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Thread: When did you first crossdress?

  1. #26
    Senior Member Jaymees22's Avatar
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    I know I was 7 because I was in the second grade production of "Cinderella". I played one of the ugly sisters, type casting? Anyway I looked happy so it must have been the start of something, I wonder what?
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    Last edited by Jaymees22; 04-07-2018 at 10:23 PM.
    I enjoy being a boy, being a GIRL like me!!!

  2. #27
    Platinum Member alwayshave's Avatar
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    I know I was about 4 or 5, my mom kept stuff on the stairs to the attic which was in my room.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  3. #28
    Senior Member Tracy Irving's Avatar
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    My best guess is somewhere in the six year old range when I discovered how wonderful it felt to wear my mothers panties.

  4. #29
    Senior Member kayegirl's Avatar
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    It seems so long ago now that it's hard to be precise. I had been playing dress up since the age of 5 or 6. Somewhere I even have a photo of me wearing my sister's bathing costume. But I was 13 when I first consciously dressed full girl. Home alone and again with my sister's clothes. For me it was a true epiphany, and I knew that I wanted to be that girl forever afterwards. Sadly it took many years before I could be as open as I am now, but that's another story, and too long for now.

  5. #30
    Member Megan b's Avatar
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    I was 12/13 when I tried on a pair of my moms pantyhose for the first time. I was hooked from that moment on. Shortly after the hose came panties, then girdles, slips, bras and finally a dress. No wig or makeup till years later. But now I can't really imagine not being a crossdresser, it's just part of me.

  6. #31
    Resident Polymath MarinaTwelve200's Avatar
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    I started with Mom's lipstick at age 12------Since I was 8 In the late 1950's,I remember the (joking) threats by Mom other women and older girls at our consolidated School, to put that red 1950's lipstick on me. The idea horrified me. especially since I thought it would not come off. The worry was for naught, none of them ever followed through with their threats----Although I came pretty close when, at a whim, Mom had dad hold me down, one time, to actually do just that, but "chickened out" at the last second "I don't know, it might give him a complex" was her excuse.-----But the prospect fascinated and horrified me for years later---at about age 12, I was left alone at home for some hours, and decided "what the heck, GO for it!" I first tried a touch on my wrist---and behold! it wiped OFF!---Then on my lips it went.----at age 13 I tried on a girdle, some panties and nylons from the laundry---THEN, (why not) a bra (stuffed with my underwear) and a slip and finally a housedress to top it off---Then Lipstick (of course) and a scarf to cover my head.---I was Completely Dressed! ----And continued (with some breaks) when I could, to this day.

    I still have some "holdovers" from my roots--I need the darker shades of red Lipstick to really feel "dressed". Yes, I have tried other shades, and I really look good (if not better) in them, but I just cant get my "rush" in anything without the red lipstick. (the 50's influence is still there, I suppose) Perhaps it is a "fetish"
    Last edited by MarinaTwelve200; 04-08-2018 at 02:14 PM.

  7. #32
    Member Anna Stouf's Avatar
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    The year was 1954. I was 10 years old. On Halloween that year, Mom sent me to school completely dressed as a girl. Panties, slip, and pretty dress. I loved it soooo much.

    Been doing it ever since.
    My favorite dress is a Dirndl.

  8. #33
    Member mdavis's Avatar
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    I started in about grade 6 or 7. Same as many. Tried on a pair of my mother's nylons. Loved the feel of them. Progressively would try on some of her clothes as well. There was a pause for several years until shortly after I got married. That was about 27 years ago. I've dressed on and off since then but, for the last three to four years have dressed more and more fully (wig, full outfit, at the very least lipstick) and today purchased some of my own makeup to try.

  9. #34
    Member michelleg's Avatar
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    About 11 or 12, home alone and got the urge to try on my Mom's slip, it felt wonderful and I loved it. So then came the panties, bra and stockings, heels that didn't fit but still looked nice. Took a look in the mirror and was hooked, anytime after that when the opportunity was there I was dressed.

