Perhaps because my first time crossdressed was forced when I was made to play a girl in a show when I was eight, I always love to hear of first time stories that were fun.
If anyone cares to share a warm 1st experience, I'd love to hear it. I'm happy to hear ones that were similar to mine, but honestly, I have no interest in hearing dirty nasty stories.
Hugs,
Emily
Age 6.
Was fun and totally knew what I was doing.
And yes, basically was my idea also.
Hi Emily, it was 68yrs.ago and I'm sure that I must've been fun and it's still fun.
Having my ears triple pierced is AWESOME, ~~......
I can explain it to you, But I can't comprehend it for you !
If at first you don't succeed, Then Skydiving isn't for you.
Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!
I left cding alone for a while. After moving from Wyoming to Colorado I was without a job for a while. So I was taking care of the house and doing all of the housewife's duties I thought well shit if I am going to this might as well act the part and does it ever feel good to be dressed. and yes I still do some of the household chores.
Leann
Emily, please provide more details on your first time!
I enjoy the first time stories too!
I was around 12 and my mother had stored some things in a dresser in my room. I found a vintage nylon nightgown and could not resist. I loved the way it felt and wondered how it would feel on me. I stripped down and put on the gown and was soon sexually excited and well.... you know. The next day I did it again adding pantyhose, etc. As time went on, I started trying on other things like heels, bras, slips, etc. It is a sexually exciting for me to dress to this day (45 years later)
Michellecd9999
My first was a pair of my moms black panties, I just had to try them on.
I can't remember if I got aroused but I do remember I wanted to do it again
Never had the house to myself that much so it was a while before I finally put on one of her dresses.
It was mint green cotton not real pretty but it felt great.
I was with my wife when she was shoe shopping. She asked me if I liked a pair of stiletto heels she tried on and I said yes. She then started a discussion - how much? how did they make me feel? And then she asked how I would feel wearing a pair of high heels and made me buy a pair of 4 inch black stiletto heels. I was nervous and very excited. I put them on at home and we both could immediately tell I really enjoyed this experience. She continued the earlier discussion - how did they make me feel? She asked if I wanted to wear panty hose and gave me a pair. Obviously I liked them too. Then she suggested black boy shorts and a camisole. The next question was if I wanted to try makeup. Gulp - yes. She applied foundation, lipstick, black eyeliner and mascara. She applied hair gel to spike my hair - then gave me a mirror. Total excitement. I loved the experience and the transformation. She also liked the new girl she created. She gave me my name - Heather. I immediately knew that I loved being Heather.
Last edited by heatherdress; 06-26-2014 at 11:12 PM.
I have 2 first time stories, depending on the depth... My wife like to use her toy on me, and I liked it too, so I put one of her hot little club dresses on one night that she never wore anymore and it felt more appropriate for the scenario, but didn't change things too much, it was after I got totally done up with breast forms, corset, dress, heels, wig, etc that it really made a difference. It made such a difference, that first time I didn't even want the sex! We just enjoyed a nice date night being girls! :-)
Hi Emily. Actual CDing (dressing en femme) was when I was 17 and going out with a girl who was in to all sorts of experimentation. So at her urging I dressed like a girl for night out followed by some great . . . well a lady doesn't discuss such thingsbut I am sure you get the picture. That was my true first and last time for 32 years.
Now if you are just talking about clothing of the opposite gender then my first day on earthIt is a bit of a funny story. Everyone expected me to be a girl as my mother had already had two and all her brothers had daughters (something about the way she was carrying me). Anyway with the thought of girl (my name would have been Michelle) there was not rush to buy baby clothes as she had plenty. I came earlier than expected and to everyone's surprise the plumbing did not match the expectations. So when they looked around for clothing to dress me in . . . pink was all that was available. So I wore my sister's hand me downs that first day on earth. Naturally my dad went out and immediately found gender appropriate "blue"
Hugs
Isha
Whe I was four I learned to play mothers and fathers....
Later in life I did it for real.
Work on your elegance,
and beauty will follow.
Is this like a kind of voyeurism? My first time was a milestone in my human existence and not just a matter for your entertainment.
REBEL WITHOUT A CLOSET!
All trans* girls are NOT created equal. https://www.flickr.com/photos/emi_again/
After many attempts of asking the wife to wear a thong she angrily replied "why don't you wear one to see how uncomfortable they are". So I did! Immediately memories of me trying on mom's and sister's cloths as a young boy came back. I don't know why I stopped dressing and Don't know why I never remembered until I put on that thong.
