I'm facinated by first time Crossdressing esperiences:

[emily606]

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

[dana digs sweaters]

Age 6.
Was fun and totally knew what I was doing.
And yes, basically was my idea also.

[BLUE ORCHID]

Hi Emily, it was 68yrs.ago and I'm sure that I must've been fun and it's still fun.

[LeannS]

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

[michellecd9999]

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)

[Rachael Leigh]

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.

[heatherdress]

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.

[Sc0rp10N]

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! :-)

[Marcelle]

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 things :battingeyelashes: but 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 earth :confused: It 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

[Beverley Sims]

Whe I was four I learned to play mothers and fathers....
Later in life I did it for real. :)

[Emi_]

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.

[Jackie F]

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.

[Desirae]

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.

[emily606]

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

[shawnsheila]

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

[Karren H]

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.....

[Teresa]

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 !!

[emily606]

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

[Jennifer_Ph]

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.

[JoanneCDSydney]

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 :-)

[Deedee Skyblue]

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

[NicoleScott]

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.

[Tera bytes]

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.

[Leslie Langford]

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

I agree...This response was mean-spirited and totally out of line.

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."

[AliyahS619]

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.

[Leslie Langford]

A very insightful and gut-wrenching post, emily606...I'm sure that it took a lot of courage to bare your soul this way, even if this is still a forum where we can remain anonymous if we choose to.

My heart goes out to you for having had to endure such an unfortunate experience as a youngster while you were at that day camp, and of course, "Lou" exhibited the classic behaviors of a pedophile. Just be grateful that he didn't carry his actions any further beyond the quick "crotch grab", unlike the fate suffered by so many other vulnerable young boys who have been caught in similar situations. Yes, summer camps, Boy Scout meetings, military cadet activities, sports teams, church groups, boarding schools etc. - these are all the favorite haunts of these types of perverts, and sadly, too few of them get caught because they capitalize on the shame experienced by their victims to continue flying under the radar. As for those who do get caught eventually, it is often far too late, and countless lives will have been negatively impacted by the time that finally happens. Of course, that also begs the question of what the motivations of that female "accomplice" were in participating in that unusual drag-inspired activity

As unfortunate as your experience at that day camp might have been, though, I highly doubt that it would have triggered your descent into the world of crossdressing in and of itself. More likely, you had already felt those inclinations previously, and were therefore far more resistant to being drafted into playing this "girl" part (not to mention being more fearful of - and affected by - the subsequent taunting) because of the paranoia associated with possibly being "outed" as a result of this. Within that context, it would be interesting to hear what your mother thought about all this. Did she naively see this as one big joke and an amusing skit with no deeper meaning, or was she also disturbed by it on some level?

All that said, this is one experience (and reaction) that I can personally identify with very closely. When I was about 9 years old, my mother bought a dress for a female cousin of mine who was the same age and about the same size as I as a birthday present, and I was drafted into trying it on to see how it would look after she brought it home. Naturally, I resisted this request as strenuously as any self-respecting "real" boy would be expected to do for the sake of appearances, but secretly, I loved the idea, couldn't wait to get into that dress, and enjoyed every moment of it (including the way my mother fussed over me as she was checking it for the fit).

I think my mother "bought" my act, and there was never any repeat or follow-up activity on that score, but I also know that my crossdressing urges were already developing at that time. I had been vaguely aware of how different I was from other boys in that respect from about age 5 years onwards, and this particular episode simply reinforced feelings that were already present and developing independently on their own at the time...

[luizapink]

my first crossdressing experience was with my ex-girlfriend. one day, we were boring at my home, and she said that i would be nice in lipstick. after she put it, she did all the makeover and said that i look better as a girl!!!hahahahaha

[6inchheels]

