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Thread: When did you first crossdress?

  1. #601
    dressed and loving it michelle az's Avatar
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    as all of us very young moms petticoat around 8

  2. #602
    Aspiring Member StephanieDragg's Avatar
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    when I was 8-9 trying on my moms nylons she hung over the shower rod

  3. #603
    New Member GirlyTGreen's Avatar
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    Around 5 or 6 my first was much like Tasha's, i needed a pair and my aunt gave me a pair of my cousins panties. Something about wearing those panties felt right....then i started trying on my mom pantyhose and eventually my babysitters dresses when i got the chance to sneak in her room. Its grown from there ever since.

  4. #604
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    Early twenties but I don't know what triggered it.

  5. #605
    Junior Member Underdressed's Avatar
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    Aged 5 or 6 trying to get plastic christmas stockings on under the table (after I had eaten all the sweets), aged 10 wearing mums heels, aged 13 progressed to nylons and suspender belt. it's been a long journey.

  6. #606
    Cougar in hiding kymmieLorain's Avatar
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    I think I was 12-13 I tried on a pair of my sister panties. I had the love for lingerie much farther back than that.

    Kymmie
    Just your average harley riding crossdressing biker

    Why be normal??????

  7. #607
    Evolution of Self Erica William's Avatar
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    Wow what an awesome topic. It's taking me a few days to get through to the end of this thread , but its got me really thinking. I can remember maybe being 7 or 8 years old going to my moms dresser drawers. But when I was 10, I found a books that my dad had. They were these little paperback dirty novels with a story line like you would find on literotica or somewhere. Most of them were straight porn type stories. But there was one that started out with a young boy dressing in his sisters clothes and getting caught by his father. The book itself was about incest. But little Tommy was always made to dress in his sisters clothes. And as I sat there reading this book I was so incredibly aroused. And when I went home after the end of the summer I took it with me. I can remember a week after I returned home I was stealing the neighbor girls panties so that I could wear them. So I think that's when it really clicked in my head I like this and not only do I like it I love it. So it's been on and off at different degrees for most of my life. This time I no one to answer to but me.

  8. #608
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    i did start dressing at age 15 mom stuff got makeup at 17 now ever time i can love it

  9. #609
    Member trisha11's Avatar
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    I was 7-8 and I found my sisters satin panties and matching bra, from that point forward I was hooked, have never looked back
    Trisha Simone

  10. #610
    Member tiffyjo's Avatar
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    I was in 5-6th grade in school. My mom had a "rag bag" in my upstairs closet she threw old clothes in to use for rags at a later date. I was looking through it once and found some of her old panties. I had to try them on,,, and that was it, I was hooked. Panties and pantyhose mostly. Expanding soon!

  11. #611
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    Age 6-7 i think, my best friend then was a girl the same age and used to spend a lot of time over her house on sleep overs, she also had a sister and we used to hang out a lot and get very messy as kids do but my clothes used to get messed up so my gf and her sis used to give me thier clothes to wear, i was never short of things to wear lol they always made sure i was well looked after lol at the time i never thought anything of it, it beats getting cold and having nothing to wear so yea i was quite young, lol its no wonder i like dressing like a girl.
    Last edited by JessicaJJ; 05-06-2014 at 06:39 PM.

  12. #612
    Platinum Member Angie G's Avatar
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    It was better then 50 years ago. Up in the attic. Shoes adress undies when I could find them.Loved it from the start.I think I was 10 or 11 at the time.
    Angie

  13. #613
    New Member Alexand's Avatar
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    At 12, I wore my mom's pantyhose. It was a new one right from it's package. I wore it and I felt so high I could not believe it! After that I carefully put it back into the package and the drawer. Now that I think about it my mom could definitely tell that something was wrong with her "new" pantyhose when she opened it, but she never said anything. After that, I remember stealing 2 pairs from a neighbour's yard where they where hanging to dry. I kept them hidden in my room but my mom found them after a couple of months and threw them away, again without telling me anything. Later I started wearing my teenager sister's bras and panties (no teenager wore thongs back in the early 90's) and I was wishing I were a woman. I am not gay, I never looked at or thought of another male in an erotic way but I know that I would feel more comfortable being a woman.

  14. #614
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    I wouldn't calling it totally crossdressing, but in 6th grade trying on friends' sisters panties and pantyhose...

  15. #615
    Aspiring Member fun4metoo2004's Avatar
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    12 or 13. Loved it but really did not understand the feelings then.

  16. #616
    New Member redwildberry7's Avatar
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    I dressed up around middle school. I went all out. I looked really hot, and danced around a little. It was so amazing. I did it every time I had the chance.

  17. #617
    New Member Thom2332's Avatar
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    Summertime last year, I was sitting around in the usual mens baggy cargo shorts thinking to myself damn these things are uncomfortable. I envied the girls who got to walk around in short shorts and tank tops. I bought a couple of pairs of women's shorts to wear at home. I wore them off and on and am really just now starting to get more into dressing.

  18. #618
    Junior Member savannaxdrsser's Avatar
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    First time

    The first time i started wearing was when i was around 11 or 12. For some reason puberty hit and i got an interest in wearing my sisters panties. After that I would dress on and off, but never fully. Started dressing more fully last 5 years and it has been wonderful.

  19. #619
    SamanthaSatine
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    Back in the 1960s..
    Found mum's silky slips, bras, girdles, stockings, make-up and heels..
    Seemed natural to play dress-up as liked girls and what they wore..
    The rest as they say is history..

  20. #620
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    I was 14, mom's panties, slip, panty hose and heels. Added a dress later. Due to circumstances, I all but stopped about a year later, and completely stopped by the time I was 20. Restarted again, very recently.

  21. #621
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    Well I have to say that this isn't the first time I've cross dressed! When I was about 11 years old I was getting to the age where I was hitting puberty and became curious about my sexuality. My mum showed me this black and white skirt that she had and even let me try it on. I loved it, so I kept putting it on. However, as the years went by I became more and more nervous about putting it on and I certainly didn't want my parents to find out, so I would wait until they went out and left me home alone, and nick it from her drawer! I did this on and off until I was about 15 when I just stopped. Until, that is, one day last week when I suddenly got an urge to do it again. It started with me shaving my legs, then making DIY skirts out of old leisurewear shorts, and this week I got some tights.

  22. #622
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    Probably around age 10 or 11... I used to paint my toe nails red, wear my mums stockings and black stiletto heels. I started to wear my first proper girlfriend's skirts and tops around age 17.

  23. #623
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    I think I was 10 or 12 the first time I tried on a pair of my sister's panties. I knew I shouldnt be doing even then. I remember being immediately jelous that girls got to wear such soft fabrics all the time- I felt almost cheated! From there, it just expanded, from panties to bras to outfits. I love it haha

  24. #624
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    Probably around age 10 or 11... I used to paint my toe nails red, wear my mums stockings and black stiletto heels. I started to wear my first proper girlfriend's skirts and tops around age 17.

  25. #625
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    What really stands out to me is when my sister got married and at the time I was living at my parents house, my sister after the wedding brought over all the bridesmaid dresses, my parents went on vacation and I decided to try on the bridesmaid dresses, ever since then I have been alot more embraced to crossdressing.

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