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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 35 People

    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 2 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 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 6 Responses Nov 24, 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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    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 41-45, M 1 Response Mar 16, 2012

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    Related Experiences

    Any crossdressers in Northern Ireland? :) x 18 cd ni here
    Crossdressheels Crossdressheels 18-21 7 hrs ago

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    I've always loved the idea of dating a crossdresser. I'm what some people might call a "tomboy" and I just always found the juxtaposition ( I that's the right word I'm not really...
    BrahmaDonna BrahmaDonna 22-25, F 16 Responses Mar 22

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    I am falling for a crossdresser. I love him and who he is and I would never change him. I told my family, which consist of my mother and sister. Mom was accepting, my sister was...
    bbsw1963 bbsw1963 46-50, F 2 Responses Mar 24

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    ...and he is not my husband! I fell out of love with my husband 5 years(?) into the marriage. He traveled a lot with his job and we were in the middle of building our home,leaving...
    SweetPeaLove SweetPeaLove 51-55, F 1 Response 8 hrs ago

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    Online dating. I hate it so much. You put yourself out there only to find out it isn't enough.
    Chilchat Chilchat 36-40 2 hrs ago

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    My boyfriend and I have been dating for over a year now, and I am completely in love with him. He' my best friend and the love of my life. I can't imagine life without him. He...
    lithium123 lithium123 22-25 6 Responses Mar 30

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    If there any girls here willing to add me or help with a 0% chance of girls clothes for me to wear or you wanna be friends please message me i am a male crossdresser and by the way...
    lovepink73 lovepink73 13-15, M 1 Response Mar 22

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    I absolutely adore crossdressers. I kind of run a small business where I help boys and men get dressed up. I would love to hear all of your stories. Any age can message me, and I...
    ShainaNichole ShainaNichole 18-21, F 12 Responses Mar 29

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    I live in GA and would like to meet other crossdressers and transgenders.
    sexidancer sexidancer 41-45, T 2 Responses Mar 30

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    Any sissy or crossdressers here from central Ohio? I'm a sissy admirer and would love to meet some girls! Muah!!!
    ChrisP1279 ChrisP1279 31-35, M 1 Response Mar 31

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    Illinois area - any crossdressers or even girls accepting near the La Salle area?
    lovepink73 lovepink73 13-15, M 1 Response Mar 31

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    Would love to meet a UK girl that likes crossdressers, message me xx
    Jessicatv2012 Jessicatv2012 36-40, T Apr 1

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    I'm a female, born on and completely one and I love crossdressers. I'm open to help you with any questions but I won't date a guy over 35. I'll be anyone's friend. Please message...
    ShainaNichole ShainaNichole 18-21, F 3 Responses Apr 1

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    I am interested in finding crossdressers in Washington State, Bremerton area for chat and maybe more?
    Danielle1967 Danielle1967 41-45, M Apr 2

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    I want to meet a Cambridgeshire crossdresser to help me
    deleted deleted 26-30 Apr 3

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Please contact me via EP, my Facebook page under Jess Angel or JessAngel6y@gmail.com to join our new male Christian Crossdressers group. I'm looking to generate support for each...
    JessAngel JessAngel 22-25 1 Response Apr 5

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    22 year old crossdresser is there any one in peterborough cambridgeshire to come and give me a good **** naver had anal and want to try so badly
    messycindy messycindy 22-25, M Apr 5

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    Look at mycrox-d.com Lingerie for crossdresser
    fercrox fercrox 46-50, M Apr 6

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    Look at mycrox-d.com Lingerie for crossdresser
    fercrox fercrox 46-50, M Apr 6

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    Seeking crossdressers, or sissy men in the southern mo. northern ar. area. Want to talk and share thoughts. Best case scenario, FWB.
    mabiguy mabiguy 36-40, M 1 Response Apr 6

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    Any sissies and crossdressers living in midland Ireland?
    cindytights cindytights 36-40 Apr 7

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    Any crossdressers living in Australia
    Jess967 Jess967 18-21, M 1 Response Apr 8

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    I am married to an amazing man, a fabulous father, talented lover and my very best friend...oh yeah, he's a crossdresser as well.
    Happiegurl Happiegurl 26-30, F 1 Response Apr 9

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    I too am a crossdresser and I love to wear feminine clothers. I love the feel of pantyhose and silky clothes. I used to fight my urges, but now I have come to realize this is a...
    JaimeCD JaimeCD 46-50, M 3 Responses Apr 10

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    Um... Hi im a aspiring crossdresser Id kinda like help crossdressing if anyone would want to My kick is josef3303664
    deathtrap12 deathtrap12 18-21, M 2 Responses 6 days ago

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    I'm from Milwaukee, Wisconsin and would love to meet a local crossdresser! I"m looking for a gurl friend that loves to dress as much as I do. Please message me if you're nearby!
    Cassie153351 Cassie153351 18-21, M 1 Response 1 day ago

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    GarthPasche GarthPasche 26-30, F Mar 24

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    likeyoungerwomen likeyoungerwomen 31-35, F Mar 31

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    likeyoungerwomen likeyoungerwomen 31-35, F 1 Response Mar 31

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    Couples have a higher chance of reaching divorce if they are having deep financial trouble, and for this reason, finding a wealthy mate is not something that a person should be...
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