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Thread: When did you first crossdress?

  1. #301
    Member laura.lapinski's Avatar
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    I remember I had erotic thoughts at age 5 or 6 ? about wearing women's underwear. I don't remember actually putting anything on until about age 12 when I put on my cousins one-piece, body-hugging bathing suit in the privacy of the bathroom in their house. It felt so great.

  2. #302
    GG ReineD's Avatar
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    Quote Originally Posted by laura.lapinski View Post
    I remember I had erotic thoughts at age 5 or 6 ? about wearing women's underwear. I don't remember actually putting anything on until about age 12 when I put on my cousins one-piece, body-hugging bathing suit in the privacy of the bathroom in their house. It felt so great.
    Thanks for mentioning this. A lot of people think that starting to CD at a young age means that it is not sexual for them, when in fact, children do begin to experience sexuality while very young.

    http://nctsn.org/nctsn_assets/pdfs/c...ndbehavior.pdf
    Reine

  3. #303
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    the first time i cross-dressed i was about 10 trying on my sisters underwear while everyone was out and it was only until about 6 months ago i started wearing dresses and other womens clothing. it feels great and even better as my wife enjoys me doing it.

  4. #304
    Member alicia45's Avatar
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    I was about 4 and trying on my mom's clothes and pantyhose. I did it openly but then my step-dad wigged out a bit when he came into our scene. My mom didn't like it but let me do it. I was a kid after all and playing at being Peter Pan with nylons as tights. Later from about 11 to 14 years old, I'd hide it but would go out when my mom was at work in the city and would take me with her. I'd stash some clothes in a backpack. Back then my hair was a bit on the longish side and I could muster a decent pass but without makeup or very little since I had to remove it in order to check in. I'd walk to shops and try on clothes and shoes. Did anyone notice? I'm not sure, but I felt I was believable. Once I did get busted buying pantyhose when the clerk asked in a snarky tone if they were for me. Another time was when I was trying on Mary Jane china flats that were popular back then. The clerk told me to scram because I was a boy. I had it out with her, but I don't think she was convinced. Others didn't seem to mind.

  5. #305
    Member Marissa V's Avatar
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    My first memories are from when i was 4-ish. Dressed in clothes from my grandma (very tiny and slim woman), with a self made 'microhpone' singing along with Waterloo from Abba. I never really wondered about it until i was 7. First soccer match and we had to hit the showers after that...but that was a big no no for me. No way i was going to shower with the boys...
    You can't fly with the eagles if you sleep with the pigeons.

  6. #306
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    Mine was when I was five. I only really remembered this a few years ago. At primary school, once you had finished your work you were allowed to play with the toys and so on. There was a Wendy house in the corner of the classroom with a dressing up box. I remember a turquoise dancing leotard that had a frilled skirt to it. I would sometimes put this on (and so would some other boys, if I remember). It was definitely my first sexual experience and i remember feeling all tingly.

  7. #307
    Junior Member StephanieCD21's Avatar
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    It was mom's shoes when I was about 5. Over the years the occasional piece from mom, aunts, girlfriends, etc. Oddly, it would be over 20 years before I figured out what was really going on. So may years of not dressing wasted. <sniff>

    ...OK, I am glad I missed 80's fashions.

  8. #308
    Lingerie Girl Andi.Devine's Avatar
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    I don't remember exactly when my first time was, I was probably about 10, but I do remember exactly what I put on. It was a matching satin and lace pink camisole and short set. It was my Moms. I believe that I can still remember how I felt when I put it on, quite erotic.

  9. #309
    Jessie White
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    I must have been around 7 years old. I remember sneaking into my sisters room and trying on underwear. From there it was 'borrowing' skirts, tights and underwear when everyone was out.

  10. #310
    New Member billy419's Avatar
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    when I was about 17 I would wear panties sometime, in the last year I have been dressing up some

  11. #311
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    when i was 12 i seen this lepord bra and matching panties on this porno and i got trund on so the next day i whent in my moms room and got into her bras and panties and the rest is history

  12. #312
    Coulda, woulda, shoulda.. PattiMichaels's Avatar
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    I was 4 years old at my grandmothers house. Mom was working nights in retail and Dad was out. I insisted on being allowed to wear a pair of her pantyhose, which is ironic since I now prefer bare legs nearly all the time.

