I was about 6. Mom always wore pantyhose, 24/7 and I loved how her legs looked. I took a pair out of her hamper and tried them on. It led to her skirts, bras, slips, dresses, heels and wigs, as I got older.
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I was about 6. Mom always wore pantyhose, 24/7 and I loved how her legs looked. I took a pair out of her hamper and tried them on. It led to her skirts, bras, slips, dresses, heels and wigs, as I got older.
Used to wear mum's shoes in bed when I was 12.
Bought my first dress at 25. "Late-starter" doesn't even cover it. I sometimes wonder what it would have been like to do it at e.g 16. The logistics would have failed at some point I'm sure......
I was about 12, hitting puberty and wondering how girls "worked", and investigating how girls' clothing worked led to me trying on a bra to see how they went on and came off... and it felt so good, I kept going.
About 5 - 7 sister's pantyhose ))
... age 8 or 9 ,I wore my mother's bathing suit, My interest started at 3 or 4.
I vividly remember the beautiful sounds of my grade 4 teacher's undergarments as she walked by... the shh shhhh of fabric on fabric.
It sounded beautiful and I wanted it for myself.
nope, I was too busy feeding my animal masculinity. As described in other thread responses, it was likely brought on by 2 things that only came together at that time- my wife refusing to dress sexy for me, meaning our relationship was lacking in femininity, and that I was embarrassed about her doing me as a guy with her toy. It felt much better to pretend I was a girl. That sums it up rather snugly, but there's a lot of periphery.Quote:
Originally Posted by Xandra
I was in my early teens staying at my aunt's house for the weekend. She called me to zip up the back of her dress, no problem. That one simple act led me into xdressing. I had to figure out how she got everything on. She wearing a longline bra and a zipper OMG with a slip. After she left, I discovered the hidden joys that were in the dresser.
I got into when i was in elementary school. i dont know why but it was just something i did when there was a window to do it in. i wish i could read my mind back then, have a pair of panties on and curling up on the floor. i wonder why that was.
My sister tells me about age 5, I don't remember that tho, I do remember at about age 12 my first dress tho. Pink satin dress in the older "puffy" style :)
I was around 6. Most friends that I can remember where girls then. And I can remember one of the girls wearing hose. I was so jealous, so I tried my moms on. From there bra's, dresses, wig.
I tried on a pair of women's satin gloves when I was an 8th grader. I loved the feeling of it and it's only grown on me. Now I like to wear dresses, heels, and full-blown lingerie. It's a sexual feeling rather than one of wanting to be a girl. I just feel sexier in women's clothing!
My first time would have been when I was around 10 years old. Tried on a pair of pantyhose too.
Around 5 to 6 years old. I was not yet in Kindergarten yet. Put on what ever I could of my sisters that fit.
I am Guessing around 7 or 8 tried on my mothers stuff, i think my first article was her slip, and it progressed from there. I remember the first time i tried her lipstick i was scared i wouldnt be able to get it off, LOL. Been hooked ever since.
Around 7 or 8, I tried on my sister's dress. Then, around 12 or so, I fully dressed on night when home alone -- panties, nylons, slip, bra, dress, makeup, and I became absolutely hooked.
Around 12 or 13. I had been watching Get Smart and I liked the 'damsel in distress' theme. So I borrowed one of my mothers' dresses (very short on me) , pantyhose and bra. I knelt in the bathtub, started filling it with water. I used to imagine that I was trapped in a phone booth that was filling with water. Strange, I know but it's my first memory.
I think I was around the age of 6.
At about the age if 11 or 12. I first tried my sisters one piece swimsuit. About the same time, I also tried on her gymnastics team leotard. .... I was always caught, and it never went over well at all.
I stopped.
Until I was about 40 and made a "deal."
I worked in a hot restaurant kitchen. Always envied waitresses in there skirts. So one saying "joked" with thedinningroom manger saying" if I wear a skirt. Can I wait tables?" She replied "if you war a skirt. You can do whatever you want."
I called her bluff. And I got a skirt. She didn't know that to say accept. "I didn't really expect you todo it!"
Surprise!
And IMO dressing has snowballed from then.
(Side note) I never did wait tables that day. But that was rather exiting and I dress in everything. But... In the closet.
