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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 42 People

    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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    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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    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 5 Responses Nov 24, 2009

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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 4 Responses Feb 17, 2013

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    Related Experiences

    I had this beautiful girlfriend who had no idea about how much I love to dress up. It killed me a little inside to keep that part of myself from her. It almost felt like not...
    kins101 kins101 26-30, M 4 Responses May 11

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    I've always loved crossdressers! I've learned half my makeup tricks from them. They're gorgeous, and definitely my "crowd". I've noticed half my friends are drag queens...
    muckwitch muckwitch 18-21, F 2 Responses May 5

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    i am a crossdresser. i like wearing female clothes,makeup,jewellery... i wear my moms saree, petticoat, nighty as i dont have a sister ..am really feminine and i like doing...
    Anjanacd Anjanacd 22-25, M 2 days 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 7 Responses Apr 27

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    Looking for crossdressers in the fort Myers Florida area
    booboo74 booboo74 36-40, M 1 Response May 3

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    any crossdressers want to chat?
    jallen93 jallen93 18-21, M 4 Responses May 6

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    I think there's something sexy about a crossdresser in a short skirt
    jryall500 jryall500 41-45, M 2 Responses May 7

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    Hi 14 year old crossdresser here anyone want to chat?
    Michael2000K Michael2000K 13-15, T May 10

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    i am a straight male crossdresser. i have always been attracted to women and and am very comfortable with my cross dressing desires. Oddly though, i've always had this "desire" to...
    quirkysquirt9 quirkysquirt9 18-21, M 9 Responses May 11

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    I would love to dress up and play with another crossdresser we can be *****
    twistedfrek twistedfrek 36-40, T May 17

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    So I just discovered that I have high estrogen levels. To my crossdresser me(15%) that means yay more enhanced boobs! But to the other side of me(85%) that means oh yay all my...
    fizzy711 fizzy711 13-15, M 6 days ago

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    I love crossdresser a they make me so hot
    hannah357 hannah357 18-21, M 3 days ago

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    i like dating with bicome and find me here:http://www.bisexualsdatingsites.com/
    bilina123 bilina123 22-25, F 10 hrs ago

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    He told me he was divorced. We've been dating for 9 months. Now he's talking about settling down, marriage and moving my 2 kids and I in with him. I'm 27 and he's 40. I see so many...
    nellinaples nellinaples 26-30, F 2 hrs ago

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    I am dating my mm again for a few months now. He said he cant bear the spectacle of losing me. But last night when his wife didnt text him and looked for him, he looked so anxious...
    AtPeaceEros AtPeaceEros 31-35, F 1 Response 57 mins ago

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    Relationship is one step ahead of camaraderie in which look for some better relationship bond and additionally two people meet jointly to understand one another. Nearly the whole...
    smitha143 smitha143 26-30, F May 8

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    There are numerous older men in the world who are single and seeking someone special in their life. For all such men, AgeMeet.com has been created as a reliable online platform to...
    sarahccaa sarahccaa 26-30, F May 18

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    There are numerous older men in the world who are single and seeking someone special in their life. For all such men, AgeMeet.com has been created as a reliable online platform to...
    Janetccaa Janetccaa 26-30, F May 18

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    Just like its title suggests, people who've STD and additional people within the same vessel to meet up and welcome us STD internet dating sites. In this manner, you relate to them...
    smitha143 smitha143 26-30, F a week ago

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    Herpes dating is a part of human mating practice whereby two herpes singles meet socially for companionship, and for marriage. And herpes is a STD(Sexually Transmitted Disease...
    harryyang1990 harryyang1990 22-25, M May 12

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    Herpes dating is a part of human mating practice whereby two herpes singles meet socially for companionship, and for marriage. And herpes is a STD(Sexually Transmitted Disease...
    harryyang1990 harryyang1990 22-25, M 1 Response 6 days ago

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    Hey, You know age gap dating? I’d like to recommend a current popular dating site ~~? – AgeLessWoo.c'om — It is the best, largest and most successful age gap dating site for...
    AgeLessWooCom AgeLessWooCom 26-30, F 1 Response Apr 28

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    I'm sick of getting hurt all the time by guys I was dating this really nice guy who has been my best friend for 5-6 years now..and all threw the time we knew each other we have...
    deleted deleted 26-30 3 Responses Apr 30

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    I am 27 years old and Im dating a man who is 42. Not only is he much older than me but he is also white.I did not introduce him to my family until this past February. We were...
    auntwinnie auntwinnie 26-30, F 1 Response May 17

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    I've thought about this everytime I have a crush for someone, where I wonder how my everyday life would be if I were dating them. based on what I see and hear from those around me...
    Sil833 Sil833 18-21, F 4 days ago

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    I do not think dating is my thing. I have not ever been on a date, nor do I wish to... For one, I ABSOLUTELY hate small talk and awkwardness. Second, I am a very sarcastic...
    RocaAzul RocaAzul 18-21, F 3 days ago

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    You know I hate when people say you only do online dating because you're ugly. Um excuse me, but did you morons ever think that it's hard to find someone in the real world...
    LonelyRollingStar LonelyRollingStar 18-21, F 2 Responses Apr 28

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    I want to share my story. I contracted HSV from a one night fling, he never told me. I'm not sure if he knew or he was in denial, because he was still in denial when i told him...
    jokerrrr jokerrrr 26-30, M May 11

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    Personally I find online dating as equal to real life dating. I used to have a girlfriend (bisexual) and we as the best online relationship. I loved her we were both very...
    EverPsycho EverPsycho 13-15, F May 13

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    I was dating a guy for two for a bit, it seemed he was more into me than I was into him. He was awesome and I was falling for him. First guy I have. Liked in a while. After a...
    ashder ashder 18-21, M a week ago

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    I am a 27 year old female and i am dating a 21 year old Indian American male.. His family is from India... He was born and raised here in the US.. He tells me he was not raised the...
    curiousgirl0824 curiousgirl0824 26-30, F a week ago

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    Hello everyone! I have been dating a widower for almost 8 months now. Overall we have a great relationship and our children are crazy about each other, even his family likes me and...
    charity82 charity82 31-35, M 1 Response Apr 28

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    I am 28 and have been dating a 54 year old married guy for 2 years. He is in LA and I am in NYC. We met thru business. I am always super careful about sending him pics, texts, etc...
    BrokeninBrooklym BrokeninBrooklym 26-30, F 6 Responses Apr 28

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    Well I'm not necessarily dating this older guy yet, we're at the early stages of talking and getting to know one another. But the issue (of it's actually considered an issue) is...
    SincerelyLorissa SincerelyLorissa 18-21, F Apr 29

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