The first time you wanted to?

[laurie103]

I can't remember the first time I felt the urge, but the earliest memory I have of it happened like this:

Early 1990's. My parents owned a thrift store. I was probably 6 or 7. The people who ran it had grandkids who were the same age as my brother and I. The place was really huge. Lots of clothes and other items. We were playing in stuff one day, and I suggested we dress like girls. So we did. I remember it being really fun and exciting, and the other boys thought it was great. My brother never mentioned it to my parents, and I don't remember ever talking about it again.

I've been re-watching the Simpsons recently on Disney+, and there's an episode where Bart and Milhouse do the same thing. I remember seeing that when I was a kid, and it makes me embarrassed/ashamed now like it did then. I hate that. Kids shouldn't be ashamed of things they want that don't hurt others.

[Brianne_bc]

Dont know if I was 4 or 5. At the baby sitters house and ide go into the shoes at the front door and put on any highheels that were there. When I was five ai different baby sitter had a daughter a year younger than I and she always wanted to play dress up. I liked it, and often wonder what she is like today. When I was 6 my mum caught me wearing her highheels and I was spanked and told boys dont do that. In grade school I stole maryjanes from the coat room, ad little girls cried when they couldnt find their maryjanes.

[jenabrooks]

When I was 4 or 5 it was before I was at a babysitters watching twilight zone. It was about a woman who has her niece age 5 or 6 living with her in a big two story house. She hired a man that was passing through town to do some work around the house. not sure how it happened but the little girl saw him using the restroom and she told her Aunt she was a boy because she had the same thing man had. I could not believe she was a boy. This girl had shoulder length hair curly wearing pretty dresses. That turned the switch on, I wished I was her. This sounds unreal it's true story, 1959 or 60

[Geena75]

Actually have 8mm film of a time my sister dressed my 4 yr old self in my grandma's petticoats and such. I have no memory of it. My first memory is trying on my sister's thrown out pantyhose -- about 10 yrs old. Next milestone was when we acquired a big garage sale, and there was a purple dress that would fit me, back in '75.

[laurie103]

Next milestone was when we acquired a big garage sale, and there was a purple dress that would fit me, back in '75.

That's so awesome...

[Karren H]

I was 6 or 7 and my baby sister had just been born. Mom had told me for years that I was supposed to have been a girl.. So after "she" came along, I started sneaking into my mom's walk-in closet, when mom and dad were out and we had a baby sitter... and I would try on all the clothes that I was supposed to be wearing... if I had been born a girl. That was over 6 decades ago.

[Kelli_cd]

My earliest memories involve wearing my grandmother's petticoats and mom's heels. I was 4 or so.

[JennyMay]

When I was 4 or 5 it was before I was at a babysitters watching twilight zone. It was about a woman who has her niece age 5 or 6 living with her in a big two story house. She hired a man that was passing through town to do some work around the house. not sure how it happened but the little girl saw him using the restroom and she told her Aunt she was a boy because she had the same thing man had. I could not believe she was a boy. This girl had shoulder length hair curly wearing pretty dresses. That turned the switch on, I wished I was her. This sounds unreal it's true story, 1959 or 60

I remember that story too. The aunt was horrible so I was conflicted but I so wanted to be a girl.

[kayegirl]

I had been playing dress up for as long as I can remember with my older sister and her friends. But then one Saturday evening aged13, I was home alone, and I knew that this would be for the next three hours. So I went into my sisters room, took off every last stitch of boy clothes and dressed fully as a girl. I can still remember the exact outfit. Now fully dressed I stepped out onto the landing and was shocked to see a girl looking straight at me. It took a few anxious seconds before I realised that I was the girl, I was looking at my own reflection in a full length mirror at the top of the stairs. That was my epiphany, and the rest , as they say is history.

[ronny0]

Ok, so it was in the late 50's, I was up in the attic, found a girdle and I fell in love with the super tight compression of woman's optional clothing.
Wore pantyhose on and off for a 'zillion' years, till I acknowledged the need to incorporate them into my lifestyle.
Wasn't long after that I was 'hooked' on super tight girdles etc....

I hope and PRAY we are able to recover from Coved & the other problems we have.
It would also be a "pipe dream' to have a world that we could all live in that would accept us as who we 'desire to be'
2020 has finally passed, hope 2021 turns out to be better.

