My First Time.

We all had our ‘first time’ dressing. For some of us it was fun, for others it was shameful and humiliating. Poor Julie – have you read her story? It’s worth joining our Premium Members group just for her story. You can get a glimpse of Julie’s story here:

I know it’s helpful for my members to tell the stories of their first time dressing up. So, you can post your first time story right here, in the comments below. You may find that others have had much the same experience as you.

This is a process that seems to help take away some of the awkwardness and stigma associated with dressing. As you tell your story, and see that others have often had an experience that is not dissimilar, you’ll find you become more comfortable with it.

Remember, this is about having fun. Tell us what your journey into the world of dressing entailed. Tell us how you felt about it, and if you like how you feel about it now.

Feel free to Register, (if you haven’t already) and then use the comments section below to tell your story.


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359 Replies to “My First Time.”

  1. Hello Fiona,

    my first time really was two years ago…
    I had been already and alone wearing girly clothes, enjoying the thrill of wearing panties, stockings, heels, and dress or skirts…
    But the real first time for me was when i had the urge to meet a man and being Lola…
    We texted and called each other, and he said he would welcome me at his house…
    I was so nervous, anxious… But i took my little bag, after carefully choosing my clothes.
    A jean short skirt, a white half transparent top, leaving my shoulders naked, a nice black lace shorty and black garterbelt with stockings. White heels.
    I got to his home, he opened the door and my heart was beating. I asked him where i could prepare myself, and i went to his bathroom…
    The whole process of quitting my “man” clothes, and slowly and sensually becoming Lola was so much a thrill already… I was aroused… Slight make up, eyeliner, mascara, and liptstick…
    Then i got into his living room…
    Walking nicely and sensually up on my heels, my hip bouncing gently while walking toward him…
    I will never ever forget his eyes on me, as i was scared to be ridiculous or awkward…. He was looking at me with the most intense lust i had ever seen in a man’s eyes.
    I felt achieved. I saw I was making him totally excited, and the massive bulge in his pants was quite obvious 🙂
    What happened next for some hours was the most intense experience of my life, as Lola was a virgin so far (well, as Lola) and i knew at every instant and then after this was me, this was right, and this was what I was craving for.

    I am married, my wife doesn’t know about my femme side, but I don’t care since i know what i want and who i want to be.
    This was my first time.


    1. Hello,
      Très très beau récit Lola. J’aurais tant aimé être à la place de cet homme… cela a du être un moment intense et magique pour vous 2

      1. Hello everyone. I’m in the free membership at the time. Just checking things out.

        My first time dressing I was 11 yrs old. I had a friend who was 15 and he was very handy let’s say. I resisted for a long time not really understanding what he wanted. But one day I was staying the night at his house. We were sleeping on the floor in the living room.

        I woke up in the night to find his head resting on my stomach and his hand wrapped around my cock. I was stunned and didn’t know what to do, so I pretended that I was asleep. His head on my stomach and hand caressing my cock felt so good. I put my hand on his head and ran my fingers through his hair while still pretending to be asleep. I eventually came. It was my first time other than a wet dream.

        He and I fell asleep shorty after, leaving cum on my belly. We didn’t talk about it at all. But a few days later he asked if would wear some of his sisters clothes. So I did. He would tease my cock through the panties and I would moan slightly letting him know that I liked it without having to say so.

        I’ve been dressing on and off sense then never telling anyone.

    2. I had already crossdressed quite a bit. But the first time I saw myself fully dressed up as Joyce was when I was about 53 years old. I had found a store that catered to crossdressers and went there to buy a dress. Cher, The owner gave me about 10 or 15 dresses to try on and I found one that fit perfect. Black, long sleeves and turtle neck. Form fitting.

      I waited until I was home alone and gathered everything together and put it all on and the last thing I put on was my red wig with bangs and lipstick and when I looked in the mirror I was mesmerized and I fell in love with Joyce. A cherished memory that I will have forever.

      1. It’s the most wonderfull sensation when your done dressing , look in mirror and see your inner feelings weren’t wrong. You’re a woman in a mans body, however if your fortunate you will get to experience a gay experience before your brain completely recognizes the difference to what you should be.

        1. I was probably about 14 when I first put on a pair of panties. My Mom had these silky panties in her clothes drawer. They were different colors and had a different day of the week sewn of them. I really like the feel of them on me, but felt a little strange with them on me. Over the years I’ve worn panties of and on. I even started buying some panties, bras and stockings. I bought a pair of 3 inch heels and practiced walking in them. I really felt feminine in them. I went to an adult book store where they had video booths. I had my feminine attire under my male clothes and my heels under my coat. When I entered a booth I took off my male clothes and slipped on my heels. I was so excited and I hoped someone would come in and see me like this. I left the door unlocked. A man did open the door and looked but didn’t come in. I was relieved but also disappointed. It was probably good that he didn’t come into the booth since he was a stranger. I hurried and got my male clothes over my dress up clothes and left. I was highly excited on the trip back home, but sorry I didn’t stay there longer. I’ve never told this to anyone.

          1. You should have stayed! Once quite a while ago i also went into a video booth. Under my sweatpants i was wearing silky black pantyhose. Before i took a seat, i removed my sweatpants. Horny i sat down in my pantyhose and began watching a tranny and crossdresser video. Then as i watched, a huge hard cock poked thru a hole in the wall. After a few minutes i shyly began to stroke it. Then i started sucking this giant cock. Well, that massive cock exploded a huge load of cum all over my pantyhose

          1. I don’t think so Daphanie! I am not really comfortable having sex with men as a man, but somehow it feels different dressed. It is important to me to have a good relationship with my Mistress and I brought her here with me so we share the experience as we always have. I was upfront from the beginning because going through a divorce once was enough. My first time was at eight years old when my sister and I dressed up in a bunch of second hand clothes that my mother brought home. Lingerie and dresses. I wore panties sometimes when my boys briefs ran low. I definitely enjoyed silky nylon. Halloween had me dressing up as a woman at least several times over the years. It was not until the internet age arrived that I really began to explore on a more consistent basis. I read a lot of erotic stories and gradually discovered I preferred cross dressing stories. Today I have a Tumblr blog with a sissy theme that allows me to express my feelings and chat with others. Sometimes I dress and go out in public, and even pass some of the time. At the moment I am in Mexico which gives me a lot of freedom to dress . Mostly I enjoy maid service for my Mistress in our condo but now and then I venture out for a bit of fun.

        2. Since the last post I had here I’ve got a new first time story. Last month I had my first time experience dressed completely femme in public. I went to a shopping mall not close to where I lived. I had talked to someone on twitter and she turned out to be a Mistress. I found this out accidentally because of something I said that made me a bad gurl. She told me as punishment I had to get dressed up completely feminine, makeup and all and go shopping at a shopping mall. And she wanted proof. After I had showed her proof, I had to post on twitter that she was my Mistress. So I drove in high heels in my femme outfit to the mall.
          I was very nervous at first especially walking that long in high heels Should have used flats but that was too late. As I walked in the mall I got smiles from men and women. I took pictures of me as proof that I was in fact there. Finally I went t into Victoria secret where I purchased 5 new pair of panties. The sales ladies at Victoria secret pretty much knew I was a crossdresser but they were very nice and helpful to me.
          I’m sure my face was red even through my makeup. When I got back to my car I felt kind of proud of myself. I sent my proving pictures to my Mistress and declared on twitter that she was my Mistress. She said I was a good gurl. It was such an exciting experience. I might never have done it if I hadn’t accidentally met my Mistress. I can’t wait to do it again.

          1. Daphaine,
            You have to be very careful with the Twitter and Tumblr mistresses. I recently had encountered one that was persistent in trying to blackmail me. Exciting story though.
            Honey Loines

          1. Just go to a thrift store and find something you like beause they don’t care who you are buying for. Though if you need some help you could ask them for it.

          1. Dunno if anyone has replied in past. Sounds too simple an answer but just own it. No need to be nervous. It’s cloth and can say anything when lingerie. Who would suspect it’s 4 u? Every day of the year there is a birthday. Does the shop assistant know when ur partners birthday is? Unlikely. So buy with confidence not nerves. Even if you’re single the cashier don’t know that. Buy buy buy. Then off to the next store.

          2. Just go about your business pay attention to what you are doing and don’t worry about what others think. Believe me you will never see them again. I personally started to shop at the mall for lingerie when I was in my early twenties. The first time I went to the women’s department I had butterflies in my stomach. I thought to myself I am never going to see these people again. If someone asks what I am doing,which no one ever does I am buying a gift for my wife. Easy enough. I went through and purchased three panty and bra sets one set had hearts and bows, another had poke a dots and bows white and red, the third was farm girl style blue and white checkered with ruffles. I left the store not a care in the world. When l got home I immediately changed into the set with the bright red and put my male jeans and t-shirt on . The feeling of the bra and panties under my clothes gave me such a sensation that overwhelmed my body I just tingled. Until this day whenever I dress in femme that same sensation returns. I love feeling feminine and girly . If that is wrong well then

          3. Just realize they don’t care. Most people are more worried about how they themselves look than worried about how you look. Then relax in that knowledge. The alternative is to buy online at VS or Land’s End or J C Penney. They have clothes for tall framed women, so torso and arm lengths make a better fit even if you are a size 4.

    3. My first time is just like every time now. 1996 and I’m 16 spice girls are topping the charts who I claim hate and I’ve been getting unusually high with my friends while my folks are away. Once they leave and get my sister and mothers clothes listen to aforementioned pioneers of girl power and play dress up.

      At the time I see I want to be deeply dominated by femininity and brainwashed. This is my finally accepted fantasy has finally taken me 20 years later . Completely

      1. Andrew we r around the same age. I’m a 38 yr old married two kids. And I love to dress up. My first real time is come up. I told my wife and sister that I want to go out dress as a girl. So she has alot of gay friends that do drag and r gonna transform into a beautiful women. I use to dress then but not as much as I do now. I do wear men’s clothes when my kids r around be rest assured that I always have on panties.

    4. Speaking for myself & perhaps many other married men I would love to be flitting around ‘en femme’ for a handsome manly man with a big hard cock, to be his ‘love puppy’ to bring pleasure to his manhood. Everyone is different in their kink towards wanting cock, mine is to be submissive and feminine. Some guys focus on only cock in their latent homosexuality, not me. I know I’m gay because kissing a man turns me on, makes me feel feminine and gay. Alpha males are very turned on by femme submissive betas like me, turned on by this desire to express our gayness through feminine mannerisms. Panties? You bet! Stockings and high heels? OMG yes! Silky dresses, wigs and lipstick, yes please. Did I mention PINK panties? Guys that wear panties and suck cock are intoxicated by the color pink, the deeper shade of hot pink the deeper the desire to be gay and suck cock.

      With my alter ego sissy mindset I know I would love to have a boyfriend. Someone I could secretly meet just to be naked with, to kiss him hungrily and most importantly suck his cock. I could easily be a sissy wife to a man. The thought of being able to paint my nails and dress in feminine attire all day stirs a smoldering longing. To be walking around the house in sexy panties & camisoles & nighties & stockings & high heels & dresses for my ‘hubby’ is a stimulating thought beyond belief. To be adored for being feminine and to please him sexually all the time, that is the secret longing, to be free to express our gayness.

      And like you Lola, my wife has no idea. Its just so intoxicating to dress and act feminine for a man…..

      1. So good for mommy. Such a little bit of good fun and sinfulness. I could not be more excited about this. Just let go of any inhibitions and the most erotic ideas that are not guilty pleasures.

      2. You are so right I can only dream of pleaseing a hubby and whering sluty cloths all day thinking of new ways to suck him off and make my self sexy and satisfying for him when he comes home from work. . But that is far from my day and it’s only part time for this Sissy.

    5. My first time was when my superhot daughter in law left her see thru white panties in the bathroom. I just had to have them. After watching her for years i decided if i couldn’t be with her, i at least wanted to wear her panties.

      It was so sensual. I started to take some of her clothes little by little. I wanted to be her! That got me over the fear. Now i buy my own dresses bras panties and lingerie. My next goal is to meet a female to accept this. I am dying to have a hot women or sexy male to bend me over in my short skirt.

      1. Did much the same thing….but with my older cousins panties….was fasinated with the feel and scent. I had to make them mine….feel free to write.

        1. My first pair of panties that I took into my possession were my friend’s sister’s. Pink bikini nylon, felt so good. Intoxicating they were. Now, after several purges, I’ve accumulated multiple pairs of different styles, colors, textures, love all of them. Just wish I didn’t have to keep everything a secret. I joined this site today as a basic member, hoping to gain an outlet for my hidden feminine self. Vanessa

        1. I bought a wig recently at a store in our mall. I told him it was for my wife. I think he had his suspicions. He knew it was for me I think. Since I’ve gotten the wig I’ve gained more confidence and have gone out dressed femme twice. Both times shopping as a woman. I talked about the first time before. On my second time I was really relaxed. I wore flats instead of high heels and casually browsed in the ladies department at Walmart. I seemed to fit in better this time. I’m looking forward to going out again.

    6. Hi’ya………..hmm, my first time was like mostly everyone else’s. I wanna share my first time, actually looking & feeling femme. Living alone, after each work day I’d race home, first stripping outta of the uncomfortable”man attire”. Then picking the perfect bra & panties. Usually lounging in those as I delicately & perfectly painted my finger nails & toes. Finally after letting the polish dry I’d pick out just the right outfit for the night, sometimes changing 3 or 4 times. Then I’d choose the perfect pair of high heels. Finally, the final step……. applying make-up & putting on my dark brunette wig. I remember as, all this takes place I begin to evolve into the woman, that just feels natural. Once the transformation is complete, it totally feels like I can finally breath, relax & just be myself. Oh how I truely miss those days. I struggle daily as the male version of myself. It isn’t fair!!! I just wanna be, no NEED TO BE ME!!!!
      And that is Jessica Nicole…….
      Thank you being here & letting me share.

    7. Lola. That is a fabulous story. I can relate to it as I too have been secretly dressing in my sexy clothes for quite some time as a married man although it started many years before. Only I have never done it outside the privacy of my home or hotel room when away on business. As far as being with a man, I’m sure it’s just a matter of time for me. Other than chatting with Fiona earlier and commenting now on your story, I have never revealed my dirty secret to anyone. I think I am going to enjoy this site and hopefully make some new friends and family.

    8. My first time was when i was 27, I always have had this way of picking out my wifes clothes and outfits. One day I decided to dress myself in her clothes. The full deal, i shaved everything and applied the make up, put on a cute skirt, bra and a top to match. I didnt feel complete. Went to the shoes and find my wifes hottest pair of heels. You know the ones that can get a you going on a cold morning. That was it, for the first time i looked in the mirror and said this was who i was mean to be. Just as i was walking into the living room my wife came back. At first she was furious! Then I explained to her everything. It took some time for her to adjust and accept me from being her husband to being her husband who can dress and be Ashley. To this day we have time for us that allows Ashley to play and its the best thing. My wife has actually helped me start growing a natural chest, shown me how to put on makeup without being to much and even comes home with cute clothes for me. I love it so much and i want to experience the whole thing. Just like in the clothes make the man.

      1. Ashley you are so lucky your wife understand
        Aftering many years I finally told a old girlfriend from high school
        When you finally come out the closet
        It’s so intoxicating
        My old girlfriend and I fantasize about getting together and playing dress up

    9. Well, a lot of these first stories sound similar to mine…
      First started with moms panties and lingerie. She had a lot of satin bikini cut panties and curiosity got the best of me. I tried on a pair if her satin panties and everything bloomed from there… After the first time trying on panties it went to nighties, bras, pantyhose…
      That all was around 5-8 years old… Then i quit for a while, then came the early teen years and i started wearing mom’s clothes again… Now i was wearing everything from panties to dresses amd heels when i was alone… Continued dressing up in secret until i was 17 living with a friend whom happened to be a girl.. Found myself with access to her clothes and internet started chatting with people who had similar interests meet up with a couple different guys over that year, figured i was bi and experimented with masc men after a while figured out i really do not find masc men attractive so been looking for a woman or another crossdresser…

      1. I also started with moms undies at about six. Processed to anything I could get my dirty crossdressing paws on. Dresses, heels panty hose until I left home..never stopped..have a great wardrobe of my own.

        1. wow.. thats soo me too.. i have a great private robe now.. my GF knows i cross dress but we havent been able to do it together. though she does embrace my pantie collection.. i have been out a few times fully dressed up.. not as much as id like.. i fear ill be too old by the time i`m fully comfortable with myself as a gurl..

      2. ³my first time was 13 halloween momie told dad that she was going to dress me up as an old lady mommie started with silky black panties and matching bra stuff with nylons then she wrapped a garter belt with four hooks around my waist then a pair of silk red stockings rolled up each leg and clipped on the garter belt mommy laughed as my tiny penis poked out in my panties she asked me if it felt good to be dressed like a lady i said yes mommy i love it she sat me down on her knee as she put a cute pair of black pumps with a 3 in heel on my stockinged feet i got off her lap and stood before her dressed completely fem my penis poking out slightly but so hard from this wonderful feeling she told me stand still and close my eyes because she needed to make my tiny bulge dissapeer she started to rub her stockinged foot up and down on my pantied bulge i couldnt help peeking at her beautiful foot rubbing me up and down i started to squeal mommy said does that feel good little girl i was so overwhelmed with all that was happening i said yes mommy yes it all feels so good then she said are you mommys little girl and i couldnt help saying yes yes im mommys little girl she pulled my tiny throbbing penis out of my panties and rubbed it up and down her sexy nyloned foot she made me say im a good girl and will always let mommy dress me up i didnt know what was spurting out of my hard penis and all over mommys foot but it was the first time i had exploded like this the few wet dreams i had were nothing like this

    10. Hi I have to say I think some of you gurls are rather wonderful and better looking than many a genetic women. You seem to know instinctively what to wear and say and act to turn a guy on. Stockings and suspenders on a gurl and a shortish skirt are a must for a guy like me and you ladies wear it so well. Lovely stories of your first time. Keep up the good work ladies, you certainly have an admirer in me xxx.

    11. Hi Lola, this is a slightly different take on my first time as I’m an admirer and don’t dress , yet strangely enough my early teenage years brought me to to where I am today. It first started before my teens or at least very early teens. My grandparents often took me to a pub in Kennington, south London, which put on afternoon drag shows. My very first time I saw a and I hope you don’t find the term queen offensive but it was a two queen drag show. Most of the punters were working class blokes who were only there to take the Micky, at least that was what I thought. But the two drag queens were absolutely hot. I still remember it like yesterday very short skirts long legs stockings and suspenders lots of make up. I can’t remember their names unfortunately but you can imagine they were rather vulgar.

      I was young and not to put too fine a point on it, horny. They both had microphones and one much to my embarrassment sat on my lap and announced to the room that she was sitting on something very hard. Well you can imagine my embarrassment, because truthfully if she had wiggled one more I think I would have cum in my underpants. Thus started a lifelong obsession which has led to quite a few sexy encounters via the Vauxhall Tavern and other such places. I just thought you might enjoy a slightly different perspective on this theme.

      Lucky enough to have spoken to Fiona this morning. Best wishes to you all, and keep up the good work.

    12. Wow Lola what a hot experience you had I certainly hope he enjoyed it as much as I would have I have posted before about my first time when very young and inexperienced now I shall share a true story about my first time with a gurl a special gurl if you know what I mean and I’m sure if your reading this ladies you know exactly what I mean . It was the 1980s and the goth look was seemingly everywhere I was on my way to a drag show at the Vauxhall Tavern as they had a drag night twice a week for those unaware the Vauxhall Tavern was a gay pub in you guessed it Vauxhall before you got to the pub you had to go under a poorly lit underpass that was when I saw her and had my first real experience she wasn’t tall like so many of you ladies in fact she was about 5ft 6 possibly 7 and slightly on the rounder side though not at all fat she was wearing heels a very short ra ra style skirt stockings and suspenders which is a total turn on for me I was incredibly nervous it was my first time I was about 19 I’m guessing she was a little older but not by much as I walked past her I Said very nice indeed under my breath she looked at having heard me and said I’m glad you approve want to go somewhere I don’t know if any of you remember the Vauxhall tavern from the 80s but there was a place called the Vauxhall gardens quite close by often used for illicit sex we went there together and had a rather sexy old time . PS that was when I first heard the term Daddy do hope you enjoy the true story from a much older man I’m now 55 and still look back on those days with a lot of fondness

    13. Hello. I am new to the site but feel that a big kiss and hug to Fiona for putting such a good venue together for the rest of us to find support, ideas, comfort and sanctuary from an often times judgemental world. I grew up the youngest of four with three older , bossy sisters. My father was a career Air Force pilot and was gone on some top secret mission quite often. I got use to being around alot of estrogen and always liked hanging out with girls more than boys. I was facinated by everything girls did and watched them constantly, studying the way they dressed, related to each other and small things like how they would flip their hair back or adjust a bra strap. I was envious of their creative options in fashion, hair and accessories. For them the possibilities seemed limitless. Boys on the other hand were restricted to pants, shirt and shoes. No enhancing our looks with makeup, No matching our lipstick with our eyeshadow or nail polish, shit , we couldn’t even part our hair on the other side without ridicule and suspicion! Our clothes were boring by comparison and I thought it was unfair. When I was around 7yrs old my sisters called me into Victorias room. Vicki was the oldest and the dominate mastermind of all that went on with us kids. I was summoned into her room one afternoon and found Sue and Jenny in the room waiting as was Jennys best friend Sherry who lived next door. Vicki came in behind me and told me to sit down and the three girls to shut up. We all did what she told us to do , like always. She shut her door and began to talk in her big sister serious voice. She , and they, thought that it was time for me to know the truth about me and she wanted to be the one to tell me because mom and dad didn’t know how. I was, she said, supposed to be a girl not a boy. The doctors had all said I was gonna be a girl, mom and dad wanted another girl and so did my sisters, who had been excited she said , to have a baby sister. She told me that everyone had been so shocked and disappointed that I was a boy. Mom had already picked my name. Brenda, she said sadly, I was supposed to be Brenda not Bruce. Sue said Mom had cried for days and days. So, Vicki said, we have decided that we don’t want a little brother, we want the little sister that you were supposed to be. As she was finishing the sentence Jenny told me to stand up and take off my shorts and shirt. Sue was picking up some clothes from the bed and holding them up for her eyes to size up. I was scared. Nervous. Confused. And excited all at once! Before I had time to think about it the girls began removing my shirt, shorts and underwear. Sherry was giggling, my sisters were masters at getting me to obey them and employed several strategies. Blackmail, coersion, sweetness, bribery and force were all part of the tactics used and they were all effective tools for getting what they wanted. Before I could say bibady bobady boo I had a pair of Sues white cotton panties on and a light blue sun dress. Vicki told me to twirl around for them. Ooh. that was fun and what was this feeling that had come over me? I felt so….normal suddenly. Vicki told me that from now on I was Brenda and that I would only wear my boy clothes at school but as soon as I got home from school she would tell me what I would wear the rest of the day and if I refused to be their sister they were gonna tell the neighborhood that I was a bed wetter and tell dad that it was me who lost his leather flight jacket and tell mom that it was me who stole all of her bowling money. The girls knew where all of my skeletons lived. And so, without knowing how to articulate the effect this was having on me my sisters had given life to someone who had been living inside Bruce all along only occasionally revealing herself. I was always more emotional than my friends. I cried at sad movies. My friends didn’t. I loved all the things girls did. My friends could care less. I liked to look nice all the time and I loved to go shopping. Not so my friends. I was sensitive. They were oblivious. I was a boys boy yet somehow different in so many ways. It all made sense now. I was supposed to be a girl. When Vicki told mom what they had done she was amused but said that if I wanted to go along with it then it was fine with her. Mom was in charge at home and her approval kept my sisters motivated, Dad never found out. For the next 6 years I was Bruce at school and Brenda at home. It was only after Vicki moved out that Brenda was neglected and eventually silenced….at least for awhile because Brenda was as much who I am as Bruce was and she would not be content to be confined after so many years of freedom. I struggled and cried my way thru high school and as soon as I graduated moved into an olld house in Kirkland with 3 girls, all of whom were very pretty and very girlie girl. I was in heaven and thrived with so much pure estrogen so close. I loved being around the girls and learned much from it though I still kept Brenda a secret. Then, in 1978 I met Lucy and Lucy was the catalyst that would set Brenda free forever. Brenda would be allowed to become my alpha personality and push Bruce to the side. Lucy and I started dating and eventually got a place together. She was drop dead gorgeous, bi, kinky as hell and worked as a dancer at a strip club. I was a rich coke dealer and had just begun to embrace my own kinkiness. We were folding laundry together one night when she noticed how I seemed to nearly worship all of her lingerie as I carefully, reverently folded her panties and lingerie. She looked at me and said, “you really like my stuff don’t you”? Duh, Ya think?, I said. What’s not to love, I asked, A few minutes passed when suddenly Lucy holds up a pair of her cutest panties and tells me to put them on for her. At first I pretended to be something similar to insulted but after a minute or two of her telling mr how much she would enjoy it I caved. It had been many years since I had worn any fem clothes and i was clearly excited, I could hear Brenda urging me to put them on. I took off my pants and boxers. Lucy grabbed my semi hard cock and gave it a firm squeeze. I took her panties and wiggled them up into position. They fit me perfectly. Lucy gasped as I turned towards her. I looked at myself in the mirror. The feeling was Back. Brenda was clawing for freedom. I couldn’t get to Victorias Secret fast enough! Since that night I have wrestled with Brenda several times. Purging and banishment. Only to buy more clothes and let her back. I was still fighting myself and not admitting who and what I was really, Many years would pass before I finally made peace with her and accepted her right to exist. I was as much female as I was male. Two genders, one body. And instead of denial there was acceptance and approval. I had to give myself permission in a way to let Brenda and Bruce share my body. And that’s what I did and they both have time to be alive. I feel like a human hybrid, designed with the best qualities of both genders, Brenda is sweet, empathetic, sensitive and tender while Bruce is tougher, thick skinned, assertive, alpha and decisive. Brenda is submissive and has a hard time deciding between the red skirt or the blue one! Bruce would eventually meet and marry Patricia, a strikingly beautiful, very bi Dominant woman. We were together in an FLR for 13 years. I told her about Brenda a few weeks after we began dating. She took Brenda and made my transformation to full time female her mission. She mentored and trained me to perfect my walk, voice, vocabulary, style and made me practice constantly. She put me on hormones so, she liked to say, I could grow my own tits and leave hers alone! Sadly she passed away a few years ago but Brenda continues to flourish. The two of us share tho she gets more out time than Bruce and has a wardrobe that is very large. She has more clothes than most women do and she’s a boot whore and shopaholic. Bruce gives her a long leash!

      1. I love your story. I’m non binary…male and female but lost my 10 yr marriage due to me being unable to suppress my fem side. My ex claimed to love me but is really enjoying her new relationship with a male. She deserves happiness. My love for her was real but hers love for me was based on my denying who I am.

    14. Hello everybody. “My first time”. I was maybe 11 when I started dressing back in 1970. I has been accosted and masturbated a man in park when I was 10. I still remember the man saying I looked like a little girl. That stuck in my mind. I think it was 11 when i started. I still had the thoughts of that man in my head and decided since i was home alone, i would dress like a girl. I went and looked threw my sisters drawer. She was at point in her like where she had training bra and panty sets. I think they were “Barbie”. I looked threw and found a silky yellow pull over dress in her closet. I loved the feel of the cool material. That was my starting point. I chose it and back to her drawer for undies. I pick a yellow matching set of Barbie undies. I undressed completely and pull the panties on. I was only 11 so penis was very small. I stuffed it back and I looked like a female down there. I put the pull on bra on and twirled around as I admired myself in the mirror. I was raised back in the long haired hippie days so I already had long blonde hair. What I seen in the mirror was the girl I wanted to be. I got a pair of white silky pantyhose from her drawer and put them on next. The feeling on my legs was incredible. Made me tingle all over. Next I slipped the yellow dress over my head, it fit me perfectly. My sister and I are 1 year apart and her clothes fit me perfectly. I put on a pair of little white heels and it again stirred feelings within me as I strapped them on and admired my feet and legs. I looked in her jewel box and put on some bangle bracelets and pearl necklace with matching ear rings. More and more as this experience unfolded before me I thought about being with a boy like this for my first kiss. I was done in her room and went to my parents room. I looked over my mothers makeup and chose a sparkling pink lipstick. It took me a few times to get it on properly and was pleased as I puckered my lips and blew a kiss at my reflection. I put on perfume as i had seen my mother do plenty of times. The smell was intoxicating. Make me feel even more femme. I put some barrettes in my hair and before me, Becky stared back at me. I wish I could have stayed Becky forever. I grabbed a few of my dad’s playboys and off to the living room I went. At that point in my pubescent journey, I did not get hard or horny. I leafed threw the Playboys and imagined myself as the beautiful women. I read some letters and imagined myself as the women in the stories being made to do things to the horny men. Being kissed by a man, feeling a man’s hardness in my hand, I closed my eyes and imagined kissing a man’s penis all over and sucking it into my mouth and when my mind excited to the point of feeling a man’s hardness, I sprang back to my senses. I looked up to see the clock and remembered my parents would be home soon. I rushed threw the process of undressing quickly. When i was down to panties only when i pulled them off, they were wet. I was terrified as i folded them, putting them into the back of my sisters drawer to dry. When all was put away i still smelled of woman so i took a hot shower and washed. As i was drying i could hear my parents enter our home. When they asked what i did while they were gone they asked what i did. I said i went for walk in park. What a lie, your son was doning his sisters clothes like the sissy he is. I smiled in my mind…I loved being the sissy and knew at that point there would be more of Becky to come. I hope my story broke no rules in content. That was my first time and there were many more to come in 48 or so years. Thank you for letting me share this with you all


    15. I was dressing as a girl since as far back as I can remember but when I hit 16 years of age, I now wanted to go out completely as a female. I waited until Halloween, I got my older sister to do my hair, makeup & nails telling her there was a costume contest & the winner would get $500.00 which I would split with her. She went all out on me, piercing my ears, shaving my body & plucking my eyebrows to ultra thin, highly arched lines, when she finished, I looked beautiful. When I left the house I started hitch hiking to the mall, a guy picked me up & made me blow him for the ride, half way thru his blow job I realized I was really enjoying having his cock in my mouth & I started sucking him harder & faster until he filled my mouth with his sperm, I loved the taste of his cum & I wanted more right then & there & I told him so. He told me to wait about 15 minutes then I could start sucking him again, I waited then took him in my mouth again. When he was super hard, he pulled my head from his cock, lifted up my skirt, slid my pantyhose & panties down & bent me over the hood of his car & put his cock into my ass hole. It really hurt at first but as I got used to the feeling I started pushing back against him, trying to get every inch of his dick inside of me, he exploded inside of me & I loved it, I never wanted it to stop. After cleaning off his cock with my mouth he made me get out of his car, he gave me his phone number & I planned to call him tomorrow night. When I finally got home my sister was waiting up for me, I told her I didn’t win the contest, she told me to go to her room & take off her clothes, she came along to help me. When I took off my pantyhose my sister started saying “you little slut, you went out & got fucked tonight” I tried playing dumb but my sister told me to look at the giant cum stain that leaked out of my ass & into her panties that I was wearing. She asked me if I liked getting screwed, I told her I did along with sucking cock, I told her that I wanted to be a girl all of the time. My sister told me we couldn’t let our mom know about this & a few nights a week my sister would dress me up & we would sneak out of the house after everyone went to bed & walk around town looking for guys for me to have sex with.

