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.


64 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

    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…..

  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.

  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.

    1. I loved 1 million BC. I bumped into a producer who worked with Ms. Welch recently. I hear she can be a little bit of a dragon! She’ll always be an angel to me, though!

  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…

  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 … 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. Mine was when I was around 10 years old, I found my mothers lacy knickers and I’d feel my cock hard and rub myself against the floor, hoping no one who come and catch me.

  21. 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…

  22. 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

  23. 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

  24. 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 🙂

  25. 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.

  26. 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.

  27. 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

  28. OMG don’t stop know your story has got me so hard and to relive in your experience!
    Thank you for sharing 1/2 your story

  29. 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

  30. 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!

  31. 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

  32. 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!!

  33. 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?

  34. 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

  35. 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.

  36. 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.

  37. 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.

  38. 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!

  39. 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.

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