  10. #35
    Aspiring Member krissy's Avatar
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    I was 6-7 i used to wear my sisters clothes .when mom didnt do laundry i would wear her panties .loved it

  11. #36
    Aspiring Member Lacey New's Avatar
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    I guess that depends on how you define crossdresing. If it is the very first time that a person wears an item of cloting of the opposite sex or is it the very first time that a person wears an item of the opposite sex specifically for their pleasure? I remember one time when I was about 10 at my Aunt and Uncle's house playing with my female cousin in the creek. We got all wet and muddy and my Aunt put me in a pair of her side zip bluejeans while my boy jeans were in the wash. That was when I was about 10 and I thought nothing of it. However, by the time I was 13 or 14, I was "borrowing" my mothers and sisters panties for my pleasure. And while I don't remember borrowing any other lingerie at that time, I knew that I wearing women's clothing was exciting and that I wanted to wear more. So I guess that was the start of my crossdresssing.

  12. #37
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    I was around 11.

  13. #38
    Silver Member stephNE's Avatar
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    When I was about 5, I remember going into my mom's dresser and getting out a bra and panties. I loved hooking the bra and spinning it around. Of course the panties were too big, but I would put them on overtop of my little boy clothes, and tuck the panties into my waist band to keep them up. I would put them on, and go back to my room to play.

    There were two boys in our neighborhood that were about the same age as me, but I didn't like playing with them, they liked playing outside and getting dirty. The house across the street from us had three daughters, all older than me. I loved to play with them. At least once (also about age 5) they dressed me up in a dress with shiny black patent leather shoes and white socks with ruffle tops.
    Stephanie

  14. #39
    Aspiring Member Georgina's Avatar
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    I was somewhere between 6 and 10 years old and my first garment was my mom's slip. Never looked back since.

  15. #40
    Silver Member Elizabeth G's Avatar
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    I was right around 11.

  16. #41
    New Member Satellite's Avatar
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    It was when I was 13. I was home alone for 2 days and I went into my mom’s lingerie drawer. It was full of panties, stockings and pantyhose. I was in heaven. I put on my mom’s panties and stockings attached to a black suspender belt and I started walking around the house. It felt so nice. I could not resist and I took a pair of pantyhose for myself. I would wear them everywhere I go, under my jeans of course. I used to hide them under my pillow until my mom found them while cleaning my room. We had a conversation and she told me that I should have spoken to her about my curiousities. She asked me if I tried on anything else while I was home alone and I told her that I tried on her panties and stockings. My mom was surpised that I was honest to her and she told me that I shouldn’t wear someone elses underwear without permission. She also asked me if I liked wearing panties and I told her that I fell in love with them because they were so comfortable. She told me that we will go out shopping tonight. That night we went in town to a lingerie shop (i don’t remember the name of the shop, sorry!) and she told me to pick the panties that I liked the most. I remember choosing some purple hipster panties. I tried them on until I found the right size. The experience was so nice. She ended up buying me panties so I wouldn’t use hers again. The next day she came home from work and she told me that she bought something for me. It was a pair of black pantyhose. I hugged her and then I thanked her. A few weeks later, everytime I went shopping with my mom I was asking her if I could get another pair of panties and she never refused me. Best mom ever!

  17. #42
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    Don't remember the exact age but pretty young. Put my mom's bra on and then her nylons, no pantyhose back then. As I got closer to my teen years I developed gynomastia and then bras started to fit better. No one ever knew, other that probably my mom as I'm sure she could tell when I had worn some of her stuff. She never said anything and I would have died if anyone ever caught me.

  18. #43
    Member Cherylgyno's Avatar
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    I was 6 year's old. I wore my mom's pantyhose, rib knit body suit and bra.

  19. #44
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    I was twelve years old when I slipped into my first pair of panties. They were purple with tiny white stars. The panties were a bikini cut made of soft cotton with a tiny lace trim along the waist. I felt excited and nervous as if I was doing something deliciously forbidden. My head was spinning. Around the same time, I paired the panties with a demi bra. It was lightly lined for a subtle lift and had underwire cups. It was probably made of nylon and spandex. I distinctly recall it was coconut white. The feeling was sublime!

