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Thread: When did you first crossdress?

  1. #401
    New Member Shar's Avatar
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    I started at the age of 17 and by 18 I was full time,going to college as a coed. Never looked back.

  2. #402
    Member Billiejosehine's Avatar
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    I don't know exactly when, but I do remember wearing my moms stuff sometime at a young age. I think it was at the of 15 when I really began CD and I have been doing it ever since.

  3. #403
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    I started when I was 8 or so, and trying out mom's clothes and lingerie and along my teen days.

  4. #404
    Happy tranny MsPriscilla's Avatar
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    aged about 13. got this urge to try on Mum's clothes while she was out and got that sexual buzz, loved it and still do

  5. #405
    New Member Courtney Ramona's Avatar
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    I believe I was 5 when I found my mom's clothes from when she was a kid in a suit case. I didn't give it much though but I kept on dressing never felt bad never felt wrong
    Last edited by Courtney Ramona; 12-12-2013 at 06:03 PM. Reason: misspelling

  6. #406
    Member Algoma's Avatar
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    I remember being 5 or 6 putting and on my mothers jewerly, clip on earings and lip stick. By jr high I had taken her fishnets, loved them. By college was into my girl friend clothes. Put dressing aside for 20 years and didn't buy my first pair of pumps until much later, 40's then the dam broke, with clothing, corests, wigs and makeup. The rest is history, Algoma

  7. #407
    Valerie G valerieg's Avatar
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    My earliest memory is from when I was about 4 years old. My mother had a short black gaucho that I could wear like long pants. I'd put them on an run around in the laundromat on Saturday morning laundry runs.

  8. #408
    New Member Arianny's Avatar
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    When I was about 5, tried on some pantyhose and have loved it ever since.
    But I only do it for the sexual thrill, once I relieve myself I put on my regular clothes.

  9. #409
    New Member VickieFairfax's Avatar
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    Growing up with 2-older sisters that are close in age, I was always jealous of the attention and clothes that received. I'm not sure if at what age (7 or 8) I first tried on a dress, but I've been hooked since.

  10. #410
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    Started about 8 whn I was "used" as a model for a flower girl's dress for a neighbor girl's wedding...told to my face I was too pretty to be a boy

  11. #411
    New Girl On The Block NikkiBeth's Avatar
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    I don't remember exactly but I remember trying on my mom's stockings and white fishnets in our laundry room. I was probally around 4 or 5. The rest is history.

  12. #412
    Silver Member Stephanie Julianna's Avatar
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    I'm the youngest with four older sisters. I was 6 when my oldest sister was 16. That was 1955 and the girls' dress were to die for. I think I started around then because I was old enough to be left home after school until my mom came home from work in an hour or two. In that time I tried on every bouffant petticoat and dress my sister owned.

  13. #413
    Member SarahBJackson's Avatar
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    Over 5 years ago, I dug into my wife's drawers looking for pantyhose or tights because of a sexual fetish. However, in May 2012, Sarah emerdgeed and I started dressing then again NOT sexual fetish, but because I'm probably a transgender.

  14. #414
    Member LadyInRed's Avatar
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    For me it would have started at about 9-10, I realized there was something not fair, girls got all sort of fun clothes, skirts pantyhose, makeup, and that wasn’t even including underwear, I started playing with my moms makeup trying it on, at some point I would sneak into my parents bedroom and I tried on some of her clothes, then my parents caught me one day, boy did I hear about that. And that ended that while I was under their roof

    So the first time I actually tried full on when I was 20 and living on my own

  15. #415
    Full-Time Duality NathalieX66's Avatar
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    This is the classic and famous question, and it appears on this forum from time to time, and every now and then.

    Without getting into specific times and dates in our lives, it often begins in that very moment in our childhood lives where we ask that question "why do girls wear dresses, and boys wear pants?"

  16. #416
    Member Jamie Christopher's Avatar
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    As I remember, I was about 11. We had a big house, 8 kids, 3 girls and 5 boys, the girls all my elder. I went up in to the attic one day, and was going through some boxes of stuff, and found a white full slip. I remember taking off my shirt, and pulled that slip over my chest and pulled it down....the feeling was intoxicating...and the eventual result is what you might imagine; a first for that little boy...lightening! There was no turning back after that, I was changed forever! After that my mom started finding me hiding one of her bras between my mattress, oye! Still one of my favorite things: pick out a pretty white bra, insert my breast forms, and pull a nice lacy full slip over and down over my body...heaven! I always wished I could look down at my chest and see female boobs.....
    Last edited by Jamie Christopher; 12-17-2013 at 12:37 AM.