I feel like I've had many first times. Perhaps because after the experiences I often distanced myself from the whole concept and essentially forgot that it was real. (Funny how the mind works when we think we're doing something reprehensible haha)
(1) When I was a kid, maybe 5-10 years old, a friend of mine and I used to wear his older sister's clothes when I would sleepover at his house. I didn't know anything much about it except that I liked it.
(2) Fast forward a few years and there is the time that I was staying with one of my brothers for the night and was accommodated with a room that had a lot of his girlfriend's clothes in it in bags. I guess she was sorting them out to give to charity or something but I tried on lots of them and enjoyed it at the time but then felt quite ashamed.
(3) When I was 19 or 20, I was trying to get my girlfriend at the time to be a devil for Halloween because I thought it would be super hot. I bought her red thigh highs and a red vinyl type dress. Conveniently, she left these items at my apartment along with a sexy, strappy pair of sky high, red stilettos. I'm not sure what led up to going for it but I paraded around my apartment in those things for a couple of hours and it was phenomenal. That was the first time I had ever worn heels and I was in love. It's funny now to think that my calves were horribly sore the next day from the heels since now I wear super high heels for at least a couple hours almost every day.
(4) Strangely even as much as I had enjoyed the prior experience, I guess it seemed so forbidden that it was another 4 or 5 years before I tried again. The rest of my firsts :) have been since I've been with my now wife. I dressed in secret for a while before finding the courage and proper time to discuss it. She was totally against it at first but has pretty quickly warmed up to the idea. I think she likes it more than she admits honestly. Although it's probably mostly because I do housework while dressed and never decline to give her massages. I'm pretty sure I wandered off topic. :) Thanks for reading.

[Zoe B]

I am not sure if 'first time' is full dressing or just trying things out.

I loved (love) women's gloves and I had tried quite a few as a child, formal, casual, Sunday best (all in secret). I think I started trying other clothes when I was around 10 or 11 and this carried on throughout high school.

Now if we are talking first full dress experience that happened over an extended period of time. My SO and I were talking about fashion and I was pointing out shoes that I thought were nice, can't remember how it happened but she bought me a pair of 5" black heels and herself some (which I have here in the closet).
Over the next year or so one thing led to another, we went shopping together and discovered new stores like the vintage clothing shop we have locally (great choice and prices), and now I have a lovely selection of clothes. From this we have girly nights where we get dressed with make-up and we both have wigs (I bought her the long black one she loved).

[emma30]

This is a good topic, my first time was when i was 13, i envied my sister cus she could wear nice underwear and clothes in the summer that were cool ie short skirts and summer dresses all of which fitted me. When i was alone i would put her stuff on and feel really feminine. I didnt feel aroused but more liberated. I never messed with my mothers stuff , i thought that felt wrong. When i started work at 16 i started buying my own panties,skirts tops etc. How i kept it all secret? I still dont know how i managed that! I look at women today and think i would love to be liberated and look exactly like them but hey ho maybe in the next life. When im en femme i still feel liberated inside.:-)

[NANNETTE]

I was twelve when I first wore Womens clothes. I always wanted to be a girl from childhood. When I was in High school all the girls would wear tights underneath their school socks I so much wanted to be like them. Eventually I plucked up the courage to wear my Mother's tights underneath my gym shorts. I could not believe how wonderful my legs looked in tights. After a while I graduated to wearing my Mother's skirts as well. Whenever my parents went out for the evening at weekends I would dress up as the girl I wanted to be. I was very shy at school and probably seemed a little bit feminine to my boy class mates. I was very shy with girls, I often wished that I could share my girly feelings and be one of the girls. Forty two years on I still can't help thinking about this.

[autera24]

i first wore a 4'' high heels leather black boots without zipper which belong to my mother, so wonderful experience i love boots as a child and until now

[charlenesomeone]

I remember wearing my Grandma's nite dress one time really young.
I wore Moms panty hose often from about 6 to 7. Got caught by my
dad once, then it stopped for a while.

[typhoidmary]

i'd been wearing makeup since I was 18 or so and had been interested in looking feminine since way before that, but I didnt start wearing women's clothes until sometime around my 21st birthday. i'd told my girlfriend at the time that it was something I'd wanted to do for years but was always too self conscious about shopping in the women's department so she took me out shopping. we went out for a drink later with me wearing some of the stuff I'd bought for the first time, it felt amazing. I just wanted to always look like that and I've pretty much kept that up since, even if my look has changed a lot in three years. It's such a nice memory for me and thinking about it actually makes me really sad that things didn't work out with her, it lasted a year and was the only real relationship I've ever been in.