    16. Hi Y’all I am new here ! My first time was at age 3 I wore my sister’s bathing suit and cap to swim in . I was rewarded with a matching tan my hide
      With Sea and Ski 2 piece outfits the tops said tan my hide and bikini bottoms said with Sea and ski

    17. Ty Lola
      My gurl name is Patricia
      My first time similar to yours after talking online and texting I finally asked Deoante to come over
      He asked if I would be dressed and I told him yes
      I didn’t have much to.wear
      White stocking pink lace white panties with pink trim a silk slip top
      No wig just a pink mask
      I was so nervous he open door Nad I saw how his eyes lit up
      We sat down and had a couple drinks and then he kissed me I was shocked I liked it I kissed him.back and he showed me for a few hours amazing sex I never thought possible

    18. Fiona,I started out dressing when I was around 10-years-old after my parents got divorced. I went in to the lady’s bed room and tried on her wig, clothes, and lingerie. My cock immediately got aroused wearing them. Then in college I was dared to dress up as a girl. I love wearing panties and not male underwear

    19. Hi Lola
      I started when I was just 10-years-old when my parents got divorced. My mother and me moved in with another lady, and I was bored so I went into the lady’s bed room and tried on her wig, clothes, and lingerie. I immediately got aroused wearing the panties. Since then, I wear panties everyday.

    20. I can only imagine how exciting that was. I could not even begin to look feminine when I tried dressing. I knew I wouldn’t be but wanted the feeling of having tried, at least. I’m happy for you. I
      I’m also married but now know what I like best and no longer feel guilty for liking it so much.

  2. I was about 5or 6 years old my mom had some of her lady friends over for drinks one day and started dress me up in girls things – a bra and panties, a nice sun dress – and then put make up on me. They did my hair all up and I had to walk to all her friends getting a kiss from each of them.

    1. At five I first noticed my mommy’s pretty lingerie when I would watch her dress. She had two lingerie chests full of pretty things she would show me. Well, I thought I would like to try her pretty lingerie on too. So, I began sneaking into her roomand I would sneak a pair of nylon brief panties (she had dozens in assorted colors–Olga, Maidenform, Vassarette to name a few) into my room and put them on under my pants and wear them all day.

      I would put my used ones into the laundry–she had so many she won’t notice I thought–the next day and start all over again. My panty fascination and sampling continued into my teens. Mother worked then, so when I came home from high school, I would venture into her bedroom and furthered my exploration into her lingerie. Only, I expanded my curiosity into the rest of her finery–garter belts, bras, nylon stockings, slippers, nighties, nightgowns, heels, wigs, and on and on and on. I had two and a half hours to play.

      I would try on different sets of her lingerie and pretend I was her. I would even put on her wigs and makeup. It was so fun! She worked all day Saturday so I would take extra time (2 hours) to look oh so feminine and spend the rest of the day parading around as mommy. I didn’t think she suspected anything because I was careful to fold and hang everything up, showered clean well before she came home to her slim handsome son.

      I loved sashaying in front of the windows when one of the neighbor ladies ( I even snuck into their lingerie drawers when house sitting) was outside–I wanted to get caught. Well my wish came true one Saturday afternoon. I was dressed in her prettiest Red lingerie to the T. I was sitting in the living room admiring my looks, reading a Woman’s Day–in heaven.

      I just lit one of her Virginia Slims when the back door opened.

      “Honey, I’m home” she called out as she marched through the kitchen and into the living room. Her eyes lit up when she saw me.

      “Uh, honey what are you doing dressed up in my clothes” she exclaimed. “Oh, and you look so cute too! Stand up sweetie so I can get a look at you. Well, well, well you look darling. Your hair, makeup and sexy lingerie. Your even smoking one of my Virginia Slims. You look…like me and I love it. But, I lost the bet…. Just hold on for a minute cutie.”

      Mommy hurried to the kitchen where she picked up the phone and dialed. “Oh hi Marilyn. I have some good news for you, honey.” She motioned me over to the phone and handing me the receiver she said, “say hello to Marilyn and tell her what you are wearing.”

      “Hi Marilyn, I just surprised mommy with one of my favorite looks, I am dressed up in her sexy red lingerie looking exactly like her. Can I come over and show you?”

      “Why of course you can sweety. I want to see you, doll. And when you come over I have a surprise for you honey.”

      I looked at mommy with a smile and said, “Mommy, Marilyn wants me to come over to her house and be a girl.
      I would love to meet with you and have you help me dress up. Please?


    2. Michael, I too, started out early, at about 2 or 3, when I graduated from diapers, and plastic pants, to real clothes. Unfortunately, my family was poor. My parents had 4 small children; and I was the 3rd one. The money for new clothes every few months for growing kids to have their own wardrobe was never there. My mom came up with a novel solution; put the next child in the oldest one’s hand-me-downs as they grew bigger. My brother was the 2nd child, so he got the treatment first; wearing my sister’s no longer fitting castaway items. This attire was of course, girl’s cotton flowery panties, camisoles made like Tshirts, but with lace, also in cotton, then the usually white cuffed anklet socks, and, of course, either black & white, or brown & white saddle shoes. Over all this ensemble was a short cotton shift patterned dress. He was a boy, didn’t like wearing girl’s clothes[ and rebelled. They broke down; and got him boy’s clothes. Now, it was my turn. These became my usual things I’d put on when I began to dress myself for the 1st time. For the next 3 years, I was happily ignorant that there was a huge difference between what girls and boys wore. I stayed in that bliss until I started school at 5. Then, a battle ensued; but, then, that’s another story.

  3. My first time I was 12. I tried a pair of my cousins underwear on. I wish I still had them. I was at her house. We played with eachother a lot. We got naked with eachother and felt each other for hours, played together fingered and stroked each other. It was great! We still love eachother! Occasionally we still get together. It’s fun.

  4. I was 11 the first time I tried on my mom’s clothes. I was going from the bathroom into the hallway and the door to her bedroom with ajar, and I could see she had a bra and a slip laid out on her bed. I felt a little tingle and it came in my mind to try on the bra and the slip to see how they would feel. I liked what I felt and what I saw in the mirror. I found her lingerie drawer and pulled out some stockings to stuff into the bra. I felt the shape of my “breasts”. I was hooked from there. Two or three times a week after school before my mom would get home from work, I went into her bedroom, opened her lingerie drawer and picked out what I would wear. I got so aroused! I discovered that wearing a pair of panties under her slip allowed me to lie down on the bed and rub the panties against the slip material to get an incredible erection and release. I also used pictures of women and girls in lingerie from catalogs that my mom kept to further my excitement. I sometimes tried to stop, but I couldn’t for more than a week or so. I repeated this often until I went away to college and lived with other guys in a dorm room. Later on, after I got married, the urge came back, and that’s where I am now.

    1. My story is pretty similar. A little exploration of moms satin slips and panties, years of suppression, occasional wearing of spouses stuff under man clothes and now as a senior, a deeper exploration including some femme hypnosis, finding a few friends in an online friendfinder site . One of these hosts parties that includes a makeup pro who did me the first time. It was pretty amazing.

      Now your program is guiding me toward next steps that is leading me to some “dates” with others I’ve found . I’ve bought stuff and am ready to play! Life’s to short !

      I hope I know what I’m getting myself into!

      1. Wow that sounds like fun I’m a cross dresser as well I love wearing and slepping in woman’s lingerie I’ve dated men and it’s the upmost feeling of having him make me his little girlfriend, I enjoyed being with a man as a woman I’m going to check that website and see what adventures lie ahead.

        1. i’ve played with gurls now and am looking fo r my first guy seduction.
          I hope he’s not just a horny guy who would fuck anything.. I keep getting compliments on my femme look despite being tall

          1. Update: I finally had a date with a man who lives about 20 miles from me. We met for breakfast at The Eat and Park restaurant near where he lived. He greeted me with little kiss and walked in the restaurant holding hands. I had already told him that I was a crossdresser through many text conversations that we had. He liked the pictures of me dressed femme very much and he sent me a picture of himself also. I was going to have him order for me but a summoned the courage and a surprisingly feminine voice and told the waitress that I would like the entre called Bananas Foster. After we ate and he paid we decided to go to his apartment. When we got there we started kissing, easy at first, then we got into French kissing. We were both getting turned on by now and I felt his hands rubbing and squeezing my cheeks under my skirt. Wanting more, I suggested we move to the bedroom. I didn’t have to ask him twice. Needless to say I found out how a woman feels making love to a man. We were both so horny.

        1. Hi all
          I am new to the site which seems wonderful. Back in 1984 in London, England I was coming out of relationship and on my own. I saw an ad, ‘ Make Up Lessons For Men’. I followed it up and visited Kathy in Chelsea. She was so helpful and had a wonderful array of dresses Tec. She gave my wonderful tips on make-up. I still remember the thrill of dressing for the first time. I had never been so aroused in my life before then. Been through many ups and downs since then but now more accepting of who I am.
          Love to all here

  5. I was 10 we just got home from the laundromat and I had started putting my stuff away and found a pair of black panties in my stuff. I knew from the style they were not my mom’s and I got curious and tried them on. It was like a switch was flipped in my head and I knew that this was the first of many more times to come.

    1. My first time was at age 7 when I walked in my sister’s room feeling curious I open her dresser drawer and noticed she had very beautiful panties and me being a curious I decided to pull a pair out not knowing why but I put them on but for a reason I didn’t understand but they felt comfortable and very natural

  6. I had been playing around in my sisters stuff for quite a while and she knew, so when I was 11 she dressed me up for halloween from head to toe. It was a short pink dress with little strawberries on it with nylons, bra. panties with ruffles on the bum, high heels and makeup, the works. That was when I knew I was Heather. I had such a great day and night and when I went home I pretended to fall asleep all dressed up so I could spend the night as the real me. My sister was great, she talked to me about it and started buying me stuff and keeping it in a special place in her closet, so when I went to visit we would have girls night.

      1. Thank you both Sarah and Crystal. My sister was and still is great, she still supports me 40 years later and tells me her love is never dying no matter what. I went to her 60th birthday party in Heather mode which I live like most of the time now, and she thought it was just great. Even if I’m not fully dressed I’m Heather on the inside, I’ve finally realized this is who I am.
        I used to go stay at her place when her husband was on the road, he was a trucker, and she had a special section in her closet with my stuff in it. I would get dressed and we would hang out and have a girls night, doing each others nails and eating junk food. I loved those times, just to bring back our youths for one day would be a dream. She even gave me tips on how to give a blow job when I got my first boy friend.
        Anyway, I’ve rambled long enough. Take care girls and thanks again, Heather.

    1. On Halloween my sister and her girlfriends thought it would be fun to dress me in her communion dress. They didn’t’ know at 11 I had already had been wearing my sisters clothes when she wasn’t around. I made a big stink that I didn’t want to be a girl but really couldn’t wait for them to dress me. They put white lace panties on me then white thigh high stockings and a white lace bra. I felt so wonderful. Then they put my sisters communion dress on me and did my face and hair, OMG I almost wet my panties!! We went out Trick or Teating and I got the most candy of them all! I loved every minute of it. I kept wearing sis’s clothes until we moved and she stayed to finish to school. I always will miss those days. I’m married now and my wife thinks I’m crazy and will not support me in my CD life at all. Love, Edie

      1. Fret not your not alone. Im going through a rough time w my lady. We have had a couple role reversale cd nights that were 100% perfection. She looked truely in her game. But pretty much thinks im nutz. Its a hard road so far.

  7. My first Time when i’ m 13 years old, i try my mother’ s green satin panties, the sensation On my skin Are very horny and beatiful !! And Everyday i put it with pantyhose and high heels . It’ s very beautyfull and i love wear feminine lingerie and clothes !!

  8. Fiona … My first time.
    I was 14 yrs old and had two older sisters and I remember I would wear their tight skirts and tops and always involved panty hose.

    I would always employ some type of bondage and red lipstick. Things really haven’t changed 30 years later except for the fact I have an entire closet filled with my own clothes.

  9. My first time I was a young boy in the year 2002. Age 11. It wasn’t my first feminine experience as I’d had a neighborhood friend as a kindergartener and she loved to play barbies and the like. And it was then I started wishing to be a girl. But at age 11 I was a 5th grader. The school had just held a womanless pageant that I was too “proud and macho” to enter. As I watched it, I felt deep regret not volunteering to represent my class. I went into a storage closet to find something for a teacher and there it was. A cheerleader uniform just there in a box. I looked around and stuffed it under my shirt. I snuck it to my locker and backpack. After smuggling my treasure home I hid away in my room and locked the door. I stripped and put on the tight form fitting dress. It was designed to fit a girl and I was small and skinny for a boy (what I wouldn’t give to be small and skinny now) so it gave me the appearance of a feminine body (for an 11 year old, I just remember having a slight hourglass). I danced and twirled for hours on end, almost daily. It was wonderfully addicting. I felt pretty for the first time and I was hooked for life. I kept that dress until I hit a growth spurt later that year and I returned it to the school when it didn’t fit anymore.

      1. Thank you! It’s a very personal and dear story. It was the first time I realized that there was a beautiful girl living somewhere inside me. She rarely gets the chance to come out. But when she does you can tell she grew up from that little girl who just loved to cheer. <3


  10. I don not remember the first time. I was about 2 years old and mother told me I was crying to be dressed like my twin sister, so somewhere is a pic of me in a nice red velvet dress.
    At thirteen or so, I ran across a picture of the movie One Million Year BC starring Raquel Welch and just wanted to be like her. So once in a while I would sneak into my sisters clothes. It felt like I was Me. Felt natural and also erotic. Been doing it on and off all my life. Working at home now for last 3 years or so, I I am dressing every day to varying degree.

  11. Uh, it was a long time ago with a friend and his mother’s lingerie strung out all over the laundry room. The panties, bras and lingerie hanging to dry, or dirty on the floor… waiting to be cleaned and worn again. I was fascinated by it. The fabrics alone were limitless. And it changed, every week there might be something different. It got weird, it got straight, it got motivated. Now I can sew full custom mens wear… hmmmmm I may have gone too far… lmfao

  12. i first started dressing up when I was a teenager, my parents had accidentally locked the house and hadn’t left me a key so I spent the time in our travel trailer until they got home. My mom had some of her clothes in there, soft silky nylon panties…it’s hard to write this it’s making me so aroused..umm i found the panties out of boredom and the soft fabric was amazing, and I started masturbating with them then I put them on and the way the fabric pressed up against my balls and kissed and made out with my cock with how it slipped up and down…

    1. You’re making me horny just reading this, finish the story. I’d loved to have been there to rub those panties on your hard cock and taste your love juice when you finished. Tell me more, PLEASE!

  13. I started dressing after I left the Army and been loving it ever since. I am loving embracing my femininity and letting my feminine side out! I love being a guy but I love becoming a woman.

    Victoria has made my life so much better and I love putting on makeup to feel pretty. I just want to show off Victoria and have friends see her.

    1. It was a strong committment being enlisted. The year before i got out they abolished the dont ask dont tell policy. So in the military i never let anyone know my kink fetish. I always maintained my bull side. Helped because it was some seriouse shit being found out at the time. It always felt so wrong to me. Half my friends were something or another. And even tho i earned their trust i still could never confind in anybody until years after getting out. So mad respect for having the mindset drilled into you and still being able to hear your heart speak

  14. My first time dressing happened because the girl i was seeing then and i were invited to a halloween costume party. She wanted to dress me up … my makeup….the whole look as a woman which i strongly resisted with an adamant no. The party was still a few weeks away and she was very persistent about what she waned to do to me.

    Soon there was only 4 days left and i,m still not sure why but i caved in to her desire to make me a woman for the party. She wasted no time finding a dress and heels fishnet stocking a corset a bra with matching thong panties etc etc. at this point i should probably mention that i felt different growing up. I knew I wasn’t like the other boys but had no idea why except that this feeling of being different was getting more intense not going away.

    Back to the day of the party, my gf had everything she needed including accessories to make me over. She refused to let me see what i looked like until she was completely finished. This took about two hours. The dress was low cut low back short little black dress. The heels were 4″ open toed black leather . I had a bracelet on each wrist and a nice necklace. Topped off with a short waisted jacket and a clutch. She finally allowed me to see myself in the full length closet door mirrors and it was the most amazing experience. Suddenly i understood what all of those feelings i had felt were about ……and the rest is historry as they say……

    1. Do you two keep it up now? Make a thing out of if. Halloween seems like the perfect night for me to hit it hard and nobody would ever think a thing about it. God how much easier if it started out as my ladies idea. Every halloween that passes i feel sadness for not maybe finding my own party to go to. Its like oppertunity passing me bad

  15. Out of curiosity, I tried on two of my sisters’ bras and panties when I was a teenager, and I even tried on the bra and panties the mother of a child that I babysat in high school. I was especially curious about her bras because her breasts were so small. But I never got an erection, only a little thrill about trying something “forbidden.” But then about three years ago, I got into videotaping myself masturbating while talking about porn and it suddenly hit me that I could be gay. This led to videotaping myself more and more while being naked and talking about my thoughts and feelings.

    Then one day I noticed that I made some sort of gesture that could be seen as being “feminine” and I though “Wow! That kind of turned me on!” So the next time I had a chance to videotape myself, I was struck with the urge to try something REALLY feminine and I got out my wife’s sheer white babydoll lingerie. I became super turned on and very hard and that led to trying on more and more of my wife’s lingerie and taking photos of myself, which I eventually posted on Flickr because I found out about other cross-dressers on there by doing a Google search.

    I’ve chatted with a couple cross-dressers and then eventually admitted to my wife that I like to cross-dress. She will tease me about it from time to time, and I wish she’d be more into it. Unfortunately, she also threw away all of her lingerie when we moved earlier this year because they didn’t fit her anymore, and I only managed to retrieve two of her bras, one of which was my favorite, a leopard print Victoria Secret padded bra. I bought a couple lingerie items myself, but I was disappointed with them and only save a pair of pink , flowery lace crotchless panties that I am wearing now.

  16. Well it all started when i was in the 7th grade i found my mom pantyhose and put my hand in them to jackoff it worked OK , but not well so i put them on and it felt so well i got so HARD i keep them and would wear them under my pants to i would go from there I started wearing more Panties bra.

  17. MY first time ??? About when I was 4yr old. I was joking around with my sister – she a cowgirl costume I had cowboy one. Hers came with skirt, mine had pants.

    I put her skirt on and I said, “yahoo, I am a rooting tooting cowgirl!” just joking around and then we started play dress up. That was my first time and it was fun and great.

  18. My first time was when I was about 14 and found a satin pair of panties in an old box in our basement. I don’t have any sisters so I could only assume it was my mother’s from a younger period in her life. I put them on and the excitement took me. For the first time, I felt sexy and the feeling was addicting. I started wearing the panties under my clothes and even added a bra on some days to school. I would have been mortified if someone caught me but the thrill of it happening was intoxicating. The eroticism of that feeling never wore off.

        1. Any ideas on “my first time (and hopefully only time) getting caught”)
          For me…that wasn’t a pleasant experience as you can imagine! If you like I could submit my story for starters…
          Or is that too much of a negative?!?

          1. I wouldnt mind hearing it. I have humiliation fantasy about being caught but of course in those it always turns out well. My real life one i had thought my lady had left for the day so i went to have a little me time before dealing w the kids for the night. I didnt have my collection at the ready because she didnt truely know about this side 100% so i grabbed a pair of hers to make it quick. Got naked and pulled her big girl panties up as i sat down on the toilet getting ready to start my bizez. Now mind you my lady would loose her mind if i wasnt in her life to tell her right where she left it. So really i should have known better i suppose or maybe i had it coming but seconds after pulling up tumblr and getting into it BAM!!!! The bathroom door flys open and i know all she sees is me sitting just off to the side in front of her no hidie her panties around my knees and a hard on. And she just goes, “God Dammit $_* wtf is wrong w you” as she grabs her ID off the counter and leaves with a massive pist off slam to the bathroom door. . . . With what she said cutting through to my sole like a katana i sit there thinking, “do i have it in me to try and finnish or has there been enough shame for one day” and BAM!!!!! Well thats the front door. And BAM!!! Well theres the car door. Surprised i didnt hear her peel out and all the way down the street and knowing i was gonna have to explain something to the kids about momz sudden pissedoffness i just gave up. Damn that was long. Sorry. But im sure thats not impossible to top right.

          2. My first time cross dressing was when I was like 6 or 7 and my sister had a friend over and one of us got the idea to dress me up in a dress and it was one of my sisters dresses that was velvety and kinda polyester at the to and a normal cotton at the bottom. The top had was black and then at the end of the rib cage it went to a flower pattern. We also had the idea to grab some pears and have them be the breats

  19. I was about six years old. My Grandma took me into one of the back rooms in her house. She said I want to see what you would look like as a girl. Then she dress me in My sister cloths. Then she said you look like a pretty little girl. She didn’t know that I like the feel of the cloths then. I started dressing every chance I could get. I used my sisters cloths and I don’t think my sisters ever knew what I was doing. Or My Grandmother.

  20. How about the first time, after accepting yourself…

    Recently set up a small space to get some respectable shots… the teddies, stockings, gowns… the jewelry… this girl is still short on a few things but the look is coming along nicely. Missing shoes and cosmetics, some hair accessories… Still the opportunity to girl up, and woman up was nice.
    Getting dressed between sets was great. Arousing at times…
    “Down boy… I SAID DOWN BOY….” almost lost it…
    its girl time. Tea or a Bloody Mary, either will do.
    click, click, click, click…. take a thousand pics, or two. some will be of great quality, some not. Select the best and roll with it girls…
    I have a tattoo, and scars for days. Man hands, tan lines, its ugly.
    Get that shot, you will love it… I do…
    If you don’t think you can, check my profile… you might be surprised…

  21. I still remember looking at my aunt’s pantyhose hanging the bathroom when I was in 4th grade and finally slipping them on one afternoon when no one was home – I was hooked immediately and have remained so since. But what I remember most was the day I got caught. It was late at night, I was 17 and came home a little drunk. I thought no one was awake so i put on the “foundation garments” that were hanging in the bathroom, and pulled the stockings up and applied lipstick – it was bliss – but then my younger brother burst into the bathroom. He freaked out and woke up my parents.

    My parents made me go to church and to confession the next day

  22. Hello, my story started when I was 7 years old. My mother and I went to my Grandmothers house. At the house we sat down for a nice lunch and then to play some cards. My job was to set up a card table and some chairs.
    I could not find the card table. My Grandmother told me the card table was in a closet in the bedroom. Went into the bedroom, opened up the closet and there were her sleeping clothes and the card table. Some silk stockings were on the edged of the table. I picked them up and they felt divine. I was hooked then for the rest of my life.
    It just progressed to clothing from then on. I never looked back. Simply love being a feminine being. Started with cosmetics which are wonderful and do feel delightful. What can i say after that, giggles. tvlace

  23. Hello misstress 🙂

    Well… My first time was around when i was 14,at that time i already felt like something super exciting to be transform into a woman (even before to be cd), at that time the only thing that aroused me is to feel like a woman, go shopping, feel inlove as a woman, etc.

    But this memory was attached to a dark memory of mine, because i took advantaje from a cousin of mine, stole one of her panties and touch her breast without her permission. For me it was awful, because the guilt that that situation caused me. I know what i did was wrong… But more specially, i know why i didi it, because i was jealous of her and her body.

    After years of self-punishment, i’ve continued to use my mom’s underwear and masturbating using it, but i became more interested on how i looked and how it felt.

    Right now i still feeling ashamed of my decisions, except the decision of follow this path, right now i’ve learned about my past mistakes, and especislly whst i want for my life.

    Im into this, feeling wonderful and being happy, i’ve even fixed my relationship with my cousin a few years later.

    Maybe there was a time when i wanted to kill myself and felt like a monster…. But after realizing more and more about my development as a woman… I could finally forgive myself.

    I’ve learned to makeup, dress, feel like a marvelous and desirable woman using panties and bras. But most importantly, i learned to embrace myself finally

    Hope not to get to sentimental, but this really have saved my life a few times. Who would wonder that a lipstick and eyelashes could gave me this happiness 🙂

  24. Hi Fiona,

    My first time took place when I was 15 (although I had the desire to dress up much earlier in life). My mother owned a couple of wigs, and one day, as I was getting out of the shower, I noticed that she left one in the bathroom. I just couldn’t pass up the opportunity to try it on, and from that moment, I was a different person. My mother also kept all of her makeup in the bathroom, along with her long silky nightgown, which hung on the bathroom door. I put on the silk nightgown and it felt so good. Next, I put on some bright red lipstick, and some mascara and made my eye lashes much longer than they needed to be.

    I looked in the mirror and initially felt guilt and shame for doing this. What would cause me to do such a thing? At the same time, I felt so comfortable and relaxed. It was a very enjoyable experience.

    The confusion soon gave way to desire and it wasn’t long before I would be wearing my mother’s panties, bras and nylon stockings. I would race home from school every day, knowing that I had a couple of hours before my mother came home from work, to master my skills. I became very good at applying makeup and removing it before she came home.

    I now fully accept and love who I am and proudly embrace my beautiful femininity.

  25. I love the feeling of woman’s clothes on my body. I have only dressed when alone. I have never gone out dressed or dressed for another person. I am hoping to gain skills to be more feminine and confident so I can go out dressed as a woman.

    1. I ‘ve got out crossdressing under my male clothes. I went to one of those adult book stores with the video booths. When I entered into the booth it was empty, so I took off my male clothes. All I had on were thigh high stockings, bar and panties. Oh And I also slipped on a pair of 3 inch high heels that I’d been practacing walking in. I left the door of the booth unlocked hoping some man might come in and see me crossdressed. One guy opened the door and peeked in, but didn’t come in. I was so excited but scared. After he closed the door I hurried up and put my male clothes back on and left the book store. I was very excited driving home, but probably a good idea that I left because he was a stranger. Still I wonder what would have happened if I would have stsyed.

  26. I can still remember that first time that I was caught by my Sister: In hindsight, I’m sure that she had planned it.

    I had told you that my nipples, aureole and papilla had shown signs of growing for some time: Nothing that would show through my shirt but enough that my parents had become worried about me. I had hardly shown any of the normal signs of puberty and my penis had not really grown at all. My testes had descended but they too were very small and hardly noticeable and would remain tucked up even when I was very hot.

    I was taken off to various Specialists and none of them seemed to think that there was much wrong.

    My sister, who was about ten years older than me and was making her way in Life as a Lawyer, had noticed my nipples and she and her friends would tweak them if they got the chance. Sometimes two of them would grab me while a third girl would gently stroke my nipples until they became hard and very long. My areola would swell by a considerable amount and I would groan with a pleasure that I didn’t fully understand. Also, my little Penis would stiffen and sometimes it would leak some sticky substance. I was not sure what it was as I had not ejaculated at that stage

    I had been drawn by a fascination of my sister’s clothes for some time and when she had gone out, I would sneak into her room and try some of her panties, bras and slips etc on.

    She announced that she was going over to see a friend of hers who lived several miles away. I knew that meant that she’d be gone for at least 5 or 6 hours –

    Bliss! That meant I could indulge to my heart’s content.

    I started by having a shower. I carefully shaved myself paying special attention to my lower parts. I tried Imac on my bottom and it really stung when it reached my little sphincter. I hastily washed myself and in doing so my finger inadvertently entered my bottom. I gasped with the shock but then tried again. One finger and then two but three digits was far too much and I gasped at the pain. It felt divine though and I spent several minutes soaping my fingers and pushing them in a wiggling them about inside me. I then followed it by having a warm bath and dried and powdered myself.

    In the Sixties, young men were just beginning to grow their hair and I had grown my hair to almost shoulder length. I started to brush it out and put some large curlers in to give myself a light curl with a bit of bounce. I’d watched my sister do this many times and she used to let me help as she found it amusing.

    I would like to have dyed my hair blonde but that would have been a step too far.

    I stood there in front of a Cheval mirror admiring myself and just running my hands up and down my body.

    Then I selected a light little Bra which I knew fitted me perfectly. I had some balloons and I’d filled them with water to help pad the bra out and give me more bounce when I moved around. I felt my nipples stiffen immediately.

    I found some little white panties and slid them up my legs. My little penis was straining for all it was worth.

    Tights had just started to become available and so I tried two pairs on and the feeling of being controlled started me leaking.

    I sat down at her dressing table and spent some time putting on foundation. Sis had shown me how to this and so it wasn’t new experience. I stuck on some false eyelashes and used an eyebrow pencil and some liner to emphasize my eyes and the effect was stunning – even if I say so myself. Some pale lipstick and the person who looked back at me was Pippa!

    I’d always secretly thought of myself as Pipp and there she was in the flesh.

    I put on a light slip; every girl wore a slip in those days even if it was only a half slip but this was a full slip and as it slithered down over my body I felt wonderful and girly. I found a little button front, pale powder blue dress and slipped that on as well and Pippa was complete.

    Some Baby Jane shoes with sweet little gilt buckles and I was complete.

