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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 81 People

    Needing Advice

    I have been with my husband for nearly 10 years and we have 2 kids early this year we decided to have a trail separation while all this was going on he came out and told me he wanted to dress like a women, now I have had my worries before as he likes shinny things and wearing...
    Reeni2006 Reeni2006 36-40, F 1 Response Sep 15, 2013

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    Please Help!

    I just recently found out the my boyfriend likes to cross dress. It at first started out as him just telling me he liked to wear pantyhose. I was ok with that it bothered me a lil but i just thought i would get used to it. Then it turns into he likes high heels and skirts. now he...
    confused728 confused728 22-25, F 6 Responses Jan 26, 2010

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    My Cross Dresser Beau Wants Others To Join Us!

    My boyfriend and I have been dating for almost 3 years. He didn’t tell me he was a cross-dresser until we were 4 months in, when I had already fallen in love with him. I was slightly amused at first, then curious. I asked him to model anything feminine he had in his...
    MG1023 MG1023 46-50, F 7 Responses Mar 27, 2012

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    I Just Found Out

    About two weeks ago I found all the undergarments and nighties, a wig and two semi blown up balloons. First I was in shock and now am trying to accept everything because he is a wonderful man. We have only been dating for six weeks. To show I am trying I bought him some new...
    confusedinw confusedinw 56-60, F 10 Responses Dec 5, 2009

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    I love my boyfriend more

    than anyone! He tells me that a lot of people don't like dating cross-dressers but I don't know why! Here's a few reasons my cross-dressing boyfriend is better than anyone else! 1. He actually enjoys clothes shopping with me. 2. He gives me valid fashion advice. 3. The sex is...
    madmae16 madmae16 18-21, F 1 Response Jun 25

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    Im not dating a crossdresser

    but I joined in hopes of finding a woman who would date a crossdresser.
    Averageguy41011 Averageguy41011 41-45, M Aug 12

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    I Am A Trans

    I am trying to learn what to do so I dont have to stop being me but I dont loose her because I do love her
    TGMegan TGMegan 36-40 2 Responses Aug 17, 2010

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    New To This World And Looking For Some Support

    I have been dating my boyfriend for 2 years this month. Very shortly after we met and began seeing each other he told me about his cross dressing. I was very taken aback by it but, I thought through it and couldn't wait to see him later that night to tell him that I was very much...
    bldbeauty bldbeauty 22-25, F 6 Responses Apr 20, 2012

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    Love My Cross Dressing Man

    I have been dating a wonderful man for a couple of months. He told me he likes to wear womens underwear after a couple of dates . I really wasn't shocked and felt happy that he was able to share this with me. He has recently started wearing more womens clothes , only indoors when...
    pinglasgow pinglasgow 41-45 5 Responses Jun 5, 2011

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    I Am Dating A Cross Dresser

    This weekend I found out my boyfriend of 15months who I live with is a cross dresser. I found pictures on his computer, I then found he had a secret account and persona and has been encouraging people to email him all the time we have been together. Our sex life has never been...
    confusedheretoo confusedheretoo 31-35, F 6 Responses Nov 18, 2013

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    Liffes Shocking Moments!!

    i met this great guy who at first i thought was like all the rest, but it turns out he was nothing like them! he not only was a real good man, but a man that likes to wear women's clothes.... the way he told me was after we had dated like a week he had came over one day and i...
    fashionablylostinga fashionablylostinga 41-45, F 4 Responses Apr 17, 2011

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    Related Experiences

    I love to dress up and make myself look pretty. I love wearing makeup especially red lipstick that matches my red nails. Slipping sheer pantyhose over my freshly shaved legs...
    Cindy7611 Cindy7611 41-45, T 5 Responses 1 day ago

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    I am a crossdresser who would love to talk with other CD's or anyone interested in crossdressing
    Cindy7611 Cindy7611 41-45, T 2 Responses 1 day ago

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    I don't have experiences but I want to know other cross dressers to advice me
    jafej jafej 36-40, M 1 Response 2 days ago

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    I was with my wife and 12 year old daughter in the supermarket today. At one point my daughter had wandered off somewhere, so I went to look for her and I found her in the...
    SerenityCD SerenityCD 51-55, M 2 Responses 2 days ago

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    It was a long time before I took the "plunge, if you like, into womens clothing. I now look at "womens" clothing more often than I do "mens" clothing when I am in the stores. I am...
    MarieJosephe MarieJosephe 66-70, M 2 Responses 2 days ago

