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Thread: The first time you wanted to?

  1. #1
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    The first time you wanted to?

    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.

  2. #2
    Member Brianne_bc's Avatar
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    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.

    No Heel is Too High.... When it's Pointed at the Ceiling

  3. #3
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    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

  4. #4
    Silver Member Geena75's Avatar
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    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.

  5. #5
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    Quote Originally Posted by Geena75 View Post
    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...

  6. #6
    Miss Conception Karren H's Avatar
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    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.
    Current Obsession - Breasts and Lingerie!

    .......My Photos

  7. #7
    Aspiring Member Kelli_cd's Avatar
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    My earliest memories involve wearing my grandmother's petticoats and mom's heels. I was 4 or so.

  8. #8
    Member JennyMay's Avatar
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    Quote Originally Posted by jenabrooks View Post
    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.

  9. #9
    Senior Member kayegirl's Avatar
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    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.

  10. #10
    Member ronny0's Avatar
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    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.
    Last edited by ronny0; 01-04-2021 at 01:10 PM. Reason: too_long

  11. #11
    Member Brandi Christine's Avatar
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    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...
    ...Damsel in distress.
    Not exactly natural, Stunning none the less...

    (As Girls Go by Suzanne Vega)

  12. #12
    Aspiring Member Georgina's Avatar
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    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.

  13. #13
    Senior Member Angela Marie's Avatar
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    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.
    Last edited by Angela Marie; 01-01-2021 at 08:46 AM.

  14. #14
    Aspiring Member josie_S's Avatar
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    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!

    pom pom socks.jpg

  15. #15
    Member Deborah G's Avatar
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    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.

  16. #16
    Miss Judy Judy-Somthing's Avatar
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    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!
    "This is ME" I am not CRAZY, I'm just a GUY who likes dresses!
    Since allot of men dress up in woman's clothing that makes it a manly thing to do!
    Much more fun than fishing.
    I do construction like house building and I love CD-ing, what's the difference?

  17. #17
    Aspiring Member joanna4's Avatar
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    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
    I don't dress to impress, I dress to outdress

  18. #18
    Member Deborah G's Avatar
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    Quote Originally Posted by joanna4 View Post
    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.

  19. #19
    Gold Member Lana Mae's Avatar
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    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
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  20. #20
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    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.

  21. #21
    Member KristyPa's Avatar
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    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.
    Last edited by KristyPa; 01-01-2021 at 12:16 PM.

  22. #22
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    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.

  23. #23
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    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.
    Last edited by Melissa in SE Tn; 01-01-2021 at 01:43 PM. Reason: Auto correct

  24. #24
    Aspiring Member Star01's Avatar
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    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.

  25. #25
    Silver Member LilSissyStevie's Avatar
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    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.

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