    I went downstairs and was so happy that I danced around every room without a care in the world.

    As I walked back up stairs I thought I heard a key turn in the front door but dismissed the idea. After all, my parents were away in France and my sister would still be put for hours.

    I had just managed to take of the dress and hang it up and taken a refolded the slip when there was thundering on the stairs and the bedroom door burst open.

    It was my sister and three of her friends.

    I grabbed a pink quilted House coat and hastily pulled it around me.

    She screamed at me “You filthy little pervert!” and her friends were in paroxysms of laughter.

    “Stand up” she shouted “And take that ridiculous coat off”
    I stood there in her bra, panties and tights. She hit me and I sat down on the bed with a thump. At that moment I had a shuddering climax for the first time. One of her friends hauled me to my feet and there was a blossoming stain across the front of the tights for all to see. It was massive and just seemed to spread everywhere.

    The three of them then burst out laughing again and told me to go and get cleaned up and that they would decide what to do next.

    “Perhaps you ought to tell your parents” Gill said

    “Or perhaps maybe he should see a Doctor” said Heléné.

    “No, I think we’ll deal with him ourselves” Sis replied “I’m sure we can think of something for him or should it be Her “

    2Witht that, they bundled me into the Shower, stripped me and proceeded to clean me up. They took a while to do this as my little penis kept growing and then I’d erupt again, much to their amusement.

    While they were washing me and they were very gentle. Heléné was washing my bottom. Suddenly she, she pushed an enquiring finger into me. I tried to pull away but she persisted.

    “Gill” she said “Grab his pathetic little cock”. Gill did as she was asked and held onto my cock and balls quite tightly so that I couldn’t move. I felt Heléné’s finger being withdrawn and then two fingers being pushed in. Then she was pushing in three fingers. I felt like I was being split in half.

    “I’ll be back in a minute “she said and with that, left to room only to return a minute later with a huge jar of Cold Cream. She slopped it onto her whole hand and then began to slowly massage it onto my bottom cheeks.
    First one, then two then three fingers disappeared fairly easily. The she started to bring in four. I was …

    to be continued

    1. I concur. Thats the kind of thing that only happens in porn. I hope you recovered well from all of this. I have fantasy that runs along these lines but its always in my benefit. I hope that ended up being your conclusion

  27. Thee first time for me i was 11 or 12, got some of my moms lingerie and it grew from there. My Grandmother caught me dressed up one evening and I thought i was a goner. She began to compliment me on how well i had dressed and then asked if she could help a bit, WOW. She gave me some pointers and would check on me once and a while. I continued for a while and she held our secret till some things in our family changed.

    After about 2 years i started in again. my parents were divorced and mom worked a lot so I had 3 hours after school and whole summers to Dress up. I was pretty good with matching lingerie, dresses and makeup. Alternate Saturdays and Monday thru Friday in the summer when school was out was my Fun Time. I’d get partly dressed and clean house, then change mow the yard when it needed it. But other than that part from going to the Pool to go swimming. all the other time i would be Dressed Head to toe. I got very good at it and if my mom knew she never let on.

    Years later I still dress in lingerie and in fact i just bought a Black bra and Black Lace Back Panty which i am wearing. I do Love Lingerie, especially fro Secret in Lace They have be very helpful to me as far as size goes and nylons, I really Love them, I can’t seem to wear High Heels anymore which is all right. I have been working to grow breast and so far they are growing slowly but not to big, A or B cup would be fine for me and my wife.

    I will say that I’m not comfortable anymore unless I have a bra, panty and nylons on. Till breast get bigger i don’t wear bras to the Doctors office

  28. When I was just 13 years old I was seduced by my teacher. It started out as an innocent time at his cottage during the summer holidays. I was invited to do lawn work and clean his pool and stuff. In no time at all he had persuaded me to dress as woman… he just wanted to take boudoir style photos of me to sell, he said I would make way more money this way than doing odd jobs, so I went for it. He had me dress complete with heels, make-up, the works. I styled my long red hair to suit my new found look. I was somewhat hesitant at first, but it was really fun. I was naturally smooth so it didn’t take much shaving to get me perfectly smooth, and I had natural female hips and curves to make it so right. This was the birth of Michelle.
    It wasn’t very long before he had seduced me and taken my virginity. He was romantic and very sexually driven. He was a great teacher in the bedroom as well. He had taught me everything! By the end of the summer I had fallen in love. I had come from a broken home and decided not to return. School was done as well. I had a new happy life pleasing a man who was over 30 years my senior. I will never forget my first time!

  29. Hi, Peta here, unlike most of the other girls I would love to be a lesbians lover, I prefer the taste and feel of a pussy, the pretty smell of having my mouth over the Clint sucking all the sex I can out of her. I love to be in lingerie while making love, all I require is a great woman to share this with

  30. I was fifteen and living with a female friend at the time. We were bored and she decided she would enjoy it if I wore some of her clothes and modeled them for her. I wasn’t sure about it but to make my friend happy I decided to go along with it.

    What a life changer! I ended up modelling lots of her clothes. I wore dresses, skirts and camis, bras and panties, nighties and nightgowns, lots of lingerie, and some of her feminine footwear (high heels, girly flip flops and some strappy heeled sandals).

    I loved every second of my crossdressing modelling session and never wanted it to end. Now, many years later, I still dress up as a woman and lovevit more everyday!!

  31. My first time actually being in public view was in 2008 or 2009. I was going to visit a therapist for a first consultation to help me with my guilt of being a crossdresser. I started dressing in ladies clothes when i was 12 years old (1976) and to this day i still love it.

    Okay back to my story. I was now going through my second divorce and blaming myself for the failed marriages . Though both wives knew about me and my secret they accepted it and thought we could have fun. But the truth was I was only allowed to dress up in the bedroom by myself. This was not working. Both of them had multiple affairs and I only blamed myself.

    Then finally divorce came about twice. So I found the therapist, a female of course, because for me women are superior and this is part of my humiliation I seek. So i was encouraged by her secretary to come in dressed up. I brought my clothes and changed in the parking lot down the street to not be seen. I drove up and sat in the car for 45 minutes trying to decide if i could get out of the car and walk in. The secretary finally came out and said ‘come in, it is okay’.

    I said okay let me change back first. She replied, ‘no come in it will be fine’. My knees shaking my stomach turning a lump in my throat. I finally stepped out and went in. The therapist was not human she was an ANGEL. She encouraged, listened to me and worked with me. At times she was disappointed in me if i wasn’t dolled up for our sessions. God, I miss her.

    1. That’s really interesting. My wife and I had been seeing a therapist, and after several joint and separate sessions, our therapist asked me if I would be willing to come in dressed. I told her I’d think about it. When I got home, I asked my wife if she would be willing to come in with me while I was dressed as Melissa. Not surprisingly, she said no, but encouraged me to go ahead and go to a session alone, dressed in my women’s clothing. So far, I haven’t done it yet, although based on your therapist’s positive reaction, I’ll bet mine would be most accepting and welcoming. I should get busy and do it, right?

  32. My first time that I remember wearing women’s clothing was when I was roughly 14 years old. I was in the kitchen in my parents house and they were all in the living room, I noticed a pile of my sisters washing sat on the counter and right at the top of the pile were two thongs and other underwear items.

    I always remember how excited I felt seeing them. There was a swirly purple design on one a union jack on the second I felt this feeling overcome me to pick them up and look at them more. Upon going back into the living room I just couldn’t get them out of my mind I knew I had to try a pair on to see how they felt I didn’t know why I wanted to I just knew that I had to try them. later on I went back into the kitchen slipped my boxers off under my dressing gown and stepped into the purple ones first. I always remember such a warm happy excited feeling in me when they were on I just cant explain what it was.

    I will always remember that night 14 years ago as a changing point in my life as I have been crossdressing in private ever since, not all the time but quite frequently and have went from sneaking around dressing up in all of my sisters thongs bras skirts dresses anything I could find while everyone was out the house to living myself and having a whole collection of sexy clothes, casual ones outfits everything really wigs and makeup I just love it soo much when I get a chance to be alone and play dress up. Well that’s my story anyway I hope I didn’t bore you all too much with it thanks for reading.
    Lots of love

    Robyn xx

  33. My first time was when I was 9 or 10 I tried on my sisters pantie hose and I loved how they felt. So after that every time I was home alone I would sneak into her room and try her clothes on. I was taller than she was so I couldn’t wear much or even try on her heels. But I had fun none the less.

  34. My first time was when I was 15 I tried on my mothers pantie’s and I loved how they felt on me. So after that every time I was home alone I would sneak into her room and try her clothes on. I was taller than my mother, I couldn’t wear much but all of her heels I could wear and it was great.

  35. I’ve loved to dress in women’s clothes literally as long as I can remember. My first experience dressing as a woman was when I was only 7 or 8 years old, when I would spend a lot of time at my grandmother’s house, as both my parents worked. I already had strong feelings of wanting to be a girl. I was too afraid to tell anyone, except for the most kind and wonderful person I ever knew, my grandmother. She was completely supportive, and would help me get dressed and would apply my makeup. She even had a wig that she let me wear. I would spend many days at her house being the girl I wanted to be.

    As I grew up, I no longer felt comfortable dressing in front of others, even my grandmother. I still wore my sister’s skirt or mother’s dress when I had the chance, but not in public. By the age of about 15, I was getting too big to fit well into their clothes. For the next almost 30 years, I could only occasionally satisfy my desire to be the woman I wanted to be by slipping on my wife’s panties when home alone.

    A few years back, my need to dress as a woman began to be too strong to ignore. I began ordering clothes on line, getting bras, panties, hosiery, skirts, blouses, pumps, everything. I then had the opportunity to go to San Jose for a business trip. I had discovered on the internet a transformation salon in the city, run by a transgender woman – who truly turned out to be an angel! My experience of fully dressing, then being professionally made up and fitted with a beautiful wig, was amazing. Looking into the mirror, I was stunned to see the woman that I always new was in me! Part of the transformation package was also a “gurls night out” with other patrons of the salon. We went to a local gay bar. I flirted and danced with a few men, who seemed very attracted to this tall, slender gurl from the Midwest. I danced with one man in particular who was very handsome and seemed quite interested in me. He must have loved the way I wiggled my hips in my tight little mini skirt, because he pulled me to him with an intense look of lust in his eyes. He kissed my forcefully on the mouth. My initial feeling was shock, as I had resisted my urges to have sex with men for all of my life, but I quickly felt so feminine, so soft in this man’s strong embrace, that I was instantly kissing him back and wanting much more.

    He took me back to my hotel that night, and I had the most intense and wonderful sex of my life. He made me his woman that night in every way, and I know now that being a woman for a strong, alpha male is all that I want.

  36. First time ( i got caught) i was in my step-sister’s swimsuit and they, my step-mother and step-sister came home early. I didn’t know they had come home , I was masturbating when my step-sister walked in on me, I was in her room. She screamed and my step-mother came in too! She was so mad she made me take the swimsuit off right then in front of my step-sister! I was 11 years old, my step-sister was 15. My step-mother started spanking my bare ass and i cummed all over myself, and ran to my room! They called me a sissy with a little pp (penis) Thats how i got my nickname (sissylilpp) my step-mother used to say my tiny penis was a sign that i should have been a girl and why i liked to dress in girls clothes. I always thought she was right? Think she was? I kept on dressing and getting caught. I still dress today!

    1. Such s cute story! Having a sister would have been so wonderful! Dad raised us, stepmom was in and out! I stole my cousins panties and it was magical. I still have never hit my chin while cumming since that first panty encounter!

  37. My first time was when I was 6 or 7, I was in the bathroom and there on the counter was my mothers revlon lipstick. It noticed me and started calling me to it, as i got closer, PICK ME UP and I did. I stood there trembling as it called to my soul, OPEN ME, TAKE IN MY SCENT i did it was exilerating. WEAR ME, oh no what am I doing I am a boy i thought as i watched this girl put on her first lipstick in the mirror. Then great amazing pleasure and a weird wetness in my underwear. WE ARE ONE.

  38. I’ve worn lingerie for longer than I can remember.
    Spent my teenage years wearing my mom’s panties – satin, lace, cotton etc. Also spent many enjoyable hours going through my sister’s panty drawer. Then started stealing bras and panties from clothes lines my neighborhood. Wearing my wife’s lace intimates, sexy panties that she wore when she sucked my cock, gave my a burning desire to suck cock wearing slutty lingerie.

    I have only ever worn clean panties (soiled panties are a turn off). Buying lingerie at department stores is a massive turn on for me. Browsing the women’s underwear aisle with slutty whore women then going to a checkout staffed by a panty and bra wearing cheap slut women gives me the urge to stuff a big cock into my mouth.

    I have become obsessed with lingerie and cock.

    Two years ago, after several failed attempts trying to meet a guy, I hooked up with a stranger I met on a gay website. I drove to his house, changed into my wife’s clothes and walked into this guy’s lounge room and in a sissy voice stated “I’m Claire. I’m wearing sexy panties and a bra and I want to suck your cock”. And suck his cock I did. I was so aroused and came very quickly. I felt no shame. In fact I felt empowered (maybe a little bit slutty). That was a turning point for me. Now I want to perform oral sex on men all the time. I have since sucked a random guy’s cock at a glory hole.

    Two weeks ago I met a young crossdresser online. With a large bag full of women’s undergarments, and wearing a pair of the most gorgeous, sexy blue lace panties that I recently stole from my MILF sister-in-law, I knocked on his door. When he answered the door I said in a girly voice “I’m a cock sucking whore and I’m wearing my sister-in-law’s hot panties”. I straight away stripped off down to my panties, got his uncut cock nice and hard in my mouth and sucked it like a possessed slut whore. “I’m a slave to cock and I want your hot cum in my mouth and on my face, dripping onto my sexy bra” I said between moans of sheer pleasure. I changed panties several times and rubbed his hard penis all over my sissy slut face, loudly stating that “I want to suck multiple cocks at once and be a filthy cum covered slut”. Sadly he didn’t cum because it was his first time and a bit nervous. I blew a massive load in my sexy panties. Again I felt no shame, only disappointed that I still hadn’t had a man ejaculate in my mouth and on my face.

    My desire for cock and cum is growing. When I wear my sister-in-laws panties I desperately crave cock to the point of crying. In two weeks time I’m going to spend two nights alone in a hotel in another city. First I’m going shopping for some sexy panties in a department store, then I’ll troll gay web sites looking for random guys to blow. If that fails I’m heading for a glory hole at a sex shop. One thing is for certain: I wont be heading home without having had the sensation of a throbbing cock cumming in my mouth.

    I fantasize about getting caught wearing lingerie in public, just as a guy covers my face in cum. I want to be caught by a slut, cum drinking slut whore woman. I also want to tell some of my female friends that like them I’m a cock sucking slut who wears lace petites and desires to pleasure men orally.

  39. When i was 4 or 5, I was usually around when Mom put on makeup and her nylons. One evening my Aunt and Uncle came over to go to a banquet with my parents. My Aunt had a beautiful gown on and she showed lots of cleavage. From that moment on I wanted to have a body like hers. Over the years I would put on Moms panties, bra, and lipstick and pretend to be a voluptuous woman. This continued on into my teens. By this time I would get Moms clothes from the hamper an get all dolled up with full makeup.

    I started stealing Moms cigarettes and smoked them and acted as a woman. I did this just about every time Mom took my sisters out shopping . I would even use a scarf to make it look like I had long hair.

    One day my Uncle came over and kept ringing the door bell. I though it might be the paper boy coming to collect for the paper. So I opened the door. My Uncle looked at me for a while than called me by name. I was so scared he’d tell my parents and begged him not to. I never dressed again. I got married while in the service.

    At work one day one of my co workers told my about a club he and his brothers owned. He invited me there but my wife did not go with me because she had a migraine. The club turned out to be for female impersonaters and I spent most of the night there. My coworker friend introduced me to a lot of the entertainers that night. He gave me some magazines – some of them had she males in them. I hid them in my car and brought the into the apartment when my wife was at work late one day.

    After that I used to sneak the into the bathroom a jerk off while reading them. I was invited back to the club and went a few more times. One night after working late my wife had found my hidden magazines and needless to say we separated.

    I will continue my story at another time.

    1. continuing: A few months after getting my own place, I continued to go back to my friends club the Queen Mary. By this time I had started dressing as a woman regularly. I met a guy at the club one night and went to his place. He loved to dress up too and we spent weekends together doing so. He gave me a blow job on several visits and I gave him one several weeks later. I felt guilty about being gay and ended our meetings & my dressing for a few years.

      Needless to say I always wanted to be a woman. I loved the feelings I had when feminized . I continue to dress off and on till this day. My only wish that I had started on hormone & sex change a long time ago.
      Thank You Fiona I love this site.

  40. When I was 12 I found a pair of my moms pink lace panties in my pile of clothes. I was so fascinated by them, I put them on. I reallized instantly, it was right and I wanted more. I experimented every chance I got. It was very hard to find clothes or time to dress up.

    My family caught me a few times. And I was punished because it was not natural. I even got married and have kids. I love women and men. But wish I could be a woman. My family and my wife don’t condone the behavior. I still keep some clothes and dress when I can. But when I am not dressed up I feel empty. Even though I look very masculine and would never pass for a woman, it’s the way that feels right.

  41. I was 14 and touring the city my brother lives in. While in a museum a man started a conversation with me. He asked me what do I do when my cock got hard. I replied “nothing”. So he lead me to a stairway where he said he would make me feel real good. For my first orgasm it was great. Than he told me that if I come to his place he can make me feel even better. How could I say no, and off we went.

    Once at his apartment he told me to take off all my clothes and handed them to him. Telling me to stay there, He walked into another room and came back shortly with panties, a bra , stockings, heels an a dress. Slowly he dressed me while licking and fondling me everywhere. Tossing a pillow on the floor in front of where he was sitting he told me to kneel an take him into my mouth. After sometime of me sucking him , a friend of his walks in wearing a robe which he took off as he closed the door. The first guy told me that I can only get my clothes back if I act like the girl I am dressed like and than commanded me to suck his friend , I compliantly obeyed while he took me from behind.

    The entire time the two men had their way with me they called me a girly (names) while slowly loving my body Ever since then wearing women’s clothes has been my fetish , and being dommed over just makes me hot

  42. Though I had been sneaking clothes since I was 5, I consider my”first time”, and what led to me dressing regularly, to be just over 10 years ago. I had broken up with my girlfriend and moved into a new apartment.

    After unpacking and meeting some neighbors I decided to hit some of the local stores. I went to a local wig shop and bought a long strawberry blonde wig, a bodycon dress at a small local shop, some heels at Payless, then off to Target for a bra, panties, make up, and thigh highs.

    I spent the next month working on myself, getting my look down until I was confident enough to go to a local gay bar that was about a mile away from me. I was looking quite statuesque with my 38DD rack, fresh shaved legs with sheer black thigh highs and 5 inch pumps, black satin panties, flowing strawberry blonde hair and make up to perfection featuring slut red lips and a hot smokey eye look.

    I was leaning up against a post table at the bar, trying to look femme fatale and noticed a lesbian couple looking at me. They looked friendly so I decided to talk to them. Drinks and conversation flowed and I had a short make out session with the cute redhead in glasses, and were having a great time. During the conversation the couple asked me where I lived and after I told them their jaws hit the floor and they started giggling.

    “What’s so funny?” I asked.

    “We’ve already met, we are your 2nd floor neighbors!”

    I almost hit the floor at being outed like this. They assured me that all was safe and good and a beautiful friendship started. The red head I was making out with has over the years regularly brought me clothes like my first little black dress and numerous skirts. When we all decided to go out together, I would change and get ready with them up in their apartment, just us girls in our bras and panties getting ready for a night on the town. Their acceptance and encouragement overt he years has helped me become who I am today.

  43. First time I really felt giddy was about 19, dressed in blue dress black nylons and 2 inch pumps, walking to the train, I was noticeably being followed by some teen boys who were not so covertly enjoying my backview. They musta jumped off the floor when they saw my facial stubble, but being ogled that day was something I’ll never forget!

  44. I am a 79 year old crossdresser, was happily married to a wonderful
    lady who I lost 10 years ago. She had known of my dressing but let
    it slide until she found my breast gels on her dresser. That led to the honest impass of OK, just don’t do it when I’m here.
    Now that I’m alone I dress daily except to go out if to be seen by neighbors. Still in that big closet!
    I am the old patriarch of two generations of close family, I fear that
    an outing would destroy me.
    Any helpful ideas to help me grow safely in this situation would be helpful.

  45. I’ve been wearing panties for some years now. I’ve tried bras and corsets, but getting the right fit has been difficult. My favorite style of panty is a bikini cut with sheer fabric. It gives me a thrill like no other. I love seeing my cock covered in that see through fabric, and also the times when I have him tucked away.

    Just recently I tried some makeup but made a mess of it because my vision is not great and without my glasses I couldn’t see what I was doing. All the same it made me feel sexy just trying. Wearing lipstick is very exciting as well! I actually wear it much of the time. If someone asks me about it, like one of my macho type friends I tell them I mistakenly took my wife’s lip gloss instead of my chap stick. Then I’ll ask them if they like the color!

    I’m sitting here in my dark blue, almost black sheer panties with a very sexy tingling in my cock writing this first time story. My nipples are erect and soooo sensitive right now. The first time anyone realized that I am a little different than what my image presents is when I went to see my cardiologist a couple of weeks ago.

    I had been feeling weird and not altogether healthy I guess you can say. The cardiologist said that I needed an electrocardiogram to see what was going on. When I took my shirt off the woman that was performing the procedure was a little surprised to see that I shave my chest! And really to be precise I don’t shave the whole landscape I just shave around my little breasts!

    Being an older male has some advantages, one of which is that my testosterone is in short supply now and breasts are a result of the estrogen that dominates my hormones now. Anyway there were my soft and really, if I’m being honest, perky little breasts with my stiff and sensitive nipples. They are completely and totally devoid of hair, peeking out of a furry carpet of silver and black hair on my chest! She was applying the electrodes but I could tell she was totally distracted by my tits. It probably took her five minutes longer than usual to get this done than normal.

    As for me I had an erection which I seldom get anymore, that was about to bust my zipper. My pucker was excited and ready to go, making those little kissing motions that feel so exquisite. And needless to say my nipples were on fire and when she brushed both of them with her hand as she applied the electrodes I let out an almost imperceptible moan, and just about blew my load in my panties.

    I was so turned on I almost couldn’t walk out of that office. My only wish is that they had required me to take off my pants. That would reveal my panties and the fact that I shave all the way past my anus and around my balls, leaving a little triangle just above my cock! That would have made my day, week, month and possibly my year!!

  46. Hi Ive been reading loads of the replies and they are brilliant.i really can’t remember my first time it’s only lately the ice started again and love it.i always try to borrow panties from friends it really turns me on wearing them !!!!!!!

  47. The other day I went to see my physical therapist, because I had been at work and taken a terrible fall. I hurt both hips and my left arm. Much bruising occurred and pain ensued.

    I’ve been seeing David for 13 years now and we have become friends, in that we are quite comfortable with each other. We talk about everything as you can imagine.

    The bruising on my left hip was so severe that he decided to use this machine on me that would get the blood flowing and reduce the bruising. When he told me I had to expose some skin as he put it, I panicked. Under my pants I was wearing my sky blue sheer panties, and he had no clue this was something I do.

    I sucked it up and opened my pants up so he could get to where he needed to be. He didn’t say anything but I could tell he was somewhat shocked. To ease the tension I said to him “wouldn’t you know, I decided to wear my best panties today, and you decide you want to look at my ass”!

    He mumbled something and went about his business, and I was secretly thrilled that he had seen me this way. Now I know every time he sees me now he’ll wonder what I have on.

    I was excited for the next couple of days just thinking about it. My only fear was that it would alter our relationship in some way. That remains to be seen.

  48. My first time was when I was 26. My girlfriend (now wife) began playing with my ass while we had sex. It felt so awesome! Things progressed over several months until she got me hooked on prostate massages as she got me off. Each time the orgasms were more intense. When she asked me to wear panties, I refused.

    The prostate massages stopped….until I agreed to wear the panties. Which I eventually did because I wanted the amazing orgasms of prostate stimulation. She had me under her…index finger.. more to come.

    1. Haha thats the kind of lady im looking for. That relationship for me would progress as fast as humanly possible but make sure you make moves with in your comfort zone. Dont over due it and scare yourself or anything.

  49. After reading several of these stories I just had to share mine. I started about 13 with just panties here and there while I jerked off (won’t go into detail as it isn’t very exciting). My real start into crossdressing started last year at Halloween.

    Last year me and my wife were trying to decide what our costumes were going to be, that year we decided to do a couples costume. So I said we should do Mario and Princess Peach, she likes the idea. But to start having a little fun with her I jokingly said she could go as Mario and I’ll go as Peach. She more than loved the idea. So I played along thinking she’ll change her mind, but she didn’t.

    The night of the party came and as I was showering I was starting to get nervous. When I got out and started to get dressed in the pink princess dress I started to relax a bit. She couldn’t believe how I looked in it, she laughed a little because it was kinda ridiculous. She did my makeup and put on a blonde wig that she borrowed from a friend. She stood back and told me I looked good. I was having fun while we still just in our apartment.

    When it came time to head out to the party, that’s when I started to panic a bit. (This party was happening at a local bar where everyone knew us). I told her I was going to drop her off in the front and that I would park in back and to have her let me in the back door. She said the hell I was and made me walk right in the front door, now I was getting really nervous, she told me to calm down.

    I was a little relieved when I saw I wasn’t the only guy dressed as a girl, but I was the only one dressed as a princess in a pink dress (kinda typical guy doing drag poorly without shaving on purpose) I was still nervous as hell and it took me a while before I went to the bar to get a drink, kinda hid in a corner till now. I asked my wife if she’d get me a drink and she said no, that I had to go get it ( she actually made me go get it) It was kinda funny when it actually took the bartender a minute to figure out who I was, then she said how awesome I looked. After my first drink I calmed down a lot to the point where I started to feel comfortable enough to mingle a bit.

    I felt much better when so many people kept saying how awesome I looked and that our costumes were amazing. A few people actually thought I was a girl from across the bar and asked my wife “who’s that cute blonde with you”, they almost didn’t believe her when she told them “that’s my husband” at which point she would call me over to show them. I was feeling pretty good by now from drinking that I started to have fun with it. One guy told me that I had the biggest pair of balls ever to go out dressed as I was. At the end of the night I didn’t want it to end, but at closing we went home and got out of our costumes.

    The next day after she posted pics from the night online, more compliments on how awesome we looked. I didn’t think much about it after that. A few weeks later we had a friend stay with us (he’s gay and does drag), he was saying how awesome we looked in our costumes and was saying how he could tell I enjoyed it, I told him the alcohol helped. Then he suggested that I dress up again and go out on a double date with another couple we knew where the husband recently came out as trans (won’t go into that), we both said no to that and my wife said I wasn’t allowed to wear a dress except for Halloween (I basically agreed to that as I didn’t think much of it).

    Well, a while after this (like probably a week or two) I started to think about it and the thought of dressing as a woman again kind of excited me, tried to shrug it off and say to myself “what was I thinking”, but I kept finding myself thinking of it. I let the idea rattle around in my head for a few months.

    Then in February 2017, while me and the wife were having a little after hours party alone I finally came out to her and admitted everything. Her response was amazing, she was totally cool with it and we pretty much started planning a night out where I could dress up. Luckily our gay friend lives in the Best area for me to go out dressed, the gay capital of the world, Provincetown MA. A short drive away.

    We talked to him about what we were planning and he almost couldn’t believe it, he was excited for it, he even offered to do my makeup for me (like I said he does drag shows). Thus began my process of picking out an outfit and other things for this night out (it was about 2 months away, we wanted to wait till it was a bit warmer). Well the night finally came, my friend did my makeup and kept saying he couldn’t believe he was doing this. After my makeup was done my wife helped me get dressed and then they both helped fix my wig. When I was finished, they both couldn’t believe it.

    Our friend said it wasn’t fair that I looked so good my first night out, and my wife said it wasn’t fair that I looked better in a dress than her. We then headed out on the town for the night, I was a bit nervous but not that bad. At our first stop I got a few weird looks, I did my best to just ignore it. We headed to our next stop, on the way we bumped into some people our friend new and had met us earlier and saw me in guy clothes, they kept saying how great I looked, kinda was a confidence booster. After a drink we went to our third and final stop.

    At this point it seemed that it was a regular thing to see a guy dressed up and out, we had a few drinks and they called last call and closing. It was an amazing night and I didn’t want it to end. We went back to our room and I got undressed and cleaned up, we relaxed a bit and then went to bed. It was an amazing night out and it was over so fast. A few weeks later I decided I wanted to do it again and made the arrangements to go back in September. We also went back again this past October too. I hope I’ll have more nights out dressed up next year when it gets warmer. Oh, and my wife and our friend gave me the name Rosalyn.

      1. Im with Kim on this one Rosalyn. It hasnt been an easy run. Has taken a lot of strength to keep from shattering. So it fills me with hope to hear a story likes yours. And makes me feel happy to hear how your Lady and friend took you under their wings. I hope you get to exsperience everything you dream of in such a way

  50. As a kid I was shy. I did not like it. But I was. I remember going to 1st grade with my moms stockings on one day. I held them up with rubber bands. No pantyhose back then.

    That in retrospect probably was wrong to do looking back now. My self confidence was low. I blame it on my awkwardness. My eyesight was very poor. I not could see without my glasses. As a teenager I could not get a Girlfriend. I figured everything work out some how. But it did not. My theory is that girls could get anyone they wanted. The jock or the bad boy seemed to be what was desired. I was none of those.

    So dulled my pain my smoking cigarettes and pot. I kind of because my own girlfriend. I would smoke pot and dress up. One day when I was 17. I actually kissed a girl. I didn’t want to stop. The kiss lasted at least two minutes. She wrote me a love note. I cherished that note. I never saw her again. So I kept on my pot smoking way.

    Fast forward age 26. I am of legal age now. I have added drinking to my habits. When I was 18 drinking was legal then. I have been hanging around all my High School friends. I was was not doing anything my other friends did. At work there was a girl how worked at the bar where everyone from work went to. She was interested in me. We went out. She had me over her house. Her name was Bonnie. Bonnie coaxed me into bed. I finally had sex with a woman. I was 26.

