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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 37 People

    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 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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    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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    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 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 2 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 41-45, M 1 Response Mar 16, 2012

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    Related Experiences

    i adore crossdressers so much!!! you all look so good. i have no idea why but im just so attracted to crossdressers. a bunch of cuties.
    sutsuki sutsuki 13-15, F 8 Responses Jul 28

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    Do I think crossdressers are gay, you ask me? Are they honest, is my counter question. I know is not exactly legimate to answer a question with another question but. But this...
    gypa gypa 26-30, M 6 Responses Aug 5

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    (Not a Crossdresser) Hmu on kick : 735218 i'm down to talk or maybe more ;) no kids please , Crossdressers only
    14674RF 14674RF 18-21, M 1 Response Aug 15

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    I don't consider myself a crossdresser. I do wear a lot of things that women wear... nail polish, panties, nylons, skirts, heels, sandals, sneakers, hiking boots, shorts, jeans...
    steve66oh steve66oh 46-50, M 3 Responses 3 days ago

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    I want to cry right now I've taken up drinking because it numbs the pain of my self disgust I'm drunk right now and want to kill myself I hate myself because I crossdress I thought...
    JulieCakes JulieCakes 13-15, M 1 Response 3 days ago

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    Are there any crossdresser boys in Illinois I can meet? I like to dress up too and have fun ;)
    noLimits5252 noLimits5252 16-17, M 1 Response Jul 27

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    I do support them but I've got one problem. So I go to meet ups and I'm going to Gay Pride tomorrow and the thing there will be a lot of crossdressers, mostly males. And well...
    CallMeChelsea CallMeChelsea 16-17, F 6 Responses Aug 2

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    I had joined this group and thought I should really add a story no matter how short. The above type of man can also be termed as a Transvestic Fetishist Under-dresser not simply a...
    manslip manslip 56-60, M 4 Responses Aug 7

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    Any Crossdressers in indiana
    pantyhoselover33 pantyhoselover33 61-65, M 3 Responses Aug 10

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    I'm going to be posting and sending nude pics or will be on Skype so add me kik: missjazzmin Skype: misscrossdresser and also looking to talk to other crossdressers
    missjazzmin missjazzmin 18-21 2 Responses Aug 11

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    I would love to have a crossdresser and a transsexual friend
    ShadowTech ShadowTech 22-25, M 3 Responses Aug 12

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    Hello! I am a crossdresser who is looking for a female to dress me up. If your interested i am also looking for a girlfriend or a owner. If your interested comment or message me...
    CuddlesNSnuggles CuddlesNSnuggles 13-15, M 1 Response Aug 13

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    I was a teen when I discovered I liked the dark lash look that mascara gave the user. I asked an older neighbor girl, her makeup was always immaculate and tastefully done, if she...
    CdKimmi CdKimmi 61-65, M 2 Responses Aug 14

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    Hi myself Rajesh. Want to meet crossdressers from Bangalore. Real admirer and lover
    Rajesh900 Rajesh900 36-40, M Aug 14

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    Hmu on kick : 735218 i'm down to talk or maybe more ;) no kids please (CrossDressers Only)
    14674RF 14674RF 18-21, M 2 Responses Aug 15

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    Hey u crossdressers in Bangalore meet me for a never before experience
    Rajesh900 Rajesh900 36-40, M 1 Response Aug 18

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    i have always wanted to be a crossdresser but dont wanna be gay or ewt what should i do
    ilovestorys1963 ilovestorys1963 13-15 1 Response 6 days ago

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    I don't consider myself a crossdresser. I do wear a lot of things that women wear... nail polish, panties, nylons, skirts, heels, sandals, sneakers, hiking boots, shorts, jeans...
    steve66oh steve66oh 46-50, M 2 Responses 3 days ago

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    I've always wanted to find someone to love who's a Crossdresser. But more than just sex a real relationship. Where I'm from it's very hard to impossible to meet anyone.
    skijunkie10 skijunkie10 22-25, M 2 days ago

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    I would love a crossdresser pen pal from New York i'm from Ireland
    jodiK33 jodiK33 41-45, M 1 day ago

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    So I would really like to meet other Crossdressers. I live in NC, but I am going to be moving to S. Korea soon. Is there anyone living over there I could start talking to now?
    Freja14 Freja14 31-35, T 1 day ago

