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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 38 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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    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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    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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    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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    Related Experiences

    I am dating a older woman who is 10 years older then me. We have been going out for 1.5 years and we stayed together for a while but not anymore we are staying in different...
    burnoutchanu burnoutchanu 22-25, M 10 hrs ago

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    My parents upset me so much. My soldier and I have been dating for two years. We want to get married one day. I'm a senior in high school getting ready to go to college. My dad...
    AaronsGirl9112 AaronsGirl9112 16-17, F 1 hr ago

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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 6 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 4 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 Sep 12

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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 15 Responses Sep 14

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      Just wondering if there are any girls out there that want to chat with a crossdresser in the uk. Nikki x
    Nikki1988x Nikki1988x 22-25, T Sep 21

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    any crossdressers want to chat then please feel free to add me as a friend
    girlyAndrea1987 girlyAndrea1987 26-30, M 1 Response Sep 22

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    I'm new to EP and want to meet a crossdresser. I'm looking for a sexual and emotional relationship. I'm 20, 5'11, 160 ibs, good looking and from Cambridge Ontario. Add me up if you...
    nick191 nick191 18-21, M a week ago

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    Are there any girls from New Jersey that like crossdressers? I'd love to hear from someone and chat
    Lovethembig Lovethembig 18-21, M 1 Response 3 days ago

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    If you're a girl that likes crossdressers you are automatically cool in my book. Y'all are the best!
    rachelmarie13 rachelmarie13 18-21, T 2 Responses 2 days ago

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    Looking for another crossdresser to talk to or be friends with in Michigan!!
    need4speed28 need4speed28 18-21, M 1 Response 1 day ago

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    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    tessacc11 tessacc11 26-30, F 1 Response Sep 22

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    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    sandycc11 sandycc11 26-30, F Sep 23

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    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    sandycc11 sandycc11 26-30, F Sep 23

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    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    sandycc11 sandycc11 26-30, F Sep 23

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    YoungerWomenWithOlderMen.com Focus on Connecting Younger Women with Older Men Recently launched online age gap dating site, YoungerWomenWithOlderMen.com, has become popular between...
    sandycc11 sandycc11 26-30, F Sep 23

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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 2 Responses Sep 7

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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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    I've tried online dating for years on and off. I've met a few really great matches for myself and just recently tried on a dating website that advertised free weekend communication...
    Owleeeeease7 Owleeeeease7 36-40, F 2 Responses Sep 20

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    I'm 17 years old and my boyfriend is 28 years old. We haven't been dating for long and we meet online but I can't express the feelings I have for him. I never thought I would be...
    nigerianigbo nigerianigbo 16-17 1 Response 3 days ago

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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 76 Responses Sep 10

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    Goa Hot Model Dating Top in Goa Dating 09702448444 
    jesikagoa725 jesikagoa725 22-25, F 1 Response Sep 18

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    I posted a story with the heading l live in a,sexless marriage....it changed to l am dating. I can categorically state that l am definitely NOT dating. I will repost my story and...
    2BlossomBlue 2BlossomBlue 51-55, F 1 Response Sep 18

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    One of my Friends came Up to Me and said "OMFG, Preston is dating Amanda and she isn't even pretty, ew,," Can I just say I hate when people do that? Dating isn't about looks, it...
    Bflyboo14 Bflyboo14 13-15, F 4 Responses Sep 20

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    www.cougardatingnow.com is the best sugar momma dating site for sugar mommas to date younger men. Sugar Mamas are a rarity in our culture but we are breaking the door wide open and...
    MaggieJohn MaggieJohn 26-30, M 5 days ago

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    Not sure if this is where I should post this but I feel the need to get this out. So, my ex boyfriend and I broke up a while ago for the umpteenth million time and i ended up...
    Pinklily87 Pinklily87 26-30, F Sep 1

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    I have been on Plenty of fish for 4 years on and off. I meet two men that I spent maybe 3 months with tops. I was not really looking for a man just dating friends first type of...
    OneTooManyTears OneTooManyTears 36-40, F Sep 4

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    I saw this girl's profile on a dating site, and it said "I'm tired of people who only care about how someone looks." I decided to send her a message. Her response? "I don't date...
    AgentSickler AgentSickler 18-21, M 2 Responses Sep 4

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    I am for sure not on this great site looking for a date or anything really..I just like sites like this one where I can be who I am all of the time,I do okay on the dating scene in...
    mrpampers2 mrpampers2 26-30, M Sep 5

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    Is this place actually a dating site? Never mind the fact that about different countries and long distance do people actually meet on here? No I don't want to date. Not from here...
    CeeAirAHH CeeAirAHH 13-15, F 3 Responses Sep 6

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    Dating? Lol hell no. I dont even know how to make friends in Ep. Real life is so much better, sometimes. In my opinion :)))
    daneean daneean 18-21, F 2 Responses Sep 6

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    Sometime I think I should just give up on the possibility of me and him. I met him a month or more ago. What started out as something that made me so hopeful has turned into more...
    emelon12 emelon12 18-21, F 1 Response Sep 6

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    For me, connection needs to happen at multiple levels before I fall in love, and some of that connection requires face-to-face time. I can learn a lot about a person's personality...
    Kerennya Kerennya 46-50, F 1 Response Sep 7

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    how thing they can find a life partner on the internet dating online?
    robinwill robinwill 26-30, M Sep 8

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    If she's on a dating site, memorize her profile pic and avoid with all effort.
    CrushedCrusader CrushedCrusader 46-50, M 2 Responses Sep 10

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