I know I was 4 or 5. I think I used to play with my mother's shoes. But, I do not know how the first time came about, whether I saw some shoes and decided to put them on or if my evil, older sister(s), while babysitting me or something, decided to dress dress me up or something like that. I just can't remember back that far, at least in regard to CDing. Some things when I was 4 or 5, I remember well. Maybe my CDing started even earlier than that.
Emi, it's not for "your entertainment." I'm genuinely curious about those of us who had pleasant first experiences into girlhood. I am sorry if I offended you.
Emily
I was between 4-6... I can't remember exactly when but I remember putting on my mom's make up (messy of course) and stepping into her heels because I wanted to be "pretty" like mommy
I was 7..... after years of my mother telling me I was supposed to have been a girl.... one night when my parents were out on the town and we had a baby sitter.... I wandered into my mothers walk in closet and started going through her clothes.. . next thing I know I have on silk stockings, a girdle, bra, riffled nightie,
, high heels..... and I was hooked... the baby sitter never came in to see what I was up to. she was watching TV..... also my sister was just born... coincidence? That was 5 and a half decades ago.... I kept sneaking into her closet for another decade.... went out enfemme my first time when I was 16... started acquiring my own clothes in High School and College.....
My first time may not be labelled fun because it was more an association with my GF, I was about 8-9, I became attracted to a shapely swimsuit possibly because it suggested her body. I knew nothing about sex and erections were more of an embarrassment but within ten minutes of trying it on the inevitable happened, but I didn't know what had happened or what had caused it, and initially it scared me !
My first time had locked in my brain girls-clothes -sex and it's never gone away ! After that I just couldn't get enough, I just wanted to try anything on and it then became fun before the guilt set in when I started secondary school !!
Some one asked me to tell my first experience dressed up in girl's clothes. It wasn't a fun day in my life, but I feel it profoundly affected me:
In 1962 I went off to a summer day camp. The day camp was located in Calumet City, Illinois, surrounded by what was still farmlands and forest preserves. The owner and director had been in that business for years and was a respected PE teacher in the Chicago School system.
I think what happened to me could be described as the perfect "how to" manual. How to rob a young boy of confidence, self worth, and dignity with a single insensitive and perhaps a crimminally abusive act. Near the end of the summer, the camp invited all the parents to spend an afternoon visiting their sons and daughters at activities and to watch each age group perform some kind of skit.
Some time prior to this visiting day, my age group was gathered into the drama hut and we were sat down with our counselor and there was a lady who seemed to be in charge of the show. Our counselor said, "We'll sing a song and half of you need to play girls. Raise your hand if you want to be a girl?"
Some of the boys laughed, but I thought, "want to be a girl?" Who would WANT to be a girl in a skit for everyone to see? I couldn't imagine and no one volunteered. The counselor asked again and then said that if no one raised his hand, he'd choose. Then he declared that his first choice was Mike. As in me. A chorus of laughter rang out amongst the boys. He continued and, in a pattern I couldn't discern, chose who'd play boys and who'd play girls.
In retrospect, I suppose, I was chosen because I was cute, small, and not one who caused this young man trouble at day camp. Of course, those qualifying traits meant nothing to me. My companions who'd be allowed to portray boys quickly cut to the core issue by taunting the so called "girls." We were told we were "fems," sissies, in fact they declared we were girls. I felt dread, humiliation, and even a bizarre guilty notion that being chosen corroborated a truth.
I was too embarrassed to tell anyone. I didn't tell my parents. I had this belief that somehow I'd get out of doing it. I'd pretend to be sick. Hopefully someone would offer to trade parts or who knows, maybe a big meteorite might smash the Earth. As a seven year old, I didn't know what to do and I was too ashamed to seek help.
As we rehearsed for the show, the drama lady paired each "girl" with a boy and we were taught a love ballad. We were told to sing and walk around the stage arm in arm. Parent's day arrived, and I'd convinced myself that if I simply, meekly, performed, most likely no one would have any idea of what I had done. After all, I'd be dressed up as a girl so who would recognize me? If asked, I'd deny it and undoubtedly get away with it. How painfully naive and innocent a child can be.