When I was about eleven, I had a curiosity about what it might feel like to wear women's underwear. So I took a pair of scissors to mine and did the best I could. It didn't take long for me to figure out that a bikini shape was improperly suited to holding my junk, but in retrospect I blame that on insufficient leg-hole elastic (which had all been cut off to give the new shape its form).
Then I pulled a bit of a u-turn in the next couple years. Lord of the Rings had just come out, and I was obsessed as any boy could be with Frodo Baggins. I wanted to grow out my hair to be like his, dress up as him for Halloween, carry around the One Ring on a necklace, et cetera. Eventually, after growing my hair out to about shoulder-length, my infatuation with the hobbit subsided and I got tired of people saying I looked like a girl, so I got a buzz cut.
CD urges flared up again at about sixteen or seventeen. I was finishing high school, still discovering myself, and wondering again what it would be like to wear female undergarments. At this point, the easiest thing to do was to knick some of my mom's. It's only ever increased from there, and I started growing my hair again at eighteen.
7 or 8, mom's girdle and pantyhose
I was about 4 and living with my grandparents as my parents were separated and going thru a divorce, It was the late 60,s and they were in their 40,s and every weekend used to have parties in their basement, my sister and I used to sneak out of bed and sit on the stairs and watch through the railings all the women in their beautiful cocktail dresses beautifully made up, drinking martini,s listening to Dean Martin and Frank Sinatra. My Grandma would let me have my naps in her bed and would often find me fast asleep in her stockings that she would leave on the bed. After the divorce My sister went to live with my Mother and My brother and I went to live with my Dad, I wouldn't see my sister again for 10 years. My father remarried and my stepmother who was only 22 always resented me, Growing up I was small and often mistaken for a girl, although I didn't start really dressing until I was about 12 or 13 one summer when my parents were at work when my brother and I went into their room and discovered all of her sexy lingerie and would dress and play Mommy and Daddy.
Uhm... think I was about 4-5 years old... the rest history :)
Around 10 or 11. First my sister's panties, but since she was smaller than me they hurt o I quickly graduated to my mother's nylon panties and dresses.
My first time was with pantyhose.
After a long infatuation with pantyhose and puberty starting to kick in, I put on Mom's L'eggs Sheer Energy and was hooked. They are the foundation of my fem side and CDing. From there, I put on mom's leotard with them and lipstick. It was an incredible rush that came over my body. The feel of tight, smooth garments, and the look, smell, taste, and feel of lipstick. Still feel the same today about it, except now, it has evolved into dresses, full makeup, nails, wig the whole 9 years baby! YES! Love it and love my pantyhose and heels!
around 11 or 12 it was nice crossdresser and feeling more feminine than now
At the age of 6 or 7. My mom had her old heels and purses in our toy box played with them quite a bit. But 8th grade pushed me over to pantyhose and then I was hooked.
I was 8. Tried on my sisters old majorette uniform. I loved everything about it and still remember it vividly after 47 years.
Have been dressing up ever since.
The first time was when I was 10 years old. I took note of my Mom's & sister's swimsuits and when I saw them drying in the bathroom I saw it as a glorious chance to try one or both on. So I did and loved how it felt. I loved the tight, body hugging feeling and have been hooked eversince. I remember my Mom asking me why I was in the can for so long so I lied and said I was sick to my stomach and, well you get the picture. Luckily she bought it. Shortly thereafter, since my Mom & Dad have been separated since I was 7, my dad's x girlfriend had this hot looking pink one piece that I just had to try on, so when the opportunity presented itself under the same circumstances I tried on that pink suit and stared at myself in the mirror for a few minutes just noticing how sexy it looked on me and how I loved the shiny spandex material, then it was interrupted by a loud rap on the bathroom door with my hard ass father saying "What the hell are you doing in there!!??" So I made a few fake puking noises and told my Dad I was puking in there so luckily he bought that too. 30 years later I have about 15-20 swimsuits and I am always looking for more.
My cousin made me try on her ballerina outfit when I was about 8, her and her sister had been left to look after me. It was fun but I was only 8.
My first voluntary cross dressing , I was probably about 12/13 and I tried on my cousin's (a different one!) bikini. I loved it, wasn't long before I was wearing her underwear and it all went from there!
My grandmother sparked my curiosity in pantyhose which later lead to full on crossdressing.
When I was around 8 or 9 I would lock myself in my mom's room and take a pair from her drawer and put them on.