    It kind of scared me. I never had a girlfriend before. I think she would have married me. But in the back of my head I heard Smoky Robinson singing. You got to shop around. Don’t let the first one get you. After about two months of going out I just stopped calling her. I preferred hanging out with my friends. I went on a few more dates after that. From a introduction service. Not much happened from that, due to my lack of experience.

    One girl I went out with was really nice. We went to a baseball game. Then the beach. We went to dinner too. But I screwed it up by hanging out with my friends instead of her. Again I stopped calling her. She probably was a keeper. I was TOO STUPID to see that.

    Moving on to 30 years old. My friend and I went to the local bar. I met an older woman there. She was 53. We went out a few times. I really enjoyed myself. She had me calling her everyday before work. Low and behold this tightened our relationship. I began to see her everyday. Eventually we had sex. We did everywhere in the neighborhood. Our favorite place was behind the car wash.

    Any ways this bar was the same bar my Dad went to. He knew who I was going out with. He warned me that this may not be good decision. I did not care at that point. A woman. Who wanted ME. I could not stay away. We met in June 1988. It is now July 2017. I am 59. She is 82. We no longer have sex. I see her everyday. It is more about companionship then anything else. But Lorraine has no idea I like to wear women clothes.

    She does not like the idea of it either. So I remain in the closet so to speak. 29 years is a long time to be with someone. A lot of marriages do not last this long.

    Lorraine and I have our own houses. So I CD at home. I’ll stop now. As you can see I have a lot of pent up feelings. I always wanted a girlfriend as a teenager. When people talk about how they met. It is mostly we met in High School or College. Those trains sped right past me. In hind sight I suppose Lorraine has given more than I ever thought this relationship I ever thought. I am rambling again. I will stop. I look forward to hearing from you Dawn. I hope you enjoyed my life story. Of course there is more. Just like anyone else.

    Opps starting another paragraph. I got to call Lorraine before she calls me.

  51. Wow, Reading these stories really does help. I’m like Rosalyn, I first dressed when I was young. I was home alone and happened to see my mothers makeup and dresses and decided to try a dress as well as shoes and lipstick. not much to it. It all came off pretty quickly.

    What I consider my first true time was a time my wife was out of town for several months. Home alone, i figured it wouldn’t hurt anyone, so I decided to try on one of her dresses. The feeling was so AMAZING, the fabric agains my skin, the feeling of a thong between my cheeks as well as the softness of them, I couldn’t even explain. I then noticed that she had a pair of sandals the fit me, that did it. I was in.

    I think I started wearing her clothes around the house almost every day she was away. After a couple of weeks, I had even ordered my own pair of Booties with leggings as well as a top, and a waist cincher. I had it all.

    One day I decided to go out in public. I decided to wear my wife’s gray Skinny gray pants, with my black 3″ suede booties, my wife’s purple halter top with her leather jacket. Definitely wore the waist cincher and bought a layered curly medium length wig. Makeup was in a light smoke with pink lipstick with a touch of a plumping gloss. I felt like I looked GREAT, the confidence was AMAZING.

    It wasn’t until I had to walk out the door that I had trouble. It took me about an hour to work up the courage to walk out the apartment door. I live on the fourth floor and had to walk down due to not having an elevator. The first step out the door, listening to see if anyone was in the hallways, walking back in. then finally walking out and locking the door. The rush that ran through my body cannot be compared with anything in this world. It was such a high that half way down the stairs I almost had an orgasm, yes, that great. I finally proceeded to walk outside and went for a walk around my neighborhood. It must have been around 2am but I must have walked around my neighborhood for several hours. It was exhilarating. I walked back into my building around 4:30am and decided to have a glass of wine on the roof en femme. I love every second of it.

    I still haven’t had the courage to tell her. I do love women. I find them extremely sexy and am very attracted to them. But I find that I am also very attracted to men when dressed en femme. Since that time I have been out in public twice to a bar on Trans night and it feels amazing. I just wish there was a friend I could tell. It feels great to tell someone. It feels so lonely to not have someone to dress with and talk to about this, especially when your best friend is your wife.

    I hope this help anyone out there. I love you all


    1. I will NEVER forget that feeling of walking out the apartment door dor the first time! I had my mind made up that once I eas out the door I was going out on the town. The 15 steps it took to get to the elevator compared, in my mind, that of a death row inmate. Then the elevator ride, what if somebody eles gets on with me? It was the longest 15 feet, 5 floor ride of my life but I am glad I took the plunge!

    2. It truely does help to hear. Your more daring then i am. But i have issues talking w my lady as well. I have no desires for men. Ladyboys and traps dont bother me but then again it is a lot of what im trying to accomplish so i feel is obvious to take tips from them and others like us. Still i worship the lady and before here had nobody to talk to. Nobody who knows me. So hopefully youll find some peace here as i do. I still have yet to do my first time. Im trying to pay my respects to everyone who came before me. Similaritys here and there along the way but i still havent yet come accross my second. Gd luck to you. Maybe we can trade tips if i stick around.

  52. So I promised I would tell my first time story after I mentioned on Tumblr that the question I see on Fiona’s posts there really hits home with me… “Remember the first time you put on your sisters panties?”

    Like many here that’s where I think it all started for me, looking back. When I was in my early teens and had recently discovered the joys of self pleasure I came up with a little game to play with myself to make it even more fun. I got myself a deck of cards and a pen and paper and assigned the 4 suits a category. Can’t remember exactly what they were now but it was along the lines of something to do, someone to think about, something to wear, location respectively for when I would masterbate. Then for each card in the suits I would write down and assign something/someone/somewhere depending on the category, but the picture cards ( jack, queen, king, ace) were assigned as “forfeits”. For example in the someone suit I would have to think about someone I didn’t really fancy when masterbating if I drew that card. Looking back now I wonder if this game was my budding submissive nature trying to express itself and encourage me to give up control even to luck!

    Anyway, one time, and I’ve no idea why, I assigned “Wear my sisters panties” as one of the forfeits. I cut the deck and guess what came up…..! So, despite being alone in the house I found myself nervously tip-toeing across and into her bedroom. I eventually found her underwear drawer and was amazed at all the sexy knickers my sister had. I tentatively pulled out a pair of purple Lacey French knickers that caught my eye. That surge I felt as I slipped them on is something I will never forget and I still feel it every time even now in my 30s. Needless to say I had a hell of a time that afternoon and soon moved wearing her knickers out of the forfeits and it was assigned to more than one card. I eventually progressed to her bras too and then more and more clothes and make up. I even started adding my mothers into the game!

    Throughout my life I have often found myself unable to resist the temptation to try on the panties of various women that have been in my life given the chance.

    Even now I can’t resist dressing in my wife’s lingerie and clothes if I have the house to myself for a while and have even been know to wear her panties to work on occasion. I am only really recently beginning to accept myself and my desires but I hope to someday find the courage to reveal myself to her. I guess the fear of losing her holds me back right now.

  53. My first time….

    Just out of college I had a female room mate. We casually dated, but we never really clicked. I had a voracious appetite for sex – that when not with woman, I needed to relieve myself daily with a steady diet of porn (straight female at the time). When she went on vacation, that became a real opportunity for some all day sessions.

    Passing Paula’s room, I spotted a full length slip and some fishnet stockings. I had this uncontrollable urge to explore. I have no idea what prompted me to try them on — my hand were trembling as I slipped my clothes to the floor and gingerly pulled the slip over me. The feel of the lace on my chest was utterly arousing and my cock was throbbing! Lying down I pulled the stockings on ever so slowly. It’s as if I was making love to a woman, as I caressed my own legs. The sensation of the stockings on my legs was absolutely mind blowing!

    As this progressed over a few days, I was craving some penetration and found a suitable broom handle with a condom to satisfy my curiosity. Sliding into myself, the penetration was making me a bit short of breath with excitement as I was overcome with an intense newfound pleasure that was hard to explain. I still craved girls, but this was beyond words. Not long after I started buying my own panty hose from time to time.

    The “cool” sensation of pulling my legs in always get me rock hard. As far as masturbation goes, nothing beats coming in a tight pair of pantyhose!

    Thanks for reading!

  54. It was 1964 and I was 12, going on 13. I was reading teen-oriented magazines and back then there were usually features about the latest “Beach” movie with Annette Funicello and other girls. Something clicked inside my head – “What’s it like to wear a bikini?” Next thing I knew, I was slipping on my mother’s bra-slip. It was magical – the luscious feel of the fabric, the curves of the bra cups and an overwhelming sense of femininity. Every time I had the house to myself I would try on her lingerie. I felt that it was wrong to be dressing up in feminine lingerie and then again, I felt so good and so right. Dressing up became part of me.

    Over the years I’ve purged and tried to stop but the urges always came back, stronger than ever. Several years ago I found a level of comfort and confidence that enabled me to go out en femme in public. Now I enjoy make-overs at Sephora and just going out shopping en femme. There are a couple women in my life who support and encourage to me enjoy my femininity and I cherish their friendship — I am very fortunate to have them in my life.

    These days, a candlelit luxury bubble bath, perfume and makeup are essential to my feminine expression.

    Even if my outward appearance is in drab male clothes, my feminine self is always there — and I love it!

  55. When I was 5 years old I the and a side by side duplex and the next door neighbor had a 10 year old daughter and one day she caught me stealing her panties off the clothesline. She asked me what I was doing I was scared to answer her she asked me ‘what you want to put these on?’
    I said ‘yes’, so I did.
    I went in the garage and put them on then one day her parents went out for a few hours and ask my mom if she would watch her and my mom said yes. I went up to her room where she pulled out a pair of panties out of her drawers. She handed them to me – her Strawberry Shortcake panties – and she pulled out a pair of pink tights. She pulled out one of her Sunday dresses out of the closet and a pair of Mary Jane shoes, a pair of pink ruffle socks and then she had me put it all on.
    I put it all on and she did my makeup did my hair cuz my hair was long enough and then her and I walk the neighborhood.

  56. My first time was with a shemale I’d been visiting for a couple of years…
    She have hade me in every way she wants but always as a man.
    After the first meetings our sexual relationships went bareback.
    Visiting internet sites, I began to fantasize been produced like a CD.
    We planned with her a meeting and Rocío (thats her name), prepeared all the stuff to transfor me.
    Rocío missed no detail at all- Make up, thong, 3 inches heels, dark curled wig …all in red an black . The colours of lust.
    She spent half an hour prepearing me…wen she finished, I walked to a mirror and I can´t describe my feelings watching a masculine man transformed in a whore. She named my Fabiola
    I realized that if a man enters that moment in the room, I only have to bring myself to him.
    But that afternoon Rocío wanted me all for her.
    After ejoying her cock and feeling it growing in my mouth, she guided me to her bed an make me put on my knees with my chest touching the bed and my arms extended in front. “The submissive possition”
    A mirror in front of me, reflected the image of myself in that situation and my goddessbehind me ready to satisfy her instints.
    Feeling the thread of my thong skimming my ass cheeck as Rocío slipped it to one side to leave my pussy-ass ready for her cock, was one of the wonderest sensations I ever had.
    Then she took me in every way she wanted. I was her whore for more tha an hour….and it was forever.
    She has some problems now and I’m looking for the way to continue with a next step in my feminization. But I’m married and it’s no easy to me.
    The story “Clothes maketh a man” is so powerful and well written that I have developed stronger feelings to be Fabiola again.

    1. Jorge,
      Or should I call you Fabiola, actually the name Georgina just came to my mind, It might be a little more fitting with your real name. You’re the first person here that has had a first time affair with a shemale. I’m really curious. as I’ve always thought I’d like to be a shemale. That is, if I couldn’t afford to have SRS and have a vagina. I’d much rather be involved with a woman or shemale than a man. I might be able to give the right person a BJ, but anal penetration. is an absolute no-no for me.

      I’d like to ask how and where did you meet you shemale friend? Did you have a long time affair with Rocio before or after you married? Would you like to be a shemale yourself? You seem to be enamored with Clothes maketh the Man. Would you like to be “BEN”?

      if you read Jenna177 above you’ll understand that I had a real turn-on to shemale’s when I went to the CLUB all the time. Love Jenna

  57. My first time l had skipped school just to get dolled up I had found. A tremendous amount of womens clothes in storage so I had plenty to choose from well. The more I put on myself the more aroused I became then I used my mama’s makeup by the time I finished I just had to get myself off

  58. My 1st time was when I tried on my mom’s pantygridle. I always had a thing for my mom. she was so fine her tits were so perky, I asked her to marry me one time when i was 10. I had a bad dream so I got into her bed. I got a hard on, she was laying on her side I started rubbing my dink on her ass. She didn’t move I tried to turn her over on her back so I could give it.

  59. Its tough for me to really pin point a “first time”. Over this journey there are many milestones. Let’s start with the big cliche (although true). When I was young, I would steal my sisters panties. When she went away to college, she left 3 pairs of satin panties in her dresser. The first time I tried one on, I knew it was ridiculous but I almost came right off the bat. I kept those pairs for years and used them every time I jerked off….and that was a lot.

    During high school and college this urge subsided. When I entered the real world, I was quite a party boy and I loved cocaine. Cocaine and porn became hand in hand and I stopped going out as much and I’d get my stash and start staying home. Just me and my shemale porn (regular porn became boring quick). Unfortunately, the downside here is that coke makes your dick shrivel and regular masturbation almost impossible. So I started looking for things that would get me more turned on and able cum during these moments. Panties reentered the equation…then anal toys….then lingerie…

    I held on to these kinks and evolution took hold. For about a decade that held me over… However after I got married and had a kid, the partying had to stop (ok…slow down more like it). Eventually, my lingerie sets, panties, and stockings just weren’t doing it for me. I wanted…needed something more.

    I found a store in our town (as luck would have it) and invested in some heels (which had been hard to sneak around and find a size 14) and a couple of dresses and a wig.

    Eventually I told my wife (who was aware of my previous kinks) that I wanted to try to go full femme and see how it looked. It was the first time and I even got her to play the domme role. Strap on and everything (first time and I had always wanted it). She even did my makeup which really opened up my mind. I finally actually kind of looked like girls. Not just a dude with a beard in ill fitting lingerie. Shaved the beard the net day (which was tough but internally it was a sign I was ready to commit. She was cool about it but was doing it to spice the sex life up…we had a 1 year old baby and we were exhausted 24/7 and weren’t having sex, so anything was worth trying.

    I LOVED it…but didn’t want to tell my wife how much…so I started experimenting on my own. A few more pairs of heel and dresses…but sneaking them around my house hiding these things I paid good money for was becoming unacceptable. I had to tell her where my mind was at. I couldn’t accept living the rest of my life hiding it so fuck it… There was a good chance she’d be cool with it but it was a risk anyway.

    So on Christmas Eve eve, I couldn’t sleep it was all that I could think about. When she woke up in the morning, I turned to her and said, “I can’t sleep anymore, I have something on my mind you need to know. I can’t hide it but every night when you go to bed, I get a dressed as a woman, and I can’t live my life hiding it and I have to be open.”

    Her reply? “Awesome, I kind of already knew this, but if that’s who you are, then I’m all for it”

    Over the last 4 months, our relationship has never been better (except the credit card bills). Going shopping together is SOOOOO much fun. I now have my own panty drawer, bra drawer, lingerie drawer, stockings drawer and half the closet full of dresses, skirts and blouses. Even moved my dude clothes to the guest bedroom. I work from home…so dude clothes only get used a couple times a week.

    Anyway, my name is Alexis now. No one knows but my wife…and daughter (but at least shes growing up in a more accepting world). Every day I go a little bit further. Yesterday I tweezed my eyebrows. That was fun…. Anyway, this became more of a life story, but if you made it this far…thanks for reading.

  60. Hello Fiona,
    My first time was discovering my mother’s dresser. I was around 12 years old and a ‘latch-key’ kid. There were times that both my parents weren’t home when I got home from school on the bus.
    My father worked the typical 9-5, but also had about a 90 minute commute each way for work. My mother was gone out for the night and left food for us after my father got home. As a curious child I checked out their bedroom and I was enthralled by the discoveries in her dresser and closet.
    I felt all the fabrics and was excited by the feel of everything. There were so many fantastic sensations. I got excited and wondered if I would look pretty too. I put on a pair of her satiny underwear and then nylons. It was the most incredible feeling I had or have ever had.
    My father unfortunately came home and beat the ever living crap out of me.
    Unfortunately, I think I was already hooked. I cooled off dressing for a while.
    I got a job and used some money here and there to buy knee highs, nylons, skirts, panties, makeup and the like. I didn’t have anywhere good the store ‘my clothes’ so I was found out. I was forced to go to all kinds of tests and therapists for this ‘deviant’ behavior.
    That caused me to find other outlets for dressing. I found theft was acceptable in my adolescent mind. So what did I steal? Women’s clothing.
    I broke into our neighbor’s and took some panties, leotard, denim skirt, bra and nylons.
    After my parents and neighbor’s found out I was beaten again.
    The local police were notified as was the local schools. I was expelled from school and shipped to a day program/group home environment school.
    Apparently, if you talk about a problem it goes away.

    1. Oh hun, i often wonder what life woulda been like if i was taught by my parents to embrace myself rather then woop my ass. Try to beat it out of me or shame me. I prolly wouldnt have made a lot of the same mistakes to begin with or they wouldnt have been concidered mistakes. The best i can do now as i see it is to try and surround myself with encuraging people who accept ne for who i am. And try to break that chain when it comes to my own kids. Im sorry. Nobody deserves to live like we did or be left by their own parents thinking something like this is a sickness. Although secretly i know its gonna be real hard to convince yourself of that

  61. my first time i was around the age of 11. i had become interested in the female body, but not in the way most men are. i would look thru my moms victorias secret catalogs when they came in the mail, and soon, i began to fantasize about wearing womens clothes and ultimately being a girl. i dont remember my first time exactly, but it started with my moms used panties in the clothes hamper. they were often lightly crusted with some sort of discharge, which i now assume was vaginal fluids from becoming aroused. i would usually smell them, and as i pulled them up my own legs, nestling my young clit into the fabric where my moms pussy had been, i would immagine the crust was mine. i would immagine sitting in my own vaginal discharge. i soon began digging for more clothes. first in the hamper, then moving up to clean clothes from her dresser and closet. we were the same shoe size then, and i soon found my way into heels and pantyhose. the feeling i got from the lingerie, was absolutely perfect. i knew i wanted my dressers full of pretty panties and nylon stockings. i was terrified of being caught, but at the same time i fantasized about getting caught and forced to undergo a complete transition to being female as punishment. instead i became good at my male persona, snd i battled with myself for over a decade before i finally gave in to the woman i am inside. now i seek to become a more polished sissy girl, and complete my transition into womanhood.


  62. My first time as I can remember was when I was pretty young. My sister dressed me in her dress when I was about 5 and I loved it even then. Mostly I remember teen years wearing my sister’s stockings and garter belts. Then on to pantyhose. Always getting me excited. Still only interested in having sex with women but I do enjoy seeing CD’s all dolled up as well.

  63. Hello to all and thank you Mistress Fiona,

    Like a lot on here I started early. I was maybe around 8 or so when I noticed the difference in the material of my yuckie underware and the color and feeling of nylon ones.

    I started stealing from my 3 aunts the neighbor and her daughters, friends moms. Any i saw and liked I would take. I had over 60 pair at one point.

    I love the feel of them on my body and the way they moved and felt and made me tingle inside. Around 12 My aunt who’s only 6 years older than me still lived with my grandparents. We lived on a farm and they were maybe 1/4 mile across a field. I use to watch their dog when they went on vacations. I would spend hours down there dressing in my aunts clothes and use her bikini’s and go swimming in the pond behind their house. This was in the mid 70’s and no internet or anything like that to let me know it was ok. I use to also wear my grandma’s granny panties. I loved the way my young little boy parts felt while i walked around in the with noting else but maybe my aunts bra or bikini top. one day walking around feeling them rub me i started to shudder and had an orgasam in them. I was excited and confused also courious. I tasted what came out it was good a little weird but i liked it i licked it all clean even sucked what I could out of the nylon. This went on a lot after that. I also started wear all my aunts skirts, dresses, panties, shoes, boots. all her things when they were gone.

    One time my dad said that they were going on vacation again. I took that as take care of the dog. I was 14 then and my aunt was in college this was during the summer and I know they went to AZ to see my uncle. I was dressing in my aunts clothes trying new combos. I had a cute white top very tight and a pink bra stuffed with panties for the look. I had one of my favorite pair of her panties on. the had and elephants front on the front and the elephant behind on the back. I just took off a cute skater skirt and had a leather mini in my hand getting ready to put it on and the door opened to her room i heard people laughing and talking til they saw me then it was giggling from the 3 girls with her and her yelling. I am standing in front of 3 pretty college girls and my beautiful but very pissed aunt who starts yelling and calling me names i don’t remember everything she said my head was spinning and knowing how I was dressed and seeing all those beautiful girls laughing it was to much i squirted in the panties with out any touching or rubbing. That made them laugh more and my aunt more pissed. she grabbed the skirt and said your ruining my stuff. she smacked my ass over and over which made me cum more. 1 of the girls finally stop her and the other girls and said calm down everyone out i will clean this up go have a drink and relax girls.

    By this time I was crying at first the smacks were exciting but my ass was red and purple with her hand prints all over. The girl closed the door after everyone left and walked over and sat me on the bed. She wiped my tears and started asking me questions and saying she is sorry for the laughing they just never expected anything like that. I calmed down and she went to the bathroom to get a towel and I was reaching in the panties cleaning up my mess with my fingers licking them clean. she came back out and said well i don’t think we need this. i stopped she said if that how you want and like it go ahead, I finished eating my cum and removed the panties and sucked them clean and put them back on. She said you have done this before and you like the taste? I nodded and lightly said it was ok the first time but taste good and feels right now. she sat down on the bed beside me put her arm around my back and said lets hang her stuff back up.

    I started to remove the top and then the bra. she said the bra looks good but lets find a diffrent top. She gave me on out of the closet and said put this on. I did and we finished hanging up the rest of the things I had spread all over. She went to the closet and picked out a skirt, slacks, a pair of jeans and lay them on the bed. she knelt down in front of me and asked which one i wanted to wear with the shirt she picked. I pointed at the jeans. She looked up and asked why I wanted to wear girls clothes instead of mine which were right there. I told her I like the look and feel of girls clothes and they are so beautiful and I want to feel that way.

    For some reason she made me feel at ease. I told her I always watched my aunt and what she wore and shes is so beautiful I wanted to dress like her and I loved the thought of being able to be a girl. so her clothes are wonderful and I wear them when I can. She said stay here I’ll be right back and walked out. if felt like days before she came back when she did she knocked and opened the door she had my aunt with her. when my aunt walked in I started crying and went to my knees and held her legs and kept saying I’m sorry. Jolene grabbed my arm and pried me off my aunts soft legs and sat me on the bed again and had me explain and tell my aunt why I was wearing her clothes which i did. Jolene explained the 3 thing on the bed and asked my aunt which would you pick to wear with that blouse she has on. the first thing I heard was Jolene called me her. my aunt pointed to the skirt. Jolene told her I picked the jeans. My aunt said not with that blouse its a dressier and sexier and deserves more of a nicer combo than jeans. I started to explain why but my aunt cut me off and said I will prove it put the jeans on, which i did then said look in the mirror. now put the skirt on and look. I did and she started to point out why the skirt was a better choice.

    Jolene walked over and hugged me and said relax and talk with her and listen. She walked to my aunt and hugged her and whispered in her ear. she then said the girls are up on me in drinks by an hour time to catch up walked out and closed the door. my aunt walked over to me and hugged me and said I am sorry for freaking out and beating you like that. I told her it’s ok I kind of liked it at first she giggled and said we all could see that. then she reach down and straightened out the skirt and said now lets fix this right. She got a different bra and said this will look better under that blouse and these hose and these shoes would look good, she sat me in her bathroom and did light makeup and stood me up and said after talking to Jolene and thinking about it you are now are little sister but will listen to us and learn.
    She kissed my and took my hand and lead me out to the pack that was laughing just hours ago. after Jolene talking to them and my Aunt I was suddenly their little sister. they all promised to protect and help as long as I followed and listened to everything they said. I nodded and sent to get drinks. I listened to them talk about their boyfriends and the bad things and the good things even in the sex department. I just sat there and listened to it all.
    My aunt called my mom and said I was spending the night because she was lonely. I learned a lot that night we didn’t go to bed til around 4 in the morning and my aunt gave me a cute nightie to wear but said I was making the breakfast in the morning for them.

    I have taken enough of your time sorry it was so long the week was also. more about if later if your still interested.

    Thank you

  64. I don’t remember exactly when I started dressing but, probably around 12 if I had to guess. I used to try on my older sisters panties and bras. Never my mothers. My sister loved going to the beach so there was a lot of opportunity to steal a bikini from the wash and it not be noticed. We had a large above ground pool in our backyard and late on hot summer nights I would put on the bottoms under my jean shorts and stuff the top in a pocket. With the lights out I’d quietly go swimming. When I was confident I was alone I’d take off the jeans and put on the bikini top. The feeling of the water going through it and how girly I felt was intoxicating.
    Later in my teens , when I’d sometimes work late at a flea market , I’d steal some lingerie from a couple of shops I’d have my eye on , waiting for the opportunity. I started experimenting with makeup and put my stolen treasure on . This went until my early 20’s and then stopped. Maybe it was all the hormones that finally balanced out .
    Believe it or not it was coming across Fiona’s hypnosis on you tube that has reawakened my inner girl to come back out after lying dormant for so long.
    I’m now starting to share this with another woman who is unsure how she feels about it but allowed me to dress in a bra and panties for her. She came pretty quick though when we fooled around. We’re having a motel date soon where I’m getting fully dressed and she is doing my makeup and hair.
    My fingers are crossed.

      1. That never materialized after all but I did put out an ad looking for women who would help in my feminization. After sorting through lots of fakes and guys I have found two that are sincere. One I have met already a couple of times and is really sincerely helping me and allowing me to go through a ton of clothes in her closet as well as makeup and jewelry. The other I have talked to and we’re trying to adjust our schedules to meet. She also seems very excited to help me.
        It’s a very positive time for me.
        They only call me by my feminine name and it is understood that if they have to introduce me in guy mode for some reason my name is Nate instead of Natalie. That way I only hear the name that I want to hear them say and it keeps my true identity covered.

  65. Hi’ya………..hmm, my first time was like mostly everyone else’s. I wanna share my first time, actually looking & feeling femme. Living alone, after each work day I’d race home, first stripping outta of the uncomfortable”man attire”. Then picking the perfect bra & panties. Usually lounging in those as I delicately & perfectly painted my finger nails & toes. Finally after letting the polish dry I’d pick out just the right outfit for the night, sometimes changing 3 or 4 times. Then I’d choose the perfect pair of high heels. Finally, the final step……. applying make-up & putting on my dark brunette wig. I remember as, all this takes place I begin to evolve into the woman, that just feels natural. Once the transformation is complete, it totally feels like I can finally breath, relax & just be myself. Oh how I truely miss those days. I struggle daily as the male version of myself. It isn’t fair!!! I just wanna be, no NEED TO BE ME!!!!
    And that is Jessica Nicole…….
    Thank you being here & letting me share.

  66. My first time was quite a few years ago, I was 13 or 14 and dressed up for halloween as a girl.. I knew just felt right.. i never had much opportunity after, until about 10 years ago… I have tried to slip into something more comfortable off and on, but until now, I just haven’t been able to shake the inhibitions to step out.. I am hoping I can push those limits here…

    1. Just let her out.
      You’ll feel much better.
      Trust me, it won’t just go away.
      Your body doesn’t lie to itself like your brain does.
      When you put on feminine clothes it lets you know the truth.

  67. This is a true and real event of the first time I dressed up with the intent to see a man’s reaction.

    I was late teens & up to this point, I had only dressed and admired myself in the mirror.

    I was home alone and knew I would be alone all day (parents at work) .

    I put on my mom’s black padded bra (a b-cup), tight jeans and a blouse.

    I ordered pizza to be delivered and put a 20$ bill in my bra.

    The door bell rang and I answered it. The pizza man was I guess in his late 30’s-40’s and was decent looking.

    I was so nervous and I didn’t know how he would react or what to expect.

    I opened the door and took the pizza inside, I came back and started to undo a few of my top buttons and I took the 20$ bill from my bra, leaving my blouse undone so my black bra was kinda vissable. As he counted out my change, I could see he was peaking at my bra, boobs. He left and I felt so so sexy, I was so curious to know how he felt, how he saw me?

    The next day I did the same thing and the same driver showed up, this time I opened a few more buttons and unzipped my jeans. I had no panties on and I hiked my jeans down a bit so he could see some of my bare bum. I hid myself partially behind the door.

    Again he left with a smile and I felt so turned on.

    The next day the same but, this time I had my blouse undone already and I hiked more of my jeans down. I hid myself behind my door again and let him see my bare bum again and some of my pubes, I even pretended to finger myself and then suck my finger, once again he just left with a smile.

    The next day when I opened the door he had a magazine with him, it was an XXX magmagazine with scenes of sex, from intercourse to bj’s. He flipped through the pages to show it to me and asked if I liked it.

    I said yes, then he asked if I was alone and I said yes and I invited him in.

    I couldn’t believe what was going on in my head. I was so scared, but excited too.

    He came in and I closed the door, I turned towards him and before I could say or do anything, he took my hand and placed it on his cock.

    He had taken his cock out as I was closing the door. I just went with it, I stroked his cock as I led him to the living room.

    I couldn’t believe what was going on, this was the 1st cock in my hands besides my own.

    I remember it feeling very warm. I felt it grow and get hard too in my hand as I held it and stroked it.

    I sat on the sofa with his cock in my hand as he stood in front of me. I took my other hand & started to play with his balls.

    He then took my head in his hands and gently pulled me towards him, he pulled my head to his cock.

    I opened my mouth and took his cock between my lips. WOW, it was awesome, his cock felt like silk in my mouth. His cock head so warm and soft.

    I bobbed my head up and down a few times and then slipped him out.

    I started to kiss his cock and lick the shaft. I tongued his shaft up and down and licked his balls. Then I slipped him back between my lips and sucked some more.

    I must have been doing ok, cuz he just moaned and kept saying oh yea baby oh yea baby suck me.

