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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 74 People

    My boyfriend, whom I've told you about on my

    last post, told me he cross-dresses. He was very afraid and insecure to the point where he believed if he told me, I'd leave him. But I am not bothered one bit by it at all like some girlfriends would be. It took a lot of guts on his part to tell me about this, and I respect him...
    takethispain takethispain 18-21, F 3 Responses Mar 7

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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 3 Responses Apr 20, 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 9 Responses Dec 5, 2009

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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 6 Responses Mar 27, 2012

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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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    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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    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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    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 4 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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    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 1 Response Aug 17, 2010

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    Related Experiences

    I've actually never been in a relationship with a cross dresser, but I am seriously attracted to hot guys in women's clothing. Would like to understand more about the lifestyle and...
    danabug danabug 46-50, F 2 Responses Jul 2

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    On 7th July 2014 I became an underwear cross dresser when I wore my 1st ever pair of girls knickers. It was an amazing day. Im always going to wear girls undies from now on.
    knickersguy knickersguy 22-25, M 1 Response Jul 9

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    I wrote my story in "I Am A Closet Crossdresser", so I am not going to rewrite it here. Please read it there. I am just posting that I live in a very small town in western...
    closetedcd60 closetedcd60 56-60, M 3 Responses 4 days ago

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    Is there anyone out there from East Midlands or Leicestershire who'd be willing to help me cross dress
    benblowers96 benblowers96 16-17, M 1 Response Jul 2

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 1 Response 2 days ago

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    They're so perfect in my eyes, I like talking to all kinds :) you should message me!
    aussieboi123 aussieboi123 18-21, M 1 Response Jul 2

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    I like to ********** while wearing panties and stockings. I am not attracted to men, but do find some M to F transgendered women rather arousing. I like to take anonymous photos of...
    LemonSqueezer515 LemonSqueezer515 41-45, M 6 Responses Jul 2

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    I am biologically straight, and get very turned on by wearing panties, stockings, heels, and bras. Anyone similar like to chat about their experiences?
    LemonSqueezer515 LemonSqueezer515 41-45, M 3 Responses Jul 6

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    Hey I'm not one but would love to get to know some !!!!
    kerw94 kerw94 18-21, M Jul 7

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    Stunning aren't they! Love you people :) message me!
    aussieboi123 aussieboi123 18-21, M Jul 8

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    I love dressing every day not passable but keep my toes painted and wear panties bra every day light lipstick and perfume when I go to grocery store
    renelynn renelynn 46-50, M 1 Response Jul 9

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    Type "Bridget Guilty Gear" on the web and you understand who I'm referring too - always drawn and fictional, never real, because fiction is one, real is something else entirely.
    psycopower90 psycopower90 22-25, M Jul 19

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    Thong thong thong thong thong thong
    windfarm2000 windfarm2000 31-35, M 4 Responses Jul 20

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    I have been a cross dresser most of my life. I have purged several times, but the desire always comes back. Lately I have been just underdressing. A strong urge came and I started...
    davis36a davis36a 61-65 6 days ago

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    I am an 16 year old gay cross dresser. I absolutely love dressing as a girl. My parents know that I cross dress and every weekend, me and my mom have some "girl fun". I dress as...
    SissyBoy7 SissyBoy7 22-25, M Jul 13

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    Hey every one I'm am a Cross dresser and not able to fully cross dress in my house so I'm look for mainly a female friend or a guy that has friend that would like to dress us up...
    Anime1234 Anime1234 18-21, M 1 Response Jul 20

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    Hi guys. I moved to Canada a few months ago and I live in London, Ontario. I have always been a crossdress we in closet. I want to increase my spectrum and explore my sexuality. I...
    deeplycurious deeplycurious 26-30, T 3 days ago

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    I would love to chat with a cross-dresser. You guys are soo hot
    fromBK718 fromBK718 26-30, M 8 Responses Jun 30

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    I had never thought of myself as a cross dresser. I have never dressed to look like a girl, but I do like and prefer to wear girls panties. I discovered this when I was a young...
    Myotheridentity Myotheridentity 46-50 3 Responses Jul 3

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    This is a continuation from my last story and happened not long after my secret stash of panties had been thrown away... I am going to bend the subject a little, but for a good...
    Myotheridentity Myotheridentity 46-50 1 Response Jul 4

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    I love cross dressers! My favourite people!
    aussieboi123 aussieboi123 18-21, M 2 Responses Jul 15

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    Looking for lady friend who will accept and support me as a cross dresser and guys who are into dresses, heels and pantyhose
    annieinhose annieinhose 46-50, T 2 Responses Jul 15

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    This is so true for all cross dressers once the secret is out!
    Brandie1960 Brandie1960 41-45, M 2 Responses Jul 19

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    I would love to meet a girl that likes cross dressers. Message me girls/ladies!
    wjk1849 wjk1849 46-50, M Jul 20

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    Not a full cross dresser but I like to wear panties and thongs. Message or add me if you want to talk about it. I'm kinda new to this. Guys or girls but I am straight but open...
    Bradhowd Bradhowd 22-25, M 5 Responses Jul 21

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    My problem is, I have no cleavage, I know there is tape out there that might work, but how good is it, any suggestions. Also I have artificial breast's, 50 DD, they had glue on...
    sweetcharlene41 sweetcharlene41 70+, M 1 Response Jul 21

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    Here is another installment of my secret cross dressing experiences. I never thought of wearing panties as cross dressing. When I was 19 I was dating a girl who did not know I...
    Myotheridentity Myotheridentity 46-50 Jul 4

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    So basically the title applies to this but I'm just asking for advice for someone who'd be going out to the dating world for the first time I'm recently coming out of the closet...
    phoenixx37 phoenixx37 18-21, M 1 Response 3 hrs ago

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    Animal Crossing: New Leaf has to be my all-time favourite game right now. I've been working on my town since April (I've been playing over a year, but I deleted my last town), and...
    SensitiveSelf SensitiveSelf 13-15 13 hrs ago

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    Please don't try. I'm only 15 and I came to find friends. If you like me, it's fine but don't ask me out please. Besides, I'm not allowed to date yet, and I don't trust online...
    adrianacecilia14 adrianacecilia14 13-15, F 14 hrs ago

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    Work in Progress Hello, I'm new to the Experience Project so please do forgive me if I do something wrong or break a rule, it is not my intention. I'm a recent college graduate...
    CupcakeVenom CupcakeVenom 22-25, F 1 Response 4 days ago

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    so I left Vegas. found work. found a decent place to live. got clean off drugs. separated from my spouse. what's next? I feel like there is something missing. not sure what to do...
    mierdamundo mierdamundo 31-35 2 Responses Jul 22

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    ARE YOU AN OLDER MAN SEEKING A YOUNG GiRL? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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    ARE YOU AN OLDER MAN SEEKING A YOUNG WOMAN? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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    ARE YOU AN OLDER MAN SEEKING A YOUNG WOMAN? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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    Well me and my boyfriend have been dating for 2 months and we have been wanting to kiss Eachother but then all of a sudden he didn't want to anymore and I didn't know why and it...
    kdub13 kdub13 13-15, F Jul 9

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    I've struggled with being a crossdresser all my life, and be Christian crossdresser for the last 21 years. When I was only a crossdresser I just though I was sick and something...
    DawnR59 DawnR59 51-55, T 9 Responses Jun 30

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    Sometimes people think that crossdressing automatically would make someone seem gay, but that isn't it! Crossdressing is just a thing that some men (or women) like to do! It makes...
    naco26withcheese naco26withcheese 13-15, M 1 Response Jul 19

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