[Brandi Christine]

My aunt lived with us when I was a kid, I was about 6 or 7, she was three years older, I liked to play dressup with her, I always wore her clothes, my choice, not her pushing it on me. I liked wearing girly things. Before that I remember putting on my Mom's lipstick and getting caught, I'd have been under 5, and she told me not to and that it was poison. I was afraid to kiss girls for years after that...

[Georgina]

The first time I wanted to I wasn't able to. My first desires began in the latter part of the fifties. Around 5 or 6 years old, in primary school, we had one teacher for all classes. She had just qualified, so was not much over 20 years old, and she loved wearing the petticoats that were fashionable at the time. She took PE classes as well. In a small country school this was outside. On windy days her dress or skirt would get blown up which revealed her petticoats. I was mesmerised by the display of colour and variety of the petticoats that she wore. For some unknown reason my immediate thoughts were I want to wear those lovely garments. That was the first time I got the urge to wear female clothes and sixty years later I still remember those days with fondness. I began searching through my mother's clothes looking for petticoats but only found remnants. I did however discover slips and thus began my dressing and dreaming of having my own clothes some day. A dream well fulfilled.

[Angela Marie]

I was about 11 or 12. I was fascinated by my mothers tights. This was the 60's so tights would be considered leggings now. She had a black and a blue pair. Once I tried them on I was hooked. It accelerated from there. I never fully dressed until I separated from my first wife when I was about 50. At 66 I still love wearing my leggings as often as I can; in addition to my other clothes lol.

[josie_S]

I was 7 or 8 and we lived with my girl cousins for a time. In a family of all boys except my mom, I'd never been around girls stuff like this before. One thing I remember is really enjoying playing with Barbie, especially dressing her up. But I also noticed that, to my silly mind anyway, girls wore low socks while I wore tall white socks. I would roll down my socks, almost like I would roll off pantyhose today, so that my legs were exposed and the sock balled up around my ankle and I thought it looked like those pom pom socks that girls wore in the 80s (see below LOL). It gave me such a thrill--OMG I hadn't thought about this in forever!

318295

[Deborah G]

It was my sister's high heels and Keds that I first experienced. She wore one or the other constantly. When I was 12 or 13, I finally indulged and tried on both and it was just like nothing I've worn before! Later, I tried on her panties and garter belts and hose. WOW! Eventually it was skirts, tops, and dresses. She and I were about the same size and she had a big closet so, there was always something new to sample.

[Judy-Somthing]

My 1st time was when I was about 5.
My older sister dressed me up in her Ballerina outfit and I was hooked after that.
I remember putting it on every chance I got after that day.

One cool thing about that day is that she took a photo that I still have of day one!

[joanna4]

Wow that gives me memories to my childhood for two things 1) my parents owned a clothing store 2) I love going to thrift stores and seeing things like leather pants and leather skirts that I would have loved to try on but sadly those were the 90s and a lot of those items don't show up in thrift stores anymore besides the faux leather stuff you can easily get brand new anywhere

[Deborah G]

Wow that gives me memories to my childhood for two things 1) my parents owned a clothing store 2) I love going to thrift stores and seeing things like leather pants and leather skirts that I would have loved to try on but sadly those were the 90s and a lot of those items don't show up in thrift stores anymore besides the faux leather stuff you can easily get brand new anywhere

Joanna, My SO at the time had a pair of those leather pants and a little leather skirt and I always wanted her to wear them. Was great going to those leather shops and taking it all in, including the smell of all that leather! A leather skirt is on my wish list.

[Lana Mae]

I was 4or 5or 6 and was playing with a younger little girl! She threw her white dress over her head! I was amazed and wanted a dress of my own so I could do that! I got boys don't wear dresses! (1950's) Well, that started it all! And guess what...her name was Lana!!!
Hugs Lana Mae

[Stephanie47]

I cannot remember the age I first became interested in my mother's slips. When she did the laundry she'd hang clothes to dry on a clothesline strung down the hallway to the bedrooms. I had to duck under the clothesline to get to my bedroom. I loved the feel of her nylon slips. The fabric was like none of my boy clothes. I would fondle them. She also hanged clothes to dry on a drying rack in the sole bathroom in the apartment. When I finally took the plunge and took one of her slips of the drying rack and put it on I was hooked. Full slips are my favorite women's garments. I have over 400 slips. Given the sales prices on ebay these days for vintage slips in larger sizes I have a small fortune at my finger tips.