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    I am married and a secret crossdresser. I have some clothes, lingerie and shoes and my body is a bit girly and with proper makeup and a wig I bet I might be ok. I am desperate to...
    cdjanine cdjanine 41-45 6 Responses 13 hrs ago

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    Living in a small town makes it hard for some folks to meet decent dating material. But I live in a big city bustling with single people from all ages and let me tell you, it doesn...
    Bellamae Bellamae 41-45, F Aug 8

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    Dating is hard enough, and it will be more difficult when it comes to dating with STDs. Thanks for the online dating platform provide a new chance for people living with STDs to...
    stdaustralia stdaustralia 22-25, F Aug 11

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    Dating is hard enough, and it will be more difficult when it comes to dating with STDs. Thanks for the online dating platform provide a new chance for people living with STDs to...
    stdaustralia stdaustralia 22-25, F Aug 11

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    Dating is hard enough, and it will be more difficult when it comes to dating with STDs. Thanks for the online dating platform provide a new chance for people living with STDs to...
    stdaustralia stdaustralia 22-25, F 1 Response Aug 11

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    I don't know why, but dating and I don't seem to get along. I've been thinking about getting back in the dating scene, but based on my past experiences in finding a date, I know it...
    jamie1292 jamie1292 22-25, M 6 days ago

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    So I've started dating again after my emotionally abusive boyfriend left me a few months ago. We were together for 9 months and even though there is still scarring there I felt...
    Equine228 Equine228 18-21, M 1 Response Aug 12

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    It did not work out the way that I'd hoped. I won't name the site that I used, but I created a profile about 2 years ago (2012ish), and figured it give it a shot. I answered a...
    moonchile moonchile 31-35, F 2 Responses Jul 28

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    So I have learned online dating really sucks!! I have also learned guys are way more pickier then the girls. They want the girls who look like models and hurt then in the end...
    feelinglost84 feelinglost84 26-30, F 3 Responses Aug 2

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    The Reasons of Older Men Younger Women Dating . Older men date younger women for many reasons. It does not depends on age most of the time as much as depend on Passion, love and...
    caitlincc11 caitlincc11 22-25, F Aug 7

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    I dont understand some people make this platform for dating and talking dirty. Some even start getting cozy and start calling you sweets when you dont even know them properly. I...
    TrueLoverN TrueLoverN 26-30, F 1 Response Aug 7

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    I've always had really great experiences with online dating. It's great for going outside your social circle and meeting new personalities. I would have to say my most...
    blazeee blazeee 22-25, F 1 Response Aug 8

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    I suppose the most realistic attitude a woman could have towards online dating is cynicism. The British musical artist La Roux's "Bulletproof" seems to captivate the aforementioned...
    Chaotician Chaotician 22-25, M Aug 8

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    Hey guys its been awhile some people asked me if I still wear diapers cause in some old stories I said I did. Well I was always incontinent and I used to be embarrassed. But I...
    Hope2456 Hope2456 13-15, F 4 Responses Aug 10

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    I joined EP for charity work and other things not to talk and date haha. I have a wonderful boyfriend and in a happy relationship no need to experience guys and dating. Love this...
    Klcataldo Klcataldo 18-21, F Aug 14

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    Well, I feel I'm progressing.. The biggest struggle I have is believing a person finds me attractive (mind and body) and not jumping to unhelpful conclusions because of that...
    liltree liltree 31-35, F 2 Responses Aug 16

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    Why does dating suck. Im so sick of letting myself getting hurt. I knew better and I still let it happen. Why do i always pick the emotionally unavailable men! **** Dating!
    AdelaideKane AdelaideKane 36-40, F Aug 18

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    I was suppose to meet the guy I'm seeing for the 4th time on Friday but had to cancel due to child care problems.. it's been a few days and I haven't heard from him which is...
    Mama86 Mama86 26-30, F 2 Responses Jul 27

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       My current boyfriend is a drummer for a local band around my area. I have dated musicians before but nothing is like dating a metal-head drummer. I have been and...
    LuckieCharmz93 LuckieCharmz93 18-21, F Jul 28

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    Saw that my bf is a member of many dating websites. A slapin the face.
    lynnys lynnys 36-40, F 3 Responses Jul 29

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    I never looked at EP as a dating website. Who wants to be friends with me? :D