    Then I felt his cock twitch and get even harder, he held my head again, with his cock deep in my mouth and let out a louder ohhh yeaaaa as his cock started to squirt.

    I felt like gagging and he sensed that so he eased up on my head and let me pull back a bit. I was able to keep him in my mouth and I did manage to swallow most of him, but some did ease out of my mouth on lips and chin. I took my finger to guide it back between my lips.


    It was awesome, and I knew that would not be my last time with a cock in my mouth. I felt so sexy and sluty too. It was such a thrill that I seduced him and that he had no idea I was just a cd.

    That was the start of me being a slut and seducing unsuspecting guys and blowing them.

  68. My first experience crossdressing happened when I was very young. I was four or five years old at the time. I had two older sisters that were always dressed in girls clothing. Dresses, skirts, tights and frilly underwear. My mom and my sisters called their frilly underwear “tickle pants.” I didn’t have any of my own so naturally I felt left out. I associated being tickled with fun and a pleasurable experience. I wanted to be included.

    So it didn’t take me too long to try on a pair of their tickle pants and I was hooked. I loved the way they felt, even at that young age. Every chance I got I would sneak a pair into my bedroom and put them on. They were quite soft and the frills on the leg openings were extremely stimulating and exciting. It didn’t take too long for me to decide to sneak a dress into my room and try that on. I loved the way it felt too.

    It didn’t take my mom too long to figure out several pieces of my sisters clothing had gone missing. All of which were found in my bedroom. I wasn’t punished at the time but I was made to feel as though what I did was wrong and I should never do it again. I was teased by my sisters for many years after that. Usually when they wanted to embarrass me in front of other family members.

    Not too long after getting caught wearing my sisters clothes I got caught again and that time I did get into trouble. I got spanked and was restricted to my bedroom for the rest of the day. Instead of getting me to stop, it just increased my desire for wearing girls clothes even more.

    As I got older, I continued to dress in my sisters clothes at every opportunity. My mom never said anything more about it but I’m sure she knew. I’m sure my sisters knew too because whenever I was alone at home I would be into their clothes. Putting on whatever would fit, get super stimulated, then I’d masturbate. It was just so much fun. The more I dressed, the more I masturbated and the more I wanted to dress up. I loved the way I looked in girls clothing and I loved the way they felt too.

    As a teenager I did begin to acquire my own stash of girls clothing as well. Mostly underwear at the time but other pieces of clothing too. Bras, panty hose and a couple of skirts. I was busted by one of my snoopy sisters. I offered up some lame excuses but she wasn’t buying it and started teasing me again. But it didn’t make me stop. I was addicted.

    This all continued throughout high school and throughout my college years. Once I got out of college and into my own place my crossdressing really took off. Having my own place and a good source of income enabled me to really get fully into crossdressing. I started to buy shoes, wigs, all kinds of sexy lingerie, dresses, skirts, stockings, make-up, the works. At that time I was also becoming aware there were other people like me out there that crossdressed too. Knowing that just got me even more into it.

    By my mid twenties I was dressing up every day. Mostly at home for my own enjoyment. I didn’t think I could really go out dressed up so I was content to dress up by myself. I’d check out the good looking girl in the mirror and dream about what it would be like to be able to pass as a girl. I went out a few times, drive around and go for walks in areas where there weren’t many people around. It was fun but kind of scary.

    I eventually met several other crossdressers and found that I really enjoyed dressing up with them and having sex with them. I didn’t think at the time or now for that matter, that I’m gay, but having sex with another crossdresser was a dream come true was and is really fun. I think about it all the time. But it has been a little hard to find someone to dress with lately. I’d love to meet either another crossdresser or a sympathetic woman. Both would be fine too.

    I’ve been a committed crossdresser for a long time now. I really have been working hard at looking good and getting up my nerve to go out dressed. I’m really excited by Fiona’s program. The encouragement and support will really enable me to get myself to the next level.

    Dressing up and looking good is one thing, but getting my mind into a girly girl place where I can really become who I really am is kind of scary, thrilling and super exciting. Almost like starting a whole new life. A new me, new friends, new experiences.

    I’m ready.


  69. My first time was when I was in Grade 5. The teacher I had wanted to do a play for Christmas in front of the school and so she choose the them of Santa in Florida on vacation at Christmas time. Three of us guys were chosen to be bathing beauties. So we were dressed in girls bikinis, given wigs to wear and some makeup was put on us and we were ready for the play. When we stepped onto the stage the whole school roared with laughter at us but we were having a good time.
    My second time was for dressing up for Halloween. I wanted to dress into something different so my mother put a dress, a wig and some shoes plus a bit of makeup and off I went to enjoy the party. I was about 12. For a while after, I continued to wear my mother’s underwear whenever I was home alone usually after school.
    Last January, my legs were freezing every day as I had to walk across a wide parking lot to the building where I was working. I thought of the idea of nylons but nylons for guys are so expensive. Sp I began looking at lady’s nylons which were so much cheaper and more affordable for a low paying wage. I bought a pack of 3 and enjoyed the little more warmth they provided each day. A female friend of mine who lives in Denmark, suggested why just nylons. Why not wear more of the ladies underwear since wearing guys underwear and ladies nylons just doesn’t seem to fit together. So I began buying ladies stuff. Then came the ideas of makeup and wigs and experimenting with different styles and colors.
    The first time I tried putting on makeup myself, one would not want to meet me in a dark alley. As time has progressed and through reading books at the library, I have been better perfecting my look.
    Last February I was also encouraged to find other crossdressers in my area. I found a transgender group that met once a month so that meant that I needed to try to look more passable as a woman. Needless to say, my first experience as an adult was not good but made it through the evening nonetheless.
    Since then, I have had two makeovers and purchased more clothes on my meager budget. As long as not being swarmed by too many ladies around the clothing section, I have no problem as a guy shopping for women’s clothes. Plus I am always on the lookout for good deals on makeup and clothing.
    My time with the transgender group is coming to a close as a casual crossdresser really does not fit in with a support group for transgenders even though they tried to make me feel welcome. But the general idea was that serious crossdressers eventually become full time the opposite gender. I feel differently.
    I consider having a woman within me and that is why I crossdress, to let her out for fresh air so to speak. Most of the time is crossdressing in the privacy of my own home where I live alone. But I greatly enjoy the fun of crossdressing and looking to experience more.

  70. My first time was at the urging of a guy who’d charmed me out of my pants a few weeks earlier and had popped my cherry at age 27.

    We’d been at the laundromat washing clothes and had just returned to his place. I was sitting on the couch while he put his clothes away, when he nonchalantly tossed me a cute little panty and said, “Go into the bathroom and change. I’d really like to see you in these.”

    I was pretty tiny at the time – a leggy 6-foot-1 but only 150 pounds – so the small cotton bikini was tight but looked cute on me. My cock was hard, so it wanted to poke out, but my ass looked to die for in those tiny undies.

    “Come on out and let me get a look at you,” my lover crowed.

    I slipped a T-shirt on and walked out into the living room, wearing just it and the panties. My heart was beating in my ears I was so excited.

    Ron licked his lips when I walked over to him. His rough hands were on my ass immediately, rubbing and spanking and pinching it. I squealed as I tried to get away. But he was too strong.

    Soon, my T-shirt was being pulled over my head and there I was, standing in the middle of the room wearing only those soft little panties.

    Ron was upon me in an instant, and his hands were inside my undies. I moaned as he pulled them down to my knees before he entered me as I stood bent over and holding the back of the couch. I remember looking down at the faded stains some girl had left in the cotton crotch.

    Over the coming months I purchased more panties and a couple of bras, a sundress that flowed down my body, a garter and stockings.

    My favorite piece, though, was a black sheer babydoll nightie and matching panties. The bunching just below my chest made my A cup breasts appear bigger, but I loved how it hung on me and covered my cock but barely reached my ass.

    I was shaving my body smooth, and with my long legs, skinny arms and deep summer tan, I looked very striking in it. That babydoll often ended up hiked up around my neck with Ron between my legs behind me, his hands on my hips.

    I still wear panties every day, ranging from boy briefs to thongs. My favorites are tiny tangas and cheekies. Some days I pair them with stockings and, during the winter, I’ll wear a bra in public under my clothes. Men rarely notice, but women sometimes do.

  71. The first time I wore anything for girls was when I was about 7 or 8 and I found this purple bikini panty with the scalloped trim from Hanes Her Way (like they used to be) and I was curious to try them on. After I cleaned them, I felt that sense of taboo but also fell in love with them. The way they looked and fit just felt right to me. It wouldn’t be until 5 years later that I would try panties on again but by then I wanted to try on more things. Half of my teen years my parents would bring in tons of bags of clothes they were donating and while nobody was around, I’d check each bag and pull out everything from underwear to pants and blouses to skirts and dresses which I also loved but really struggled with the guilt of what I was doing. I, like many cd’s and gurls like me, would find myself buying my own underwear and clothes only to panic and throw them away at some point multiple times.

    In 2013, I had just moved back around where I grew up and I had told myself once again that I could beat this… whatever it was. But then I was walking through Macy’s around Christmas time after I had been looking around for gifts when I once again felt the pull to look at all the pretty dresses, skirts, bras, panties, and beautiful displays for makeup. I fast walked my way out of the store, drove to my friends where I was living at the time and felt so exhausted from what I had been doing to myself. Denying myself of the way I wanted to express myself in turn for forcing myself to stick to the mold. I had just overcome how much I hated myself and started to like myself and this feeling came on fierce. I looked at myself in the mirror and laid out my only two options in light of my personal growth. I either keep doing what I said I was going to do by beating this “princess boy” (dad referred to me as this on a few occasions) essence of myself down for the rest of my life, or if I went back to Macy’s, I was going to commit to figuring out what I was bottling up and never turn back.

    I knew either option wasn’t going to be easy and it still hasn’t been. But I felt that self-abuse after all the growth I had done aside from my crossdressing had felt wonderful and denying myself of my true self expression was a huge part of why I hated myself in the first place. It didn’t take but a few minutes to decide which direction to take but it was a few minutes of intense thought and reflection. I went back to Macy’s that night and I started over once again but with the promise that I would never turn back and figure out who I was and what I was experiencing. In 2014, after doing a lot of research and speaking with others who are trans, I came to the realization that I wasn’t just a crossdresser but that I’d really truly rather be a girl, and that girl resonated with the name Kimberly.

    In 2016, after losing sleep for months, I texted one of my closest friends and took the risk of telling her who I really was. After an agonizing hour of feeling regret for texting, wishing I could take it back because of the negative things that could happen, she responded back with such a positive and enthusiastic acceptance of Kimberly. I’ve since used great discretion in who I tell but have continued to tell some of my closest friends to build confidence. It’s been incredibly liberating and I wouldn’t turn it back for anything.

    1. Discretion is gd. Ive told only the people ive loved and some of them didnt react as best i could have hoped for but your so strong. Your a little more then i am. Confronting your demons like that shows so much character in strength. Makes me feel proud. Gd luck out there. And be safe

  72. Skimming through these posts I realize some similarites to my evolution. Ignoring that I might have tried on Mother’s silky slip once or twice as a boy, my 1st guilty pleasure was as a married reaponsibleyoung adult.
    On days off, after my wife had gone to work, I was getting into the shower when I noticed a pair of pantyhose that she had thrown aside due to a run. Who knows why, but I just had to try them on. Ohhhh, such a nice feeling encasing my legs, butt, etc. They felt like heaven but I guess good is never enough. Before she got home I had to get out of my now crotchless pantihose and he panties, bra & strapless sundress. (still miss that dress).
    Years later, fessed up & spent some good times dressed with her. Best yet was shopping together for things we both loved (corsets, garters, etc). Wonderful times, but so is sitting at home typing my experience while lounging in a Snow White costume (satin & sequins) being myself.

  73. My first time happened a few years ago when my wife was out of town for business..I was home alone and have always thought about dressing in her clothes, I’ve always loved girly things (my guiltiest pleasure is a nice pair of knee high fuzzy socks and uggs!! ), I decided to put on a pair of her ridiculously soft Pink panties and bra…I didn’t like how my body looked in just her underwear, so I put on a nice blue sweater dress and leggings along with a nice pair of nude high heels…I looked in the mirror and noticed a bulge in my dress…I don’t think I’ve been happier… unfortunately, I’m not sure how she would react to me dressing (she’s very traditional and a little up tight!) especially with a young child at home…so I’ve been forced to keep Madison Grace locked in the closet, but dress every opportunity I get and still love it just as much! Maybe one day I’ll venture out of the closet and see what happens! I’ll be following along this blog that’s for sure!! Thanks Fiona!

  74. Hello Mistress,
    I was about 7 or 8 years old when I first crossdressed. It was early on a Saturday morning, only I was up in the house. When I went into the bathroom I noticed that my mother’s clothes were hanging from the towel rack. I still don’t know why, but I felt an irresistible urge to put them on, so I did. As soon I as was fully dressed up, my sister burst into the bathroom (I had neglected to lock the door) and discovered me. She was 6, and she found the picture of me dressed in mom’s clothes hilarious. I was mortified, and mumbled something about ‘just wanted to see how it felt’. I promised myself I would never do it again, a promised that I promptly broke just a couple of days later. Since then I have never been without the compulsion to wear women’s clothing, and finally, after many decades of keeping it secret, have revealed my true self to my wife. She has been very accepting and my life is so much better for accepting who I really am.

  75. The first time i was dressing was actually for a school musical when I was around 12 years old. I was playing a mom and had a really long dress on. I still know that it was really nice to spin around in it because it was a wide dress. I also had my mom’s wedding shoes in my closet on my room so I sometimes weared them when I was alone. The next time I dressed it was probably around 1 years ago (I am now 20) it was just so very nice and relaxing to crossdress again and now at this moment I have a full crossdressing outfit and it feels wonderful.

  76. Hi I’m Brittany. My full girl name is Brittany Kayla Marie. I have been wearing girl clothes around the age of 8 possibly earlier whenever I would be spending time with my best friend who is basically a sister to me. She would dress me up as a girly girl and I actually loved it and enjoyed it but I am not sure if she noticed I did. I haven’t been doing it anymore after that until recently. I am in a relationship with my girlfriend who is accepting it and actually loves it. Apparently it is a turn on for her. I told my girlfriend about what I did when I was younger and asked if I liked and enjoyed it. I told I did and she told me that she wants to continue it. Now not only are we in a relationship and want to marry each other but she also wants to be married to Brittany Marie who is a total girly girl. I have never been out in public as Brittany before but do become her when I have time off work. Will be more often after me and my girlfriend are living together. I love crossdressing but I am still a straight guy and live normally as a guy but my girl side is an ultimate girly girl that is in cheerleading and loves it. Me and my girlfriend have gone out as girls together yet but there is always a possibility of it starting to happen from time to time.

  77. I had a similar experience to many here. I would wear my mom’s pantyhose, bathing suits, but i loved the heals and jeans skirt the most.I would do this through most of my preteen teen years.
    In my twenties one Halloween my buddies and I were invited to a party. We were told the more extreme the better. So I decided to upstage as many people as i could. I went as a French Maid. I bought stockings, heels, a wig, and the costume. My mom did my make up for me. I looked good. I was tall, 6″2″, 150 pounds. and I looked hot. Guys were hitting on me. My ONLY complaint of the night I had to take my heels off to drive.
    I kept the outfit,And like many crossdressers I threw it all out on day because i felt “Gay”.
    I would not dress again for years. But I did discover the fact I am Bi-Sexual. I had sex with men I would meet on the old AOL Chat rooms. but never dressed, I had nowhere dress.I met a nice girl, and got married. We moved to an area that has the video booth places, I would go there and suck men’s dicks. I had a guy cum in my mouth after I told him not too. So I stopped going for a while. I went back, and made them wear condoms.I would not hurt my wife, but there was something missing. I went to a sex shop and bought a little outfit, a pink top and tong. I would were it under my clothes, and men loved it. I threw out at least 3 of those .
    I one day around Halloween(see trend here) bought some stockings and a wig. I went to the dollar store and bought some cheep makeup. i used a pair of my jeans and made shorts out of them, and borrowed one of my wife’s tops.And went to the video booth place, I met(and fucked) a real women there who was there to have sex and she and the men were all cool. they recommended I go to a thrift store and buy a skirt and top, she helped me figure out my size(I’m no longer 150 pounds),and i went.I have gone every chance I get. And yes I have thrown out 3 other outfits since that day, what i have now I am keeping, I love it too much to stop. I think about dressing and I get hard, I think about sucking men’s dicks as Sara and I get horny, I love it. I have up graded to make up(not just lipstick), perfume and have 3, going to be 4 outfits.
    I feel so sexy dressing, I know I am not passable, but the men I hook up with love cross dressers and don’t care. So I go.

  78. My first time? Wow, so many years ago…I was probably about 12 or 13. I’m the oldest of 5. I had (have) a younger sister and was very curious about her “underthings”. So I started sneaking into her room, trying on her panties and bras. It felt soooo good! As she became older, and her “things” more feminine, the feelings intensified when I donned her unmentionables. I eventually got caught, and of course, had to discontinue my adventures. To jump ahead many years, now I have my own “unmentionables” to wear any time I choose…

  79. Hi
    My first experience was around the age of 5. My slightly older sister persuaded me to wear one of her night dresses so we could both play at being princesses.
    From there I progressed to trying on a pair of tights and was then hooked. When I was in my early teens and was trusted to be allowed to stay at home when everyone else was out I would try on my mother’s panties ,bras , nighties stockings and dresses. Then the usual story got married and had a family so repressed the desires as much as I could. Occasionally I would be home alone and the desire would be too much so would wear some of my wife’s clothes. One time when away for work bought and wore panties and stockings all day under my man clothes. I am not out but find it comforting to come here and enjoy the connection with others who have similar views. Love Clothes maketh the man series. Having a real life Devina would be a fantasy of mine but if it really happened would probably run a mile. Thanks again to Fiona for this wonderful site.

  80. My first time was at 11 and I noticed my mothers bra and panties in the hamper and decided to try them on. The feeling of the soft and smooth fabric on my skin was intoxicating. I still love this feeling but have to be discreet because my wife thinks I’m disgusting as she has trolled my computer before and found my sissy websites, etc.

    1. You wife may not be quite ready to accept this, bt that doesn’t make you ‘disgusting’. Her response is something she is responsible for, not you. There are some interesting discussions on how to address this type of response within the Premium Program, and also how to manage the communication and appropriate levels of a crossdressing practice, with partners who may not be entirely accepting.



    2. That really rough hun im sorry. It was a very stressful way for me to live. Its one thing to be in the closet. Its a whole nether to have taken the chance to come out and exspress yourself to your lady. And have a part of your sole cut out. I hope this site helps you like it already has been me. Mistress has been kind enough to be attentive and help me see a few things straight. Be patient as possible.

  81. Hi
    my first experience is at the age of 15
    one day my mother was going for a function
    before she leaving she told me to my aunts house and i agreed. then she left home and me the key. i waited a long and night i left home on my way there is heavy rain and my clothes become wet. when i rached my aunts house she told me to shower. when i am back i asked her for some clothes to wear because i didnt pick any spare clothe. she asked me to follow her and she welcomed me to her room gave some clothes. i was shocked. it full of girls clothes. i rejected it. she told me that their is only girls clothes and she is alone at home and she is divorced 5 yrs ago. so their is no male clothes. then i got forced to wear her t shirt and skirt that night passed. at the morning mom called me and told she return after a week. i asked aunt to buy me some clothes and she agreed. unfortunately we dont go for purchase and the second night i was wearing another skirt and t shirt. next morning i asker her to go for purchase she told me that she is alone at home and it looks good for me and adjust for few days more. i agreed to her openion and i started loving to wear girls clothes. i told her that i dont like to wear like. i want to be like a proper boy or like a proper girl. she told me to go to her bedroom and she gave me pink padded bra and panties and applied make make on me and gave some sexy clothes. i got shocked. i look like a beutiful girl and remaining days i was fully a girl…..
    now wear girls clothes when ever i can
    and i love to aunts house because she treat me like a girl and having fun with her

  82. Hi everyone & all my dear sisters,
    I’m a crossdresser – transvestite – transwoman for about 57 years now 🙂 Yes I started when I was 8 years old by trayting my granmothers old fashion costery and I have been cached about 4th or 5th time when I was trying and garnd mother sad that it is not right what I was doing. But it has not been stoped me. As quite all of you gurls I started to use my moms underwear. I was addicted and still addict the bobs and the bra… When I was about 13 years old I already had my own bra and some tights. When I was alone in my room and aspecialy at night I was wearing my bra and filling it with cottons also wearing my tight and hiding my manhood behing myself for having woman looks on the front.
    I also liked & like the silk touch and was masturbating with a silk scarf when I was wearing my bra and tights…
    They all were happened when I was living in Turkey with my parents.
    1979 I went to UK (Weymouth) for my study and was having my own room at a house with other students and I was wearing more woman’s things when Iwas alone in my room and have my girlfriend and made her you wear more sexy as she did…
    After I went to London and stayed a girlfriends house for about 5 moths and most of the time she was away and her shous were at my size also her dresses was just for me.. I started to use them… And also got some for my own, but never went out.
    at the end of 1980 I got maried with my first wife. Before we maried I told her that I am crossdresser and she sad that it was my color…
    1982 I started my business! Guess what? Ladies underwear…
    But I had my moustage as I was not looking old enough as a businessman…
    I found “Friends Place” in London which is not exist anymore and went there Ms. Yvone helped me so much how to make up how to dressup etc. We even visited this place one with my wife and she sad that she doesnt want to partisipate this life of mine but I am free what I like to do.
    I went out to the public first time in Lonodn with a group of “Friends place” with the help of Yvone… It was great time.
    After this first time I started to have my own lingerie as I was selling them and also started to buy some clothes and even got the silicone bobs to fill my bra.
    Each time I was out of Turkey for business I was going out as woman but not had any experiance with a man.
    1985 or 86 I do not remember I was staying at the hotel in London and wanted to have the experience. at this time there was no internet like today. I had a magazine and find out the male escort called them and rcvd a nice guy who was from New Zeland. I had such a good experiance with him and took photos kept them for many years. After we met with him in Mykonos island twise and one I invited him to Turkey and arrange a nice hotel room for 3 days. I never forget him…
    During 1996 I decided to leave Turkey and came to France, no more business and first time I had my epilation all my body, had enough lingeirie and dresses to go out. I was living at the French Riviera and dressing up at nights and going to Cannes where there was a trans bar enjoying myself. I was regulary out.
    2004 I divorce for other reasons and went to Paris and started to be out quite all the time but only during the evenings.
    Long long story….
    Lets make it short…
    Today I’m living 60% man 40% woman a real bisexual but mostly having sex with man. I never go out with other gurls as you all are my sisters. But getting a man at a bar or a club is a ral fun for me…
    I have my long hair and today I know what to wear how to make my makeup etc. Even some times I am traveling I go to the bus or airplane as woman… It is a real good feeling.
    The only thing I regret that I did not have the operation for having real bobs…
    Kisses to all of you…

  83. My first time ever wearing girl clothes was when I was only 5 or 6. I was at my best friend Zoë’s house (who I had a huge crush on) and she told me she wanted me to dress up like a girl. She had told me the week leading up to me going over to her house that she was going to put me in a dress and treat me like a girl. I always told her no way! The day came and I went to her house. She and I were playing in her room and I found myself wanting to be dressed like a girl. I asked her if she still wanted me to dress up and she said “oh no, I was kidding” I was so upset! I must have showed that I was upset because she grabbed my hand and asked if wanted to. I shyly said yes. So she said how about we start with a skirt. I felt so cute and girly and I was so happy! Then my mom got there and I had to quickly change back to boy clothes and go home. I went years without thinking about that day. Next, I was 13 and home alone. I quietly opened my sisters bedroom door. I crept in and threw open her closet door. I started with a bra and panties and was quickly hard. I threw on a pair of heels and a dress and started prancing around the house. I caught a glimpse of myself in the mirror and found that I made a much better girl than boy. This went on for years, dressing by myself, masturbating, taking the girl clothes off and telling myself it was the last time. When I was 15 I discovered Omegle. I started dressing up, getting on cam, and showing off for men. I always said I was 18 and most of the time they bought it. It turned me on so much watching men masturbate over me while I showed off my ass and young girly dick. I know i shouldn’t have done it but I was hooked. I’ve still never been with a man while dressed though, someday soon I’ll try.

  84. Fiona – Thinking back it probably started in the fourth grade. I was in a school play and as part of my costume I had to wear girls leggings and boots. I remember the feeling to this day. Moving forward to high school. Freshman year I went to school in the afternoons. I was home alone all morning. Just me and my mothers clothes and makeup. The amazing feeling of slipping into pantyhose, applying makeup, eyeshadow, mascara and lipstick. Then I would do my nails. I could not help myself. I did it nearly every day. The worst part of my day was having to wash it all off to get ready for school. I recall one time being in the cafeteria when a friend asked if I had mascara on. I made up some excuse. Reality was the excitement that came over me. The rush of almost getting caught. To this day I get so excited to come home, put on my makeup and dress up. I always felt that girls were so lucky to have such incredible options when it came to “getting ready”. Going to the hair salon, manicures, pedicures, fashion, high heels, ankle booties .. OMG there is so much more. I’m so glad I found your site. Hopefully, I will learn so much more about my femme side. Maybe I will even get lucky some day!

  85. The first piece of women’s clothing I tried was my mothers swimming bikini which I put on while I was alone and stroked myself I think I was about 15, not long after one of our cousin’s stayed with us to start her nursing career, she was pretty hot and a few years older, she had a boyfriend and obviously flaunted her looks by wearing lacy lingerie under her nurses outfit as I found out by going through the laundry basket to find some slightly moist lacy red panties and an underwire bra which I immediately had to try on along with her blue nurses outfit and have a great stroking session, this went on for a few years before she finished and moved on in life so I needed to get some from somewhere, the adult store had some and it wasn’t too awkward, then the internet took of and I started watching alot of ts porn and had my first transexual experience before I was 21.
    But here is where things get crazy but awesome, 2years ago I was inbetween jobs and my lease finished so my cousin, yes the hot one who’s dirty lingerie I liked, let me stay with her, she was divorced now and I told her and her sister when I was moving in that I like to dress as a woman they were both very supportive, the first night I head to bed and she asks where I’m going and tells me to come with her so I do and we talk in bed for a while, but she can’t help herself she hasn’t been fucked for over a month so she says and begins to suck my cock, it was weird for about a second then I asked if I can get a dildo, and from that time on we fucked and sucked each other daily and I wore lingerie to bed every night, eventually I was the woman in the house wearing dresses and heels occasionally a wig, so now I was her bitch she needed to be the man so I brought a strapon harness and dildos which she would get me to suck after I had showered and dressed before telling me to get on and fuck.

  86. My first time was a halloween party. I was about 21 married with children. the night of the patry my wifes sisters help with the clothes and make up. When they had completed the transfor.ation I couldn’t even recognize myself.I remained in the attire all evening being groped by all the other husbands. I have to say I did like all the attention especially since nobody knew who I was but my wife. The party continued for hours and everyone changed back into their regular clothes but I didn’t bring any spare clothes. When the party was over and we got home we were a little lit and my wife still dressed as robin hood suggested We stay in character have sex as the characters we were. I agreed and she put on her strapon and made me pretend to give her a blowjob and then said get on the bed face down and ass up. I obeyed so she proceeded to fuck my brains out. We never did that again because she said it was kind of weird. Truth is I enjoyed that experience and miss it. Sometimes I’Ll shave and wear pantys under my man clothes but it just isn’t the same as that party night. Still married love her alot but seriously need an occasional gurls night out.

  87. Hello Fiona,
    Thank you for putting this site up and maintaining it.
    Hello to all (others) on here, I don’t want to leave any one out??
    I assume there are more than cross dressers on here, admirers??
    So hello, and I first tried on a pair at 16, A bubby’s 13 yr old sister. They were at work, school and I was staying there that week and I was not feeling good that morning. I read her diary, she was all about how hot I was… Reading while wearing her panties…. I was Hot… and Hard…
    It would be many years for the next time. Now my wife is well aware and has donated a few she dislikes for whatever reason. I haave bought many more since myself. I have several on the way now. I think I have hundreds of pics. I love the way I look in a lacy pair with silk panels…. Feels good. Looks good. I have 2 bras and couple pair stockings so far. It took two years for her to adjust, so hang in there closet dressers. I want to try for this Halloween to dress fully. fingers crossed… No Pun… Marcia

  88. My first time was when I was 8 years old and my two sisters dressed me in there dress and pantyhoses when I wore them it just felt so right so after that I would borrow my sister clothing and where there outfits when they were out when I got to grammar school I stopped for a long time untill my sister started working in a hotel and her uniform was a dress and tights I just couldn’t help myself and would wear her uniform just for fun after that I stopped dressing untill I left school and started working in a grocery shop with a lot of women and of course there uniform was skirts and tights after a while I just couldn’t resist and I bought a dress tights high heel shoes off the internet and I have dressed ever since that day.

  89. My first time came up when I was 11 years old. My mother dressed me as a girl for carnival and she put some make-up on me too. I won the second price of the local costume competition 🙂
    This was an unbelievable experience and I was so disappointed when carnival was over again.
    As a common boy at this age, it was impossible for me asking for another dress up session again, unfortunately. However, I will never forget this first and lovely adventure.

  90. I’m really not sure how it all started. Having 3 older sisters had something to do with it I’m sure. In a 3 bedroom house, mom and dad have one room, the other two between the four of us. Underwear and girly clothes everywhere. I remember putting on the silky half slip and matching little bra. It felt like I was doing something naughty and I shouldn’t be doing it but I did it anyway. Whenever i could, i would try something on. Skirt, underwear, walk in their girly shoes. Growing up, I played soccer up north. And a trick to keeping warm was to wear stockings underneath your shorts and long socks. A lot of the guys did it. So if it works for soccer, it works underneath your regular clothes. I spent many days in pantyhose in math class or science.
    Fast forward to my mid twenties living in my own place, I would order all my girl clothes from Victoria’s Secret. Everything from panties and bras to dresses and denim jeans. Continued to date and made it a point to go to her place instead of mine. Until I met my future wife. Purged everything. Thousands of dollars of clothes gone. I’m separated now and I’m so much happier being who I want to be.

