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Thread: When did you first crossdress?

  1. #1
    Discovering the Gurl Xandra's Avatar
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    When did you first crossdress?

    Do you remember the first time you tried on an item of women’s clothing?

    I remember putting on my mum’s fake fur coat around age 7 and getting a thrill from my appearance in the mirror. I knew at once that this was part of my future. How about you?

  2. #2
    Gold Member ~Joanne~'s Avatar
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    I remember having an pantyhose fetish at an very early age. I think I was 10. I loved The way they looked on women, how "see through" they were, The shine they gave off and how cute they made feet look. It was within that same age that I wanted to know how they felt on me so I stole a pair of my mom's. They didn't look as good as they did on other women (to find out it came down it brand and such) yet they felt amazing! There was little turning back after that.
    Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!

  3. #3
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    Probably about the age of 10. Those pantyhose just hanging there in my grandmothers bathroom were just too much to resist.

  4. #4
    Junior Member artofbalance's Avatar
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    I used to be dressed up in ballerina outfits my sister had as she was growing up... about 4 years old I think. I remember about age 4 trading underwear with a girl my mom babysat for. They were white with strawberries on them.

  5. #5
    Silver Member I Am Paula's Avatar
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    My sister and I were very close. She'd dress me up starting around 5 or 6. Alot of kids play dress up like that, but I liked it too much. By my early teens, at pajama parties I was my sister's make up manequin.-Celeste

  6. #6
    Platinum Member kimdl93's Avatar
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    As early as I can remember...probably around 4 years of age.

  7. #7
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    Probably as a single digit midget. I fondly remember taking my mother's nylon slips off the clothesline and trying them on. I loved the feel of the material. I had no conscious thought that I would like to have been born a girl. I had no sisters or female playmates. No one dressed me up. Maybe, if my mother wore cotton slips I would have turned out differently????

  8. #8
    California Dreamin Michaelasfun's Avatar
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    I am a late bloomer, I guess..it was about 10 years ago, my wife and I were playing around and she put her bra on me for fun when we were "messing around" one evening..shortly after I suggested we go find a lingerie set for me at the dept store, so we went and she helped me get one...the novelty kind of subsided for several years..then last year for whatever reason, I got that outfit back out and tried it on..then went on an ebay spree and slowly gathered more stuff until i was "evolved" enough to go out in public..anyway I digress lol
    Michaela


    If you choose not to decide, you still have made a choice. - Rush

  9. #9
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    I might have been 4 or 5, I would go into my moms closet and put on her girdle,
    Then try walking around in her heals.
    That was OK for a while, but when she caught me wearing her girdle and
    nylons in bed when I was 10, I got the "TALK".
    Had to hide stuff better, Under the mattress was no good anymore; so I went
    to work and built a false bottom to my built in dresser drawers. Worked like a charm.
    Then when I went off to the Navy, I had to purge everything, That hurt.
    I left a note in the hiding space saying, "HA, I caught you looking at my Hiding Space"
    The old house is still there, all though we moved out 40 years ago; I wonder if anybody
    found the note.
    Rader

  10. #10
    Gender Outlaw! vikki2020's Avatar
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    about 4 years old---slipped on some nylons, and never looked back!
    "And if you want some fun, sing Ob-Bla-Di-Bla-Da!"

  11. #11
    Member Charlotte Haynes's Avatar
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    School holidays, ten years old, and I had the house to myself during the daytime. Went through my Mam's drawers looking for tights/pantyhose (I'd been obsessed with them since I was about five) and pulled out some sheer black ones. I put my arm(!?) in them, then panicked and went back downstairs. A few minutes later and I was back up...this time putting one foot in over my sock...panicked again and back downstairs. Sat down, and then promptly went back up, took my trousers and socks off, and pulled them on. I can sometimes recall exactly how I felt at that moment... but it only lasts a second or two...a "first hit" type of experience, never fully recaptured. I couldn't keep out of them after that...
    Last edited by Charlotte Haynes; 01-05-2013 at 06:43 PM.

  12. #12
    Member Ariamythe's Avatar
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    I don't remember precisely when I did it the first time, nor what compelled me to. But it was in high school, with my moms clothes.
    Ali Edwards

    Transgender Science ~ Blogging with WrodPress ~ Tweeting on Twitter

    "I am half-sick of shadows," said / The Lady of Shalott.

  13. #13
    Almost full time (90%) Phoebe's Avatar
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    Arrow When did you first crossdress?

    Four and five years old, my mother had me put on dresses she made then have me get on a chair so she could make the hem straight. Sometimes wore those dresses all day long. My father was away in the hosptial then and never knew my mother dressed me in dresses.

