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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 39 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 6 Responses Nov 24, 2009

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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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    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 9 Responses Dec 2, 2009

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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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    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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    Related Experiences

    I suspect that transgender and cross-dressing individuals are in the same invidious situation that gay people were several decades ago. Hopefully, prejudice against those who have...
    Ashanti Ashanti 51-55, T 1 Response Jan 6

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    Full drag doesn't make me look any younger, on the contrary, I look 50ish as a woman. That's okay, I'm not doing it for dating or picking anyone up for a one night stand.
    Doviov Doviov 41-45 5 days ago

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      I'm an 18 year old crossdresser and I'm just getting into this community. I'm buying my first toys, chastity cages, high heels (OMG), lingerie, clothes and makeup. I call...
    xxxSissyGabriellaxxx xxxSissyGabriellaxxx 18-21, T 2 Responses 4 days ago

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    im a secret crossdresser aged 23 size 8-10 in the uk from peterborough love wearing dresses tights and high heels favorite look is deffo school girl look id like to meet other...
    messycindy messycindy 22-25, M 1 day ago

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    I was just organizing my gurl stuff and took a quick inventory: 9 pair of boots of varying styles, 7 pairs of pumps up to 6 inches tall, 2 pairs of ballet flats 6 pairs of...
    JessicaDale JessicaDale 51-55 11 Responses Jan 1

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    I wanna skype with a crossdresser xxx
    lifeaintshit lifeaintshit 18-21, M Jan 1

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    I'm not ashamed of it tbh I have a feeling I'll grow out of it though but still right now the thought of a girl dressing me as a girl sounds fun and interesting. I don't see what...
    ChristianCrossdresser ChristianCrossdresser 13-15, M Jan 2

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    I'd like to talk mostly to girls who are interested in talking to someone that is a crossdresser. Not to be sexist or anything it's just my preference...
    ChristianCrossdresser ChristianCrossdresser 13-15, M Jan 2

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    I don't know what it is but crossdressers make me so horny
    maxi54321 maxi54321 18-21, M 1 Response Jan 3

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    I want to talk to women who like crossdressers
    Yoloswag2211 Yoloswag2211 16-17, M 2 Responses Jan 4

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    When I was younger and in shape I did an okay as a passable crossdresser. I was a football player and wrestler so I stayed nice and trim. When I was 18 I spent almost a week as a...
    Medic72880 Medic72880 31-35, M Jan 6

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    I would like some tips! I am a "crossdresser". I put the quotation marks since I hacent gone too far, but I do have ny own skirt. If someone could message me and give me some tips...
    mygirlskirt mygirlskirt 22-25, M 3 Responses Jan 7

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    i was looking through so many sites for ireland and to be honest theres nothing good to find so im curious if theres any other irish crossdressers on this site too would love to...
    dawncutie dawncutie 18-21 Jan 10

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    this is my crossdressing support page join if you support crossdressers or are any of the above
    guyindresses1991 guyindresses1991 22-25, T 2 Responses Jan 11

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    Yesterday I created a twitter acount with my crossdresser identity, and its such a thrill right now! Hope nobody I know finds out my true identity... *wink* *wink*
    jokkki jokkki 18-21, M 1 Response Jan 12

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    Crossdressers make me so horny I'm just stroking right now thinking about em
    maxi324 maxi324 18-21, M Jan 16

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    Any crossdressers want to trade pics or cam2cam
    maxi324 maxi324 18-21, M Jan 16

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    I'm a Crossdresser from northeast ohio
    rachael68nuome1 rachael68nuome1 46-50, T Jan 16

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    Sometimes I think about being a female to male crossdresser! Wouldn't it be something to wake up some morning as a woman and finding out I want to be a man and then dress as one...
    Cassandrajoan Cassandrajoan 61-65, M 1 Response Jan 16

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    Any other crossdressers want to talk?
    Autoxer Autoxer 18-21, M 2 Responses Jan 18

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    Yes I Would:) I am a 17 year old crossdresser in training, i'm abit shy, but sure after a while i can open up about things, as I am becoming more and more confident as the days go...
    Tyrone147 Tyrone147 18-21 4 Responses Jan 21

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 12 Responses Jan 22

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 1 Response Jan 22

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    I wouldn't call myself a crossdresser, but I order things from guys catalogs and buy guys clothes (tshirts, shoes, pants sometimes)
    Ashthewolf7601 Ashthewolf7601 13-15, F 3 Responses Jan 23

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    They make me so hard especially h e.nt. ai crossdressers
    hannah357 hannah357 18-21, M 1 Response a week ago

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    Crossdressers get me so hard I love em
    hannah357 hannah357 18-21, M 2 Responses a week ago

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    So last year I shared my experience on this page about my wonderful caring, beautiful loving girlfriend whom of which I love with all of my heart and as does she. And even though...
    need4speed28 need4speed28 18-21, M 8 Responses 6 days ago

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    i started to crossdress a couple of weeks ago. but i stil feel not completely happy with the result. annyone wanne help me being a better crossdresser
    dannyb1994 dannyb1994 18-21, M 2 Responses 4 days ago

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    I'm looking for crossdressers or female friends in the New Orleans area. I enjoy dressing in my feminine attire to go shopping, clubbing, movies and anything else thats fun :)
    Kimber1973 Kimber1973 41-45, T 3 days ago

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    i want some crossdressers experience
    karizma9007 karizma9007 22-25, M 3 days ago

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    Hi am chris... this is to all you crossdressers that kept it a secret for to long you need some advice or help. Message me and ill help you as much as possible this gose out to you...
    24chris24 24chris24 22-25, M 1 Response 14 hrs ago

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    My experience with dating has basically been "I love you" after 1 week...0 interest in me...a total feeling of wrongness when we kissed...and one healthy relationship that lasted...
    ForeverAloneForeverFriendZoned ForeverAloneForeverFriendZoned 13-15, F 1 day ago

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    Younger women dating older men mainly because younger women are attracted older men. older men mature, confident, stable .Mature guys always know how to treat their women.These...
    minnieccaa minnieccaa 26-30, F Jan 19

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    If you are a single biker and seeking a riding buddy & motorcycle club and serious relationship , you have to have a look the first , largest and most effective single biker dating...
    karallylong karallylong 26-30, F Jan 16

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    Society has long become more open to the idea of older man - younger woman relationship and older woman - younger man relationship as well. Hollywood has brought in the practice of...
    angelacc11 angelacc11 26-30, F 4 days ago

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    I really hate online dating sites because they are very boring and dangerous. You don't know who you are talking to. I tried dating sites before but none didn't work out for me. I...
    elana453 elana453 41-45, F Jan 14

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    Do Men Really Like Dating BBW big beautiful women? I Asked 25 Of Them.Jared, 28Yes. Men are hardwired to care about looks. That’s just a fact of evolution.Garrett, 28I think...
    LissaCoffey LissaCoffey 41-45, F 2 Responses Jan 2

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    Okay well I've never dated before and I know myself too well. If I were to date someone I couldn't. I don't know the basics to dating! I can barley find a way to express my...
    Bonshaquitalafondria20 Bonshaquitalafondria20 18-21, F Jan 4

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    ive only dated one person in the last year. yet, i see people dating multiple people for a short amount of time. which i think is stupid. i believe in patience. i am a very honest...
    Ebolaa Ebolaa 16-17, M Jan 4

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    I love dating white men instead of black men. I'm a black woman who will date a man of any race. I love white men. I wouldn't mind dating one right now.
    winnie19 winnie19 41-45, F Jan 5

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