  91. My very first experience with crossdressing was when I was really a little boy and touched my mothers slip. The satin feeling was heavenly and I really liked the look and feel. The urge to touching and caressing the slip grew and grew until one day i tried it on. The feeling on my bare skin was very nice and from that day onwards I was hooked. I “stole” slips from my mother on a regular basis and went from slips to nightgowns in which i slept. Early in the morning I dropped them in the hamper and I really don’t know it my mother noticed it. I can’t ask her since she passed away last year.

    I think it was during my puberty that the feeling increased from slips and nightgowns to dress a little more. That was a difficult situation because I’m the youngest from 3 brothers so the only female in the family was my mom. One day, while riding my bike to school, I noticed a very nice pink skirt in the window of a shop. I think I was about 16 or so and felt that I really had to buy that skirt. It took some weeks to gather enough courage to enter that shop and ask the salesgirl for that skirt. I told her that I had to buy it for my sister and she asked no further questions. I raced home to fit the skirt as soon as possible but I had to wait for the night. After dinner I told my parents that I had to do a lot of homework and I room the first thing I did was fit the skirt. The size was good and the feeling on my legs was heavenly. I was hooked !

    As said living with my parents and brothers didn’t give me a lot of opportunitiers to dress. That changed when I started a relation and went living together with my wife. I never told her of my crossdressing because it was at a low level but always in the back of my head. You should know that I’m talking about 1984, no internet, no social media, none. Living together with a female gave me a lot of opportunities. To be confronted with pretty lingerie, dresses, skirts etc on a daily basis was too much.

    One day, when I came back from work, I couldn’t resist the urge to dress completely (which I never had done before). I picked panties and a lacy bra, a pencil skirt and a lovely silk blouse from my girlfriend’s closet and tried it on. It felt so good !! I admired myself in front of the mirror and was on my way to the couch when I heard the key in the front door. I was trapped and had nowhere to go and my heart was beating to the max. “Honey I’m home” my wife yelled while entering the hall of our apartment. Then she entered the living room ………

    That was the beginning of a very long, emotional and challenging evening…………..

  92. It all started when one Saturday afternoon my wife convinced me to join her on her weekly trip to the nail salon. She told me that lots of guys get pedicures and that I should try it. Now I was always kind of jealous of women and the endless options in fashion as opposed to the drab choices that males have to choose from. I also loved the look of a girl with beautiful nails. So on this day I decided to get a pedicure. Needless to say it was a life altering experience for me. It was incredible. Soon after I was giving myself manicures too. Before long I decided that I wanted to go all out and dress up. I recall doing my makeup for the first time. The feeling of applying lipstick. The sensation I got when I slipped on a pair of panties, garter and stockings. Sliding on a dress and slipping into a pair of heels. “OMG this feels amazing” I said to myself. My wife had been away on a girls weekend. I had the rest of Saturday to enjoy my femme side. Or at least I thought I did. Next thing I know I hear a car door shut and the front door opens. In walks my wife Sue. She dropped her bag at the sight of me. I was speechless. How could I explain this to her. She reacted by pulling out her phone and calling her best friend Megan. You’ve got to get over here and see this she said. Then Sue says to me “I own you now Alex, or should I call you Alexis?” I had no idea what to expect. Sue then told me what she expected out of me. You want to be a girl then you will learn to do everything that a man expects out of a girl. A couple of days later Sue came home from work and gave me a new outfit. Put it on she said. Next thing I know I’m dressed up like maid. Sue tells me this is your new uniform. Get to work. Friday night rolls around and Sue brings home a new outfit for me to wear. She helps me with my makeup and nails and tells me to get dressed. Next thing I know I’m wearing a cute black leather skirt, white blouse and matching leather vest. I slip into a paid of black ankle booties. My world had changed overnight. I had no idea what to expect next. Then Megan is knocking at the door. Sue says to Megan “did you bring it?” Megan takes off her coat – she is standing there wearing a big black strapon. Sue then tells me to get on my knees. Next thing I learning how to give a blow job. Before long Sue was taking me to a dressing service. Makeup, wigs, incredible outfits. They had me experimenting with different looks. How did a simple trip to a nail salon and a pedicure turn into this. My curiosity and Sue’s abbreviated girls weekend changed my life forever!

  93. My first time dressing I was 5yrs old and I put on one of my sisters pinafore dresses. I’d already fallen in love with her party dresses, but hadn’t had the chance to wear one before I got caught and disciplined. I’m pleased to say my fem side never left me to this day.

  94. I always had feminine interests and tendencies but societal reality quickly taught me to suppress those interest and desires. “No you can’t play with those toys, those are for girls.” “No you can’t wear those clothes, you’re a boy.” So I played the part.

    And then at around the age of adolescence I was home alone and happened to notice a little black dress hanging in my father’s closet. It belonged to his girlfriend at the time – a beautiful and petite Mexican woman by the name of Anna (who I just recently met again after years and years- maybe I’ll tell that story another time). I removed the dress from its hanger and went to my room and slipped it on. Apart from not quite filling out the bust, it fit perfectly. For the first time in my life I felt… right… like I a missing part of me had been restored. That sense of fulfillment immediately dissolved into a deep sorrow as it occurred to me that I cannot be complete. I was a boy – this was a dress – for girls. I fell to my knees sobbing and eventually returned the dress exactly the way I found it.

    For many years to come I would occasionally find an article of clothing, usually underwear or something else small which could be easily stolen (yes, I stole them. I’m not proud, but I did what I had to to get by in a very conservative area), and I’d take them home and hide them as if it was a box full of drugs and blood soaked murder weapons – ashamed of who I was. I would build a collection of women’s clothing and inevitably get scared and purge them – and then do it all again.

    And then, last year (I’ll be 34 in December)… everything changed. I fell head-over-high-heels in love with a dear friend, his name is Brian. Sadly, he does not feel the same – which for several reasons, which I won’t get into right now, caught me quite by surprise. And though we are still very good friends, the rejection was(is) heartbreaking. However… it was also a catalyst – and exactly the one I needed.

    A year on and now most of my wardrobe are women’s clothes, much of which I can work into my day-to-day male look without arousing too much suspicion. I’ve also come out to my son, mother and a few close friends. I can’t tell you how good it feels not to have to hide in my own bedroom. Or how great it feels to socialize with the people I care about without feeling like I’m lying to them or to myself. I can put on a dress, heels, makeup, and breast forms and go to a friend’s house for drinks… it’s so… it’s such a relief.

    But there’s still ground to cover. I need to get better at applying makeup. I need to work on feminizing my voice. I need to decide whether or not to begin an HRT regimen. There’s still fear. Each new step is sooo scary. But each step, once taken, feels as if I’m a step closer to being “Me” – the me I should have been all along.

  95. I loved to dress as different characters as a kid. I dressed as girl for a masquerade when I was 11 years old. I remember I loved it. I remember stripping on a table at that party. People often said I was girlish those days so I worked hard to be more boyish. But the time I really found out how sexy it felt wearing women’s clothes was when I was 19. I had to borrow my gf:s trousers to work one day and it really turned me on. I felt sexy, feminin, free and alive. But, some time efter that we broke up. I lived by myself for a while and started experimenting with anal play and loved. But ended up feeling bad about it, suppressing my needs and have done so for about 25 years. Some years ago the erge grew om me and it keeps getting stronger and now I’m here.

  96. Hello Fiona.
    My first time was six months ago. I played cards with my girlfriends and lost. They made me make-up, put on a dress and grandma’s wig. Suddenly there was a bell at the door. A guy came by one of his friends. He was older and didn’t live in our neighborhood. I was sitting among my girlfriends. He said hello to everyone, looking at me. I jumped up and ran outside – rather home. Pink with shame, it seemed to me that everyone was looking at me, but in fact people did not pay attention to me, except for a few guys who looked at me as a girl. I lowered my eyes and ran past them, my trembling hands quickly opened the door and slid home. Having calmed down and breathed, I looked in the mirror and got excited so that my stiff penis stood out through the dress. The next day, when I went to my girlfriend’s place for clothes, she said her boyfriend said I was a beautiful girl.

  97. My wife took me out for New Year’s Eve which was my first time out of the bedroom dressed as Molly we went to club Pittsburgh and had a great time with a lot of compliments on my outfit even though my make up artist did not show up to do my make up

  98. Darling All, so when did this start? Dressing up box was always a favourite dresses to play in. My parents friends daughter as we grew up we looked similar and gender swapping was our sweetest game. Her clothes always felt great especially touch each other playing mummies and daddies. My truely first indulgence happened during summer school holidays when I spent a couple of months living with my Grandparents. They both worked that left me at a loose end during the day. My Nan was elegant no fuss women that I adored. Her formative years were the 40’s and 50’s and this reflected her dress sense and for me more importantly her lingerie. 6 and 8 strap suspenders, silk stockings , a line dresses, slips and under skirts. Mmmmm. The joy was as soon as they left for work I would be in her lingerie collection. Being just 15 I was tall and slim with mid-length fine red hair and whilst most clothes fit I lacked the breasts to fill her bras so would wear her cams and slip. Shows another issue as only her open back mules would fit but so made me feel so wonderful. I would strut my stuff pretending to be the sweet daughter and usually ending in me masterbating into her knickers. As days past my confidence grew or perhaps restlessness set in.I would flaunt myself in heels, stockings pencil skirt and blouse in front of the windows or spend time sunning myself in the garden. Who was there to see me everyone was at work. Or, so I believed. Not long before it was planned to return home I was fully made up. Eye shadow, blush and bright red lipstick. Freckles across my nose to add to the naughty innocence. Black Cuban heeled seemed stockings, 8 strap suspenders sheer panties, silk slip and pretty white cotton blouse. I did my usual routine around the house and danced around the garden and had just walked back in the kitchen when there was a knock at the back door. A males voice called out my Nan’s name and said “only me” walking straight in. I stood there frozen staring at him in the shock of being seen like this. My Grandpatents neighbour equally stood there open mouthed. I saw the shock turn to anger and I will never forget the words “my god what are they going to say?”. I collapsed to my knees cried and pleaded with him to say nothing. His reaction was to say well your grandad would thrash me so he would do it and with that he pulled out a chair, grabbed my wrist and pulled me to my feet and the across his lap. He smacked my buttocks hard causing me to again cry out. My ass really stung as he smacked. He even pulled my knickers down to expose my glowing cheeks. Spanked me again. Something changed he was breathing harder, I could feel him stiffen against my tummy and instead of smacking me he stroked my buttocks having a good feel. He abruptly stood, I slid off his knees to the floor knickers around my thighs, and I thought he was going to leave. But no, he unzipped his trousers and took out his thick manhood. He told me to kiss it. I initially refused, but he threatened to tell everyone about my “dirty” secret. What was I to do, no choice but to be that submissive little slut and do as told. I cupped his balls and manhood and kissed the end of his shaft. My god it felt and tasted delicious. This virgin girls first touch of sweet sex. He told me to put him in my mouth which I now willing did. He grabbed my head and roughly fucked my mouth. He came quickly and filled my mouth which like a good girl I swallowed. He zipped himself up, told me to say nothing and left. I couldn’t believe what had just happened, how abused, but so turned on. My clit was so hard, harder then ever before and fit to burst. His taste still in my mouth and several quick strokes and my cock was exploding over my stockings. My good I felt so turned on, such a woman, and so sexual. Never have I felt the intensity of such a sexual encounter. Nothing else happen between us, our secret, but I still fantasize about having an affair with him. Him coming around and fucking me properly.

  99. Hi Fiona –

    My first time was back in High School. I had a job working as a stock boy in a large department store downtown. I was assigned to the Cosmetics Department. I was responsible for stocking the drawers for each of the Girl’s stations. I recall having to learn all of the different makeup lines, nail polishes, perfumes, etc. I remember the stockroom was alongside the Cosmetics Department. The girls were all so nice. They were all so beautiful as well. Sort of a dream to be able to work with all of those girls as a 17 or 18 year old. I used to watch from the stockroom as the girls would work their magic at the counter. There was Patty, Marilyn, Joan, Donna, Carol and a few others.

    Around Christmastime the girls would get together for a unit party. Since I had been assigned to the unit for a good part of the year one of the girls invited me to the party. Just stop by for a while she said. “You like beer don’t you” she said. How could I have said no. 17 years old, beer and beautiful women. Besides, I had nothing else going on that night so I decided to go. So I arrived at the party which was at one of the girls houses and one of the girls handed me a beer. I was talking to a couple of the girls, just small talk … That’s when things changed. All of a sudden Carol, the host of the party walks in and says “What’s he doing here? – This was supposed to be a party for just us girls” Everything was a blur after that. Carol says that If I’m going to hang with the girls I needed to change. Change? I said ….

    Next thing I know they are leading me downstairs to the basement. There was a long bar and entertainment center. They lead me over into the corner where Carol had her own salon set up. Apparently, she did side work on her days off. Take off those jeans and sweater they said and put on this robe. They sat me down at what I found out was a pedicure station. You are going to love this they told me. Next thing I know I’m getting my feet soaked, getting my cuticles taken care of, exfoliation, foot scrub, trimming and filing my toe nails. then they used a moisturizer on my feet. The girls were all so attentive. Next ting they are applying a base coat, two coats of polish and a top coat. They gave me another beer while my feet dried. they were right, I did enjoy it. It did not stop there though. Next they lead me to the manicure station. They started the whole process over again on my hands. Then they decided that because my nails were short they would apply acrylics. Before I knew it I had soft hands with perfectly shaped nails that were then covered with two coats of bright red polish. I remember that I couldn’t stop staring at my nails. What was happening? Then they told me to remove the robe. Next thing they shaved my legs. I was a swimmer back then so I actually did that regularly during swim season. I remember the girls commenting on that. After another beer I was feeling more comfortable.

    Then they lead me over to a makeup table complete with a long mirror and lights. I did not have much of beard back then. They started by hydrating my skin with moisturizer. Then they applied a base foundation and concealer to hide a couple of pesky zits that I had. Next they used powder and blush to highlight my cheeks before tweezing and shaping my eyebrows, applying eye shadow, eye liner and mascara. Then they applied a bright red lipstick that matched the color of my nails. Finally, Carol brought out a medium length wig with brown hair and highlights in a shag hairstyle. They swirled the chair around so that I could face the mirror. I could not believe what they had done. I was staring at a beautiful girl. That girl was me. We’re almost done they said. Once again, the robe came off. They closed the curtain around me and told me to slip into a pair of panties that they handed me. the drew the curtain and stood me up. Then came the lacy garter and sheer stockings. Next thing they were fitting me into a corset to give me some shape. The girls finished by dressing me in medium length black dress with a V-shape neckline and a waist belt. Then they handed me a pair of black pumps to slide into.

    After standing up in the heels I faced the mirror. I was not longer Alex. The girls called me Alexa or Alexis.

    That is my story ….

    1. I remember spending the rest of that night walking around in heels. I had become one of the cosmetics girls. Afterwards, the girls continued to invite me to their parties. Each time, dressing me up. The girls enjoyed it too. They always had new outfits for me to wear. It was so exciting. When I left that job and went to college I stopped dressing.

      Fast forward to last year I was with my girlfriend running errands one Saturday afternoon. She asked if I would mind if she stopped for a manicure and pedicure because she had a meeting coming up on Monday and wanted her nails to look nice. I escorted her into the nail salon and sat down on a couch alongside her nail tech’s station and started reading a paper. The Nail Tech asks Sally if I wanted a manicure and a pedicure too. She said a lot of guys get them. They both convinced me to go for it. So I pulled off my shoes and socks and all of a sudden the memories of my nights out with the cosmetics girls came back to me. Those memories and the simple pleasure of a manicure and pedicure gave me the desire to start dressing again. It’s now a part of me. My other side, My Femme side …..

  100. Hi all, I admired my grandmother out of all the family. I remember trying on a pair of her panties when I was around 6 years of age. Here in the old families in the South, things like this were extremely taboo especially in the 70s and even early 80s so I conformed in accepting my male role as a leader in the family never to do this again but the thought of silk against my skin always stuck with me. Years later after providing for so long, after the children are all grown and after two failed marriages I met the woman of not only my dreams but the woman that shared my fantasies of what I would like to try and experiment with. I was afraid to tell her everything but I knew I had to be honest with her after all I felt secure with someone for the first time in my life. I finally broke down after staying quiet about the subject and told her that crossdressing (atleast trying it out) had always been a fantasy of mine,. She seemed shocked at first but not shocked that I had wanted to do this but shocked that it was a fantasy of hers to dress a man as a woman and have a romantic evening with him/her. Since then, we share make up tips, dress eachother up in sexy clothing (female) and just have fun with eachother as girls. She has given me the confidence to accept what I have always been inside and now life is beautiful for me with a touch of femininity.
    Kisses all,

  101. I started out like most of us, just wearing pantyhose. By the time I was 14, I was fully dressing & experimenting with hair & makeup. At the age of 16, I could pass easily for a young woman & would get dressed & walk around the town at night. When I was 17, I had grown my hair to shoulder length & had been taking my mothers over the counter pills for nail growth, I had noticeable long nails which I kept shaped & I would go out every night in my car as Joanne. When my parents went away for the weekend I would go nuts, living the whole time as Joanne, I would go to the mall, get gas, buy food it didn’t matter I felt so comfortable as a girl. From all of my dressing & going out, I started wanting to look more like a girl & see if I could meet a guy. My parents had to attend a funeral out of state in September, so I had the house for 8 days, that is when I went too far. I bathed & shaved my body, polished my fingernails & toes a bright red, put on my panties & bra & suntan pantyhose then set my hair in hot rollers. I borrowed my older sisters blue, velvet mini dress along with her blue open toed pumps & some bracelets & a necklace. About 3 hours later I took out my rollers & styled my hair in a feminine look, I then did my makeup & finished up by spraying on my sisters Charlie perfume & borrowing a matching purse to keep my makeup, nail polish, perfume & keys in. I got in my car & drove to the mall. While walking around I saw the piercing pagoda, I couldn’t resist the urges I was having & went in & got my ears pierced. The woman put studs in my ears but I bought a pair of large, blue hoop earrings to replace the studs with when I got back to my car. As I left the store I seen a hair salon in the mall & walked to it, I asked the girl if they waxed eyebrows & she said they did so needless to say I left the salon with very thin & highly arched eyebrows. Luckily for me, I didn’t have enough money on me or else I would have gotten my hair frosted. I went out to my car & put in my hoop earrings, I loved the feeling of them swinging around when you moved your head, I truly felt like I was a girl. I left the mall & went to payless to look for new heels, I caught my reflection in a mirror & couldn’t believe what a difference thin, arched eyebrows made, I looked like I was born a girl, a quite attractive girl. While looking at shoes the salesman came over to see if I needed help, I said I didn’t but he hung around making small talk. We probably talked for a half an hour then he asked me if I would like to take a drive with him down to the river after he got off, now, I know that the river is where you go with your girl friend to make out but feeling like the girl I wanted to be, I couldn’t resist saying yes. His name was Adam & he said to meet him in the parking lot at 9:00 it was already 8:15 so I went to K mart & walked around looking at skirts & dresses until then. I parked in the pay less parking lot & waited for Adam, he came over & led me to his car, I got in & we headed to the lake. We talked along the way then Adam put his arm around me, I didn’t try to stop him but I did say there was something he should know about me. He asked me what that was, so I said, please don’t get mad, he said he wouldn’t so I told him I was really a boy who wanted to be a girl, I was surprised, he didn’t move his arm from around me, he just said, really ? he then went on saying I looked too pretty not to be a girl. I asked him if he was mad & he said no, he said he didn’t have a problem with it, after hearing that, I slid over closer to him & took his hand that was on my shoulder. We pulled into the lake parking lot & parked, Adam no sooner turned the key off & he was moving in to kiss me. I never kissed a man before but it actually felt right then I felt his tongue in my mouth & thought I was going to faint. I really liked the feeling of him kissing me & started kissing him back. Adam moved from my lips & started kissing my cheek & the next thing I knew he was putting his tongue in my ear, I was so turned on by this I reached down & started rubbing his crotch, I could feel he was already excited. Adam removed his tongue then whispered in my ear to take his cock out of his pants. I unbuttoned the top & unzipped his fly & took out his cock. We started kissing again as I played with Adams cock. He was getting really hard now & he asked me if I ever had a man in my mouth before, I told him no but I wanted to so he put his hand on the back of my head & guided me down to his crotch. I was about an inch away from his cock in my hand, I couldn’t help but notice how sexy my hand with shaped long nails polished bright red looked wrapped around his cock, with that I started to kiss his junk. After I kissed the entire thing, I slowly took him in my mouth. Adam told me what to do & how to do it & in no time I was bobbing up & down like a pro. I managed to take his whole cock down my throat, his pubic hairs were tickling my nose then Adam put both his hands on my head & started pushing my head up & down faster. A few seconds later Adam said he was going to cum, he stopped pushing my head & just held it there while he began thrusting his hips forcing his cock deep down my throat, it felt as if his cock got a little bigger then he exploded. He held my head firm so I was forced to swallow everything, I kind of liked feeling his cum hitting the back of my throat & I really loved the taste of his cum, he had a lot of cum but I was a good girl & didn’t miss a drop. When he finished he released my head, I kept him in my mouth trying to get every last bit of his cum down my greedy little throat. Finally Adam pulled my head off of him & told me what a great job I did, he said he had girl friends that were no where near as good at sucking cock as I was, I said thanks & told him that I really enjoyed doing it then I told him that I really wanted to feel him inside me then leaned over & kissed him. Adam said he would love to be the man that takes my cherry, so I told him that Joanne was here for the next week that I was living as Joanne until my parents get back, I wrote down my address & phone number & Adam said he would come by tomorrow & pick me up then we would go back to his place. I asked Adam if there was something he would like to see me in for our date & he said, how about you pack a bag & spend the next three days with me, I said that I would love to then planted a big kiss on his lips. We drove back to my car & after 10 minutes of kissing Adam left. On my drive home all I kept thinking about was that I never wanted to go back to being a boy, everything that happened this night felt normal to me, I sucked a guy off like I was supposed to do that & it all felt right. Maybe if Adam agrees to pay for it, I’ll get my hair colored & styled & move in with him as his girl friend.

  102. I was 8 when I first started, I had a dress, wig, heels, skirt, and panties. I took a break until I was 14. My parents and siblings were away, so I dug into my mother closet, found nice panties, a dress, a bra, leggins, makeup. I stayed feminized for a few days, changed clothes of course. That’s when I knew I wanted to crossdress. When my family went away I started going out, first with lingerie, then shaved, then with the full outfit. Only one person knew, my friend Alivia, we would go out and she would help me get over my anxieties. When I moved out I became Michaela full time. Alivia and I started going out and having threesomes. Time goes on me and Alivia are married, we have other men and women over for sex, but I am always dressed as Michaela.

  103. Hello everyone! My name is “Airika” My first time began when I was around seven years of age. I remember taking one of my father’s under tank top shirts. Of course on a young kid like me, it was like wearing a tight sexy little dress. All I know is, I just loved how I felt in it and how it felt on me. I even stepped up to wearing pantyhose that my mother had and a few pairs of her shoes. I even still remember the collection of clothes I acquired over those years. Ironically, I still wish I had them.
    A lot of those days, I would approach my bedroom window that led to our backyard. When wearing a light teal color night shirt that said “Eat Drink & Be Married” with nude pantyhose and one of my mom’s heel pumps that kind of was the same color. I would hoist my leg up and out the window. Shimmying myself onto the window sill and bring my other leg in and out. To where I am sitting on the sill dangling my legs in the air. Then I would twist around to where my stomach is resting on the sill, humped over, legs still dangling and my toes trying to find the ground. Now a days, I find myself fantasizing that someone caught me and began rubbing the back of my long nylon covered legs. Their fingertips and hands gliding up the back of my thighs and squeezing my butt cheeks.
    Other times, I would wear her white high heels, white pantyhose and a cute and soft pink shorts and top outfit. Then there was times I wore black pantyhose, a black netted dress that tied in the back and a pair of her grey color leather, open toed with a buckle strap over the toes and ankle strapped as well, wedge styled shoes. Plus, even a pair of shorts that I had cut out my pants.
    When I was around 14 years of age, I grew 7 inches in one semester. Becoming a 6′ 4″ 14 year teen. It was around this time that I surprised my best friend at the time. By showing him the wedge shoes, black pantyhose and one of my mom’s tank tops and my shorts that I cut out of my pants. I just sprung them on him. Telling him that I was wanting to wear these for him when he was about to spend the night. So, when we were in the living room. I ended up wearing the nude pantyhose and my father’s wife beater shirts as they called them back in those days. I guess in all the excitement, I wanted to wear everything for him. Then when I did, he gave me the best compliment of my life. He told me that I looked like a certain girl from our school that we both knew. She happened to be the finest and prettiest girl in school. Anyways, he laid on our couch and I gave him a blowjob. Then, he wore what I was wearing and gave me a blow job in return. He ended up spending the next night with us. Only, this time it was in our van. This is where I wore what I had intended to wear the first time. We were in the back with the seats folded down. I laid on my back and slipped my shorts up my long legs and off of them. Then spreading my legs apart in the air. He began jerking himself off and I said to him that I would like him to cum on me right here between my legs. On my crotch area. He hadn’t been jerking a minute when he came on me just after I said that to him. I then took my left hand and scooped his cum with my fingertips, rolled over onto my stomach and began masturbating and rubbing his cum smearing it all over my nylon covered crotch til I came.

    I am still dressing up as a woman til this day.

  104. My first time, I met a guy hitch hiking & got his phone number. I called him & asked if I could come over & dress up for him, he said sure so I hung up & started getting ready. I wore my panties, bra & pantyhose under my male pants & shirt, I didn’t wear any socks just sneakers. I polished my finger nails the same color as my toes, bright red & got my makeup, dress, heels, bracelets, earrings, necklace & perfume & got into my car. I was really nervous as I knocked on his door, he answered it & invited me in. We sat & talked for a little & I could see his eyes looking at my hose covered ankle. I asked where I could dress at & was directed to his bathroom. When I entered the living room, his jaw dropped, he couldn’t believe how good I looked as Joanne. I did go all out for him, I had my ears pierced & my eyebrows plucked into thin, highly arched lines. Our date went from just spending a few hours together to my spending the entire weekend with him. This was my first time having sex as a woman with a man & all I knew was that I loved it & couldn’t get enough of it. I left his house on Sunday night at about 11:00, I felt so much like a real woman, I didn’t even change back into my male clothes, I left in my dress & heels. I never wanted to go back to being a man again, I just hoped my parents would be asleep when I got home.

  105. Hi, new here, little shy but excited, love to share stories. I enjoyed the stories of first time excitement or uncertainty of trying the feel of a woman clothes on r skin. But for me I always wore clothes that was unsex , I’ve been a traveler so other places u get away w/ wearing shirts or pants that passes for girl or how ever one thought I looked. Where I had a problem was not understanding why I couldn’t use the girls restroom, other countries not a problem. But well say it’s not been easy living two lives, I’m a construction worker so showing up in panties & tight jeans is hard to pull off, yet now more women r in the construction trade so I can relax a little bit be more myself. Ty everyone for being here, saline is my chosen name so that’s all

  106. My first time was at my Aunt’s house in upstate New York. My family visited Aunt and Uncle’s house every summer as they lived on a lake. In the bedroom she had a huge vanity she would sit at to prepare for the evening. She would let me watch her prepare quite often and once her robe opened just enough to let me see the thigh high stockings and two of what I later learned was stays. I stared a bit too long and she caught me and laughed softly. She explained that it made her feel very sexy and that everyone needed to feel sexy when they are adults. I was hooked. I would sneak in as often as I could and the first time I tried putting on her panties the feeling was awesome. THAT day was something I will always remember. After that, I started adding more until I wore a skirt. I have tried over the years to stop…I never could for a long period.

  107. I remember being about 5 years old. I was at the swimming pool and a girl there was talking about how she wished she could be a boy. I remember thinking, “I wish we could trade!” I remember feeling it way down, way down deep and feeling the ache that goes with it, the ache to be female. It’s a huge longing that can’t be fulfilled, but it lives in tension with the knowledge that I really am female. It’s just that I don’t get many chances to express it.
    Around that same time, I remember going to my sister’s closet. She was in school and I was in half day kindergarten. I picked one her dresses.
    It was a glorious feeling, seeing myself femme for the first time. The change was making me tingle and tremble a bit; I was so excited. I knew there had to be more.
    At the same time, I was miserably disappointed. It just didn’t fit. Even though I am three years younger, I was already bigger than sis. I ached as I thought about what to do.
    Just then, my grandmother found me in the closet. She shared the room with sis. I thought I was in some really deep doo-doo. She just told me to stop and get out. She never mentioned it again.
    Years later, here I am. Lately, my urges have been particularly strong and I’ve become fairly proficient with makeup. So I’ve been going out en femme and am I loving it! I’m really shy so it isn’t easy but I have been sitting in my car at the sidewalk in front of the park. I love it when people pass by. I love feeling pretty!
    I’ve practiced getting out of the car a few times and doing a short walk, to the garbage can to throw something in. The feeling of the outside air against my nylons is like electric silk.
    My next step is to do some short walks in view of some people but only people far away. Gradually, I’ll let them get a little closer as I develop more comfort. I need to be my true femme self.
    I’m hoping to find a chat place to share crossdressing experiences. Does anybody know of any?

  108. Wow. I am a little envious of your alls’ stories. I’ve not exactly had a FIRST TIME in the flesh. there have been plenty of fantasies over past couple of years, and not a few of them play out like those some of you have expressed. I was 57 before I had my first encounter with CD, and that was exclusively a role playing fantasy I found myself in. It was incredibly arousing, and for the first time In my life I actually felt attraction to men. I’ve been with guys before going back as far as earliest teens. There was, however, nothing sensual or passionate about that: it was just mutual aid. Alas, the pandemic has pretty much thwarted all my hopes of being able to dip a toe into this side of myself. Ah well, maybe some day.