[KristyPa]

It was right around when I was 7. I was still sleeping with my 5 year older sister. I woke up one morning and her very plain nothing sexy dress was hanging on the back of the bedroom door. I got up, put it on and checked myself out in my brothers bedroom next door mirror.
Have no idea why I did and really didn't think much of it at the time. I don't remember wearing her cloths again until i was 12 or so then it was her garter belt type thing with hose. I did this before I became sexual, interested in sex.

At 12 or 13 I was then putting on something of my sisters until she left home when I was 14. Then I had some panties, cami's, camisoles and hose from a couple neighbor girls. I had one neighbor mother that was really good looking and wore hot cloths. I was 15 at the time and I'll guess she was 35. Started buying on own things at 15-16 from kmart even a very nice long blond wig.

At 35 I started dressing fully and going out to bars.

[Lorna]

Lots of different experiences... Not having any sisters (or brothers) I wasn't expoxed to girls' clothing at home and, for me, there was no interest in it until I was old enough (probaly around 13) to become "interested in girls". Girlfriends, as such, were still a year or two away (this was the 1950s) but I noticed plenty of attractive girls around me, often in their school uniforms or, at weekends, in their Sunday best. I particulatly noticed what girls wore but, without a sister, my knowledge of their clothes - especially the clothes that weren't visible - was very limited. My knowledge of their anatomy was also limited.
So, I was intrigued when I realised how girls my age were changing - developing, in fact. I noticed breasts and I noticed legs. The former must be held in bras and the latter were encased in nylons. My mother wore those - so were the girls wearing underwear like my mother's? I really didn't know. I realised, though, that there were some sources of information available, even if I didn't have access to real girls to investigate and find out. These sources included what could be seen in shop windows (plenty of slips, bras, girdles, nylons on display), occasional chance views of such garments on washing lines and plenty of advertisements in newspapers. None of these, though, really told me what I wanted to know: what did girls actually wear and, increasingly, what must it feel like to wear those things?
A little earlier, my grandmother, who had lived with us, died. This meant that when I came home from school (quite early on some days) I was alone in the house and I confess to looking to see what kind of things my mother wore. Of course, I found the full range of items and tried some of them. While this gave me some idea of what stockings, girdles, slips, skirts, etc felt like to wear (and the feeling was very good) most items didn't fit me well and, in any case, I could only put them on, walk around the houase for a few minutes and then take them off again. However, that was enough to spark a love of female clothes - especially of the 50s and 60s - which has lasted over the years.

[Melissa in SE Tn]

Age 7 during my first holy communion exercise. I wanted so badly to wear the white dress & not the blue suit with clip on tie. The feelings would resurface at family gatherings when my aunts & cousins wore dresses. This must reinforce that cding is nature as I then had no knowledge of sex.

[Star01]

My first memory of anything transgender related came from a very unlikely source. My dad used to take me to a magazine store (I think it may have been the original Schinders) on Wabasha Street in downtown St. Paul and let me pick out comic books. I was into Superman, Batman and the DC comic lineup of the late 1950's and early 1960's so the latest issues of anything related to those characters were always my choices. Actually it's kind of exciting to be able to tell this story now as I just recently found out what issue it was and the date.

Superboy comics included a story in issue #78 in December 1960 titled "Claire Kent, Alias Super-Sister". Superboy encounters a spaceship piloted by a woman and the spaceship is out of control and about to crash. He saves the life of the ship's pilot who is named Shar-La and makes a comment about women drivers that does not sit well with her. She showers Superboy with rays from the ring she is wearing and they both go their separate ways. At first Superboy doesn't notice anything is wrong but then realizes that he has been turned into a girl. The story goes on to tell how he had to come up with an alias and dress in women's clothes. Anyways as the story goes she eventually returns and explains that it was only a dream and turns him back into Superboy.

It took several years of searching until I finally found a record of this article and I was thrilled because I couldn't recall if it was real or something I imagined. My parents passed away separately not many years later but I would have just turned nine years old in September of 1960 so I had not gone through puberty. I have vague memories of there being an uproar over whatever I said after seeing the article but I know there was some talk of "not letting the kid read anymore of those comic books" but that eventually subsided. My mother passed away, father remarried and my step mother passed away in 1964 so there was about a six month period between her passing and my dad having a fatal heart attack the following April of 1965. My first crossdressing experience was discovering my late step mother's clothes in the attic in late 1964 and early 1965. Garters, stockings, girdles, slips, bras, and I had about an hour to myself every day after school to go up and try things on.

