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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 53 People

    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, 2015

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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 5 Responses Nov 24, 2009

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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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    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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    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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    Related Experiences

    i'm here for me. it's nice to have people to talk to, but not hooking up with EP guys.
    lifealwayschanges lifealwayschanges 41-45, F 1 Response 5 hrs ago

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    I am only 18 months out of a 22 year old marriage and 24 year old relationship. The break-up was not mutual - only he wanted it so to say the least I am still coming to terms with...
    Alleygirltoo Alleygirltoo 41-45, F 4 Responses 14 hrs ago

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    you think you suck at dating!? Check out his faillll. Day 9 - A Java Rejection https://youtube.com/?reload=7&rdm=1vq2016vm#/watch?v=ip8IUV-Svz8
    RedChaplin RedChaplin 22-25, M 2 days ago

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    Im in serious need of dating help
    jellybellyman jellybellyman 18-21, M 3 days ago

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    I need help, I started dating this guy who's black, we've been friends forever. My parents don't approve, it's really hard because I don't want to disrespect my parents but at the...
    kpool88 kpool88 26-30, F 3 Responses 4 days ago

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    Im dating a woman. I pay for everything. Now she wants me to pay for her and her friends too. Why do women play me for a trick...
    xIcexColdx xIcexColdx 22-25, M 1 Response 5 days ago

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    I've found my zen. I have reached online dating nirvana... When I look through all the profiles and I notice how many girls I find myself attracted too. And not just like, oh...
    thenicholasexperience thenicholasexperience 31-35, M 6 days ago

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    I want to find a gurlfriend that wants to get together and have sex and just enjoy each other's company, I find other crossdressers irresistible
    Jamiegirl12016 Jamiegirl12016 56-60, T Jan 29

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    Being the man in the relationship or being the play toy sissy in her life. Crossdressing in front of your girlfriend can be the end of your relationship or life time of being...
    KatrinaBoyer41 KatrinaBoyer41 41-45 6 Responses Jan 29

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    I'm In Dire Need Of A Local Crossdresser Whose Local (In/Around The Charlottesville Virginia Area.Who I Could Possibly Host and Dress and Get All Dolled Up With.It Would Be...
    BiggBeautifulBri BiggBeautifulBri 46-50, M Jan 29

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    For ***** ‘n giggles of it, I compiled only ‘some’ of the dating questions I would now ask at this point in my life. These questions are rhetorical here. I could come up with...
    OlivePhire OlivePhire 41-45, F 1 Response Jan 27

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    I've been texting with a guy I used to go to school with. It's been 6 1/2 months now and I thought he was beginning to like me... flirting and such. But twice now he's suggested we...
    vickie8669 vickie8669 46-50, F 4 Responses Jan 26

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    I've recently asked a question about what you would like online dating to be like. Please visit my page and look for the post just below this one. We are doing a lot of...
    thenicholasexperience thenicholasexperience 31-35, M Jan 26

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    I just recently signed back up. I don't think it takes very long before you want to delete and go back into the real world only. I hear a lot of complaints from guys and I hear a...
    thenicholasexperience thenicholasexperience 31-35, M 1 Response Jan 26

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    Oh yeah, I tried it alright. I've had a gut I figured out the demographics and income level. It almost in desperation for survival. I met more single fathers that were granted...
    laceset34 laceset34 36-40, F 2 Responses Jan 26

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    after my experience with online dating I decided to give it up...
    Navae Navae 18-21, F 1 Response Jan 26

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    I'm going on a date today. With a guy I met on a dating site.
    kuroijukai kuroijukai 26-30, F 4 Responses Jan 26

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    i love talking to crossdressers it's such a huge turnon when guys dress like girl hmu
    jakeypoo96 jakeypoo96 18-21, M 2 Responses Jan 25

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    I'm an Indian crossdresser, who got the habit of wearing gagras and patialas
    ASanjanaSharma ASanjanaSharma 22-25, M Jan 25

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    the only place a lot of people are going to experience that perfect relationship is in their minds fantasizing. there's so many men and women today who are under the impression...
    niceguycursed niceguycursed 31-35, M 1 Response Jan 24

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    Tinder,Skout,POF..are similar. (I still have keep Okcupid cos at least i've met two guys on this site in a six months.ZERO on other sites) In my case,i couldn't find a guy who...
    babyblueeee babyblueeee 31-35, F 10 Responses Jan 24

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    well im dating a guy 5 years younger than me and I'll say he treated me way better than the guy I dated was 5 years older than me. I just hope when time passes he doesn't get bored...
    the808heartbreak the808heartbreak 22-25, F Jan 24

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    I love to dress up in nice girly cloths like dresses, skirts, panties, bras and, many more. But the one thing I want the most is a fraiends to help me or even do it with. I told...
    Ryan050606 Ryan050606 13-15, M 1 Response Jan 23

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    I love crossdressers they are hot to me , are any of you here bi or gay ? if so message me we can be buddy's
    deleted deleted 26-30 2 Responses Jan 21

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    I'm a lady who loves crossdresser guys even tho i'm lesbian lol i still like to see men dressed in drag and lingerie and like talking to them sometimes
    deleted deleted 26-30 1 Response Jan 20

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    i want to **** a crossdresser and have him dressed while i do it and also roleplay like he's a female lol i am weird i know i
    deleted deleted 26-30 Jan 20

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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...
    kimcc11aa kimcc11aa 26-30, F Jan 19

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    People say my Boyfriend will hurt me but idk what to think... All guys do but feel like he could maybe the one that may stay longer :D I like this one and hope I don't lose him...
    joybabe16 joybabe16 16-17, F Jan 19

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    http://www.crossdreamers.com/2016/01/the-life-of-crossdresser.html
    ashwinib ashwinib 26-30, M 2 Responses Jan 19

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    I used to suck at dating till I started dating this older guy. What came with his age was maturity, and a lifetime of experience. He was well into psychology. I think I ended up...
    herdinstinct herdinstinct 36-40, F 1 Response Jan 19

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    I'm west of Atlanta, in Georgia. I don't identify really as a "crossdresser" but rather a "genderfluid girl", that is, I have a feminine self identity, but am okay with presenting...
    tiffanyjoxd1989 tiffanyjoxd1989 26-30, T 1 Response Jan 18

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    I met this guy... well not personally but we have been chatting online. I went on a dating site and that's were I first had an encounter with him. We chatted a bit on whatsapp...
    Thandiwe25 Thandiwe25 22-25, F 4 Responses Jan 17

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    I met this guy online... we started chatting, the he told me he was in prison. I was just looking for a relationship but now there's this man telling me he's in jail. But I gave it...
    Thandiwe25 Thandiwe25 22-25, F 2 Responses Jan 17

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    Ladies, please read (or listen on audio) at least one of these books before you start dating again. It will save you from wasting your precious time, and maybe heartache. "It's...
    Carissimi Carissimi 56-60, F 3 Responses Jan 15