  109. It was my lust for lipstick that lead me down the CD road. I remember when I was very young being spellbound seeing my neighbor (she was about 10 years older than me) and she had the most beautiful red lips. Then I noticed that when she smoked, the lipstick from her lips left a ring around her cigarette and I would try to find any excuse to be close to her so I could watch. When I was old enough to find the pleasures of masturbation, quite often, when nobody was home, I found myself playing with myself while looking at the models in the Sears catalogue, they all wore bright red lipstick. During my teens, when I was able to get my hands on a playboy magazine it was always the model who had the best lipstick coated lips that made me squirt. None of the girls that I dated wore “slutty” lipstick, but the real thing (sex), had allowed my passion for those red lips to subside, for a while. I went to college in a mountain town and then continued to live in mountain towns through my twenty’s, beautiful women, but not much makeup. Fast forward to my 30’s. I’m now separated from wife #1 and living with wife #2. #2 and I had an awesome sexual relationship. She had some very sexy lingerie and I loved how she looked dressed in it. She also has a box of makeup (she didn’t wear much to often) but occasionally I could talk her into putting on mascara, eye shadow and lipstick while wearing lingerie. Watching her do it turned me on to no end and I would lay on the bed naked beside her with my cock throbbing in anticipation.
    So one day when I was trying to coax her into putting on her makeup and she said to me “only if I can put makeup on you too”. I said sure, trying not to show my eagerness. She applied mascara to my eyelashes, made my eyebrows shapely with her pencil, and put green eyeshadow on my eyelids. She finished with bright pink lipstick on my lips. Oh god, I couldn’t believe how my lips felt, I was in heaven. She laughed and said that I should put on this black lacy lingerie top that opened down the front I did and instantly felt an emotion that I had never known. We made love with me dressed and made up and that started my trip down the CD road.

  110. My first time
    Gosh that was so long ago
    How can i start

    Well i was 18 or so and i use to have problems getting women to go out with me.
    I see now that it was me & I did change and now really don’t have a problem anymore but im getting married soon but we all ready think we’re married

    I would go to these adult book stores by I-94 in Kenosha county Wisconsin

    I would go there and look at movies and magazines

    These 2 places are not there anymore but i would go almost every night

    I had to build up a little will power to go down the hall to go into the video booth and watch the videos and not have to buy a video and take it home i could just it right there

    I would get men watching me and they make sounds so i would look at them and wow they have their pole in their hand jerking it and smiling

    I would follow them out to their car and do what ever

    Then i had a friend that was religious telling me and showing me in the Holy Bible a man shall not lie with another man as he would a women
    Me being me and being into Witchcraft at the time though
    Well then ill lie with a man as a women would.
    I would do the opposite of what i would do with a women

    I then started dressing like a women

    I started by get clothes from my moms closet

    Then i started go up to this area where the adult bookstores were and walk around with this skimmy dress and hosery and heels and grew my hair out. I was only 110 in wght and was skinny with not much of a shape

    I then turned 21 and then started dressing up and walking around in that store
    They heels i got that were red and about 4 or 5 inchs and came up to my knee

    I would dress all sexy and be a sissy slut but did not know those words at the time
    I still liked women very much
    But over time when i was RiJeana i was into men also
    I figured i did no wrong in this so called Gods eyes because i was dressed like a women so i was not lieing with a men as a women would because i was the women
    But then my friend blew that bubble up because then he showed me the part that man shall dress in women’s cloths and called me a sinner

    Then after yrs of going back and forth with that and in and out of crossdressing
    I came up with 2 things
    One i am baptized so i can sin and be forgiven for ever more
    Two those are Hebrew laws and im not Hebrew

    But now 20 plus yrs later

    Im dressing more all the time And going out in public because i must prove to myself i can and learn to smile at others that judge me with there eyes and soft talk
    Because this is who i am and I believe i should of been born a women
    But i know i was born in mans body i can treat my wife and other women with the respect they deserve

    The best thing is my wife supports me crossdressing and that helps me
    I thank her much

    Sorry i fell off topic a bit and went into forbidding areas but that is my story of what led me to my first time and why i dress like a women
    Thanks RiJeana

  111. I grew up in a small Midwestern town where everyone knew everyone and their business. Having the urge to dress and keep it private was difficult. My first time was when I was 3 or 4 years old. I have three older sisters and when we played together they liked to play dress up. Some times I was dressed as a boy and sometimes a girl. I didn’t think much about it, I just wanted someone to play with. The first time I dressed on my own I was 14 years old. I was slight of build, tall and thin. I was often teased and bullied by other boys. I came across some of my sister’s panties and and a bikini swimsuit. I had to try them out to see what I would look like as a girl. I remembered vaguely the fun I had playing dress up with my sisters. I tried everything on in the locked bathroom. It fit well and I looked passable as I had shoulder length hair. After that I wanted to get out dressed up and walk around. I headed to the wood lot behind our house where there was a small pond in an abandoned gravel and sand pit. I changed into the panties first and walked around feeling very aroused. Then I put on the swimsuit and it was a warm summer day I went for a dip. It was wonderful! I left the water and laid out on the sand bank to dry off in the sun. I didn’t bring a towel and didn’t want to put my dry clothes over the wet one or carry wet clothes home. After a bit, I took off the swimsuit and hung them in a tree to dry. I put the panties on and laid in the sun some more. I heard some noises on the far side of the pond and I hurriedly got dressed. It was a group of boys and girls from town coming for a cooling swim. They came over and wanted to know who I had been swimming with as they saw the semi wet swim suit hanging in the tree. I said I was alone and hadn’t been swimming and that the suit was hanging there when I arrived. They asked me to swim with with them but I declined as I did not have a suit to swim in. They suggested I borrow the one in the tree but I declined. I watched the them swim for a bit making note of how the girls wore there suits. I then left the pond and wood lot and headed home. I later returned and collected the swim suit. I continued to dress like this in the bathroom or in the woodlot in various borrowed swim suits, bras and panties for the next few years until I left for college. I then left the dressing behind until my mid forties. I have gradually increased my dressing activities and wardrobe over the years and have been out in public places such as gas stations, parks, theaters and restaurants dressed as a women but in gender neutral outside apparel. I hope to get the courage to go out dressed more specifically in feminine clothing and make up. But I’m not passable anymore as I was in my youth.

  112. Hi Fiona –

    Well it started just about two years ago. My wife received an invite to the annual Halloween Party that we always went to. My wife thought it was kind of strange because the invite was for a “Girls Night Out” Halloween Ball. This was probably early September. My wife decided to call Ashley, her friend that always organized the party. So it’s just for the girls she asked, I can’t bring Charles? As I tried to listen in on the conversation I got the impression something was up. I saw this grin on Lexi’s face. What’s going on I thought. When she got off the phone I said what’s up? Lexi said that I could go, but, there was a catch. The guys had to go dressed as girls. NFW, I said. there’s no way I’m doing that. C’mon Lexi said. It’ll be fun. All the guys will be there. Well I’m sure you can guess what happened next. Lexi put her plan in motion. She started shopping for me. For the next month I spent every evening practicing to walk in heels. Legs were shaved, nails painted, Lexi was doing my makeup every night. I was modeling for her. She bought me several wigs, breast forms, corsets, you name it. As time went on I actually started to look forward to dressing up. As the party drew closer I was actually getting excited. The morning of the party Lexi took me for a manicure and a pedicure. The nail tech shaped my short nails and gave me two coats of a shimmering red. She then gave me a pedicure which I must say was treat! After a light lunch Lexi took me to have my makeup done. It was almost time for my big debut!. Lexi said to me, tonight, you will become a girl. Off to the party at a local hotel ballroom. We had a room reserved for the night. The guys had to bring three outfits as we would be judged. First up was a maids outfit. After that we all became ladies of the night, street hookers. Finally, we all got ready for the LBD competition. Lexi helped me freshen my makeup. I looked in the mirror and said to myself wow! I actually looked pretty good. All of that practice paid off! I was enjoying myself and I didn’t want the night to end. After the party we all ventured into the hotel bar for drinks. I actually had a couple of guys grab my ass lol. I turned around and smiled at the young guy, then I grabbed his cock! Lexi looked at me and said, you little slut, you must think you’re some kind of a cougar! She was so happy that I had a good time.

    A few months later Covid hit and we all went into lockdown. Working from home became the norm and it continues to today. Needless to say, I have a whole new wardrobe to wear to work these days. My morning routine mirrors that of Lexi and I absolutely love it! I’ve let my hair grow out and now I now have a cute pixie style cut. Lexi and I go for manicures and pedicures together. She’s always buying me a new outfit or a pair of heels. I’m living a dream. I’m no longer Charles, I’m Charlie!

  113. When I was about 10ish, I had a few Friends, boys, and One Girl, Linda, Linda was not an ordinary girl, she was a tomboy, but being only 10 ish, I didn’t know what that meant, we used to play amongst the rubble of the old Colliery, in the village, going for walks along the old railway tracks.
    We were, so close, anyway, I can’t remember how,why or when, but eventually we started swapping clothes, I used to wear her girl clothes, and she mine, this was on the walks down the railway lines
    Most weekends, and during summer holidays, we went off on our little adventures, and it was so natural, we almost forgot who we were.
    Any way, one day, another of our mutual friends came along on our walk, and we changed as we normally done, and went on as normal, then changed, on the way home. All three walking home.
    Next day went out to play, and our third friend in street with other friends, then shouts,” he dresses in girls clothes” and goes on to say what we did.
    Well all of a sudden, Linda was not available to play, whenever I called, it seems our parents must have talked, and sorted this solution, I never did see Linda since.
    She did years later come out and was living with another girl.
    Myself, I think, hid inside myself, joined the military at 16, and it’s taken me 46 years to now come to terms with who I am


  114. My first time happened just this past summer. I have always known something was wrong with me and it took me almost 20 years to accept that it was my body (I am a 25 year old bisexual transwoman). Despite denying my true gender and sexuality all those years, I have always complained about my facial hair, hated what I saw in the mirror for a long time now, usually sat down to pee, secretly desired my own breasts, envied woman’s fashion, listened to lots of girl’s music, worn my hair long most of my life, been obsessed with gender bender scenes/tropes in manga & movies, acted in plays during high school and postsecondary life, been mistaken many a time for being gay, been angry at God and all of Creation for not feeling truly a part of it, always been afraid to go to therapy in case they discovered the secret I was running from, always been terrified of having to penetrate someone with my penis which I would do anything to avoid having to confront was really on my body (and to my horror, growing larger as time went on). Despite growing up in an open minded and supportive family, I was mortified by the thought of my crossdressing revealing my trans-ness and bi-ness to the world (as if the euphoria on my face would betray immediately to everyone that I was really a woman who was attracted to men, not just a happy crossdresser). When COVID-19 hit, I could resist it no longer; I bought some breast forms and women’s underwear, started building up a bit of a wardrobe, found a therapist who specializes in LGBTQ+ issues, came out to my parents and a few friends. One of which was a co-worker of mine who I had always admired for her beauty and kindness, that helped me put it all together and we went for a walk together. It was the very first time I went out in public wearing a gaff, panties, bra, breast forms, colourful sundress, makeup, women’s shoes, all shaved and smelling like a woman too. It was the very first time I really presented Connie to the world. I felt a sense of confidence and happiness from just walking down a familiar street, unlike anything I had every experienced as a man from such a simple task. That’s when I knew I was right, that it had been gender dysphoria plaguing me all these years, just as I had feared doing this would. However, unlike I had feared, the only one who saw this clear as day was me. Since then, I have been making progress in therapy, searching for a new job to afford my own place to live (I moved back in with my parents and siblings at the beginning of the pandemic since they needed some help at home and I still had to finish my last semester of undergrad to graduate), finished paying off my student loans, working on coming out to the rest of family and friends, quitting smoking, forming feminizing habits and I’m meeting with an endocrinologist this January about starting hormone replacement therapy. I still have a long way to go before I can really love myself for who I am after so much self loathing for so long, but I am really excited to watch my body develop and to see how sexy my authentic self can be 🙂

  115. I wore my friend’s panties while on a trip with her family as a 5 year old. I found them in her suitcase and wore them to sleep with her. (Her parents had us in the same bed.) It made me feel something I can’t describe. Some wholeness. Dressing is so intoxicating. The feminine sensations are overwhelming. I am chaste and dressing as I write this. 🙂

  116. My first time was when I was about 12 years old, no idea what made me do it but I saw a lipstick that my mother had left in the bathroom and i tried it on. It was a mid-purple colour and it looked and felt amazing. I had no idea what it meant to do that but i knew i liked it.

    My desire for all things feminine truly began and I would then regularly wait until everyone else in the house was asleep and go downstairs to put on a random lipstick and if I was lucky a pair of heels left around to click in on the hard floor of the kitchen.

    The rest is a long story and that was many years ago, I have dressed in secret ever since but decided this year to embrace my feminine side, will still be my secret thing but am more accepting now thanks to finding Fiona’s site. X

  117. I’ve cross dressed for years started when I was 12 with my moms clothes s I got older I bought my own, came out to a couple girl friends before, married one it lasted for close to six years was a blast I lived as a woman 70% of the time with her, but I wanted more. We divorced after she caught me messaging a man and sending him pics of me dressed up as Makayla sucking on dildos. So after the divorce. I meet a man of Craigslist we chatted and texted back and forth agreed to meet at my house. I got home from work shaved my legs, put on a sexy black lace thong, matching bra and breast forms, was wearing a cute silk Boho top with belle sleaves purple, my miss me low rise skinny jeans with angel wings on the back pockets. A sexy blond wig, did my makeup, my nails picked out some fuck me heels to wear, and waited for his text that he was close. Finally he texted he was on my road, I met him outside my house, kissed him as soon as he got out of his truck, he was fine, older than me, in shape smelled amazing. We kissed some more and I led him inside. Immediately when inside I dropped to my knees and undid his jeans took out his cock from his boxers and started sucking him off. His precum tasted amazing I had to finish sucking him off. He came and filled my mouth full of cum I savored the tasted and swallowed every drop. He kissed me tasting himself afterwards. We had a couple drinks and made out some more. I wanted him badly, he started to finger my hole omg I had to have him inside me, he lubed me up put in my plug and played with my plug sucking on my tits, my breast forms and bra where gone by now, I’m laying in bed face down on my pillows in heaven as he’s playing with my hole, my clitty is hard put I hate having it touched, he did lick it and gently suck it, until I told him I wanted him inside me. Omg I was ready and wanted him to fuck me. He pulled my plug out and lubed me up, and inserted his cock into my tight ass omg he felt amazing as he pushed in and started to fuck me. His balls slapping my ass, he fucked me until he was about to cum, I told him to keep going I wanted him to cum inside me, we were both clean and I wanted to feel his hot cum shooting deep inside me, omg it was amazing way better than riding dildos like I was used to. Feeling him cum made me cum as well, my first time cuming from a man fucking me, I loved it and love having sex with men.

  118. To fiona and admim ***

    Is there any plans to develop a page on your website similar to this first time to be a more experiences and share tips or open letter page? Think it could end up as popular and as useful as your first time page and beneficial allowing free share without assigning it to a preset topic. I ask cos I have a lot I could input and share but what page do i attach it to. Just an idea and would be useful. I dunno something like a speak free non judgemental page?? A place for misc topic?

    Elle xXx

      1. If it happens let me know page link but I’m sure you’ll newsletter it . Not always a first time and admim will clear posts or reply if attachments are included. Or just. I did this- how did it go. Not good but I went this was for me but now it doesn’t have to be that for everyone. Learn and grow. Support each other. Glad you replied and considering the page idea. Elle xXx

        1. That’s a great idea, will really help boost confidence for those of us on our journeys. I am still trying to work out what I am and where I should go with it all. Hearing more about what others are going through that might help me and vice versa would be amazing.

      2. If it happens let me know page link but I’m sure you’ll newsletter it . Not always a first time and admim will clear posts or reply if attachments are included. Or just. I did this- how did it go. Not good but I went this was for me but now it doesn’t have to be that for everyone. Learn and grow. Support each other. Glad you replied and everyone the page idea. Elle xXx x

  119. Had an eye exam Friday. I knew the assistant in the opticians from when I used to be a support worker for venerable adults at this opticians and she knows me well. I chose to use this same optician ever since for myself. Eye exam over. Time to choose glasses. Explained to the assistant who i’ve known for over ten years telling her I’m transitioning and want to select a more feminine pair…. minimal repsponse or reaction so went well, she was understanding helping me get the right look for my face shape. Good on her. More like her in this world please x

  120. First time introducimg male chastity to a gf. Seriously got misread. Maybe I went about things the wrong way. It was a gesture of giving myself and not the typical take.. She saw it as I didn’t want sex with her. NO it was as what I know and many of you know it’s about giving fully to someone. Ok she didn’t get it. Also like many of my relationships I disclose me ASAP. Saves confusion later on. Will add dispite this. This gf with me crossing found me a threat to her stating womanhood is her territory. I beg to differ. X

  121. My first time I was dared to try on a pair of my mothers panties. I loved how they felt and it felt so right. Since then I have grown into wearing hose, bras, slips, dresses, skirts, blouses, heels and anything else I could get my hands on. I have come out of the women’s clothes closet to people and admit to sales people I am buying women’s clothes for myself and I have gone for a bra fitting twice. I even go out dressed.

  122. Hi Fiona – My first time began innocently enough when I was at the mall shopping with my wife. She was shopping for nail polish. I hap commented on all of the colors. Then she says, “pick a color”. I was kind of shocked. I knew she was serious. I picked a dark blue called “CIA – Color is Awesome”. Next stop was to the Nail Spa for her manicure. After she was done with her manicure and pedicure she turned to me and said “it’s your turn”. It’s time for your first pedicure and you’re going to love it. So I slid into the chair and sat back while the nail tech worked her magic. When she was done I had perfectly manicured toes done in the polish that I had picked out. The color WAS awesome. It was an incredible experience. That experience was life changing. My wife then asked if she could dress me. I agreed and from that point on I was hooked. The clothes, the shoes, the lingerie, the hair, the makeup. OMG now I can’t stop. Just today I went out to Ulta for the first time and bought some eyeshadow on my own. I felt so liberated, so confident in the new me! Who would have thought that picking out a nail color would change me forever! My wife told me that in the Spring she is going to take me to NYC to find a dressing service. I can’t wait to go out dressed up!

  123. My first time for me was when I was eight years old. Our school always had a Halloween party and parade and my mother and her friend Marie thought the perfect costume for me to wear would be that of a ballerina. Marie seemed to take charge and Mom just went along with her. When it was time to get ready Marie produced a frilly ballerina set, a tutu type skirt with top and a pair of silky panties. I went along with the costume as I did not want to disappoint my Mother. They had me remove my clothes and stand on a chair. Marie held out the panties and helped me put them on, she slipped them up my legs until they were in place. Marie had me turn around a few times and in the process she would say “they just don’t seem to fit correct” and she would pull them down and back up again this went on for some time. When she had the panties in place where she wanted them she had me put on the skirt and top. Marie suggested to my Mother that I would need some make-up to complete the costume . This started my love for silky panties and all things feminine.I remember going thru my Moms and sister things trying on what ever I could. As the years progressed I came to realize my Moms other life. She always had a lot of girlfriends. She would talk to me like I was a daughter telling me the things men do on a date pointing to her body saying squeezing here or rubbing there . The one experience I remember the most when I was fourteen is the time Mom left me with one of her girlfriends husbands. He explained he deigned bathing suits and would I be OK with being a model. I said sure, so he left the room and when he returned he was holding some of his wife silky panties and told me he had forgotten his samples at work. He said these are kind of what I design would you be OK modeling these. I said OK and took the panties into the bathroom and came out modeling them one at a time. He said I want you to make believe your at the beach laying on a towel lay on your back and then roll on your stomach, I did this with each pair. When I got to the last pair I could not contain myself any longer and I had an emission and wet the panties. He never blinked an eye telling me it was OK. Thru the years I had other experiences when Mom left me with someone when her and the girls went out.

  124. Recently reassigning as female fullntime. Grooling hand picking who to tell and how. A lot of people to set aside and tell. Dunno if it’ll work for others but be sure of others before trying what I’ve been doing to steamline. Put on wig or I call hair extention of myself under a beanie hat. Here’s how it worked for me. Approached by others not me approaching anyone. Just by others… didn’t know you had long hair… i dont I’m transitioning. With that I’ve been elevating bit by bit. Next time out is complete exceptance of my transitioning in public. Personal comments- you’re off level confident. Why? Cos I own it. El x

  125. Hi Fiona –

    Since becoming joining your Premium Program as one of your gurls I so look forward to each of your assigned tasks. Throughout the day I try and think and act like a real girl. I’m becoming more and more confident. I believe that my femme side is really going to blossom thanks to you!

  126. First time or day one of kicking offl full time transitioning. Baby steps forward means u treaded carefully forward and limit having to step back. I won’t go back 2 male I won’t set a goal is can’t follow through with or fail.. Everyone i can think of now knows I’m transitioning and everyone so far ok with it. Wise words- failure to prepare; prepare to fail. El x

  127. I could remember as a child of 7 to 8 years old playing with my sister’s Barbie head she had and I would play with it when she wasn’t looking. Then later in my years at ages 16 to 18 I would dress in my sister’s clothes and wear them when she wasn’t. Now over the years I would do things like having my nails, eyebrow waxing and manicures.

  128. In the last 5 yrs I have been able to see myself become a more well rounded fully dressed cd. I have gathered a more extensive ware drobe have gotten make up, still far from experienced with it. I have the hair and nails I have fell in love with. Seeing Shelly become who she is now is sometime quite breathtaking to me. My breast are ample and my nipple are sensitive and plump. I have discovered a cage and anal seems to get better and better. I have never experienced the real thing but thats ok. I would love to meet more girls like me and chat and play from a far and just have fun. Please reach out if you have any questions. Shelly

  129. My first time: the first time I dressed completely was a few years ago. My girlfriend and I had split up but her voluminous clothes collection had still not been removed.
    I chose some yellow, flared trousers, wedges [ which I adore ] , a shirt , a fur coat and trilby pushed back. I walked out into the street, it was dark and walked around our block, about 800m. While I felt conspicuous no-one else seemed to :] I made it back to sanctuary wondering what the hell I thought I was doing – ahh! the wonders of societal conditioning.

    Now I’m so glad to be here and to be able to slowly grow the girl.

  130. I posted once already under Member Experiences about what was my true “first time” but, frankly could also easily just have been called “experimenting”.

    I am going to talk about my “first time” realizing that it was more than experimenting or “just a phase”.

    I was in college, 1997. I’m not going to go into too many details because if some of the people I knew then read this site then I might be too identifiable. But to put it into context, a friend of mine was having a “lingerie” party where she wanted everyone to come in lingerie, including the guys. Talk about a dream for a crossdresser, right? In retrospect I think it was because her boyfriend wanted to try out or be more public with his own dressing, but I digress.

    In any case, I was too shy and unsure of myself to dress, but one of my female friend’s did style my hair. I wore it long then, though not as long as now! It was a lovely experience with a curling iron giving me long, wavy curls, and she put one of her hairpieces in my hair, giving me a nice bundle of curls down my back (well about to shoulders anyway).

    To this day I recall being so happy with how I looked, and how it made me feel. It was so wonderful!

    The party itself was a letdown, and the hostess herself I’m pretty sure was disappointed with the outcome, but that part of the preparations was a significant milestone, turning point even, in how I viewed myself.

  131. I knew from a very early age I was different from most boys. I never liked sports or most other more traditional “boy” activities and gravitated to more feminine things. For example I loved to help my mom cook and clean house and even love playing with my older sister’s dolls. My first dressing experience happened at age 11.

    My sister who is about a month shy of being 3 years older than me would usually take her bath first and did that night. My sister was 14 at the time and beginning to develop breasts so she had started wearing a bra. She always left her clothes in the hamper in the bathroom when she finished her bath and just put on her gown and robe. One night my curiosity got the better of me and I tried on her bra and panties. It was an experience I will never forget! I think that was the moment I realized why I was so different to other boys. I continued to slip into her bras and panties every chance I got until she married and moved out. Needless to say that bra and pair of panties came up missing as did several others over the next 5 years until she moved out. I continued to dress, lingerie mostly, until I was around 45. For some reason I began to get urges to dress fully and even go outside my house dressed, which up to then was something I wouldn’t even consider. I am now 59 and it seems I am in girl mode more and more with each passing year.

    1. I understand completely. I think at about that age we begin to really know ourselves. That results in us wanting to accept ourselves for who we truly are – and then we literally wish to ‘come out’. For those of us who can this is wonderful – but by that age many of us have created lives in which such an emergence can be ‘difficult to navigate’, to say the least.

  132. My first time I was probably 10 or 11. My older sister, 15, caught me trying on mom’s girdle in her clothes basket. She ran out saying she was going to tell mom. I went running after her in a girdle crying and begging her not to tell. She made me put on mom’s bra and put makeup on me. She took a picture with our old Polaroid and said if I wasn’t good she would show mom. Now I realize she never would have but I became her dress up toy to see her outfits she couldn’t wear out of the house and to practice her makeup she couldn’t wear until 16. She would take me in the closet and play with my little weenie and let me feel her boobies and panties although I had no idea what it was for. I learned to love our little sessions and while I whined like I didn’t like it I actually feel in love with the feelings of being dressed. As she got older and stopped I still longed for it and have been dressing on and off all my life

  133. It was a long time ago but I remember it was yesterday. I was in my later 20s and been married for 8 years. There was a lingerie store in the strip mall very close to my house. In the window was a black baby doll with stockings; totally delicious. I begged and pleaded for my wife to buy it. After a long series of no’s, maybe”s and sure tomorrows; she surprised me one night. Of course, it didn’t stay one for long and we made love and fell asleep. The next morning she said it felt terrible, the lace scratched and the stocking didn’t stay up. She told me not to expect to see that “thing” again any time soon.

    Next I know, it’s in the laundry I was doing. I thought to myself: 1) there is hope and 2) how could it be that uncomfortable. So, I tried it on. The reaction was spontaneous and messy. The rest, as they say, is history.

  134. My first time… I was preteen, like 12. My brother was too young to stay home during summer, so we went to a daycare run out of a house. The owner’s son was around my age little older, like 14-15 so we hung out being the closest in age. Him being older meant he was cool to me so I went along with whatever he wanted to do, and him being a teen, well his penis is all he thought with. We used to play around, he’d have me hold his cock and stroke it, it do the same to mine but didn’t really mean much, but I was included… then one day, while playing around and avoid the little kids we came across his sister’s tutu. Somehow he convinced me to put it on (it was very stretchy and I was very small then) so there I am in a tutu, he has me show it off, spin, etc… its all a big game… and the game kept pushing further… eventually I’m lying in his sister’s bed, he is ontop of me between my legs grinding and pumping through our clothes, I think he even kissed me, not sure if that is real or wishful thinking.

    Looking back I know how wrong it was for what he did to me, but it also sparked a little fire. within a year I would be prancing around the house in my mom’s lingerie every single chance I got, playing dress up, using the vibe on my clitty to cum and cum and cum, make videos of me doing this, fully dressing up, even learning how to use my ass for pleasure. My only real regret is that I abandoned it all at 18 till I was almost 30, so many lost years and missed chances.

  135. Hi gurls
    I just have to say and reading through all the stories and it’s truly brought a tear to my eye. I’m so proud of each and everyone of you and giving me the courage to connect with you.

    I too am somebody who is just reach the age of 60 and I’ve been fighting my feelings all my life. To the outside world I have the job, the family and the friends anybody would want.
    My dilemma however it is I have felt like so many of you a big hole in my life missing. Thanks to Fiona for creating the space and I can try and fill that void.

    Out of the task at hand, My first time.
    I was the youngest in the family of all boys. We certainly did all boy things however there was always something missing for me. I was very close with my mom and was always very aware of how she was doing and surprisingly always noticed how she dressed. Being intrigued with that, I would sometimes sneak into her room and check out her panties and bras. I remember camping out side the house one night in a tent and I got brave enough to sneak a pair of her panties. I was so intrigued with the smell I love the soft touch of them. Well of course I had to try them on. I remember feeling very excited how about this. Well as a young man you can imagine the inevitable that happened because I had them on and feeling myself. It was just such a connection with this.
    Well the night came to an end and I had to sneak them back. I never was sure if mom really knew I did this or not however I think she suspected. She passed away when I was 18 and I truly did this day miss her. We had a special bond and I loved being in her feminine presence amongst all the manhood in the house.

    Of course over the years I’ve played a dress up, even tried some of my wife’s clothing on however even though we’re quite different in sizes and height.

    Finding Fiona site has really rekindled a lot of that within me. So much so that yesterday I went and did some in person shopping on my own. I had the most amazing night ever. I’ve been contemplating going clothes shopping in person for a long time. Tonight I went to a womens store and spent an entire hour trying things on. The sales people were absolutely marvellous and took amazing care of me. After selecting the clothes they offered me to try them on in the fitting room and were so attentive and making sure I found what I was looking for. I’ve got to do this again.
    I picked up a beautiful bra, panties, amazing pair of slacks and a body suit in black. I wish you could see the smile on my face
    My wife is away for a couple of days so I’m Currently wearing the items that I purchased and it feels so natural.
    As many of you have mentioned, I can’t share this with my family or my wife however I will cherish these moments

  136. I can vividly remember the first time I cross-dressed. I was about 12 or 13 and in the bathroom that I shared with my two-year older sister. On the counter were a pretty pair of her baby-blue nylon bikini panties. Something came over me and I suddenly had an incredible urge to try them on. I quickly dropped my pajama bottoms and underwear and slid the silky panties up my legs and into place. Oh, my how wonderful they felt on. I looked in the mirror and loved how they looked as well. I did not want to take them off, so I slid my pajama bottoms back on and went out to watch TV. As I sat there, I slowly caressed the front of my pajama bottoms and loved how the front of my bottoms slid over the slippery nylon fabric. It felt so wonderful. As you would guess, I ended up experiencing my very first orgasm in my sister’s panties. I continued to “borrow my sister’s and later my mother’s nylon panties from that point on.

    I can also totally remember the first time I shopped for something for myself. I have always been fascinated with garter belts and stockings. Some of my earliest memories are thumbing through the Sears catalog when it arrived. Always straight to the lingerie section to see the pretty garter belts. I just loved how the models looked and secretly wished I could try them on myself. It was the 70’s so my mother and sister both wore pantyhose at that time so I could not secretly try on something of theirs since neither had a garter belt in their lingerie drawer.

