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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 74 People

    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 1 Response Aug 17, 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 6 Responses Mar 27, 2012

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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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    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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    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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    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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    Related Experiences

    Yuck! OK Women's clothes are for WOMEN. Men ALL look nasty wearing women's clothes. I am sick and fricking tired of seeing NASTY photos of such horrible behavior online. I am...
    LadyGypsy LadyGypsy 36-40, F 4 Responses Aug 7

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    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 2 Responses 5 days ago

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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 7 Responses Jul 27

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    Why I Wear Lingerie Q) When did you start wearing womens lingerie? A) Since a young age, about 8 or 9 years old. Q) Why do you wear womens lingerie? A) When I was coming of age...
    Joeymartin1977 Joeymartin1977 36-40, M Aug 9

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    Anyone around the north west up for a chat? I'm really curious :)
    LydiaCDRose LydiaCDRose 18-21, M 4 Responses Aug 14

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    I have been coming out of the closet; a little at a time at first, but now it's really become unstoppable and I can't imagine going back. A couple days ago, my boss, who teases me...
    MollyPetal MollyPetal 41-45, T 1 Response 4 days ago

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    Can anyone give me tips on how to feminize my voice? Read reason and story on my profile
    stevemoody2468 stevemoody2468 13-15, T 4 days ago

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    Hi sisters i am a cd and would like to chat with my sister who r like me so even if u feel the same then do contact me on bbm my pin is 7E11E527 and my skype id is bhawani94210
    bhawani992 bhawani992 22-25 1 day ago

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    This was a very close call by seconds. I remember one night that my sister was out with friends till really late. It was my chance to raid her dresser. I would frequently make...
    banannasplitz09 banannasplitz09 22-25, M 2 Responses Jul 31

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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 Jul 27

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    Ten years ago I would have used the word weird, and many other similar words to describe cross dressers. However that has now changed, I use words like delectable, mouth-watering...
    kinkycoupleuk kinkycoupleuk 46-50 7 Responses Aug 6

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    Woman I think Who love Cross dressers have best of both worlds…Any girls or woman would like a chat pls do…could be fun…butterfly effect…xx
    BeingaGirl77 BeingaGirl77 41-45, M 2 Responses Aug 10

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    If I wear make-up and my sense of style is very much feminine (I don't wear women's apparels or shoes, though), am I a cross-dresser, or am I just an androgynous gay boy?
    miumiuganda miumiuganda 18-21, M 4 Responses Aug 14

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    As soon as I saw the title for this group, I wondered why I did not start it because this is the kind of cross dresser I am most of the time. I am in not in a situation where I...
    cdsubalice cdsubalice 56-60, M 5 Responses Aug 18

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    I'm not really a cross dresser because I do wear girl shorts and cute shirts but I dislike dresses and makeup
    serenagirl87 serenagirl87 13-15, F 4 Responses a week ago

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    And so does my wife, as do most women everyday. They go out dressed much like a regularly man and no one says a thing, but let a man put on more traditional women's clothing, and...
    onefourfun4u onefourfun4u 61-65, M 3 Responses 3 days ago

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    Hi, I am a cross dresser and I recently started going out in public dressed as a women. I am looking for open minded women who can be friends with me without being judgmental. I am...
    laaquila laaquila 31-35, M 2 days ago

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    I had picked up on cross dressing a little while ago and want to start wearing female clothes all the time. I was wanting to see if anyone cross dressed in ohio
    Eriborn Eriborn 18-21, M 2 Responses 6 hrs ago

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    I had joined this group and thought I should really add a story no matter how short. The above type of man can also be termed as a Transvestic Fetishist Under-dresser not simply a...
    manslip manslip 56-60, M 4 Responses Aug 7

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    I have always wanted to get caught cross-dressing and be horribly humiliated. This story you are now reading is not true, but I am sharing it as if it was true: Last Friday night...
    Robertredlips Robertredlips 56-60, M 1 Response 8 hrs ago