Those are my first memories dealing with crossdressing.

[LilSissyStevie]

It's difficult to remember what came first but a few things stand out.

When I was little, I lived in a house full of females. I was the only male there most of the time. My father wasn't around much. All of the kids our age that lived close by were girls, too. My sisters and their friends would play house and with dolls. Out of boredom I would often play with them. I usually got roped into being the dad but I didn't really identify with that. My dad was just some guy that got drunk and smashed up the cars and fought with my mother. We would sometime visit him in jail or the mental hospital. I was afraid of him and certainly did not want to be like him. Sometimes the girls would let me play the mom and I would tie a headscarf or towel around my waist to be a skirt. My grandmother would catch me playing house sometimes and, afraid that I would become a sissy by playing with girls all the time, would force me to go down the road and play with the boys. I thought the boys were stupid, mean, and cruel. They bullied me and I didn't relate to them at all. I would always come back home in tears, bloodied and bruised thinking "too late, grandma, I'm already a sissy." I always wished I was a girl so they would accept me as one of them and I wouldn't have to hang out with boys.

The first time I remember wearing girls clothing was one of my sister's rompers that she always wore. She was also taking ballet lessons around that time and I remember trying on her ballet outfit. It was exhilarating.

I was watching the Mickey Mouse Club one day and Annette Funicello, who I had a huge crush on, was doing a ballet skit and I suddenly realized that I was fantasizing about being a ballerina like her. Then I came crashing back to Earth.

[Alexis00]

When I was 9 or 10 started stealing my moms panties and bras from the hamper when no one was home.

Eventually that led to wearing them in bed. Got up to go to the bathroom and my mom saw me. First time caught....

[Cheryl T]

I was 5 or 6 when I first donned my mother's panties.
It felt so right.
Then came her bra, stuffed of course, and those silky slips she wore.

Eventually it became everything.

[Rachelakld]

5 years old, borrowed sisters clothes to ride her "girls" bike, didn't want people to think I was a boy on a girls bike, my folks saw me and soon after bought me a "boys" bike

[Alexis00]

When was the first time any of you went out? When I was 13 I’d stolen a bra from friends hottish mom. Got some water balloons and used to walk out to check the mail with these big bouncing breasts. Didn’t realize our housewife neighbor also checked her mail, and saw me multiple times. She questioned me and I denied it: but my face flushed hot red. I was never sure if she told my parents (who had already found the bra and my stash at least once) but the never mentioned it. Didn’t go out again for a couple years and not at home.


My first memory of anything transgender related came from a very unlikely source. My dad used to take me to a magazine store (I think it may have been the original Schinders) on Wabasha Street in downtown St. Paul and let me pick out comic books. I was into Superman, Batman and the DC comic lineup of the late 1950's and early 1960's so the latest issues of anything related to those characters were always my choices. Actually it's kind of exciting to be able to tell this story now as I just recently found out what issue it was and the date.

Superboy comics included a story in issue #78 in December 1960 titled "Claire Kent, Alias Super-Sister". Superboy encounters a spaceship piloted by a woman and the spaceship is out of control and about to crash. He saves the life of the ship's pilot who is named Shar-La and makes a comment about women drivers that does not sit well with her. She showers Superboy with rays from the ring she is wearing and they both go their separate ways. At first Superboy doesn't notice anything is wrong but then realizes that he has been turned into a girl. The story goes on to tell how he had to come up with an alias and dress in women's clothes. Anyways as the story goes she eventually returns and explains that it was only a dream and turns him back into Superboy. It. Is this it?

http://dccomicsartists.com/superwhoswho/Superboy078-05.jpg

[SaraLin]

I ALWAYS wanted it.

I think that probably the first time I wore anything feminine was probably one of my sisters' dresses when I was around 4 or 5.
I'd sneak it from the laundry and wear it under the covers in bed at night. I'd then imagine that maybe I'd be able to wake up in the morning and be changed into a girl.
Oddly enough, it didn't work.

