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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 39 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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    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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    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 41-45, 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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    Related Experiences

    It seems that 95% of all crossdressers are male to female, unless it is just that females are less likely to come out about crossdressing. But regardless it is pretty rare for me...
    LexyCD LexyCD 18-21, M 3 Responses Nov 20

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    Some of the best friends I've ever had are transsexuals and crossdressers. I helped one of my past boyfriends of two years even realize he was a male. I helped him pick his male...
    AlysonBlack AlysonBlack 18-21, F 4 days ago

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    Happiness is at its peak, as gays can now meet and greet the people they want to date, on an online platform. Online dating sites in today’s world is the most convenient and...
    MosesProffitt MosesProffitt 22-25 Dec 1

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    Hi everybody! I would like to introduce myself this wonderful group. I'm Amber and I am a very part-time crossdresser. I've been crossdressing on and off for a few years now. As...
    lthrnick1987 lthrnick1987 26-30, T 3 Responses Nov 18

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    I love being a crossdresser. I mainly dress in boyish clothing but I chuck in girls clothes too.
    BondageKiller66 BondageKiller66 16-17, T Nov 20

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    I'm more of a transgender then a crossdresser.. Nun the less I could use more CD/Trans friend! We could take about everything u want! Our dresses, heels, stockings, leggings and...
    CutepieTay CutepieTay 18-21, M 1 Response Nov 20

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    Having been a crossdresser for years and having purged my collection several times because my previous wives objected I now have an ever expanding wardrobe of dresses, nylons...
    PJSZ PJSZ 61-65, M 1 Response Nov 23

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    I'm a girly crossdresser who wants to meet someone like me and we dress up like princess girly girls
    sissyprincess2 sissyprincess2 22-25, M Nov 30

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    I would love to have a cross dresser pen pal, I think it would be wonderful to talk to someone like that:) if a crossdresser would like to have a non cd pen pal please pm me.
    Batman328 Batman328 18-21, M Dec 2

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    It's official my whole family know my secret of being a crossdresser and it feels super amazing it's a feeling I thought I would never feel :)
    Tigerbentz Tigerbentz 16-17, M 2 Responses Dec 2

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    mesg me plz im willing to talk talk anyone im a crossdresser btw
    imacrossdressermessageme imacrossdressermessageme 70+, T 1 Response Dec 4

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    I'm looking for friendship with males females crossdressers,I can be a loyal and caring friend xx
    stuartCd stuartCd 18-21, M Dec 6

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    I love being a crossdresser sometimes. Every time I go shopping for women's clothes, I always love trying them on at the Fitting Room. Normally I look for leggings, bra, panties...
    Pretty7Pretty Pretty7Pretty 26-30, M 2 Responses Dec 6

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    Have any crossdressers seen sissy hypno pics or vids? I've recently found them and I'm hooked..
    ConfusedSecrets ConfusedSecrets 18-21, T 2 Responses Dec 7

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    Thinking about coming out to my sister. Over the past couple of months, I've realized that I'm a crossdresser. I've already debated for a while about coming out to my family and...
    Cmoor007 Cmoor007 22-25, M 2 Responses Dec 7

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    I wanna chat/trade pics with other crossdressers or girls please message me with either your kik/skype please have a pic as i want to see who I am talking to. xxx
    lucyxcd lucyxcd 18-21, M 1 Response a week ago

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    I often dream of taking a girl home then finding out she's a crossdresser when I go down on her
    thesentinel02 thesentinel02 22-25, M 2 Responses a week ago

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    God doesn't make mistakes. I was just reading some comments to another Christian Crossdresser story, and came across these words. In the comments I was reading just now they were...
    AzabethTV AzabethTV 51-55, T 6 days ago

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    i want to find a girl that wants to date a crossdresser
    littleprincess1992 littleprincess1992 22-25, T 5 days ago

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F 1 Response Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    JessieFay JessieFay 31-35, F 1 Response Dec 2

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    MandyWilson MandyWilson 26-30, F Dec 3

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    MandyWilson MandyWilson 26-30, F Dec 3

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    MandyWilson MandyWilson 26-30, F Dec 3

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    Middle-aged men and teenagers don’t really want to get that tag of a committed relationship and fall into a long-term relationship at an early age. However, women in today’s...
    CougarsWoo CougarsWoo 36-40, F Nov 19

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    10yeargap.com focuses on younger women dating older men and it encourages age gap marriage. 10YearGap.com is not a sugar daddy site. Single women are attracted to older single men...
    MandyWilson MandyWilson 26-30, F Dec 3

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    Okay, so this is actually old news that I'm experiencing strong emotions about again. My mother died when I was 13, after about 8 months of battling cancer. That in itself was...
    jaclynhampson jaclynhampson 18-21 Nov 27

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