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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 48 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 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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    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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    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 3 Responses Apr 7

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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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    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

    hi everyone!!!! im a teen crossdresser (17), and im looking to make a long lasting friends who also crossdressers, someone who is interested in talking about anything!!! let me...
    CDArseni CDArseni 18-21, T 1 hr ago

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    Is it just me or is online dating completely pointless...??
    Katrinahu Katrinahu 22-25, F 1 Response 8 hrs ago

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    I'm married to a crossdresser whom I love and am happy to talk to anyone about it.
    crazybipolarchick crazybipolarchick 36-40, F 5 Responses 13 hrs ago

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    Sometimes I find a partner Crossdressers interesting))
    DOMINABARBARA DOMINABARBARA 36-40, F 12 Responses 1 day ago

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    I Love Older Women That Like Younger Men? Welcome to OlderWomen-Dating.com The premier Older Women and Younger Men Dating Site.We offer the matchmaking service for mature women...
    Ben60 Ben60 26-30, M 2 days ago

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    I've recently started dating this guy and to my surprise it's been real easy and fun. It kinda reminded me of how things were the very first time I fell in love. Everything seemed...
    tiara29 tiara29 26-30, F 1 Response 3 days ago

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    so, im a teen crossdresser (17) and iv been dressing since i was 10 or so. im so happy i can have this life and its so exciting. At this point i have a nice little collection of...
    CDArseni CDArseni 18-21, T 2 Responses 3 days ago

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    I've been dating younger men for the last 10 years now. Since I split from my son's father I decided to give a new fresh look to my life and decided to start dating another type of...
    angyguti1990 angyguti1990 41-45, F 2 Responses 4 days ago

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    So when I first moved to a new city, and was trying to get into the swing of being single again after my separation/divorce, I figured I'd give online dating a shot. After all...
    RisenFromAshes RisenFromAshes 36-40, M 5 Responses 4 days ago

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    How do I say this? Well, first off, I'm a lesbian. My cousin is bisexual. She is 19 years old and I'm 13 :-/ I know she's too old for me and that she could go to jail and get in...
    Sweetie6 Sweetie6 13-15, F 5 days ago

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    Look, don't mean to be brutal, but don't ask me for a date or a relationship because that's not what I'm on EP for. I'm only here for friendship and that's all so don't ask me to...
    ArtLover24 ArtLover24 22-25, F 5 Responses 5 days ago

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    Why don't some people read other's profiles more thoroughly?? I'm so sick of being propositioned for dating/relationships. I only want to make friends. I wasn't interested in...
    nightowl2015 nightowl2015 26-30, F 2 Responses 6 days ago

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    I just found a "new to me" store devoted exclusively to crossdresser clothing. It is https://www.janetscloset.com/ it is located in Wyandotte, MI WOW quite a selection
    sweetGigi sweetGigi 61-65, M a week ago

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    I am a big woman in Chicago,I don't know whether people love big women,I'm a little bit but I treat people good and I have a nice look.I met several people on fb,we chat but it's...
    Celialee Celialee 31-35, F 1 Response a week ago

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    So... A coworker asked for my number, he wanted to go on a date with me. but there's 2 problems here, he's my superior and big friend of my boss and I wanted to apply to another...
    Blackberries Blackberries 26-30, F 3 Responses a week ago

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    I just want to say... I am tired of the perverts and creeps who antagonize crossdressers for pictures. I have been the victim of this numerous times. they ask you for pictures then...
    IamKatrina IamKatrina 18-21, M 1 Response Jul 23

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    Is anyone else out there dating there best friends parent? Casting new show, need stories to pitch.
    Outsidethabox Outsidethabox 26-30, M Jul 21

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    Would you date someone who has an ex-boy/girlfriend living as roommate? But then your date tells that ex-boy/girlfriend has been trying to constantly hitting on my date? I just...
    preciouscargo1 preciouscargo1 36-40, F Jul 20

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    Actually a funny story. GUYS, do not judge me for this, I was only 11 years old. I met a girl on a forum called gaiaonline.com. I messaged her and we chatted for HOURS. After...
    Omziraal Omziraal 18-21, M 2 Responses Jul 19

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    Hello im Michael/Kaitlynn and ever since i have started dressing i have always wanted girl-friends and a girlfriend who like crossdressers. it has always been a dream of mine to...
    deleted deleted 26-30 Jul 19

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    I am a crossdresser that's me in the pic anyone wants to chat
    ssexysissyboy15 ssexysissyboy15 13-15, M 3 Responses Jul 19

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    I am just trying to find love. I don't want to be lied to, let on or propositioned. I don't want to seek empowerment through hookups or one night stands, I honour myself and my...
    brightonion brightonion 26-30, F Jul 18

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    I really don't think EP is a dating site, but I see it being used as one, I mean don't get me wrong, if it weren't for EP, six amazing people that I know wouldn't be married...
    BroknGirl89 BroknGirl89 26-30, F 1 Response Jul 18

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    I don't and won't do it on this site, because this is not a dating site.......but i have recently made a new account on an actual dating site, to meet and date people in my general...
    violet1698 violet1698 31-35, F 4 Responses Jul 17

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    Today I hung with my boo & we barely hang because of work . Today he tells me he might be moving away & I feel like he's no considering" us" he's just thinking about his company...
    sadelove sadelove 26-30, F Jul 16

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    I wouldn't mind dating one of there guys on here. We just have to hang out just to see if it's something there. It take me 5 months to date someone. I have to know everything about...
    lorrena19 lorrena19 18-21, F 1 Response Jul 16

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    I'm 15 I'm secretly a crossdresser and I'm secretly attracted to men anyone wanna chat
    sissyboy20000 sissyboy20000 13-15, M 3 Responses Jul 16

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    I'm asexual guy, I like dating with lesbian girl
    Showmelove84 Showmelove84 31-35, M Jul 16

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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...
    ultacc11 ultacc11 26-30, F Jul 16

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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...
    ultacc11 ultacc11 26-30, F Jul 16

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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...
    ultacc11 ultacc11 26-30, F Jul 16

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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...
    ultacc11 ultacc11 26-30, F 1 Response Jul 16

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    Hi I'm new to this but I am a crossdresser. At times I feel like a real girlie girl on the inside and other time just a boy. I would love to connect with a real genuine girl who...
    VANZxADDICT VANZxADDICT 18-21, M 2 Responses Jul 15

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    I've tried online dating. Needless to say that it may work for some but it hasn't worked for me yet. I've been as nice as I can be and been that guy who isn't a creep and yet still...
    CityWok88 CityWok88 26-30, M Jul 15

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    I started on OKCupid and I went on one date and it didn't work out, he was just really weird. But after that I went on plenty of fish. (POF) I talked to this guy for a few months...
    SabRaWr SabRaWr 18-21, F 3 Responses Jul 15

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