[chris80]

When I was 4 or 5 it was before I was at a babysitters watching twilight zone. It was about a woman who has her niece age 5 or 6 living with her in a big two story house. She hired a man that was passing through town to do some work around the house. not sure how it happened but the little girl saw him using the restroom and she told her Aunt she was a boy because she had the same thing man had. I could not believe she was a boy. This girl had shoulder length hair curly wearing pretty dresses. That turned the switch on, I wished I was her. This sounds unreal it's true story, 1959 or 60
Journey into the Unknown 1968 episode called 'Miss Belle' maybe the story recalled. Kim Burfield born 1961 as the orphaned boy dressed and living as a girl by his unhinged aunt. George Maharis as a US drifter in UK discovers the truth
Charles Beaumont pseudonym for Charles Nutt who wrote for the Twilight Zone. His unstable mother dressed him as a girl as a child once as a punishment and killed a pet. May be the basis for the story originally titled 'Miss Gentilbelle'
Details on IMDB and photos.318388 I've searched the precis storylines of Twilight Zone for the first five series to 1964 but can't find that episode that Jena saw

[NancySue]

So similar. I was 6 or 7. Sisters the same age lived next door. We often played together. On one occasion, I walked in when they were playing house and dress up. The invited me to join them. At first, I wasn?t too interested until they found some panties and pantyhose. They dated me to try them on. I did. BAM. That was the beginning. I loved and couldn?t wait to play dress up again. I could walk in high heels. Seemed natural. My mom still wore nylon stockings with OB girdles. You can guess the rest of the story.

[chris80]

The story was written by Charles Nutt pseudonym Charles Beaumont who wrote stories for Twilight Zone and Journey to Unknown. I searched Twilight series 1-5 and can't find a precis of that episode. His original story was 'Miss Gentilbelle'. His unstable mother had once dressed Charles as a girl as punishment and killed a pet bird.
George Maharis, still318390 alive at 92,played the US drifter in UK who discovers the deception in Miss Belle. 318389.
Miss Gentilbelle was also made as a short as 'Ursula'1961. This can also be found on IMDB with picture of a blonde girl in a polka-dot frock but no definite mention of crossdressing

[Star01]

Alexis00 Yes, I believe that is likely the issue but I don?t recall what the costume she was wearing looked like. This is the first time I have seen it in 60 years. Thanks for sharing.

[candykowal]

I found the episode of Miss Belle on youtube (https://www.youtube.com/watch?v=eLeXGFWQx0Y)...the British version of The Twilight Zone.
I was so underdeveloped and sickly as a child, I often slept with my mother when Dad was away for work.
Mom dressed me in a satin babydoll so she could change my diapers and clean my bandages without undressing me.
I spent a lot of time in that room, in my babydoll.
Mom was a huge influence in the way I watched her dress, her make-up, perfume, and mannerisms.
My first recollection of purposefully dressing like mom was in Kintergarden, I wanted to play in this giant sized walk in dollhouse they had on one side of the room.
One of my girl classmates told me only girls with dresses can play in here and told me to get out!
After school, I went into Mom lingerie chest and closet and purposefully dressed like I saw Mom do many times, even wore her wig.
Went Mom came up from the basement from doing laundry and laughed and asked me who gave me permission to dress in her clothes.
So, I started to cry and told her about the girl in the dollhouse. So I am sure she tried to explain my gender role but the dye was cast long before that.
I always enjoyed soft fabrics and pretty smelling things.

[jenabrooks]

Chris80, Thank you for finding that show I watched it again and it brought back memories while I was sitting on the floor at a babysitters house watching TV. Hard to believe a show like that in the 60's. That started it for me. If it wasn't for that it would happened later down the road.

[Christina89]

My first urge was when I was about 12 or 13. I was watching a TV show called Totally Spies. I suddenly had an urge to go upstairs and try on some of my mother clothes. The first thing I tried on was one of her bikinis. I loved the feel of how it felt on my body. After a few minutes I took them off and went back to my normal routine for the night. The next day at school I couldn't get the thought out of my head. It was all I thought about. I couldn't get home fast enough to explore it further.

[dominique]

Must've been between 10-12. I found out that I was interested in woman's clothes. it was the range and breadth that pulled me in. I would try on my mums skirts, bras etc and the feeling was amazing. When I was alone in the house I would fully dress and it felt right. Nothing has changed except I put make up on now.