  14. #14
    Exploring NEPA now Cheryl T's Avatar
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    Mom's panties and slip at about age 7 and then her wonderful pink OBG with 4 garters and lace up back.
    Can you see the REAL Me?

  15. #15
    Junior Member Wendy G's Avatar
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    I was 6 years old. I was enchanted by pantyhose. I found a chance to wear my mother's hose along with a skirt and blouse. Of course they did not fit, but I was thrilled and began pursuing crossdressing as often as possible. Over forty years later, I'm fully dressed as I type this. The thrill has never escaped me.

  16. #16
    Junior Member CdD Janessa's Avatar
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    I was 11 or twelve just watched a movie where a man dressed ad a woman and somehow wanted to be like them so id borrow my moms clothes anf do it got caugjt a couple timed but that hadny stopped me ftom dressing. I to love thr feel og nylons on my legs

  17. #17
    New Member sarahgrant's Avatar
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    Aged about six. Tried on a pair of my sister's panties in the cupboard under the stairs. Felt wrong but oh so right.

  18. #18
    Junior Member Deborah J.'s Avatar
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    I was 12. Pantyhose weren't out yet but my mom used to hang up her stockings to dry on the bathroom towel rack. One day she also had her garter belt there. I tried them on. Couldn't believe how nice they looked. Even better was how they felt! I was hooked and the rest is history.
    [SIZE="5"][/SIZE]Deborah J.

  19. #19
    New Member FeminineEmoBoy's Avatar
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    pretty much since i was 2 i think so 16 years ago. I had two older sisters who would dress me up and push me round in a dollies pram and gave me girl names, however i only really realised i was a crossdresser by secondary school as i simply didn't realize i was one before. i will just say i'm glad my parents were so accepting x

  20. #20
    Member Robyn2006's Avatar
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    I was a bit of a late starter, I suppose, 14 yrs old. It was my sister's 16th birthday and we had all gone for the weekend to the Disneyland hotel in S. California, just outside our home in LA's San Fernando Valley. It was then while all were elsewhere and I was alone that I first realized the possibilities. There in the bathroom were my mother's and sister's bathing suits hanging to dry. Really, it was almost instinctual as I pulled my mother's one-piece suit off and just… well, put it on. Without a thought, I remember so clearly, I pulled off tons of toilet paper to fill the suit's 36D cups. From there, of course, all my mother's makeup seemed just natural to try on too. To say I was excited hardly describes it. But it was when I first pressed her Avon Periwinkle Pink lipstick to my lips (yes that was the shade, will remember it to my dying day) when all came to be and I discovered my true self. With each stroke of that lipstick, I became more alive than I had ever felt. After a bit of work, blush and mascara as best as I could manage, I couldn't believe how attractive I had become, feeling and looking just like a girl… my reflection in the mirror that of nothing but a newly discovered ingenue. It was such an amazing day, perhaps the best of my life.
    Last edited by Robyn2006; 01-12-2013 at 02:33 PM.
    When lost, alone, or blue I know I can always get through the day, for I've always another shade of lipstick to make things right!

  21. #21
    Crossdressing Newbie
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    One month ago, I was in my parents room. I got to try on a couple bras, panties, and a nightie. Loved every second of it.

    I wish I found this out about myself a lot earlier. I need to catch up!

  22. #22
    New Member Amelia_Barry76's Avatar
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    I was 11 when I 1st dressed. I wore an old dress that was just sitting out in my mum's bedroom

  23. #23
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    Honestly, I don't remember. The first time I did it knowing that it was "abnormal" was around ten maybe? However, when playing house with my cousin, it was earlier. And I'm told my mother and sister enjoyed dressing me up as a girl, although I also remember rejecting the typical lace-sleeved shirts of the 70s at the time around seven or eight, probably because that was about the time outside influences began telling it was wrong to do that. Wasn't my parents, though.

  24. #24
    Happy to be me!! S. Lisa Smith's Avatar
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    I was in day camp at age 9 or 10 and the camp did Oklahoma. A bunch of the boys were dress and sang "I enjoy being a girl". I think that was my first time, but not my last!!

  25. #25
    Aspiring Member Jenny Gurl's Avatar
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    I knew I had a fem side around 5. By kindergarten I already envied the cloths the girls got to wear. Although I can fit in with the guys, I seem to gravitate towards the girls. I seem to feel more comfortable in a group of girls. Once I have been there for a short time they seem to accept me as one of them in our conversations. I started dressing very young, and did so until present aside from a few breaks.

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