My dad, to my relief, was not going to leave work to attend, but mom came. She had no idea of what I was battling inside. The parents were herded into the drama area. We were told that all of the "girls" were to go to Lou's, the camp director's house, to get ready.
He was there, along with that lady in charge. We took off our pants and tee shirts and each boy put on white tights and we were put into a white schoolgirl (circa 1920?) style dresses. Then, one by one, this lady applied makeup onto us, eye liner, mascara, rouge and lipstick. Each boy was fitted with a kind of bonnet that had curls attatched which hung down onto our faces. I looked at myself in a mirror and felt a wave of relief, in the belief that I was unrecognizable. (In retrospect, I find the amount of make up that was used on 7 and 8 year old boys odd in itself.)
The lady told us that she needed to leave to start the show, but that we should wait with Lou, we should sit and watch TV, and be careful not to mess up our makeup or our dresses. Lou carried in a tray of lemonade and he asked me to stand up. He asked me if I was being a good little girl and I didn't know what to say. He reached under my dress and just grabbed my crotch. He laughed and said that I was a very good girl. The other boys laughed. I don't know how old I was before I realized that he wanted to see if I was hard under my dress. I think he was a pervert and he was getting off on all of us sissified boys.
Next it was our turn to go on stage and I still believed that no one would recognize me. Of course, I heard my name called in a jeering manner as we walked toward the stage, but that was nothing compared to the roar of laughter as we began our song. Quickly, it was over and I ran as fast as I could back to Lou's to get out of that dress and to furiously wipe off all that make up. It didn't come off so easily and until I got home, I bore a shameful kind of Scarlett letter or temporary tattoo that identified to anyone that day that I had been a girl in the show. I was so ashamed of myself.
I don't know how the others who stood on stage that day felt because I never talked about it again. I believed that if I blocked what had happened, it was as if it hadn't happened. I denied to my friends that I had played a girl. When they teased the crap out of me, I lied about having been a girl and I denied it. They knew I was lying and I knew that they knew I was lying, and unwittingly I gave them more fuel for their taunts. Some friends didn't limit their taunts for just that day, but for weeks and some felt the need to bring it up for years.
Over time, I felt an odd attraction to crossdressing. I'd see the three stooges in drag and it mystified me as to what led them to be crossdressed. I had dreams in which I found myself being offered the chance to wear a dress to school. When I'd put it on, in the dream, it felt nice and I wasn't embarrassed. I couldn't understand why I had those odd nutty thoughts. I didn't know why my penis would sometimes be hard when I awoke from those dreams. When I was 11, I saw a boy dressed up as a girl on Halloween. I couldn't believe he did that. Then I noticed that he even had on nylons. I wondered if he'd been punished and then it occurred to me that he wanted to be a girl for Halloween. I realized I was jealous.
Sometime within the next year, I finally tried on one of my mom's skirts. Then I decided I had to try on more of her things to discover that peaceful and exciting feeling that the dreams gave me. One night, I put on her panty girdle, nylons, half slip, and yellow chiffon dress and I realized that I adored the feeling. I walked about the house, I sat down again and again, crossing my legs and I kept feeling my legs and I adored the wonderful feeling of my nylons whooshing against my slip. The swirl of my chiffon skirt felt incredible. When I couldn't stand it any longer, I took off mom's dress and I masturbated. I immediately felt guilty and wondered what kind of pervert I was. I swore I'd never ever put on women's clothes again. I broke that promise the next weekend when mom and dad were out.
I read The Catcher in The Rye when I was fifteen and I was thunderstruck by Holden's description of a transvestite he observed in hotel room window. The man's movements as he dressed himself sounded just like me. It seemed dirty and perverted. I thought, that's me, there are others like me, but I'm not a pervert.
I always assumed once I kissed a girl that my desire to crossdress would vanish. It didn't and then I assumed it would once I lost my virginity: it did not. Then I assumed once I married it would. Then once I was a dad. It's never gone away. I stopped beating myself up over this and have come to accept it. Though, I'm going to guess once I'm dead it'll finally go away or won't matter to anyone.
My wife knows I crossdress, but she prefers to not be part of it and she doesn't want me to be public about it. We have a don't ask, don't tell arrangement.