  20. #45
    Member BillieS's Avatar
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    I was 8 or 9. I tried on my mom's bra and girdle, and almost got caught!

  21. #46
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    What a memory! I love how you bring it to life with your words.

    [SIZE=1]- - - Updated - - -[/SIZE]

    It was meant to be!
    Quote Originally Posted by Esther Latour View Post
    When I was in the first year of art school, at a fancy dress party. It was supposed to be ironic but of course it really wasn't. I had been having fantasies about it for years.
    [SIZE=1]- - - Updated - - -[/SIZE]

    That's some mum!
    Quote Originally Posted by Satellite View Post
    It was when I was 13. I was home alone for 2 days and I went into my mom’s lingerie drawer. It was full of panties, stockings and pantyhose. I was in heaven. I put on my mom’s panties and stockings attached to a black suspender belt and I started walking around the house. It felt so nice. I could not resist and I took a pair of pantyhose for myself. I would wear them everywhere I go, under my jeans of course. I used to hide them under my pillow until my mom found them while cleaning my room. We had a conversation and she told me that I should have spoken to her about my curiousities. She asked me if I tried on anything else while I was home alone and I told her that I tried on her panties and stockings. My mom was surpised that I was honest to her and she told me that I shouldn’t wear someone elses underwear without permission. She also asked me if I liked wearing panties and I told her that I fell in love with them because they were so comfortable. She told me that we will go out shopping tonight. That night we went in town to a lingerie shop (i don’t remember the name of the shop, sorry!) and she told me to pick the panties that I liked the most. I remember choosing some purple hipster panties. I tried them on until I found the right size. The experience was so nice. She ended up buying me panties so I wouldn’t use hers again. The next day she came home from work and she told me that she bought something for me. It was a pair of black pantyhose. I hugged her and then I thanked her. A few weeks later, everytime I went shopping with my mom I was asking her if I could get another pair of panties and she never refused me. Best mom ever!

  22. #47
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    I was around 9 or 10 and found one of the drawers in my mom and dad's room full of sexy black thigh high hose, panties, garter belts, and black lingerie. Everything in that drawer was black and sexy and I just couldn't resist trying on the black thigh high hose, a pair of her black panties, the black garter belt and found out real quick how to attach the black thigh high hose to the garter belt, and one of her sexy black bras.
    I just had this sensual sexy feeling all over my body and in my mind. Upon further snooping that day while no one was at home, I found my father's Playboy magazine collection hidden underneath the bed.
    Well you girls can just imagine what I did myself when I laid down on the bed with all of that sexy black stuff on with my dad's Playboy's open and next to me! After that day, I've been hooked ever since.
    I've personally tried for many years to take my cross dressing to a the highest level possible and I'm always looking for ways to improve.
    Thanks for reading my note...Sincerely Scarlett

  23. #48
    Queen of Chinatown jennifer0918's Avatar
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    I was around 10 years old I wore a pair of jelly shoes back in the 80ies.

  24. #49
    Junior Member JennyLiz's Avatar
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    I was about 12 or 13. It was my sisters swimsuit, then her panties. Been hooked ever since, swimsuits are still one of my biggest enjoyments to this day.
    My wife told me she didn't want me to become Liz from AHS Hotel.
    I Promised her that I have never and do not plan on killing anyone.
    I wonder why she wasn't comforted by that?

    (True Story btw)

  25. #50
    Member jamienoir's Avatar
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    Since I can remember. I got spanked when I was 5 or 6 for wearing my sisters panties. By the time I was 10 I was full blown dresses, heels, makeup etc. I can't imagine why I started. I would go to the local library and get books in transvestim and hide in a remote corner reading the very adult theories. I then discovered the term drag queen due to an article in a magazine abt La Cage. That really gave me more subject matter to look up!

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