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    After my parents got divorced when I was ten, I was living with my Dad. He was bisexual and had a boyfriend that stayed with us. On some weekends I would stay at his boyfriends...
    Michelle1976 Michelle1976 36-40, T 4 Responses Aug 16

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    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 6 Responses 4 days ago

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    Living in a small town makes it hard for some folks to meet decent dating material. But I live in a big city bustling with single people from all ages and let me tell you, it doesn...
    Bellamae Bellamae 41-45, F Aug 8

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    Dating is hard enough, and it will be more difficult when it comes to dating with STDs. Thanks for the online dating platform provide a new chance for people living with STDs to...
    stdaustralia stdaustralia 22-25, F Aug 11

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    Dating is hard enough, and it will be more difficult when it comes to dating with STDs. Thanks for the online dating platform provide a new chance for people living with STDs to...
    stdaustralia stdaustralia 22-25, F Aug 11

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    Dating is hard enough, and it will be more difficult when it comes to dating with STDs. Thanks for the online dating platform provide a new chance for people living with STDs to...
    stdaustralia stdaustralia 22-25, F 1 Response Aug 11

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    I don't know why, but dating and I don't seem to get along. I've been thinking about getting back in the dating scene, but based on my past experiences in finding a date, I know it...
    jamie1292 jamie1292 22-25, M 6 days ago

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    Cuffed and detained during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
    banannasplitz09 banannasplitz09 22-25, M 3 Responses Jul 31

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    Do I think crossdressers are gay, you ask me? Are they honest, is my counter question. I know is not exactly legimate to answer a question with another question but. But this...
    gypa gypa 26-30, M 6 Responses Aug 5

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    I want to cry right now I've taken up drinking because it numbs the pain of my self disgust I'm drunk right now and want to kill myself I hate myself because I crossdress I thought...
    JulieCakes JulieCakes 13-15, M 1 Response 3 days ago

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    So I've started dating again after my emotionally abusive boyfriend left me a few months ago. We were together for 9 months and even though there is still scarring there I felt...
    Equine228 Equine228 18-21, M 1 Response Aug 12

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    Hi my name is ben I, live in swansea in wales, and im 17. I have long had fantasies about crossdressing, I would love to meet people on here to explore this aspect of my...
    swansea21 swansea21 18-21, M Jul 28

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    I cross-dress whenever I can. That includes usually in public, often at work and always in my downstairs office/workroom. I never cross-dress around the rest of the house because...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 3

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    Lately I've been crossdressing a lot less but, I've been having dreams where I'm crossdressing a lot more, it's been frustrating I'm trying to break my habit of crossdressing...
    JulieCakes JulieCakes 13-15, M 3 Responses Aug 11

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    I don't consider myself a crossdresser. I do wear a lot of things that women wear... nail polish, panties, nylons, skirts, heels, sandals, sneakers, hiking boots, shorts, jeans...
    steve66oh steve66oh 46-50, M 3 Responses 3 days ago

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    It did not work out the way that I'd hoped. I won't name the site that I used, but I created a profile about 2 years ago (2012ish), and figured it give it a shot. I answered a...
    moonchile moonchile 31-35, F 2 Responses Jul 28

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    So I have learned online dating really sucks!! I have also learned guys are way more pickier then the girls. They want the girls who look like models and hurt then in the end...
    feelinglost84 feelinglost84 26-30, F 3 Responses Aug 2

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    The Reasons of Older Men Younger Women Dating . Older men date younger women for many reasons. It does not depends on age most of the time as much as depend on Passion, love and...
    caitlincc11 caitlincc11 22-25, F Aug 7

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    I dont understand some people make this platform for dating and talking dirty. Some even start getting cozy and start calling you sweets when you dont even know them properly. I...
    TrueLoverN TrueLoverN 26-30, F 1 Response Aug 7