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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 39 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 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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    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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    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 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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    Related Experiences

    Hello, I would love to talk with crossdressers or people who just wanna chat. I know it is a very 'taboo' topic but I am sure there are some people out here who would love to chat...
    lwdcd lwdcd 22-25, M 2 Responses Mar 2

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    If you like crossdressers, please come chat with me I want to know all about it and you.
    69hotstuff69 69hotstuff69 22-25, M 2 Responses Mar 5

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    Herpes dating sites cater for people with genital herpes . When two people suffering from herpes date, it is obviously much safer as there is no worry about transmitting anything...
    smitha143 smitha143 26-30, F 2 Responses Mar 6

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    I am happy to chat with crossdressers
    crossdresser1065 crossdresser1065 13-15, M Mar 9

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    Is there any crossdressers on here who want to come over to my house today
    hannah357 hannah357 18-21, M 2 Responses Mar 9

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    I would love to meet a lady in Canada. I am sissy baby crossdresser who love a mommy to take me in as her daughter.
    RachelHill RachelHill 26-30 1 Response Mar 9

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    I love sissies so much Sissy crossdressers are so so hot
    Terrabyte Terrabyte 18-21, M 3 Responses Mar 12

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    I'm making plans for a sissy/feminisation school I would like to have started for insecure boys who want to become females or if it is in their best interests. When I am finished...
    JohnVBlackburn JohnVBlackburn 18-21, M 1 Response Mar 12

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    yeah ... so send me pics of you crossdresserd or whatever , in exchange for pics of my ex girl
    Soizir Soizir 22-25, M Mar 18

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    I am a female to male crossdresser, and I like it. I started wearing guys clothes when I was 12 and now, I'm nearly always in a pair of trousers and some kind of plaid or flannel...
    miskia0917 miskia0917 18-21, F a week ago

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    I am just beginning to come to terms with the fact that I am a crossdresser and need someone to talk to madre about it
    justlilly03 justlilly03 22-25, T 7 Responses 6 days ago

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    Im a 21 year old and I want to meet and talk to crossdressers! I was in to crossdressing myself when I was younger but got out of it. Ive always just had an attraction to men in...
    nick191 nick191 18-21, M 1 Response 4 days ago

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    Herpes dating sites cater for people with genital herpes . When two people suffering from herpes date, it is obviously much safer as there is no worry about transmitting anything...
    smitha143 smitha143 26-30, F 1 Response 4 days ago

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    When you intend to have a herpes dating, which one is better? Blind dating, old fashion dating or online dating, which one do you prefer? My choice is online dating, for the...
    harryyang1990 harryyang1990 22-25, M 11 hrs ago

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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...
    kelly11aa kelly11aa 26-30, F 3 Responses Mar 17

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    Life is a journey that isn't meant to be traversed all alone. It is believed that happier people find it easier to cope up with STDs. If you're looking to find a like &ndash...
    wkellylaura wkellylaura 22-25, F Mar 9

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    Why not, Herpes is a common infection which doesn’t end your life. Herpes in no way can stop you from having a lovely life like many other uninfected people. Herpes is very...
    smitha143 smitha143 26-30, F Mar 6

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    Still are you single?? Fed up in finding your wealthy soul mate?? Here is the best road to the love paradise The largest over hundreds of Rich single’s Group. The place to meet...
    smitha143 smitha143 26-30, F 1 Response Feb 28

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    http://www.dailymail.co.uk/news/article-2942381/Woman-sues-rapist-met-Christian-dating-site-mother-writes-Facebook-post-accusing-lying.html For those who think Christian dating...
    1lonelydaisy 1lonelydaisy 41-45 Mar 15

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    The last time I posted here was a while ago, and I believe I was whining about how there is no possible way that id ever find love. I've found that in dating, the best...
    misterverde misterverde 22-25, M 1 Response Mar 8

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    Is it bad that after 2 days on a dating site I have a date lined up and another potential? In the near future?! xD I am very nervous with this whole "dating scene".....lolll....it...
    MFeisty MFeisty 41-45, F 18 Responses Mar 11

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    I'm not entirely here for dating, but if there's potential for people local to NY, I won't hesitate to try dating off of EP.
    Domance Domance 26-30, M Mar 16

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    I'm not really into the whole gay scene that much when it comes to bars, nightclubs or even Starbucks that much (best friend took me once to find people to talk to; so many snobby...
    jamie1292 jamie1292 22-25, M 4 days ago

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    When I was 19 I met this Indian American guy online. He was supposedly 22 at that time. We were really just friends in the beginning. However slowly we started falling in love. He...
    thisisparadise thisisparadise 22-25, F 4 days ago

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    I met a guy on an online dating app called scout and we had an incredible connection. We used to message back and forth. After a while we decided to talk on skype. Our video chat...
    itsmeagaim itsmeagaim 22-25, F 3 days ago

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    I'm also in my 40's and starting to get back into dating, still looking for my Mr.Right and hoping he just don't exist in my mind. lol
    tonia3 tonia3 46-50, F 2 Responses Feb 27

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    Here I am, well over 30. Dating is something I'd like to stand on it's head. Many times I've dived in with hormones first...and end up with the wrong guy. Now I'm starting over...
    nvr2late nvr2late 51-55, F Feb 27

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    I am in a heck of a situation. I am dating someone with aspergers. He recently decided out of no where he wanted to break up. When he breaks up with someone he disappears off the...
    littlemisspoe littlemisspoe 22-25, F 1 Response Feb 28

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    I don't understand what it takes to be good at dating because I'm awful at it!
    Jack1230 Jack1230 18-21, M 1 Response Mar 1

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    I've been "dating" this guy for about a month , and he usually communicates with me everyday & we would see each other 2-3 times a week when we're not working...all of a sudden he...
    Shaybee1991 Shaybee1991 22-25, F 2 Responses Mar 4

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    This is hard for me as it's my first experience dating a man with a child. I'm 21 and so is he, he has a 4 year old daughter. He's truly an amazing man, he's kind and generous and...
    beebeexoxox beebeexoxox 18-21, F 2 Responses Mar 5

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    Ugh. Back to the drawing board. Not a fan of online dating but it seems to be the best option at this point in my life; a divorced mom of three young kids. Wish there was an easier...
    peach1977 peach1977 36-40, F 1 Response Mar 6

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    I'm dating a guy right now and I really really like him. He is getting really handsy with me and I'm scared. I'm not saying I don't like it but it's scary because I never...
    Megan0899 Megan0899 13-15, F Mar 6

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    Started chatting to this guy who seemed really nice and had complimented saying I looked gorgeous on a profile picture. We get chatting exchange nos and he asked for a couple more...
    Lostway28 Lostway28 31-35, F 1 Response Mar 7

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    dating a nerd or gamer girl. always a plus.
    razgrizizzy razgrizizzy 22-25, M Mar 7

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    I think that online dating is a way to chat with people and that is it! Cause honestly people think that you have to click with them right off the bat. It takes time to get to...
    jellyrolls34 jellyrolls34 18-21, F Mar 7

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