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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 76 People

    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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    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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    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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    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 3 Responses Apr 17, 2011

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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 9 Responses Dec 5, 2009

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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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    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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    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 5 Responses Nov 18, 2013

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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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    Related Experiences

    For some of ye who haven't read my first story. I am a closet crossdresser. It started with my step moms clothes and eventually moved onto were ever I could get my hands on...
    Iamconfused1 Iamconfused1 22-25, M 6 Responses Apr 11

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    Any mtf crossdressers around my age(16) want to talk about dressing? I would also like get some help with making me look more feminine. Nothing sexual please. Message me :)
    HollyTG HollyTG 18-21, M Apr 6

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    Today I crossdressed in my mom's loungewear and did chores around the house. I even ran outside in the rain and took out the garbage and got the mail. It has to start somewhere...
    Orion6 Orion6 22-25, M Apr 9

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    Hi I thought to re-start my Video uploads on cdsing channel for anyone interested in learning the ropes to super advance tips & tricks of cross dressing! Its my 3rd year of cdsing...
    cross2play cross2play 31-35 3 Responses Apr 19

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    Since I was 6 years old, I used to think I was a girl and I remember that day as one of my favorites when I went to a store near my grandparents' house and the clerk (an old man...
    Loren18 Loren18 18-21, T 3 Responses Mar 27

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    Frist time I walk in a women store it was VS and the lady I talk to help me out big I told her I was thinking of dressing up as woman I think she was turn on by it she pull me by...
    virginiacox virginiacox 46-50, T 2 Responses Mar 29

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    Please be honest but do i make a cute girl?
    HarleyMachado HarleyMachado 18-21, T 1 Response Apr 12

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    Going to Lewisville tomorrow to get another wig and some new bigger breast forms... Can't wait
    Txcrossdress Txcrossdress 41-45, M 6 Responses 3 days ago

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    desperately need to talk to someone. Didn't get any response to my story so I'm posting again. I just need to chat to other closet cd. Would love to know how you feel about it and...
    gilliian gilliian 26-30, F 6 Responses 1 day ago

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    I've been cross dressing for many years & would love to meet other cross dressers, and chat with other dressers possibly in the uk or female. admirers of cross dressing males
    mick69x mick69x 51-55, M Apr 18

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    I'm a 16 year old male and I LOVE cross dressing. I've been doing it for like a year now and I just can't stop. I mainly like to wear yoga pants and panties. I want people to...
    CamThayer CamThayer 16-17, M 1 day ago

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    Trans people and cross dressers aren't the same thing. However I support each group fully.
    theindigoboy theindigoboy 18-21, M 3 Responses Apr 5

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    looking for a gay teen cross dresser to swap with under 18
    alexwttwu alexwttwu 13-15, M Apr 10

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    I want to meet another cross dresser
    mick69x mick69x 51-55, M Apr 14

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    I am a married Male to female Cross-dresser.  I recently came out to my family.  So far its a pretty good.  I dress mostly when Im in my job.  I work alone, and usually spend...
    liziemary liziemary 36-40, M 5 Responses Apr 16

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    I finally to my sister and she is very happy for me & is quite willing to supply me with what ever I need fem wise. so if you are a cross dresser with a sister tell her as she will...
    mick69x mick69x 51-55, M 2 Responses Apr 18

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    Recently I was kind of wrestling if I was trans or not. I think mostly I felt that I had a gay guy trapped in me but at the same time I was a straight female. I didn't want to say...
    PateFist PateFist 22-25, F 7 Responses 4 days ago

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    I like talking to other cross dressers. Makeup, wigs, shoes, all the important stuff!
    jessicavamp jessicavamp 41-45, M 2 days ago

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    I started about 11 yr old when I had the urge to wear older sister's (16) panties she left on bathrm floor after showering. I remember how great they felt and the tight pressure...
    robbi95 robbi95 46-50, M 9 Responses Apr 11

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    I never did it with either, yet they both played a crucial role. It began with my mom wanting a baby girl. She was so certain that I'd be a girl that she insisted on girl's things...
    AlbertSAT AlbertSAT 66-70, M 9 Responses Apr 9

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    I would luv to date a feminine crossdresser. Message me.
    Hot4Tgurlz Hot4Tgurlz 31-35, M 2 Responses 17 hrs ago

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    I would love to have a Crossdressing friend in the Fort Myers Florida area
    booboo74 booboo74 36-40, M 6 hrs 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 11 mins ago

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    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...
    georgetta1994 georgetta1994 18-21, F 4 Responses Apr 7

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    I've been dating this guy for a week. I know this guy all my life me and my family are friends with his and we used to be childhood friends. But before me and him started dating I...
    cutemonkey cutemonkey 13-15, F Apr 12

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    This experience made me think of a story that happened 15 years ago. There was a charity all-male beauty pageant at a local Banquet hall. The group of girls we hung out with at...
    Hot4Tgurlz Hot4Tgurlz 31-35, M 2 Responses 22 hrs ago

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    Went on a date with a guy who asked me out, just walked up to me and started talking. I was alittle taken back but continued conversing. We went to Hyde park- his favourite place...
    deleted deleted 26-30 5 Responses Apr 10

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    She's 16. Her names Amber. She has black hair which she dyes green. She has dark olive Italian skin. Her eyes are hazel. She knows the risks I would be taking if I gave myself to...
    deleted deleted 26-30 1 Response 2 days ago

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    I'm a frequent crossplayer, which is exactly what it sounds like, I cosplay characters opposite my gender most of the time. It's something that is not unusual in the anime...
    TinyJiro TinyJiro 22-25, M a week ago

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    My first crossdressing was when I visited my sister at her house she is 25 years old and I was 13 years old today she was out so I was by myself I got bored so I went up to her...
    cutewolf197 cutewolf197 16-17, M 1 Response Mar 29

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    I have been to numerous dating sites, trying to take chances of finding a man to be in a romantic relationship with or even just a friendly one, because I do believe that long...
    nbsbgal nbsbgal 22-25, F Mar 30

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    Life's just so hard at times. A few months ago i was secretly crossdressing daily loving life, then the next thing i know i stop crossdressing and start going to the gym to make...
    Tyrone147 Tyrone147 18-21 7 Responses Apr 3

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    Hey all I want to share my experiences of dating a widower........ When I found out the man I was talking to was a widower I have to admit I was scared I wasn't strong enough and...
    Becky1711 Becky1711 31-35, F Apr 15

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