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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...
    earthlingcc11 earthlingcc11 26-30, F 1 Response 3 days ago

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    Your lucky hope you enjoy life.
    Lonely47 Lonely47 66-70, T 4 days ago

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    My first time I was 10 years old I was playing in my sister room and I was going through her dresser I found her bras and panties so no one was home I try them on and I though I...
    aliciafox55 aliciafox55 56-60, T 1 Response 4 days ago

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    Online dating Is so fricken frustrating. All these people claiming in there profiles to be these cool genuine loving people and they say "message me :)", "ask if you want to know...
    jhns1029 jhns1029 22-25, M 1 Response 4 days ago

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    Is this normal? I have this amazing coworker who is a cross dresser and is a really great person. I really enjoy his company but when we go out I feel somewhat uncomfortable. He...
    LisaMeToo LisaMeToo 26-30, F 10 Responses 5 days ago

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    I know this group is more about a cross dresser in a wedding gown, but I've always felt the desire to turn a boy into the most delicate and feminine presence imaginable, and I...
    watcher1978 watcher1978 31-35, M 1 Response 5 days ago

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    Not only do I like to chat to crossdressers but I myself am a cross dresser. Someone message me who really wants to chat about crossdressing, I really enjoy it.
    pantyboiCD pantyboiCD 18-21, M 7 Responses 6 days ago

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    When I was younger I would sneak into my sisters room and put on her clothes. I loved being a woman. The feeling of the soft tight clothes around my body. Every time I made a new...
    clevername11 clevername11 18-21, M 4 Responses 6 days ago

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    Hey I found a cool app "you cam makeup" you can take a picture of yourself and see yourself with makeup and a wig on. It's really great!!
    clevername11 clevername11 18-21, M 1 Response Aug 25

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    Well I told my step mom this weekend that I'm a cross dresser and all she had to say was "well so is your dad"
    Camocrossing Camocrossing 18-21, M Aug 23

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    I came to EP to find out if there were other people like me: Straight guys who dressed as women. At first I was surprised to see there were a lot of men who cross dressed and were...
    Foxanne Foxanne 22-25, T 3 Responses Aug 23

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    I am a lesbian,but would quite enjoy the friendship of a cross dresser,many of which share common interests in fashion and aesthetics. Rene'
    deleted deleted 26-30 4 Responses Aug 23

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    One of the greatest joys I have is providing cross dressers a safe,caring environment or internet forum for expression of their desires. Lady Rene'
    deleted deleted 26-30 Aug 23

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    I decided to do sort of a crossdress dare to go in public without the possibility to chicken out. If you've read my previous story, I explained how I got caught and had to dress up...
    DCYDDON DCYDDON 18-21 7 Responses Aug 23

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    I'm looking for cross dressers to share pics and talk about cross dressing :) if you cross dress we can talk and share pics :)
    FootMaster95 FootMaster95 18-21, T 4 Responses Aug 22

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    More details in the comments............................................. ........................................................................................
    wannabepreggers wannabepreggers 36-40, M 3 Responses Aug 22

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    anyone from Hampshire England please message me
    riw1996 riw1996 18-21, M Aug 20

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 Aug 19

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    Dancing on a first date...even if I´m not light on my feet, I´ll enjoy grabbing your waist and twirling you around.... I promise not to step on your delicate feet ... and be...
    SolitaireGent SolitaireGent 41-45, M 1 Response Aug 16

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    I wrote a previous story about my boyfriend being a crossdresser. About three months ago, he told me that he was transgender and wanted to transition to a female permanently. At...
    titelips titelips 31-35, F 5 Responses Aug 16

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    I'm a 14 year old cross dresser who lives in the South Texas down and in the middle of the bottomish upish right of Texas
    Crossdresserforlife247 Crossdresserforlife247 22-25, M 3 Responses Aug 15

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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...
    allisoncc11 allisoncc11 26-30, F Aug 13

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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...
    allisoncc11 allisoncc11 26-30, F Aug 13

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    Today! Me and my girlfriend have been dating for 3 years and she usually paints my toes (either red or pink). But today, she caught me in her high heels with red toes putting...
    FootFetiBoy FootFetiBoy 22-25, M 5 Responses Aug 13

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    I am looking for a young guy who wants to become a passable crossdresser. I will provide guidance
    Noregrets2015 Noregrets2015 31-35, M 1 Response Aug 13