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Thread: at what age did you first crossdress?

  1. #226
    bollywood beauty
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    was in my teens

    was in my teens when i first crossdressed... wore my mom or was it my sis's undergarments and then went from there wearing their dresses... now it is my wife's dresses...havent bought anything myself...

  2. #227
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    Quote Originally Posted by joann07 View Post
    I didn't have the urge to dress up until I turned 37 three years ago.

    Hugs!
    I started at 14.

  3. #228
    Member charlene#2's Avatar
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    i think i was about 13 and there were about 5 of us guys and girls playing strip poker and there was this one girl who really liked to lose,or just show off her body.well any way i had lost everything and was just sitting around playing hands and i made a joke of putting on this girls panties and for a while i felt so good and no one seemed to care and nothing was ever said about it,i guess from then on i was hooked

  4. #229
    Member Ashley_in_Texas's Avatar
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    Started at around 14 or 15.

  5. #230
    Aspiring Member Jaclyn NM's Avatar
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    I was about 5 or 6 years old when I first tried on a pair of my moms high heel shoes, and instantly loved it. It just continued from there, and with each new article of female clothing that I tried on, I loved it more and more, which is where I am today. If I could, I would only wear female clothing.

  6. #231
    Feelings with no outlet.. Ballerina's Avatar
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    Besides the play skirt my cousin tackled onto me (10), I picked up my first dress and tried it on at age 12.
    I'm not out to fool the world, just my inner girl
    Real men wear pink <3

    G.K. Chesterton
    “Fairy Tales are more than true; not because they tell us that dragons exist, but because they tell us that dragons can be beaten.”

  7. #232
    Junior Member DeniseCA's Avatar
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    Probably about 10 or 12, tried on my sisters panties in the laundryroom. They just felt so sexy, from there I tried on pantyhose, bra, skirts, & blouses. In a way life was easier pre-puberty ... easier to fit into ladythings!!

  8. #233
    Aspiring Member karennjcd's Avatar
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    About 13 I believe, wearing Mom's stuff. Was caught by brother, and Mom knew her stuff was disturbed, ugly scene prevailed. I think it's since been forgotten.

    Karen

  9. #234
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    I was 13 the first time I dressed, went into public dressed when I was 15.

  10. #235
    We all have our dreams... AmiFL's Avatar
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    teen crossdressing

    My dressing started in a sad sort of way. I was about 13 or so. My fathers best friend had a daughter who was causing trouble at home so she came to stay at my house. Dad liked having a "daughter" around so when she went back home I tried to become one too. I started wearing my mothers things and playing with her make-up when I was home alone. Some night I would walk around outside dressed almost getting caught once or twice. That was over 40 years ago and dressing still fascinates me. Posting my thoughts also is proving interesting....... thanks

  11. #236
    New Member JENNYgirl's Avatar
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    Frist time for me

    The first time for me was when i was 13 been hook ever since love the feel of hose and spandex

  12. #237
    New Member Aurora Rosas's Avatar
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    First time as a girl

    As most tg girls I tried on my sisters clothes before elementary school, probably at 5. And kept on doing so till I left for college. However it was not till the age of 43 when I dressed in full, great wig and make up, with the help of another transvestite, and looked as a sexy woman, and loved it.

  13. #238
    Exploring NEPA now Cheryl T's Avatar
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    I was about 8 when I first remember donning some of my mother's clothes.
    Once I tried them I only wanted more and I had no idea why. It was only a matter of time till I had some of my own and that has never changed.
    Now I spend about 1/2 of my time expressing my femininity and of course want more.
    I don't wear women's clothes, I wear MY clothes !

  14. #239
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    Oh my. Lessee...I think 6 or 7. I think I remember Mom's things and how they felt, but not much more than that. I don't remember at which time it became a sexual experience for me, but I do remember when it stopped. I remember distinctly one morning on my way to work, with painted toenails under my Kenneth Cole socks, saying to myself guiltily, "You wear women's clothes"...about ten minutes later I remember thinking, "No I don't. Those are MY clothes".

    From that moment on life was so much easier.

  15. #240
    Junior Member BecomingMichelle's Avatar
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    I was nine

    My mother stored some of her old clothes and my sister's old clothes in my bedroom. My mother had great clothes. Cute minis and sundresses. I was particular enamored with a blue sundress and my sister ruffled panties and a leotard.

  16. #241
    Princess Bunnie BunnieCashmere's Avatar
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    My grandmother was a master seamstress who made dresses and costumes for plays. After the plays she just threw most of the clothes in a big trunk in the basement.
    When I was young, like 8-9 I would go down there because that's where all the toys were, and secretly try on the dresses and parade around. My cousins (girls) and stuff thought it was cute and funny. It didn't bother them, so why should it bother me?
    Later on in life (12-13) I started trying on my mother's lingerie and stuff. I haven't been the same since.

  17. #242
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    Quote Originally Posted by joann07 View Post
    I didn't have the urge to dress up until I turned 37 three years ago.

    Hugs!
    loved your pictures. please is there more sexy pictures? love to wear pantyhose since last year. when i tryed my stepdaughter red pantyhose. now i wear her bras, thongs, pantyhoses and short dresses. love to her from you.

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