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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 49 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

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    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 18-21, F 4 Responses Apr 7

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    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?
    PStJBR PStJBR 36-40, M 1 Response Mar 16, 2012

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    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

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    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 8 Responses Dec 2, 2009

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    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

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    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 1 Response Apr 19, 2012

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    Related Experiences

    I'm still trying online dating and find it really hard.
    kuroijukai kuroijukai 26-30, F 2 Responses 8 hrs ago

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    I tried on line dating but got looked at strangely sitting with my lap top in a movie theater. It really got weird when I put my arm around it and went in for that first kiss....
    thebustierthebetter thebustierthebetter 46-50, M 1 Response 11 hrs ago

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    Any crossdressers interested in sending me pics?
    flasherguy flasherguy 26-30 1 Response 1 day ago

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    Anyone who has crafted a message on OkCupid knows that online dating is still a very unnatural act. You scan the stranger's profile, wittily riff off of their listed interests...
    rsfindley77 rsfindley77 36-40, M 1 day ago

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    so im a straight crossdresser so im i wrong for wearing panties underneath my pants?
    stoner92188 stoner92188 26-30, M 1 Response 2 days ago

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    I don't..I'm just curious to read peoples dating advice here,hence me joining this group.
    simpleandpossible simpleandpossible 22-25, F 1 Response 6 days ago

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    I used to crossdress as a child and teenager. When I went to college I stopped dressing. Now I am very attracted to mtf crossdressers and trans women. I love their strong feminine...
    tjlawrence tjlawrence 26-30, M 6 days ago

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    A new friend of mine recently loaned me a few of her cds regarding dating, marriage and relationships from a Catholic perspective. Although I didn't see much differences from the...
    niceguycursed niceguycursed 31-35, M 2 Responses a week ago

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    I am a straight male who doesn't crossdres but I have fantasies of being with a crossdresser or Transgender in edmonton
    Scotian5 Scotian5 36-40, M Aug 18

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    wanna meet a crossdresser in Hampshire England message me if your interested
    riw1996 riw1996 18-21, M Aug 17

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    Need some advice. I haven't dated in awhile but my friend is trying to hook me up with someone. He doesn't necessarily have the greatest looks but he seems to be super sweet. I...
    TheQuietOne92 TheQuietOne92 22-25, F 1 Response Aug 16

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    So I've started rebuilding my clothes and make up once again. I went through another spell of not wanting to do this anymore and feeling as though I was wrong in dressing up the...
    RubyGirll RubyGirll 36-40, T 10 Responses Aug 15

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    I've been dating my boyfriend for almost 10 months, we starting dating quite fast after we met. Now I wants to get our friendship bond stronger. I asked if he wanted to break-up...
    IbelithLP IbelithLP 36-40, F Aug 15

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    I would like to talk to and get to know a transsexual or crossdresser, always been attracted, message me
    riw1996 riw1996 18-21, M Aug 14

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    What are your thoughts about internet dating? I tried it before and hated it. I'm thinking about giving it another shot, but I probably won't. I just think it's so much better to...
    musicman99 musicman99 22-25, M 2 Responses Aug 14

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    There are numerous older men in the world who are single and seeking someone special in their life. For all such men, AgeMeet.com has been created as a reliable online platform to...
    allisoncc11 allisoncc11 26-30, F Aug 13

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    There are numerous older men in the world who are single and seeking someone special in their life. For all such men, AgeMeet.com has been created as a reliable online platform to...
    allisoncc11 allisoncc11 26-30, F Aug 13

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    I feel very confident i was born a crossdresser i reached for stockings and lingerie without anybody telling me to when i was 6 my mom when pregnant with me thought talked bought...
    alexiswcd alexiswcd 56-60, T Aug 13

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    Sort of. I've always dreamt of being a girl and I've met an awful lot of crossdressers I like online. We tend to have a lot in common, even though, personally, cross dressing...
    mickitg mickitg 41-45, T 1 Response Aug 13

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    I tried online dating and I still do occasionally. I've met some nice women online. It's hit or miss, just like traditional dating. You just don't know what you're going to get...
    RichardHertz RichardHertz 36-40, M 4 Responses Aug 13

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    not officially dating this man, met him two years ago in a beautiful place in Bali when he approached me asking for my picture. I was still in high school, he looked young. Then...
    liberaleconomist liberaleconomist 18-21, F 2 Responses Aug 13

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    Im not dating a crossdresser but I joined in hopes of finding a woman who would date a crossdresser.
    Averageguy41011 Averageguy41011 41-45, M Aug 12

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    I think that my boyfriend is gay. I heard a rumor that he was. Naturally, he is not going to tell me if I plain ask him. I do not see that there is evidence that he is gay. If he...
    TooCute12 TooCute12 22-25 Aug 12

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    Hi I'm 18 years and I'm a bi crossdresser looking for a crossdresser bi, gay, or straight to talk, meet or play with I haven't been with a crossdresser before but I want to try it...
    CDerforlife CDerforlife 18-21, M 2 Responses Aug 12

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    I am a real estate paralegal and work for a real estate company in the city. I love to work out, dance, love to try different restaurants, watch movies, camp, travel, love going to...
    mirandalongfellow mirandalongfellow 26-30, F 1 Response Aug 11

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      I am a real estate paralegal and work for a real estate company in the city. I love to work out, dance, love to try different restaurants, watch movies, camp, travel...
    mirandalongfellow mirandalongfellow 26-30, F 1 Response Aug 11

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    I am a real estate paralegal and work for a real estate company in the city. I love to work out, dance, love to try different restaurants, watch movies, camp, travel, love going to...
    mirandalongfellow mirandalongfellow 26-30, F Aug 11

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    I play word with friends but they need to call it "word for friends dating site. Currently I am being entertained by "BIG D" who I met in community match. I started playing with...
    Browneyedcurlygirl Browneyedcurlygirl 46-50, F Aug 11

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    I'm a crossdresser who just started. Can someone help me be the girl I was meant to be. Msg me
    CDerforlife CDerforlife 18-21, M Aug 11

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    fasantied by crossdressers and transgender
    scizamps scizamps 31-35, M Aug 11

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    anybody actually have luck with online dating?
    sadguy253 sadguy253 26-30, M 5 Responses Aug 10

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    I am married to a crossdresser an I love him so much
    heatherxdress heatherxdress 51-55, F 1 Response Aug 9

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    I'm a 17 year old gay crossdresser looking for a gay guy who likes doing the same
    youngadult18 youngadult18 18-21, M Aug 6

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    Women just suck in online dating. Complain that a guy just wants sex, ignores guys that don't talk about sex. They want someone to looks at their profile. Goes directly to your...
    zerofivenosh zerofivenosh 26-30 2 Responses Aug 5

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