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: http://fionadobson.com/julies-page/


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.
😊

Fiona

91 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.

    Lola

    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

    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.

    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

    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.

    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.

  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?

  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

  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.

  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

  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

        Love
        Michelle

  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.

  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 …..do 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……

  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?!?

  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.

  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

  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!

  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.

  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.

  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.
    Misse.

  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

    Andrea

  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.

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