[sweetdreams]

At around 5 years old. Neighbor threw out a pair of nylon stockings. I saw them and thought I needed to play with them. It was only a day or so before mom found them and tossed them. I had to wait another 4 years for my second push to show up.

[JennniferMcC]

I was 4 or 5 one night when my younger sister and I were playing in the living room. She had on a pretty dress and a pair of white tights. (around the holidays maybe?) I'll never know quite why but I desperately wanted to know what the tights felt like so I asked her if I could wear them. As I was struggling to get into them our mom walked in and yelled "Stop! You'll ruin them!" As she was putting them back on my sister she told me if I wanted tights she'd get me a pair of my own. A few days later we were in Baum's dancewear store. She walked me up to the salesgirl and said "A pair of tights for the boy." Suddenly I was really embarrassed. The girl showed me a color chart and asked me what color I wanted. I was mortified but I thought quick and told her I wanted orange since that's what Captain Marvel wore. (I didn't care what color-God help me I just wanted some) So we took them home, mom showed me how to put them on and I got to wear them whenever I wanted. My very own orange Danskins! Unfortunately, somehow, at some point, shame at my little proclivity entered the picture and I went totally underground with my ever growing feminine "explorations." But I've always wondered what my life would be like today if I'd only embraced this from that very first day and not hidden it. And oh my, what I wouldn't give to have held on to that very first pair of tights.
-Jen

[Confucius]

I don't remember any time in my life when I didn't want to dress as a girl. My older brother enjoyed persecuting me, while my mother treated my sister like her little princess. I wanted the attention my mother gave my sister. In my formative mind I believed that if I was a girl my mother would love me more. I recall at 3 years of age, rummaging through my mother's closet and playing with her clothes. My mother would ask what I was doing, and I would explain that I was playing "mommy". This dress-up play continued even as my mother tried to stop it. At one point she made a dress for me, but my father objected and my mother gave it away. By the time I started school I was trained that dressing up was humiliating. Then I developed this idea that all boys really liked to dress like a girl, but we had to pretend that we didn't like it.

[JenniferMBlack]

I was like 7 or 8 I had a huge curiosity what it was like to wear a skirt. All the girls were wearing skirts most days at school and I wanted so badly to try a skirt. I didn't try one until I was 12 in part because I knew boys didn't wear skirts. Then there was a skirt my strong desire to wear it and no one else around. Yet I still struggled to actually put it on. In the end my desire won out. Look at me now having not worn men's clothes for two months.

[udcd]

In 5th or 6th grade, I remember having class in the school library. The teacher asked everyone if they could be one material what would it be? My answer, without a doubt, was satin. There was zero hesitation in my answer. The girls in class did a collective “ohh satin!” I remember being embarrassed but happy at the same time. I finally got to wear panties in high school and I’ve been hooked ever since.

[CDJamie2000]

It was sometime later after we got married that I tried on my wife's wedding gown. I love the way it looked on me and the way it felt. When she decided to donate it I rescue it out of the donation box and kept it . To this day I will put it on and wear it during the day.318447

[Beverley Sims]

With the girls next door, I used to play mothers and fathers, I was about 3 or 4 and was often dressed as the baby and pushed around in a pram.

I thought it was great getting a ride in a pram everywhere, a drink of chocolate milk out of a baby's bottle, wearing nappies and a pretty little frock.

Later I had to be a mother and another smaller girl became the baby.

I think that was the early conditioning as the parents on all sides got a laugh and condoned the practice.

[Teri Ray]

Like many others here I was about 6 or 7 when I found moms panties and bra in a rag box. These items were meant to be discarded but I found them fascinating and I was drawn to try them on. The rest as many of you know is history.

[Wen4cd]

When I was 5 or 6, I found my own little lace-and-frilly 'christening outfit' hidden in a box in my parents' bedroom dresser drawer. (Even the boy outfits looked like femme doll's clothing back then, so I thought it was like, from some dead sister or something, the way it was all hidden and preserved.)

Got obsessed with wearing it, but could never find the opportunity for a long while, and it's existence gnawed at the back of my head for months... until one day I was home alone for a good hour or two, and immediately tiptoed in there and tried everything on and stared at myself in the 3 mirrors on top of the dresser

It was super small but it was really super femmy and adorable and suddenly I wanted to go put on mother's lipstick....

