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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 38 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 6 Responses Nov 24, 2009

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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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    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 3 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'm dating a man in the Air Force who is stationed in Quatar. He will be home right after Christmas! We have been together for almost a year now...I miss him so much :)
    Irishgirl456 Irishgirl456 41-45, F 21 mins 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 4 Responses Aug 23

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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 3 Responses Aug 24

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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 Aug 20

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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 Aug 23

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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 Aug 24

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    I would love a crossdresser pen pal from New York i'm from Ireland
    jodiK33 jodiK33 41-45, M Aug 25

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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 Response Aug 25

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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 9 Responses Aug 26

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    Well, many people would call me "crossdresser". I don't think of myself that way, because I've never tried to present myself as female or make anyone think I was. But, I like to...
    steve66oh steve66oh 46-50, M 5 Responses Aug 27

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    I am a crossdresser! I also love anal play x
    SluttyCP SluttyCP 18-21, M 2 Responses Aug 30

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    Hi. I'm new to this site so is thought I would post! I'm 25 and in a committed relationship with a woman. I consider myself bisexual and have had encounters with both genders...
    Nikki1988x Nikki1988x 22-25, T 7 Responses Aug 31

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    any ladies or other crossdressers please message me!
    Gmailol Gmailol 26-30, M 6 Responses Sep 2

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    hey babes, if you ever want to talk to another crossdresser, just message/add me and ill add you back.
    Gmailol Gmailol 26-30, M 7 Responses Sep 2

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M Sep 3

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 3 Responses Sep 3

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 2 Responses Sep 3

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    I would really like to have a crossdresser friend to spend girl time with, but I am about to move out of the country soon. I don't want to start a friendship with someone local...
    Freja14 Freja14 31-35, T 1 Response Sep 5

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    I am happy to chat with crossdresser, just inbox me and we can talk
    Thecdman Thecdman 22-25, M 5 Responses 5 days ago

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    I know most people on this site are in the US but I would really like to get to know other crossdressers to chat with / share experiences with. I am new to this but can't get...
    Nikki1988x Nikki1988x 22-25, T 13 Responses 3 days ago

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    Before responding consider what I am saying. Overwhelmingly dating is the way in which people start relationships and it's not that dating is the only way, but dating is so popular...
    idkanswer2014 idkanswer2014 26-30, M 1 Response Sep 7

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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 Aug 20

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    Dating online may be an interesting experience with everything dealt with properly.If not, it will surely be rather boring.That's why dating online should be made carefully rather...
    Tink0624 Tink0624 26-30, F Sep 2

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    The idea of senior dating is completely different than dating in current generation times. Usually, when people who have crossed the near fifty years mark engage themselves I...
    sophiescanlan1 sophiescanlan1 26-30, F Sep 3

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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!
    Sabr3na Sabr3na 36-40, F 1 Response Aug 18

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    Dating a married man is hard. He whips out his wallet to pay for something and I look down and see a photo of his wife tucked into his wallet. You can imagine how that feels...
    hankpalmer hankpalmer 18-21, F 77 Responses a week ago

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    I met a man on a dating site. As soon as we met, we hit it off. He was single, after getting a divorce from his wife of fourteen years. But as the relationship progressed, he would...
    mumziiii mumziiii 36-40, F Aug 18

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    The guy I'm dating seems so cheap now ! He doesn't want to go out to eat or anything just stay home and watch movies . I mean it's nice but if he's cheap I at least want to know...
    mimilsu mimilsu 18-21, F 2 Responses Aug 18

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    I'm 21 dating a 25 years old he's close to turning 26 but I'm in my "I want to drink and go to bars stage" and well he's not . He's more of stay at home watch movies all day . I...
    mimilsu mimilsu 18-21, F 1 Response Aug 18

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    The guy that i talk to is "friends" w/some1 i think likes him and wanna have sex w/him. I called him u to tell him do not answer or text her anymore. He did her pics 4a wedding and...
    sadelove sadelove 26-30, F Aug 20

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    Im 23 dating a 30 year and shes my co-worker been talking for about 8 month.. Its difficult because she has a 14 year old daughter so she always comes first, of course i understand...
    GoneeonG GoneeonG 22-25, M 1 Response Aug 21

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    I've been wary about dating someone online. I mean, they could tell you whatever they want and put up pictures that may not even be of them, but it could all just be a ruse! They...
    Whoami30 Whoami30 26-30, M 2 Responses Aug 21

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    I don't see EP as a dating site and am not looking for an online relationship anyway.
    Sourminds Sourminds 18-21, F 2 Responses Aug 21

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    I really don't understand these idiots on dating sites. Typical idiotic things guys always say and do: -"Are you a virgin?" -"I'm h*rny." -"I have morning wood." -"Want to trade...
    firecancatchme firecancatchme 18-21, F Aug 22

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    I really don't understand these idiots on dating sites. Typical idiotic things guys always say and do: -"Are you a virgin?" -"I'm h*rny." -"I have morning wood." -"Want to trade...
    firecancatchme firecancatchme 18-21, F 3 Responses Aug 22

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    I've been dating this guy for almost 2 1/2 years and we've had our ups and downs but its kinda gone into barely speaking with his either being busy and me starting senior year in...
    fallenfar fallenfar 18-21, F Aug 22

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    I am dating someone I know I do not want to marry..... Now what? Do I have that conversation? He hasn't proposed so I don't want to mention it but I know if he did the answer would...
    Millionairess1 Millionairess1 31-35, F Aug 23

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    congarconnecting. wordpress. com this blog is good for reading some dating story and checking out mature women
    tanglelau tanglelau 31-35, F Aug 25

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    Some one give me a ligit dating site please i need an online gf lol
    EBestest EBestest 18-21, M Aug 25

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