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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 45 People

    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    Dating this guy for 3 months. He works and does a lot of over time. So he usually gets one day off. We live an hour apart. I have kids at home. So when he gets a night off and...
    flydragonfly flydragonfly 36-40, F 1 hr ago

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    I do just as bad with online dating as i do with real life dating. If I could just find one guy who was honest.
    baprel26 baprel26 36-40, F 2 Responses 13 hrs ago

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    A met a guy online who was super sweet and charming. We talked, text, and video chatted every day for about a week before meeting in person. We didn't click because I thought he...
    Mo2013 Mo2013 22-25, F 3 Responses 15 hrs ago

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    Dating sites take all the fun out of Internet dating haha I had a picture of just my eyes and not a full face picture. If i were wearing a burka only my eyes would be visible. I...
    paliglass paliglass 31-35, F 1 Response 16 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...
    Junecc11 Junecc11 26-30, F 21 hrs ago

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    I have been seeing a man 33 years older than I am biologically. We have fallen deeply in love and we do not want to live life without each other in it. I do not believe there is...
    mamaML22 mamaML22 18-21 21 hrs ago

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    Any crossdressers out there that wanna chat? Just message me, I'm going to bed but I'll respond in the morning!
    CrossdresserOfToday CrossdresserOfToday 13-15, T 23 hrs ago

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    Hey guys, anybody who wants to chat with a 15 years old crossdresser, please leave a message! I'm so bored...
    Ciao00 Ciao00 13-15, M 1 day ago

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    Any crossdresser who wants to chat with me??? Please... I'm bored
    ImasexyCD ImasexyCD 13-15, M 1 Response 1 day ago

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    I just came out as a crossdresser to a friend. :)
    IamKatrina IamKatrina 18-21, M 2 Responses 3 days ago

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    I'm not a full time crossdresser but when my mom leaves (which she is about to) i wear some of her panties
    deleted deleted 26-30 2 Responses 3 days ago

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    Hi I am Jamie not real name looking for other crossdressers to chat with I have never been this brave before but game to talk with other like minded I live in queensland
    jamie05 jamie05 46-50, M 2 Responses 4 days ago

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    I have this guy who I have been talking to for about a year. I like him and all and I know he really wants to be with me. But I don't really know if I want to risk an online...
    Girl12335 Girl12335 18-21, F Jun 24

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    Hi, I am a 15 year old crossdresser who wants to chat so please message me!
    Crossdresser3333 Crossdresser3333 13-15, M 1 Response Jun 24

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    Herpes is a sexually transmitted disease that is common, According to the Centers for Disease Control and Prevention, in the USA about 1 out of 6 folks have the herpes virus. Sadly...
    smitha143 smitha143 26-30, F Jun 24

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    This is usually how it plays out: Guy: what's your number, let's chat Me: dubious, but ok Guy: chats for a while, seems human, can spell, gaining trust Me: drops my guard a little...
    jesabellica jesabellica 31-35, F Jun 23

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    One of my best dating advice is: Don't rush into a relationship, don't start out to strong. Don't ever date a guy that won't allow you to meet their parents. Don't date a guy who...
    DeterminedToMakeLifeWorthIt DeterminedToMakeLifeWorthIt 16-17, F Jun 23

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    Well,there's not much about dating,so i noticed this sector to be busy... I want to ask tip or your take on dating women and if everything just falls on the female selection who...
    Peteswords Peteswords 31-35 2 Responses Jun 23

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    I really just didn't know where to put this but umm here goes my teenage girl problems. I'm talking to someone..dating..I'm not really sure . he is 7 years older than me and has 2...
    Alylovespuppies Alylovespuppies 18-21, F 1 Response Jun 23

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    Southern ca looking to experiment with Crossdresser or chat and trade
    deleted deleted 26-30 Jun 22

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    a Crossdresser gave me a ******* once and I think about it constantly.
    deleted deleted 26-30 1 Response Jun 22

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    hi I'm an 18 year old crossdresser looking for others to talk to.
    TheSissyBritney TheSissyBritney 18-21, T 3 Responses Jun 22

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    I have read some people say I've met my husband off here and this and that I'm thinking ok cool , awesome I love ,love what can I say ... But I can't cosign on that ep is a...
    Prettibrowngirl Prettibrowngirl 70+, F 2 Responses Jun 22

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    I'm no here for dating... anymore. Just wanted to let people who try to hit on me know that their intentions are not worth it.
    Undecodable Undecodable 18-21, F 1 Response Jun 21

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    Elite dating sites, elite dating sites reviews, elite dating at www.elitedatingsites.com
    elitedatingsites elitedatingsites 36-40, F Jun 21

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    Around 4 years ago my senior year of high school I met someone who ended up having a big impact on accepting myself and being okay with who I am. I met her through a mutual friend...
    crossfitprincess crossfitprincess 22-25, M 5 Responses Jun 20

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    There is a girl at work whom i think likes me, then there is my long time crush working a few floors above me, and there is this other girl that finds odd times to just say hi to...
    backgroundguy backgroundguy 22-25, M Jun 20

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    A couple of weeks ago, someone messaged me at the dating site I am on asking if I'd like to exchange email messages with him. He seems to have a likeable profile and conveniently...
    iCuriousBabe iCuriousBabe 41-45, F 5 Responses Jun 19

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    On a whim, I joined a few online dating sites. I added the usual. A few pics, a short bio. Now I'm juggling conversations with 6 different women. I guess there are worse...
    twistedAndJaded twistedAndJaded 41-45, M 4 Responses Jun 19

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    How do you even get back in the dating scene? I tried a couple of sites and the men seem to only look for the hook ups or I get responses from people who are far away from me
    granny1969 granny1969 46-50, F 4 Responses Jun 19

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    I am a crossdresser....I have been experimenting for almost a year now and I love it. I love dressing up in cute panties, sexy lingerie, hot skirts and heels. My favorite is to...
    JessickaJaxxxon JessickaJaxxxon 26-30 2 Responses Jun 18

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    I am a 17 year old crossdresser who is looking for others. I have a supportive girlfriend and she is the only one who knows. I like to show off and it turns me on. Dressing in sexy...
    sexyjesscd sexyjesscd 18-21, M 1 Response Jun 17

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    okay well I've really decided this time because I'm ready. more ready than the last time I said I'd jump in to the dating pool and was wearing some hefty floaties. kept my...
    queenjellyfish queenjellyfish 18-21, F 1 Response Jun 16

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    I am a 17 year old crossdresser who is looking for others my age to talk! Let me know! :)
    sexyjesscd sexyjesscd 18-21, M Jun 16

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    Just because I am a crossdresser doesn't mean you can just pop up and say "be my sissy tart". Then have the audacity to report and block me after I politely said no thank you.
    JessicaPenny JessicaPenny 18-21, M 7 Responses Jun 15

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