I'm fascinated by first time stories. I suppose I yearn for soft and gentle introductions to CDing because I think mine was dark and perverted. Perhaps I'd have been a crossdresser without having been a girl in the show. Perhaps Lou grabbing my crotch had nothing to do with anything either. Maybe it was just a joke. Yeah right, I think Lou was a criminal pervert. He and his God Damned day camp should have left me and the other boys alone and had I been an adult at the time, he would have found himself investigated by the Police. I bet he masturbated that evening at the thought of us putting on our dresses for the show and he got away with it.
That's my whole story.
Emily
My first time was pantyhose. I had a crush on the girl in front of me in class, and she always wore pantyhose. I was I duuno, 12? Anyway, I was so fascinated with her legs, shoes, dresses, that I had to steal a pair of hose from my moms drawer. L'eggs Sheer Energy, sheer to waist, suntan... still my most favorite hose today some 30 years later! I loved the feeling, then my feet were small enough, so I had to know what heels felt like. And a dress. A year or so later I was alone in a hotel for an hour or so, and of course I had brought my stash. I put on my red dress, hose, and heels, and walked up and down the hall way! I passed one guy, I just looked at the floor. lol! I remember standing on the balcony just LOVING the feeling of the breeze around my legs and dress. I was hooked. I got it all off and away before the family came back from wherever they were - I don't even remember the excuse I used to stay back, I know the reason, but not the excuse. Fast forward to today, I am a waist down CD.. I love skirts hose and heels, not so interested in the wigs, boobs, makeup, etc. It is still a thrill though! Oh and for those of you paying attention, I only got to 'go steady' with her for about a month before her family moved out of town.She was the first one I told that I had worn pantyhose... and I told her it was because of HER. She loved it! I can still picture in my minds eye her blue dress and white strappy heels and suntan hose in front of me in class. It's all her fault!! lol!! Honestly, for me it's always been the desire to feel how it felt to wear something. Not how I look, but how I felt. I buy heels now because I see some woman wearing them and I say to myself, I wonder how it would feel to wear those? So I get some. Yeah, I have too many pairs of heels...wait, that's impossible. Thanks for listening.
xxoo
Jennifer
i was 19... i know late bloomer, just broken up with my girlfriend at the time, and she had moved out but had left some cloths to "get at some point latter". i wanted to know what it felt like to wear woman's cloths... thats how it all started for me :-)
Emi, if you don't want to play, don't play. But there's no need to toss in comments like that. There are plenty of other threads where you may be more inclined to join in.
I'm not sure what was my first time I dressed up. But I got caught by a babysitter before first grade, in a slip and I don't remember what else. She was probably in her 40s. I begged her not to tell anyone, and she agreed. And as far as I know, she didn't.
Deedee
It's not wrong... but it is forbidden!
I have always had a fascination with lipstick, and besides a little dabbling when I had some private time, two stories come to mind:
1) I showed up in costume for a two-night elementary school singing event. Teachers were applying red lipstick to both girls and boys' lips, so the audience could see, so they said. Of course, all the boys protested but complied, and I, too, did the obligatory complaining. The next night, I showed up at school having already applied the lipstick myself. It's more fun that way anyway.
2) Two other boys and I decided we would paint clown faces on ourselves. We got ahold of some red lipstick and went to the basement of one of the boys. The first boy drew a red circle on his nose and then a typical big clown smile, while the other boy and I applied the lipstick to our lips as a woman would. Not a word was said. We eventually went our separate ways, but many years later I wondered if I might have had a potential CDing buddy.
My first complete make over happened with my wife. She discovered I crossdressed a year into our marriage. She one day came home for lunch un announced and all the while I was in the powder room getting dolled up. She asked me what I was doing having already noticed her shoes, clothes and some draws open and lying about. My only response was to come literally out myself and explain why and what I was doing. I explained and she was receptive. I currently dress mostly when I am alone. After eleven years of marriage I still don't feel comfortable dressed around her. Even though she is supportive.
I agree...This response was mean-spirited and totally out of line.Originally Posted by Deedee Skyblue
We are a support group here, and sharing our experiences - both good and bad - helps us not only come to terms with a condition that most people find baffling (if not downright weird) and consequently attracts an inordinate amount of negativity from the public at large, it also helps us grow as human beings and become the people we were meant to be.
You chose to join this group to share in the experience, Emi - no one held a gun to your head forcing you to do so. As the saying goes, "Don't sh*t where you eat."
I don't remember how old I was. Maybe 7 or 8. After a wedding, just for fun, my female cousins all dressed me up in their various girls' clothes, heels, and makeup. I never looked back after that.
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