[Brandie.n]

When i was 15 i wore my cousins black leotard,tights and boots it was a base for a witch costume.The costume was a slinky black dress with a hat that had a wig and face mask attached.i loved that costume until i had to use the bathroom.
231388

[EllenJo]

I grew up with 2 older sisters, and about the time they went through puberty I noticed that they got a lot of new clothes and a lot of attention. One night when I was about 13 and going through lot of changes myself, I was home alone and wondered into my sisters room. I opened the top drawer of their dresser and was amazed at everything inside. Silky things in pretty colors. I selected a pretty panty girdle (it was the 60's) and tried it on. Not really knowing what I was doing I did tuck myself so I would look like a girl down there. Then I tried a bra but could not get it hooked so I tried a camisole instead. Looking in the mirror I looked like a girl from the neck down and about that time something else happened down there. When I recovered I immediately took everything off and had to wash the girdle before anyone came home. Of course the next time I got a chance to repeat the experience I did figure out the bra, found a skirt that fit and some pantyhose. I have been hooked ever since. I remember looking at the Sears catalog women's underwear section and wishing I could buy everything in that section.
Hugs
Ellen Jo

[Badwolf]

For me there were two events that I remember (probably a few other small ones), that stick out in my mind as "firsts".

I remember playing dress up in my moms stuff once (at least I think it's once), and trudging around in her way too big heels.

A few years later (I think I was around 8), there was a day we were required to bring in yellow pants for a color wars event. I mistakenly took home someone elses with a little bow around the end of one of the legs. This became the first item that was sort of "mine", and I loved them. I wore them for years at home, without my mom making a big fuss, and eventually they got hidden in my stash where my mom apparently forgot about them. She eventually found my stash and shamed me into purging (which she did twice). After that I never let her catch on again that I was doing anything and learned to hide my clothes MUCH better. When she recently found out she forgot the scoldings she gave me, and once I convinced her they were real she apologized and said she loves me (something I always thought she'd do, since I really believe it was my lack of "self confidence" as she saw it that she was afraid of).

[jeank]

The first time I fully dressed was with my first wife when we went out to a party dressed in matching dresses and make up - it was the mid 70s and we lived in a very arty community where anything went. I tried to do the same again, but it turned into very much a one off.

The next first time was many years later when I rented an apartment on my own for several months when I was relocating between jobs (and countries). I bought shoes in a store (very nervously) and then acquired a dress, tights, some make up and undergarments, and spent many happy nights dressed. It's been fairly constant since then whenever the opportunity arises.

[tammie]

Oh my what a wonderful topic to explore. My first time was after an older very sexy woman (mid thirties) touched my arm at a party and leaned forward (so I could smell her perfume and see down her cleavage) to whisper into my ear "your tits are bigger than mine honey , you should be wearing a brassiere". WEll about a week later I was home alone and as I walked past my sisters bedroom , on the floor was a very sexy black lace underwire bra and I stopped and picked it up .

Somehow it spoke to me and I pulled off my tshirt and put my arms thru the straps and leaned forward (as I had seen my mother do many times) and as I walked my hands down the band and hooked it (like a woman) I somehow knew I was on the verge of a big discovery.

Then as I adjusted my little boi tits onto those lace UW cups I almost feinted it felt so wonderful. I knew then I was a CD forever and I filled the cups (36B) like I had been measured for it . I took it and as I was leaving I saw the matching lace edged LLPG
and took it also .

Three days later my mom looking for my sisters missing bra and girdle walked in on me in my bedroom, wearing them and with a big erection. So I became a CDer and was caught in the space of 3 days . My mom made me promise to not wear my sisters lingerie , and so in about a week I reasoned I didn't promise to not wear my mothes things so.........

I got into my mothers dresser and got a bra girdle stockings and slip and was dressed up in them the second time my mother caught me. She mademe strip in frontof her and took her clothes . I was despondent and felt I was so terrible . My mother asked her gay friends what to do to "help me" and they advised her to just shop for me and get me my own lingerie .

A few days later I got home from school and on my bed was a shopping bag with my own bra (same size as my sisters) a LLPG and a slip of my own. Motehr had me try them on in front of her before cutting the tags and told me not to wear them out of the house or let my dad see me in them . The rest as they say is history , but now after all these yrs I still love putting on a brassiere just as much as the first time .

[sometimes_miss]

OK. Age somewhere between one and three. Vaguely remember wearing a white dress and a lady poking her head down at me and saying what a cute little girl. Compliments of mom's wanting a girl instead of a boy.