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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 42 People

    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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    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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    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 5 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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    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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    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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    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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    Related Experiences

    I am 15 years old crossdresser, maybe i was born a boy but its not me i want to be a girl i love wear sexy panties bras bikinis sexy lingeries and i love do my make up its me and...
    barbaraxoxo barbaraxoxo 13-15, T 1 Response Apr 3

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    I would love to join your number of crossdressers
    eile eile 61-65, M Mar 28

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    I am crossdresser and I live in Orlando, I need to meet
    KayraCasanova KayraCasanova 46-50, M 2 Responses Mar 28

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    Hi. This is really the first time I'm really putting this out there. I've been secretly crossdressing on and off since I was 6. I'm turning 18 in July so it will be 12 years now. I...
    DecrepitSundew3 DecrepitSundew3 16-17, M Apr 1

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    Life's just so hard at times. A few months ago i was secretly crossdressing daily loving life, then the next thing i know i stop crossdressing and start going to the gym to make...
    Tyrone147 Tyrone147 18-21 7 Responses Apr 3

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    Any mtf crossdressers around my age(16) want to talk about dressing? I would also like get some help with making me look more feminine. Nothing sexual please. Message me :)
    HollyTG HollyTG 18-21, M 1 Response Apr 6

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    Any mtf crossdressers around my age(16) want to talk about dressing? I would also like get some help with making me look more feminine. Nothing sexual please. Message me :)
    HollyTG HollyTG 18-21, M 1 Response Apr 6

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    Any mtf crossdressers around my age(16) want to talk about dressing? I would also like get some help with making me look more feminine. Nothing sexual please. Message me :)
    HollyTG HollyTG 18-21, M 3 Responses Apr 6

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    Where do you boy crossdresser buy your thongs at?, because I don't want to go to Victoria secret XD
    Emoji2 Emoji2 18-21 3 Responses Apr 7

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    My friends a crossdresser and im proud that im friends with him
    Katiedollx Katiedollx 16-17, F 3 Responses Apr 11

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    I've noticed most crossdressers on here are either from the UK or the US, are there actually any mainland Europe CD's on here ?
    PersonOfUninterest PersonOfUninterest 18-21, M 3 Responses Apr 17

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    Last night the gal who lives across the hall from me invited me to a party she was having with a few friends. She knows I live alone since my wife passed away a couple years back...
    HappyJackUSA HappyJackUSA 56-60, M 4 Responses Apr 18

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    I am just a guy who find crossdressers fascinating. I have not interest in being one myself but I find getting lost in the illusion intriguing. So if your looking for support...
    HappyJackUSA HappyJackUSA 56-60, M 3 Responses a week ago

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    Hi I'm a 16 year old m crossdresser and just looking for someone to either talk to or have a good time with!
    hatrickhockey23 hatrickhockey23 16-17, M 2 days ago

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    Its amazing how little it takes for a crossdresser to project a female image..I went to a hockey game with a CD I met name Angela..Despite the fact that she wore a hockey jersey to...
    HappyJackUSA HappyJackUSA 56-60, M 3 Responses 1 day ago

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    I am finding it very hard to figure out where I fit in the grand scheme of the gender spectrum. I would say that I more fluid and don't hide myself that much no matter how I am...
    JessicaMarie35 JessicaMarie35 36-40, T 3 Responses 8 hrs ago

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    I have been to numerous dating sites, trying to take chances of finding a man to be in a romantic relationship with or even just a friendly one, because I do believe that long...
    nbsbgal nbsbgal 22-25, F Mar 30

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    Hey all I want to share my experiences of dating a widower........ When I found out the man I was talking to was a widower I have to admit I was scared I wasn't strong enough and...
    Becky1711 Becky1711 31-35, F Apr 15

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    I do know one or two couples who met through dating agencies of one sort or another (internet or not), but generally I regard them as cynical and parasitical. If you are unable to...
    Perspicares Perspicares 61-65, M 2 Responses Mar 28

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    I think I need to either stop dating entirely. Or stop dating smart,educated women. Cause deep intellectual conversations seem to end badly. My beliefs and opinions are strong and...
    pecos666 pecos666 36-40, M Mar 29

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    I never thought I'd still be dating at this stage in my life. I was supposed to be settled down by now with a husband, white picket fence, 2.5 kids and a dog. And I still hate...
    CAgrlnGA CAgrlnGA 31-35, F 3 Responses Apr 2

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    There is something I need to get of my chest and I suppose that's what this is all about. I "met" this guy through a very popular online site recently.. Wow. He seemed perfect...
    wingofthebutterfly wingofthebutterfly 46-50, F 10 Responses Apr 5

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    In the course of dating smokers, I find the majority on smokers dating sites are women who started their cigarette habit in their teens and 20s. But not all. It seems while smoking...
    Freekorps Freekorps 56-60, M Apr 13

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    I am not now dating a widower. After 11 years I got tired of feeling like I was dating a married man ... just one with a wife in the grave. He was good to me overall. His family...
    FoolForElevenYears FoolForElevenYears 51-55, F Apr 13

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    So, I'm a freshmen in college, and am currently dating a black guy, I am white myself. Now, my whole family is against this, but since I was a freshmen in high school my parents...
    CollegeStudent9396 CollegeStudent9396 18-21 1 Response Apr 15

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    I just finished checking my inbox, NOT on EP. So far, I don't love what I see. Most of these guys seem so lame or are not attractive or are booring. Sigh, I hate online dating but...
    Nadine1986 Nadine1986 26-30, F 2 Responses 6 days ago

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    Good morning Ep, last night I got a letter asking to talk a little about the crazy world of dating with a disability--now to be honest I'm hardly the guy to give any kind of dating...
    ChasingSuperman ChasingSuperman 26-30, M 5 days ago

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    Guys tell me if there was a girl you haven't slept with yet but you want to really bad after 3 months of casual dating but you have been sincere with her telling her you are not...
    syntheticrhyme syntheticrhyme 46-50, F 2 Responses Mar 30

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    Online dating makes me feel like **** sometimes. If I message someone who I find cute, or not necessarily extremely attractive but not horrible, they'll message me for a little...
    idontknow2658 idontknow2658 18-21, M 2 Responses Apr 1

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    your stupid and perverted and can't use grammar if you think this experience has anything to do with oral. it means the person is really bad at dating!!
    darkprinsus darkprinsus 13-15, F 2 Responses Apr 7

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    this dating thing is mystery. Most of the over 40 are newly divorced & have the residue of the previous relationship. Not having a clue of letting go
    girleve girleve 70+, F 1 Response Apr 11

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    If I wanted to date, I'd go on an actual dating site.
    PinkChocolate00 PinkChocolate00 13-15, F 1 Response Apr 12

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    I have never enjoy the date world and I thought that I am still in this world. I have dream that I would be marry with some kids at my age but I am still single. I hate dating...
    AZraven AZraven 36-40, M Apr 12

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    So how do you exactly know if you're ready to date someone? like, you're not just being desperate... if you go looking for a potential date, does that mean, you are being...
    kmisfit123 kmisfit123 18-21, F Apr 14

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    So is it possible to find the love of your life online or through a dating app?
    coraimaal coraimaal 18-21, F Apr 14