[simoneisatg]

Well I win the award for the dumbest girl here - the first memory I have of dressing is the first time I got caught doing it.

I was on a family camping trip (oh, the irony) at about the age of 5. I had a couple of female cousins a bit older than me. I couldn't get over how wonderful their panties were, and smuggled several pairs out of their tent and into my sleeping bag. Eventually, their lack of underwear was noticed, and I was sprung. I had to return them, and even now can't work out if I was more upset for getting exposed, or because I couldn't wear them anymore.

There is actually a picture of a me in a pink dress we had in our dress-up box as kids when I was younger than that, but I don't remember it myself.

[jacques]

Hello Laurie,
I remember "borrowing" mys sister's tights when I was about 8, because I wanted to be Robin Hood.
I did some research into the age we started about 10 years ago - here it is in graphic form (I hope this works)
318992
Stay healthy!
luv J

[MindyCD]

I cannot exactly remember the first time I dressed up but I do know that I have always been fascinated my female clothing.

When I was around 8 I would sneak into my Mother's bed in the mornings when my Dad left for work. I was captivated by seeing her getting dressed. It was around this time that I started wearing her clothes and it was tights and panties mainly as everything else was way too big. My oldest Sister was born when I was 8 so it was many years before any of her stuff fitted me. I did borrow a dress from her in my 30's for a fancy dress party but that's years later.

One if the earliest memories I can recall clearly is when a female Cousin stayed with us as her Mother was in the maternity hospital. I found her primary school (up to age 12) uniform which consisted of a brown pinafore, brown knee length socks and a navy blue old fashioned type school knickers. For some reason I got dressed in my wardrobe and briefly ventured out into the bedroom. I didn't know why I was doing this but knew that it felt so good. A short while after that when I was at my Cousin's house I persuaded her to let me try on the yellow summer dress she was wearing so we sneaked off the her bedroom and swapped clothes. I think I got the better deal there. I did "borrow" the knickers and socks she was wearing that day which my Mother found which was very embarrassing at the time but quite arousing.

Some years later when some of my Sister's stuff started to fit me I was dressed in a short red skirt which had an elasticated waist, panties and socks I realized that unless I stopped crossdressing I would never be able to stop as the more I did it the better I liked it. I decided to continue and the rest is history.

[Lacey New]

I was in my early teens. Girls wore miniskirts to school and occasionally provides a glimpse of pretty panties. I was fascinated by what I saw and curious about what was underneath those pretty panties. Also, I could see bra strap under those budding blouses and I desperately wanted to experience those as well. Well, I had a young mother and a sister only a year younger and there was a common hamper in our one bathroom. One afternoon when I happened to be alone in the house, there was a pair of nylon panties peeking out of the hamper. So, out of curiosity, I tried them on and the effect was as one might expect. I found myself behaving like Pavlovs dog. Instead of ringing the bell and getting a treat, I put on panties and had an orgasm. I became fascinated with lingerie. If panties were wonderful, then panties and a bra were better. And so it began.

[Elizabeth G]

I was about 11 or 12 years old. My mother ran a pretty tight ship at home so the only thing around the house that might satisfy a young boys curiosity about girls were the lingerie sections of the Sears and JC Penney catalogs. Over time I realized I was just as fascinated with what the models were wearing as I was with the models themselves and I found myself wishing I was one of them.

[Katherine L.]

The first time I felt the urge I was when 11 or 12 and I tried one of my mom’s bras I found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any bras I could wear. One time she caught me wearing one, but didn’t make a big deal of it. I was extremely embarrassed at the time, but not enough to ever stop.

[Alexis00]

////A short while after that when I was at my Cousin's house I persuaded her to let me try on the yellow summer dress she was wearing so we sneaked off the her bedroom and swapped clothes. I think I got the better deal there. I did "borrow" the knickers and socks she was wearing that day which my Mother found which was very embarrassing at the time but quite arousing.///I “borrowed” a sun dress as an early teen that I used to wear when no one was home. Even went out to check the mail a few times. It felt wonderful!

[Blonde617]

Think I was 7 or 8, took my mothers or sisters things from the laundry. Didn’t own a wig until after college so never went out before then.

[Donna42]

I was an early teen when I first got the urge. My aunt always had very cute clothes and I found myself sneaking and wearing her panties