    First time out dressed was 17 years old, but that's another story...!

  13. #313
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    i was about 10 when i put on my moms bra and nylons and the pink fog set in and has not gone away. i would not change a thing

  14. #314
    Junior Member DanielleT's Avatar
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    I think I was in 4th or 5th grade when I started wearing my sisters bras and panties. Sadly, it took me another 20 years to admit to myself that I really was (am) a woman. Thankfully, both of my sisters have accepted me as such.

  15. #315
    Junior Member katia's Avatar
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    Aged about 10 ,tried on my mums tights and loved it then teenage years use to try on my sister clothes when they were out
    In the garden of life another flower blossoms is that really me

  16. #316
    Junior Member Margaret's Avatar
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    Aged about 4. i remember trying on a friend's lacy petticoat. then at around 6 years old I remember going to the beach with some neighbours. I had no swimmers, so they gave me a girl's one-piece to wear. i loved it!

  17. #317
    Junior Member Didi's Avatar
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    I was 8 or 9, and tried on my older sister's girdle and nylons.

  18. #318
    Member SophieKitty's Avatar
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    I was 13 when I first slipped on my sister's PVC top with a tight fitting faux leather mini skirt. By the time I was 14 I got scared and Sophie has only recently resurfaced.

  19. #319
    Member Karen kc's Avatar
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    5 or 6, tried moms pantys,she didnt have pantyhose, just garter stockings [early 60s] tried them on but didnt know about the garter belt! Remember wearing her pantys to school when I didnt have gym. Never looked back!!

  20. #320
    A happy, mature lady! Joy3's Avatar
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    It felt so right!

    When I was 5 or 6 a neighbor girl would dress me in her clothes so I could be her girlfriend. We played all the games girls enjoyed. She would put make-up on me as we would play big girls. I really enjoyed these days as girlfriends and missed them terribly when she moved away. However, I was hooked and have been dressing for many years and loving it.

  21. #321
    Sometimes Clueless Laurie A's Avatar
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    I started being interested in my mom and sisters clothes sometime around 7 or 8 years old, but I don't have a particular first time memory of trying something on.

    I scanned the responses to this thread, and it seems most replies involve not only the memory of when, but exact what each person wore the first time. Most responders started between ages 4 and 14. Most responders mentioned the specific items the wore. If you look at the replies, there are several common categories in order of popularity: 1. underwear/bras/panties/slips/girdles 2. pantyhose/tights/stockings 3. skirts/dresses 4. shoes/boots 5. makeup/jewelry/nailpolish

  22. #322
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    It is interesting that all of the replies are so specific about how and when cross dressing began. I remember the feel and look of the corset that I wore. The sunlight coming into the bedroom and the strange inner thrill that suffused my body when I looked down at the silvery panel at the front of the corset.

    Also interesting is that the urge to cross dress diminished during teen years only to appear in the twenties or a little later. I have noticed this pattern in a number of replies.

  23. #323
    Discovering the Gurl Xandra's Avatar
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    For a long time dressing was an erotic experience for me, too. It still can be, albeit less so.
    Quote Originally Posted by laura.lapinski View Post
    I remember I had erotic thoughts at age 5 or 6 ? about wearing women's underwear. I don't remember actually putting anything on until about age 12 when I put on my cousins one-piece, body-hugging bathing suit in the privacy of the bathroom in their house. It felt so great.

  24. #324
    Member AlexisRaeMoon's Avatar
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    When I was 5, I put some balled up socks in my shirt to see what it felt like to have breasts, but I don't really think that counts as wearing girls' clothes. But when I was about 13, I pulled on a pair of old pajama pants that I stretched into a tube dress, and supplemented with mom's pantyhose and red heels.

  25. #325
    Junior Member michelle-'s Avatar
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    I was around ten. I was going to have a shower and my sister had left some clothes in the bathroom. I tried on a bra and filled it up with my socks. I think I tried a top as well and red lipstick. All this while the water was rumning. I kissed a sheet of toilet paper and had my shower. I kept that paper with my red kiss on it for some time.

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