I Am Curious About Crossdressing

Personal Stories, Advice, and Support 409 People

    My boyfriend and I have been together

    for almost 2 years. I got pregnant about 3 months into our relationship, so things got "serious" very quickly. About 9 months into our relationship (when I was 6 months pregnant), I found photos on his phone that he had taken of himself wearing dresses. I confronted him about it...
    Jadedgirl88 Jadedgirl88
    26-30, F
    3 Responses Sep 23, 2015

    Want To Try Crossdressing

    I have been curious in crossdressing for four years and have never tried it. I have started desperate and dont have enough money to buy clothes and have told mutliple people i know about it. Sadly no one has been able to help me and i have no other ways to crossdress
    blacksheep6 blacksheep6
    18-21, M
    10 Responses Feb 27, 2011

    On You Tube

    It's been 8 months since I Started Uploading Pictures and Videos of me dressed as a girl. At first I was nervous but now I'm compfortable about it. I love the feel of girls cloths touching my body. I love the compliments I get from men and women alike. I  love being who I am...
    HeroBuggirl HeroBuggirl
    18-21, T
    5 Responses Aug 6, 2009

    So I'm dog-sitting for someone next month

    so I'll have a house to myself. I'm wondering if anyone has recommended tutorial video or something for make-up for complete newbies. I wanna see if I can make myself look pretty. ;) Thanks!
    k0013 k0013
    26-30, M
    1 Response Feb 22, 2015

    I'd love to crossdress

    but I'm scared of doing so, because I'm worried I won't be able to like what I see in the mirror when I do so. But I adore make-up and women's clothes.
    lyolyo1 lyolyo1
    26-30, M
    5 Responses Mar 20, 2014

    I almost got caught wearing panties

    and bra at work, but luckily I narrowly escaped total embarrassment:) has any of you had any close calls?
    happycrosser happycrosser
    31-35, M
    Aug 14, 2015

    I'm strangely drawn to womens clothes

    and have fantasies about wearing them. I fantasize about women friends sneaking up on me and abducting me and forcing me to dress up and tie me to a chair or chain me to a wall to humiliate me. Why do I have these fantasies? Should I act on them? But it would probably never...
    TooInnocent333 TooInnocent333
    31-35, M
    5 Responses Jul 27, 2014


    When I was 11 or 12 I was curious about my mom's bras and panties so I decided to try them on. Who knew back then before the internet what it was called.  And later to find out there  are likely millions of us who love to wear girls and women's clothing.I love crossdressing...
    jml2000 jml2000
    61-65, M
    Mar 5, 2013

    Been Wanting To Try...

    I'm a girl who wants to dress like a guy. And no I'm not a lesbian believe it or not I'm straight. I've been looking at ways to tie my chest down, the clothes, how to walk and stuff but I haven't got the courage to yet. I'm really scared that I won't do it right and people will...
    JarredRay JarredRay
    22-25, F
    3 Responses Apr 16, 2012

    I have cross-dressed twice (with some of my

    friends that are girls around) and I LOVED it. I don't know what to do, and I haven't done it in about 4-6 months, I don't really know who to turn to, but I've been kind of craving it lately... What should I do?
    cmk97 cmk97
    22-25, M
    4 Responses Sep 15, 2014

    If You Are Curious - Women Or Men - Please Just Ask A Crossdresser

    In my humble attempts to raise "crossdressing awareness" I have found that a number of people have a lot of questions. I have received comments to stories and messages from women that are interested in learning more about crossdressers and what makes us tick. Many of the...
    BizSuitStacy BizSuitStacy
    56-60, T
    7 Responses Jul 2, 2012
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