Hi, I posted this exact post in another thread when someone asked me why I was asking about first time experiences. This is how I started. My first time was unpleasant, over time, I realized I liked it:
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.
Hi Lisa,
You should read my first time story. I was at a day camp too, but it was not a fun experience. If you don't find it, let me know and I'll send it to you.
My crossdressing started when I was about 12 years old. I would be home from school "sick" and I was so fascinated by women's clothing. I tried on my mother's pantyhose first and couldn't believe how great they felt. I had to feel what a whole outfit felt like so I tried on a dress too. I loved how it made me feel. I remember wishing I could dress like that all the time. After taking it off I was paranoid that my mother would know what I had done so I sprayed her dress with perfume which probably made her suspicious about what's going on. I did it a lot when I knew I was home alone for a long time. I never was confronted by my mother about it though. I would try all sorts of things I found in my mother's wardrobe and I remember it being so much fun. Getting caught once by my very intolerant brother forced me to suppress it for a while until I started having those same desires to crossdress.
I dont remember - all I know is I cant remember a time when I didnt....but then i remember very little from early childhood - I must have had a good time huh
I can't actually remember the moment itself, but I do remember that it involved formal gloves.
Somewhere around 4 or 5 for me playing with my mother's heels. During the weekends when I would go over to my father's house, I would put on my sister's nightgown, which was always hanging on the bathroom hook.
i started wearing nylons and tights in my early teens.
Somewhere around 8-10 years old trying on my mom's panties. Over the years graduated to bras and pantyhose. Always just felt natural.
Curious: What are formal gloves?Quote:
Originally Posted by Zoe B
I think I was 7 or 8. The first time I wore my mom's lingerie I was hooked for life!
About 6 or 7, I tried on a girl's babushka under my front porch. Plus when my Mom and I went shopping I couldn't resist looking at the blouses,skirts and dresses when we walked past the Three Sisters Store and also wishing when we were on the 1st floor landing I wanted to have a perm in Goldblatt's Beauty Salon.
My signature says it all.
When I was 5 or 6, I put on my Mums tights and they felt so good. I've been interested ever since. I've always loved the feel tights give you but also got intrigued into how good women's clothes make you feel when fully dressed. I started with just knickers, bra and tights when I was 18 but then moved onto fully dressing when I was twenty odd. In my situation atm it is hard to dress fully so have to stick to knickers bras and tights unless I am 'away'.
I was about 8 years old, and had to wear girls tights as parts of a costume for a children's' ice skating show - I was mickey mouse :) I put them on and wow they felt nice. It was a few years later that I started "borrowing" my mothers hose, slips, bras, etc.
I was 12. I discovered some wigs in the basement then tried a few dresses, shoes then....bingo! I was hooked. I instantly fell in love with the feeling of being pretty
I was in kindergarten when I discovered pantyhose. Mom would comb my brother and my hair and put legs off of her pantyhose on our heads to hold our hair in place when we went to bed. I would then play in the ones that didn't have any legs. One day while playing in my fort in the living room I went to grab the hose I wore but ended up with a full pair instead. From that day on I would barrow moms pantyhose and even wore them to school under my jeans. Then when I was about 8 I started in with full crossdressing. In twenty years I haven't regretted it.
I'm not sure of the exact age but I was in the single digits. My first time was seeing my sisters one piece bathing suit hanging up in the bathroom. I really felt the urge to try it on. The fabric felt incredible. I soon progressed to wanting to try on clothes of more types mainly panties and bras. Whenever I was home alone, I would raid my mothers wardrobe and have a great time. I remember there was one black thong and matching bra that was my favorite.
I was at a family friends house spending the night, they were two sisters and their mom gave us a bath in the tub together. I guess I was about 4 or 5 when we were done I did not have any clean underwear so she gave me a pair of one of the girls to wear, I loved them, they were pretty and had flowers on them. Later when I was in my early teens I remembered the panties and bought myself some and have been wearing panties ever since, of course now I have about 40 of them along with all of my other clothes and don't even own a pair of mens underwear.
I tried on my mother's sheer knee highs when I was about 5 then since I had them on I went in her closet and put on her shoes she just laughed and said that I wasn't supposed to wear those i didn't try actual pantyhose until I was about 7 at my grandma's house. When I was about 7 or 8 my mom gave me an old pair of her shoes and said dont let your father see these lol