I Am Dating A Crossdresser

Personal Stories, Advice, and Support 53 People

    It's Time To Get Dressed Up!!!

    So we are planning a trip to Jacksonville, FL (only a two hour trip from us!) to go to The Metro, from what I hear, a pretty cool gay bar.  They have drag shows on the weekends and I think it will be a lot of fun.  But I really feel like this will give...
    loudamy loudamy
    26-30, F
    5 Responses Nov 24, 2009

    A Completely Unexpected Beginning

    I just went on my first date with a wonderful man. I've never had so much fun, or met anyone who gave me butterflies as quickly as he did. I went into the first date knowing that he was a part time crossdresser. I don't know if I was in shock, or simply didn't care, but the news...
    ashfay ashfay
    22-25, F
    4 Responses Feb 17, 2013

    My Wife Is Married To One, Me. Does That Count?

    My wife is married to one, me. Does that count?  She's not active on this site, but I am. I'd be happy to share with others in similar situations, but I'll keep this brief, since I'm not sure how active this group is?
    41-45, M
    1 Response Mar 16, 2012

    Dating A Crossdresser

    The other day my boyfriend of a year and eight months revealed to me that he occasionally crossdresses. He assured me it was NOT because he is actually gay, NOT for the sexual aspect of it, BUT because it gives him a chance to escape the stress in his life. When he told me, I...
    BFisaCD BFisaCD
    18-21, F
    2 Responses Apr 19, 2012

    It's Been Awhile...

    Sorry, ya'll. It's been quite a while since I've been on EP. Goodness!! So much has happened. I'm sorry to say that I and the crossdresser did not work out. Nothing to do with his enjoyment of dressing in woman's clothing. We just were not compatible as people. Still good...
    loudamy loudamy
    26-30, F
    3 Responses Feb 29, 2012

    Pantyhose Run!

    Unfortunately the pantyhose from Hooters didn't hold up as well as expected so I was asked to make another run last night.  No problem there, I don't mind one bit, but it was a bit funny this time around.  Last time I went there was a very busy dinner crowd so I...
    loudamy loudamy
    26-30, F
    7 Responses Dec 2, 2009

    I recently found out my guy is a crossdresser.

    It took me completely by surprise, lots of crying and confusion. Because I love him I chose to stay. He only wears womens bra and underwear and occasionally corsets. He said he doesn't feel feminine or want to have a full female persona or wordrobe and he also doesn't consider...
    georgetta1994 georgetta1994
    22-25, F
    4 Responses Apr 7, 2015
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