I Have Crossdressed

Personal Stories, Advice, and Support 328 People

    I remember one time when I was on the streets.

    I had met this guy with a speak inpetiment problem while sitting at a bus stop. I started talking to him just about various stuff. He didn't know I had on a women's thong, pink stirrup tights and a pink leotard that were rolled down to my waist. It was getting late and I told...
    Jasminej235 Jasminej235
    41-45, F
    1 Response Jan 31, 2015

    My First Time Crossdressing.

    The first time that I crossdressed I was 15 and at my friend's house. We had been left alone on the farm, the three of us, and we couldn't wait to be wild and crazy guys. After watching a huge block of Anime and drinking a few two liters each (possibly 3 or 4) we ran out of...
    TheUnsure TheUnsure
    2 Responses Apr 18, 2010

    so what. i have also torn the tags off

    mattresses, jaywalked,worn mismatched socks and made an illegal u-turn.
    xkmb xkmb
    Aug 24, 2015

    Yes I have. I loved it.

    I used to house sit for a friend. His wife had the sexiest clothes. When they had me stay over I'd get a g-string, sexy lacy pink bra, mini dress and heels. Some times I'd put on perfume. Hang out all day like that. At night I'd wear her lingerie. Had to hand wash things when I...
    deleted deleted
    2 Responses Mar 9, 2016

    Right Before College

    I had just graduated high school a month before and was hanging out with an old friend. She had her house to herself so we were chilling and watching TV. After awhile we had gotten bored so we decided to play round of pool; she asked me if I wanted to make it interesting and I...
    TheUnsure TheUnsure
    2 Responses Mar 5, 2011

    It's sad really, that I've only really done it

    once. Anyone who knows me could tell you that I'm not feminine, except for certain circumstances. I would wear boys clothes more, if not for my mother. I keep getting the strong aura of disapproval from her whenever I even suggest anything of the sort. I know that she wants me...
    YesThisIsJenna YesThisIsJenna
    18-21, F
    Feb 22, 2014

    Crossdressing For The First Time

    i was about 14/15 when I cross dressed for the first time I was at aschool mates house & had to visit the little boys room on the way I had to pass his sisters bedroom of which the door was open & I noticed a pair of pantyhose laying on her bed as I wanted to know what it was...
    xdpaul xdpaul
    56-60, M
    Jun 25, 2011
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