  17. #417
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    When I was about 9, my sister had a heap of dressup material in our playroom, so I was frequently in girls clothing and jewelry, my sisters had this sort of coloured lip gloss and I started wearing that. As I got older, I started wearing girls clothing more frequently, I was still using lipgloss and lipstick up until I was about 12. One day I planned to try a full girly makeover in the bathroom, so I grabbed a few of my sister's dresses, a bag of jewelry and my mum's bag of makeup. I was very rough with my makeup skills and I looked a bit subpar. Over the years I have improved greatly and could pass for a female with a wig and a bit more skill, I still can't apply blush, lol.

  18. #418
    I think I must have 4 or 5, sneaking into my mum's room as she slept, trying on here underwear and nylons.
    I remember also nagging my Grandma for lipstick at this age.
    I seem to remember having to wear green tights for a school play at a similar age. Protesting to my parents that these were for girls, but secretly loving it.

    But it really started when I hit puberty, in my mums wardrobe, and faking sick days to stay home from school.

  19. #419
    Aspiring Member
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    I understand that about 70-75% begin in early childhood. Then about 20-25% begin in adolescence. Finally about 5% begin in adulthood.

    As for me, it goes back to my very earliest memories. My mom would tell stories about how she wanted a daughter when she was pregnant with me. I was a very clingy baby, always wanting to be carried by my mom. When I was about 6 months old, my mother was pregnant again. This time she gave birth to my sister. My mother finally got the daughter she always wanted. My sister was pampered, spoiled, and I was jealous. When I was about 3 year old I started raiding my mom's closet and playing "mommy". In order to keep me out of her closet my mother made me a dress as play-clothes. My father was upset with this and the dress had to go. I had to undergo some sort of aversion therapy, but it didn't take.

  20. #420
    Junior Member autogirl's Avatar
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    12 years old

  21. #421
    Pink and Quirky FeliciaCDSNJ's Avatar
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    The earliest I remember, would be around 5 years old. It began with pantyhose and scrunchies and escalated from there. Been caught plenty of times and had my butt beat for every time too but in my opinion it was well worth it and now at adulthood, it's all fair game. I remember being caught before school wearing a bathing suit under my clothes, I had got the bad end of the belt and hand before school and more of it after I got out of school. It made me much more wise were to stash my hidden gems out of the gaze of parental figures and siblings. I didn't start fully dressing, however, until the age of 19 where it felt so natural to me to be dressed up, even it was just around the house.

  22. #422
    Discovering the Gurl Xandra's Avatar
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    There's dedication for you. Luckily I was never caught. :-)
    Quote Originally Posted by FeliciaCDSNJ View Post
    The earliest I remember, would be around 5 years old. It began with pantyhose and scrunchies and escalated from there. Been caught plenty of times and had my butt beat for every time too but in my opinion it was well worth it and now at adulthood, it's all fair game. I remember being caught before school wearing a bathing suit under my clothes, I had got the bad end of the belt and hand before school and more of it after I got out of school. It made me much more wise were to stash my hidden gems out of the gaze of parental figures and siblings. I didn't start fully dressing, however, until the age of 19 where it felt so natural to me to be dressed up, even it was just around the house.

  23. #423
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    I see a trend here...it's the pantyhose! The pantyhose companies made them so irresistible so they would have a more people to sell to. It sure worked on me lol. Probably about 10 like a lot of people here. I do remember putting on as many pantyhose as I could find at one time. Not sure what that was about....

  24. #424
    Member Carrols's Avatar
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    I was 11 or 12 when I tried on my sister’s bikini. I remember loving how good it felt. Next were her panties and a bra. I found a pair of my Mom’s stockings and a girdle with garters in the bathroom and tried them on. I wore them to bed that evening. That was 48 years ago and I still love the look and feel of a bra and stockings!

  25. #425
    Member Patty-Fay's Avatar
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    I was around 4 years old, this was 1958 (before there were panty hose, btw. I had two older sisters, 5 and 8 years older than me. I remember always being jealous of the pretty clothes they always got (I suspect this jealousy is at the root of my obsession with feminine attire). I specifically remember coveting the younger one's new red petticoat. I put up such a fuss she let me wear it frequently. In later years, I'd sneakily wear their panties and bras, and put on lipstick. When I got a job in my later teens, one of the first things I bought myself was a cute baby doll nightie. I never fully dressed until I moved away from my parents in my early 20's, and I had both the time and money to indulge myself.

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