    When I was old enough (probably about 17 or so), I went to a local department store determined to get my own garter belt. I went straight to the lingerie department and looked through the racks until I found a pretty black lace garter belt. Of course, I was embarrassed to be looking there (and actually picking something out) but I was determined to get a garter belt for myself. I guessed on the size hoping it would fit. Luckily, the stockings were close by, and I quickly snagged a pair of sheer black stockings. I took both to the register where a young lady took my things to ring them up. She just smiled at me as she took my money, said to have a nice day, and sent me on my way. Young men my age were probably not regular buyers of lingerie (especially garter belts) so I am sure she figured it might be for me. In any case, I had done it! I went straight home and tried on my very first garter belt and stockings along with some red nylon panties with black lace that I had borrowed from my mother’s drawer. Luckily, everything fit perfectly.

    The experience was unreal. I loved the look and feel of everything, and I am still hooked on wearing garter belts to this day. I look back now, smiling that my first purchase was not panties (so I could stop borrowing my sister’s and mother’s) but a pretty garter belt that I had always dreamed of wearing.


  137. The first time I was nine years old, I went through my mom’s drawers and found a garter belt, stockings, panties, and bra. I had to try on the silky material, and I did. I felt so sexy, yet so bad for trying them on. I carefully removed the clothing and put it back in the drawer. I always went back to try on more through the years. Kayden was emerging even at a young age. I started reading about cross-dressers and sissies in the 90s when the internet became a statement at my house. I was married, and there was no way she could ever find out. I used to buy her lingerie I knew she would not wear, and when she would go shopping, I would put it on. I have worn panties under my guy clothes out and to work.
    I am 53 now. Divorced for ten years, and have bought clothes and purged them several times. I currently am dressing more and have mastered 3″ heels. I want it more and more. I own a breastplate with 36C breasts, a chastity device, panties, bras, stockings, heels, a dress, unisex jeans, leggings, and a pink t-shirt.
    I love to dress and have never ventured out or even told anyone before. I have never been with a man or another cd before, but I want to try being the woman and be encouraged to dress. I want more cross-dressing friends so they can inspire me to dress and become Kayden all the time!

  138. Hi Fiona –
    My first time was actually back in college freshman year. I had become friends with Ashley, a cute girl from California. we were hanging out in her apartment one night with a friend of hers. They both commented that I had feminine features and they asked if they could make me over. I agreed to and I was amazed at what they had done. Next thing I know they were dressing me every Friday night. I loved it. Well, Ashley transferred after her sophomore year and I stopped dressing. I lost track of her. Fast forward to a year ago. My girlfriend up and left. She did more than leave me. She left me with a closet full of clothes, a dresser full of lingerie and a treasure trove of makeup. You can probably guess where this is heading! I thought back to those Friday nights in college. Next thing I know I’m slipping into a pair of panties and applying makeup. Since then I’ve been working remotely. My day starts with a Yoga class before I get dressed En Femme. There’s no stopping me now!

  139. I’m a straight man.
    But I’ve always wanted to wear women’s clothing.
    When I was a teenager I found an old pare of pantyhose in my parents basement
    But those got old (and too small for me)
    And other than trying on my sister’s bra for a few minutes I didn’t too much.
    But I would always dream about it and especially panties.
    So Finley today I got a pair of pink floral panties
    (I’m wearing them now) and it’s amazing
    I smile when I put them on (are I love how it makes my butt look)
    I’m very excited about this but I can’t share it with my family so I had to tell someone.
    Thank you all

  140. Daphaine,
    You have to be very careful with the Twitter and Tumblr mistresses. I recently had encountered one that was persistent in trying to blackmail me. Exciting story though.
    Honey Loines

  141. It was a Halloween party for people that I work with. I had to find a costume that could be put together quickly. I had talked with my wife and she decided she would go as Robin hood as there were things she could quickly assemble into a acceptable costume. I decided that it would be easy to dress a a female. To help me I enlisted the help of two of my four sisterinlaws. One was a beautician student And the other just had clothes she didn’t mind. Me using. The two of them were quite thorough. I was dressed in panties thigh high stockings and bra with a short skirt and a flimsy camisole top. The beautician had expertly applied my makeup and fit me with a long curly red hair wig. When they had finished I wasn’t me, I had suddenly changed into a beautiful woman. Well we had left for the party with a quick stop for gas. While I was pumping the gas I was being eyed over by a carload of boys at the adjacent pump. They winked and made all kinds of gestures to lure me to them. I just finished pumping the gas and put the nozzle back in the pump looking down and back towards them with a wink and a wiggle climbed into the car and drove off to our destination. Upon arrival my partner who I worked very closely with was on the porch gazing at me. He greeted my wife and asked where I was and if I was coming. Then he said who’s your friend and reached to shake my hand. I couldn’t hold it back any longer I burst out in laughter and he said NO! I said yes it’s me . He said you look amazing. We went inside and the whole evening his father followed me around with the camera. He was mesmerized. All evening long the men followed me and groped at me. Toward the end of the evening everyone had started changing into there real close and I hadn’t thought to bring a change of clothes. So I spent the rest of the evening living out the part of a female guest. When we finally arrived home. My wife said don’t take it off. So I didn’t. She said you like being a slut don’t you. I said it was fun. She walked over and retrieved a dildo that was handy and said come over here kneel in front of me. You wanted to suck all those men off didn’t you. I didn’t reply. Well you can see where this went. It was the most amazing night of sex I had ever had. There was some truth to what she had said. But more than that I had Found that I wanted to be the female but not just a female. A females female.

  142. I am a very old closet transvestite who has been doing it since I was about 10 years old. I am married and my wife wants nothing to do with my passion for women’s clothing. Since we are both retired and together most of the time I rarely if ever get to dress up anymore. The one thing I never achieved on my bucket list was to find a woman who love’s women’s clothing as much as I do, and would take the time to dress me up in a satin skirt suit and blouse and c/w all the underthings women wear as well as do my make-up and get me a wig. When she was done, she would then dress herself accordingly and the two of us could kiss and fondle each other for hours ultimately having orgasms while fully clothed (the only real way to have sex). All I have left is to look at all of the beautiful transvestites on various websites.

  143. My first time I ever crossdressed was when I was about 8. I went to use my sisters restroom and as i walked in I a black bra. I think it was a Victoria’s Secret bra. It was smooth and felt soft. For some reason I got excited about it being there. The thought of “I wonder what wearing it feels like” popped into my head, next thing I knew I locked the restroom door and took my shirt off. I hesitated a bit but as soon as I started to put my arms through, I got a sensation running through my body. I relished it. I continued to struggle to try to put it in and I finally got it to clasp in the back. OMG, it felt so good. It was like a hug. It felt so right and natural. Over the course of a few years I kept doing it. I think my sister knew because she once left a fresh pair of panties too in the restroom. A white bra was paired with it and placed on top as if she wanted to try the panties on with the bra. The feeling of the smooth silky panties riding up my legs was amazing and I couldn’t help but to look at myself in the mirror. I loved what I was looking and felt even better. Where was this all my life. As I got older I kept buying and throwing away bras and panties here and there along with other clothes. Now I made a decision to keep whatever I have now. Maybe Victoria’s secret is that bras and panties aren’t just for women.

  144. – [ ] Telling my story how I started cross dressing is a long one. Ok I can tell you of how my older sisters would dress me even before I started grammar school. I recall wearing my sisters Halloween costume it was, “Little Red Riding hood”, and her ballerina tutu and tights. How my mother called me by a feminine name when she was upset with me and threatening me with “I’ll make you wear one of your sisters dresses”. I’m sure it was to discipline me and had to do with the brutal beating I received from my abusive alcoholic father for wearing my sisters dress. So I tried to be good, I didn’t want to be beaten like that again. But I still wanted to dress. Ok I can tell you of the many times I would sneak some panties or nylons or even when I was 12 when I first wore a bra, panties, nylons, and a full slip. I was home alone for the weekend and the family was away for the weekend leaving me behind. Living with 6 sisters there was always lingerie hanging in the bathroom. And if you didn’t think I wouldn’t take advantage of it! That weekend was magical, my body tingled with excitement. Of course I masturbated. Over the years I’ve had many different genetic girls help me achieve my dreams. I even tried hormones for a short while until the doctor said I was having a bad reaction to the estrogen and had to stop, or it could be bad for me. I have a couple of small reminders of that time which my wife occasionally comments about. That’s another story. But I would rather tell you about the first time I met her. That girl in the mirror. You know the one getting ready for a glam evening. I had several days off from work so I decided I would spend all the time “enfem”. In those days we didn’t have the internet but there were underground publications if you looked hard enough you could find them. You could get tips and information about friendly shops and services willing to help, of course at a cost, just like anything but the internet makes it easier today. But there I am rambling on again. I wanted to tell you about the first time I met my female side. Yes it was even more magical than my encounter dressing at 12. She was beautiful. Now I was use to dressing by now and having my girl friends help, they were mostly platonic relationships. It’s not that I didn’t get a thrill dressing it was just different. The thrill was that I looked pretty. I think the girls were as fascinated with me as I was with becoming a girl. Or it had to do with the fact I had a hot Chevy Camaro and a good job that paid very well. It was fun to get dressed and go out with the girls with guys looking at you not knowing or maybe they did. There were guys that tried to pick me up. I think it was with Diane she liked hanging out with her older sister who hung out with a bunch of gay guys. She told me, “what do you expect dressed like that and hanging out at a gay bar.”She was right. I didn’t have a problem with gays I had gay friends but I’m not gay as I actually prefer women. I always thought I would have been a lesbian if I was a genetic girl. But that’s youth. I was in my early 20’s fresh out of college about 5ft 6 maybe 100- 110lbs small build or just skinny. I was always told I make a better girl than boy. Even my mother said it more than once, she even said I would make some woman a good wife someday because of my domestic skills. My home was always immaculate everything in its place and I can cook. But when I met her I was spellbound. I spent the day preparing. I took a bubble bath and carefully shaved every single inch of my body. I got dressed in one of my favorite skirts and blouse put on a little makeup and went grocery shopping. My hair was already very long so I didn’t need a wig although I did own several. You know for different occasions. I usually only ate home cooking because I believe it’s healthier. I am a fairly good cook if I have been told. I learned from my mother. I could share some recipes. Ok I did a little clothes shopping I didn’t buy anything because there were no sales. I stopped at the local Walgreens to pick up a new lipstick, they always had my shade then I went home. Which was a nice 6 room 2 bath condo on the 3rd floor of a high rise with a balcony where I kept a small table and chairs, facing south west overlooking a river and 7000 acres of forest preserve. The view was absolutely beautiful, the sunsets were spectacular, the wildlife was enchanting. I loved living there. I had a huge walk-in closet one side all female and the other male but as time went by more female clothes made their way to the male side there just wasn’t enough room. Anyone looking would think a woman lived with me. The second bedroom closet was all female clothing. I made a garden salad for lunch and ate it on the balcony. All the while there were a few cat calls from the guys down on the street. I just smiled and waved. Dumb dopes but still I liked it. Later I took a nap and got up in time to listen to the financial news, I always want to know what is going on with the economy. Must have something to do with my wanting to be successful. Oh yes about my meeting. On several occasions I saw reflections in windows and mirrors around the condo. I would check back periodically to see if what I thought I saw was really what I saw. What I saw was a woman walking around my condo. Holy S@$t! Damn she wasn’t all that bad! Then I realized it was me. I was thrilled. I think I achieved my dream. I didn’t want to be that child cross dressed and masturbating I wanted to be that nice girl next door, dressed in pretty dresses always smiling and having something nice to say to everyone. Hopefully I could brighten someone’s day. That night I determined I would wear my Lucie Ann by Clair Saunders a white Greek Goddess nightgown to bed. It was absolutely stunning and fit me very well. I got it at Renees boutique I actually bought several more. You know the gowns worn by Eva Gabor on the sitcom “Green Acres”. They were heavenly! They were expensive but worth every penny! Renee was a friend of mine and she always gave me a discount because I was a regular. All the same time I was seeing a girl CiCi who was helping me with my image and other things, till she tired of me and ran off with some guy. That’s another story. I was sitting at the vanity brushing my hair all dressed for bed. I still haven’t removed my makeup, and I looked into the mirror and for the first time I really saw her and she captivated my mind ever since. I looked into her hazel eyes at her auburn hair the gentle look of her face the beautiful gown. She was beautiful, graceful, gentle, understanding, thoughtful nurturing, loving, sexy, everything I wanted to be. She even smelled good, the perfume I think it was Muriel. I felt absolutely feminine, and I was enjoying the feeling. It was magical and I wanted more. I was finally beginning to understand my own feelings. I loved it, I didn’t want it to end. I fell asleep and had magical dreams of dressing up in beautiful gowns and my sisters were trying to get a look at me through my bedroom door. I had the same dream multiple times. And occasionally the dream comes back. I woke the next day I looked in the mirror as I walked to the kitchen to make coffee and was pleased at what I saw. A beautiful radiant woman. I never really stopped dressing but things really took a 180 degree turn when I met my wife. But that is another story. Now I want to revisit my past. I found you can take the boy out of the dress but you can’t take the dress out of the boy. I always watch how the girls dress and do their makeup I get a lot of ideas. I find myself being jealous that I don’t do that anymore or not as much. I usually spend more time with my wife and her girlfriends because I feel more comfortable with them. I’m not much into sports in fact my wife knows more about sports than I do. My wife knows all the players even to the point where she knows who they are married to and how many kids they have. Women take pride in remembering names and knowing about others lives. Men can be so crude talking about their conquests over women. I find it to be crude, insensitive and mostly bragging. I believe details of intimate experiences are private and not to be advertised. How do you think your partner would feel if she heard you talking about your intimate experiences? Bragging about intimate experiences usually leads to a bad relationship. Well I think I spilled my guts here, probably told you more than you would like to know, but that’s my story. I hope I don’t sound psychotic or like I’m bragging. I just have to let it out. I spent years in therapy which didn’t help. So I gave up and started to do as I felt was normal for me. So what if some of my mannerisms are effeminate. That’s who I am and I want to be left alone to make my own decisions. So far I haven’t done so badly.

  145. Hi Fiona – Well my story goes back to when I was a Freshman in High School. I went to school in the afternoon because our school had double sessions due to overcrowding. I was home alone in the mornings so I began experimenting with Mom’s makeup. I would do my nails, eyeshadow, brows, mascara and lipstick. I made sure to wash it all off before getting ready for school. That experiment ended soon enough. Anyway, a couple of years ago my girlfriend decided to end it. She packed most of her things and moved out. She did leave a few things behind though. A few bottles of nail lacquer, some makeup, a few pairs of panties, a couple of dresses and a pair of ankle booties. The weekends began to get pretty boring. After a few beers one Friday night I decided to paint my nails. I always loved looking at pretty manicured nails. Once my nails were dry I decided to take it to the next level. So I applied some makeup, eyeshadow, mascara and a little lipstick. I must say it brought back some memories of freshman year and it felt amazing. Next thing I know I’m watching YouTube videos on how to apply makeup. I was researching nail polish colors on the OPI website. I opened up online accounts for Ulta and Sephora. I started ordering makeup, lingerie, wigs, shoes and other pretty things. I would rush home from work to get dressed. On days when I worked remotely I would get up, do my makeup and dress up for the day. Then one day at the office I apparently didn’t get all of my mascara off and there was still a touch of red polish on my pinky nail. I guess I was rushing that morning. Sure enough, I was sitting in the employee lounge at lunchtime chatting with two friends, Tara and Lisa when one of them picked up on my dark eyes. Then as I lifted my water bottle she noticed the red polish on my pinky finger. The two of them looked at each other in amazement. They called me out right there at the lunch table. “You Little Sissy” they said. Then they told me they were going to feminize me. They weren’t kidding. They showed up at my house that Friday night. They were shocked at all of the beauty supplies I had accumulated. They commented on my Charlotte Tilbury makeup, my OPI nail colors and my pretty lingerie. We are going to have fun with you they told me. Since that day we have been getting together at least once a week. They have helped me with makeup techniques. They have taken me shopping, ordered clothes. Before long we were going for manicures together. I’ve become one of their besties. They have plans to take me to NYC for a weekend. They want to take me shopping and take me for a full makeover. After I will go out for the first time dressed as Alexis or Lexi as I prefer. We’ll go to happy hour, dinner and then to a couple of clubs. They are even telling me that I will definitely get lucky that weekend. “It’s time” they said for Lexi to experience life in heels. My goal is to be classy, just not too classy 🙂 Well, I guess I have some shopping to do! That’s my story. Me being Lexi. Thanks to my two besties …

  146. Hi Fiona – Well Tara and Lisa kept their promise. They took me to NYC this past weekend. It was amazing to get to spend three days as Lexi. We arrived in the City on Friday evening. Once we checked into our hotel suite the girls helped me get ready. I wore jeans, a white blouse and a black leather jacket with stiletto ankle boots. The girls did my makeup and I wore my hair in a cute mid-length wavy Brunette layered style with bangs. We stopped for a light dinner and then hit up jazz club for drinks, soft music and girl talk. The talk centered around me and what they had in store for me the next day. Saturday started with a morning of shopping for lingerie, makeup, shoes and outfits. After lunch they took me to a dressing service for a complete makeover. All I could say was WOW. A beautiful mani-pedi in a rich garnet color called “We the Female” by OPI. My smoldering eyes, bold brows and lips to match my nails. My look was complete with a brown wig with blond highlights with long, natural curls. After trying on several outfits I settled on black mini dress, sheer tights and printed heels. Lexi was ready for a night out. We took an Uber back to the hotel so we could drop off our treasures and so the girls could get ready. Next it was off for drinks and an amazing dinner. Afterwards, we hit some clubs for music and dancing. we ended our night in the hotel lounge. We were sitting at the bar when a gentleman who was about 50 sat down next to me. We ended up talking about an hour. Tara and Lisa had struck a conversation with two other guys. Although my makeover had transformed me beyond my wildest dreams, my voice gave me away. David, however, did not seem to care. He ran his hand up my leg. My body trembled with excitement. This can’t be happening I thought. I took it to the next level by running my hand up his leg. I felt his cock get hard. Next thing I know he takes me by the hand and leads me away to his room. I turned towards Tara and Lisa and smiled. What happened next was incredible. David started kissing me as soon as we entered his room. Next thing I know I was unbuckling his belt and pulling down his pants. My instincts just seemed to kick in as I pulled down his boxers and took his cock in my mouth. Then, he pulled away and lifted me to my feet towards a chair by the window. Next, he lifted my dress and pulled down my panties. I lifted my leg over the arm of the chair to expose my bum. He then gave me the ultimate pleasure. A feeling that I can’t describe. I leaned against the chair as he filled me with more of his pleasure. At that point I realized that he had changed me forever. I returned to our suite. The girls had just gotten back. We ordered a bottle wine from rooms service. I told them all about my experience. They looked at each other and smiled. Just as they had predicted, I got lucky. The next morning, they did my makeup for me once again, I slipped into a pair of leggings with a sweater, scarf and sneakers. Our weekend had come to an end. We Ubered back home with our score from the shopping excursion as well as a weekend full of memories that I can’t stop smiling about 🙂

  147. I’m new here and just browsing through the amazing content. Anyway, my first time was probably like so many other girls. I dressed up and played with makeup as a teenager. I got away from it during my freshman year of high school. One thing that I always loved though was pretty painted nails. I always admired a woman’s beautiful, freshly manicured nails. Anyway, about six ago my wife took me for a pedicure just before we were going away on vacation. There was no color, just a clear finish. I must admit I felt so excited sitting in that chair. Well, it was not the last pedicure. I started going regularly. Eventually, my wife encouraged me to add some color. The nail tech suggested blue so I went with it. I loved it! My wife loved it too. Soon she was giving me secret manicures at home. One thing led to another and soon she was buying me lingerie, makeup, dresses and heels. She feminized me! Now we dress together and shop together. It’s just an amazing feeling. Our relationship has never been stronger. The power of the pedicure I guess!

  148. Hi Fiona,
    My first time was when I was around 12 years old. I remember one day when a Victoria’s Secret catalog came in the mail for my mom. It had immediately grabbed my attention but I obviously didn’t just take it from my mom. I had to wait for a few days to find it in the recycling bin. As soon as I saw it there I grabbed it and took it up to my room. That evening I remember twirling through the pages and looking at all of the beautiful women. Alessandra Ambrosia and Marissa Miller were really the models that stood out. There was one other thing that stood out though, their underwear. At this point it was the prettiest and most feminine things I had ever seen. It woke up a strong desire within me to want to feel what the models felt when they wore gorgeous underwear. I also had a way to find out too. I’m not proud of this but I knew that my older sister sometimes left her dirty laundry in the bathroom. It’s an invasion of privacy but I had to know. The pair was in a bikini style and wasn’t that interesting compared to what I had just been looking at. It was light green in color. But immediately in my fingertips I could feel the difference. I started to shake. I was shaking as if I were at the epicenter of a magnitude 10 earthquake. I couldn’t believe I was actually considering wearing women’s underwear. Time seemed to stop as I lowered my own drawers and held up the panties one final time before I said goodbye to my man card. I slipped one foot in and then the other. I slowly slid those panties up my legs until they couldn’t go any higher. I had just done something most men would never consider doing. I was wearing women’s panties. My brain was on fire as I couldn’t deny that everything about it felt so right. I honestly don’t remember what happened directly after this event. All I know is that is the moment that has started me down a path which has lead me to here.
    I hope you enjoyed my story.

    1. I am a straight man. I remember it started with me when I was 11 and wearing women’s bearpaw boots. I just liked the feel and look of them. I began to get more interest in feminine clothing and cosmetics when i was 14. I started doing my nails and bought myself high heels, knee high leather boots, and leggings. My mom unfortunately one day found all my nail polish I had and threw it out. By this time, I was 18, I stopped for a while since I moved out of my home state for work. I Decided to get new outfits eventually once I get settled in my new home.

      After 8 months of moving out and having my own house, I could do more. One day I remembered how much I liked femininizing myself and bought some fake nails, leggings, and knee high leather boots. I would femininize myself on the weekends I had off work. I got brave enough to where I wore these 2.5 inch knee high leather boots outside to throw out trash. I was so nervous and excited at the same time wondering if someone noticed since you could hear the heels from my boots. Someone did happen to pass by but did not seem not to care or notice. I started dressing in leggings more while having on acrylic nails at night. I eventually bought myself lingerie when I was 20 from Victoria secret. I remember I went to go pick the order up from a mail store and the packaging showed a bunch of Victoria secret logos. I was so nervous and excited. My last few months out of state I started wearing acrylic nails almost all the time outside of work. I remember when I ordered food 2 times I had on these pink round nails. The first time the delivery person didn’t notice. The second time I remember the delivery lady was looking at my nails when I was grabbing the food. I was so excited and nervous. I remember when I was hanging out with one of my friends, I had on some pink square nails the whole day we were hanging out. I brought up what we thought about them and he said they were nice and I should get them done black color.

      I’m now back home and working on getting an apartment or a house for me. I’m living with family for now. I now just go full on out and buy more things like high heels, boots, stockings, fake nails, makeup, and more feminine clothing. I recently bought myself a faux black leather dress, thigh high stockings, and white crew neck sweater. I remember looking at myself with everything on and I looked completely different. I get sexually aroused a decent amount when doing this. I am going out of my home state for vacation in a week and I’m gonna wear fake acrylic nails almost the whole time and I may dress up. Im excited for my trip.

  149. Here’s one of my stories.

    I’m not sure when it started, but I do remember this event. I was a happy and content 6th grader. (A few years ago, ok several years ago). There was a camp before the end of 6th grade. We were put into groups. Girls and boys in separate groups. Each group had to do a skit. I don’t remember how many were in each group. They picked a group leader and had that group leader select a box of props. The box that was selected for our group was several different dresses. It was decided that we would do a fashion show. I was one of the models for a dress. I was in the dress when the show started. Our group wasn’t the first group or the last one. Of course I wasn’t paying attention what was happening. When our time was to do a skit, I was out in the crowd. When they called for me, I went to the meeting place of our group. When I was going there I heard several whistles and cheers. Was it embarrassing? I didn’t think so. But it was fun.

  150. A couple days ago, I decided I was going to wear women’s panties one afternoon. As I put them on, I was getting excited and nervous at the same time. My family members would be around, so I’d have to be careful. Would they show? Would I get caught? If caught, what would they say? Or do? I put on my underwear over the top of them to help conceal them. It was getting late in the evening, I was asked to go to our storage unit and get something out of there. Up to this point it was just sitting around the house not moving too much. I was asked to go right now. My wife was going too. I was nervous that she would find out about the panties. We went there got what we wanted and came home. They didn’t show and I was relieved. I was going to take them off before bed, but my wife was there and would have noticed if I tried to take my underwear off. Needless to say, I slept with the panties on under my underwear. In the morning, my wife got up and went out shopping. I finally was able to take the panties off. Almost a full day with ladies underwear on and didn’t get caught. It was exhilarating and nerve racking at the same time. I’ll have to do it again soon. Maybe other items too?

  151. On Tuesday I went to Walmart. I enjoyed this shopping event. I looked through the women’s section. I picked up a bra, a set of 3 panties, and a waist trainer. Next I went to the make up isle. I have no idea what I was looking for and left that section empty handed. 🙁 I wandered around a little more with the 3 items I selected from the lingerie area. I decided I spent enough time in the store. I could have gone to self checkout, but I didn’t. I went straight to a checkout where there was a lady checking people out. I placed the items on the checkout belt. I think I caught a smile from her. 🙂 I purchased the items and left with a grin when she said have a happy holiday. Looking forward to trying them on later this week.

  152. Today was the first time I shaved my legs. I used an electric razor. Should have used blades. It took a long time to make sure I got all the hair shaved. A lot of the hair got caught up in the razor. I had to stop and clean it several times. After I finished that, I put I nylons. I had worn nylons before, but this was different. It felt sexier and stimulating as I pulled them up. I’m hoping I can keep my legs shaved from now on. 🙂

  153. Today, I stopped at Walmart and looked through the makeup section.
    Miss Fiona suggested I get some eye shadow and lipstick.
    As I was looking at the different items, there were employees refilling/stocking the makeup section. I went along with what I was doing. I’m sure it looked like I was somewhat lost (which I was), but I ignored everyone there. I picked up some lipstick and eye shadow that I thought would be ok with me. I also purchased some wipes to remove the makeup. There were 2 ladies there that helped me check out through the self checkout. No one was at the other registers. I always have problems with self checkout. I put the items down and they were the ones that scanned each item. I’m sure they got a good laugh out of it. I didn’t care. As I got back to my room I was excited to try on my new purchases. Before putting any on, I put some on my arm, and used some wipes to see if it would come off without a problem. It did. Now the real exciting part putting it on. I tried the lightest shade of eye shadow. It looked like I didn’t even put anything on. (I may have to go out with that on). I tried the next shade. It looked a little different, but still didn’t look like I had anything on. One shade had some glitter in it. That was exciting to see my eyes sparkle. 🙂 the last shade was a little darker. I decided to put some on my eye brows. It is definitely a subtle difference. I may have to purchase more colors. 🙂 I went with a light shade of lipstick. I put some on my arm and used the wipes to make sure I could remove it. It worked. Now the real experiment, putting it on my lips. I opened the case. Excitement growing. Looking closely at my lips and the color of it. I pressed it on my lips. A small dream coming true. I finished putting it on. I looked at the finished product. Even though it is there, it isn’t jumping out. It is subtle. I couldn’t believe I purchased makeup and am wearing it. I may have to get a few more (darker) colors of lipstick too.
    Thank you Miss Fiona for this little playtime task. It was a nervous and exciting thing to do.

  154. Miss Fiona. Here is a task you could put on one of your playtime with Fiona blogs.

    While I was in Chicago for work, I went to a mall that was close by. My wife asked me to check stores for Christmas sales. As I was in Nordstroms, I walked past racks of dresses. I turned around and started looking through them for something I would like color, style and size. I picked out 4 dresses. I thought I spent the time picking them out , I might as well see if I could try them on. I found the dressing rooms. I waited for an attendant. If one showed up and asked questions, I was ready with a response of it’s for a costume party. None came. I proceeded to go to the farthest room and try on the dresses. I took pictures of each dress I tried on. I did like a couple of them. I placed them back on the hangers as I took them off. When I finished, I put them back on the racks. I couldn’t believe I had just done that. I was so thrilled with excitement, I was shaking all the way to the food court where I just sat and calmed down. Once calmed down, I was getting ready to leave the mall and I spotted another department store (Forever21), I figured why not see if they have anything I’d like. Needless to say I picked out 6 dresses and did try each one on. I like 3 out of those six. As I left the fitting room there was an attendant there and I asked if I should put them back. She said sure. There were other customers in line waiting. I’m sure there were puzzled looks on the customers faces when nobody else came out of the room I was in. It maybe even made them smile. Either way I was in dreamland. It was a fun and exhilarating day.

  155. My first time going out as Rhoda.

    Before we left, I tried to keep Rhonda down on the ground. She wanted nothing to do with it. She wanted to soar. She lead the charge. What was I to do? I went along for the ride. She drove. As we drove I started to get nervous. My knees were hitting each other it probably sounded like loud drums. Rhonda’s heart and soul were racing with excitement. Beating to a different drum. We finally entered the parking lot. I sat in the car to calm down while Rhonda wanted to run. Eventually I gave in letting her have her way. As we got out of the car, my knees were hitting each other as she was pulling me out of the car. It was a long way to the door of the club. As we got closer, Rhonda was pulling harder and I was dragging my feet. Her strength won out. By the way she is a strong woman. We went in. Each of the performers were fun and accommodating to a new person joining the sisterhood. Ok. For me it was fun. Rhonda had the time of her life. It took an hour and a half to enjoy the ambiance, capture pictures of the performers, and eat some food. I had 1/2 a burger and fries (stomach was in butterflies). It was getting late and Rhonda wanted to stay. She knew it was better to leave since it was a long drive and it was snowing. She let e drive. She was still reeling about the entire night. I got all the things ready to go into the hotel room. We exited the car together. Nobody saw us. We quickly walk to our room. We go into the room. We are safe. I can calm down. Rhonda is bouncing off the walls. I think it is impossible to hide her away. She is me.

    Thank you Fiona for the suggestion of the place. Rhonda will never forget it.

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