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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 77 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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    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 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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    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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    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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    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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    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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    Related Experiences

    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 Aug 21

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 1 Response Sep 3

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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 Aug 22

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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 5 Responses Aug 25

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    They know be name at victoria secret now :p
    QueensFinest45 QueensFinest45 22-25, M 1 Response Sep 3

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    I havent dressed in a while. I can hold in the urge of stepping into a pair of panties and pantyhose when i'm with my girlfriend and i get to do certain things with her:) but at...
    CDMichelle16 CDMichelle16 18-21 3 Responses Sep 3

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    Today I am going to come out and tell my best friend about it. I trust that he will understand. He's always been understanding and has friends with all kinds of preferences. I'm...
    Lydia93 Lydia93 18-21, T 6 Responses 21 hrs ago

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    So as my last post said. I'm right now on my way to my best friend whom I've always been able to talk to and see if I dare to tell him my secret. Also a first is that I left the...
    Lydia93 Lydia93 18-21, T 3 Responses 19 hrs ago

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    So... For those of you who wondered how it went when I came out to my best friend for support... He said that he was proud of me for being honest about who I am and that he was...
    Lydia93 Lydia93 18-21, T 2 Responses 12 hrs ago

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    I am an artists I am a cross dresser I am a man I am the artist I am the canvas I am the model Only a few will ever know my work Even fewer will ever know the "truth" Cross...
    JessicaDale JessicaDale 51-55, T 6 Responses 2 days ago

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    So here it is, I am Proud to be a Bangalorean and proud to be a Cross dresser in this City. I am as normal as most Men, I work for an MNC , Drive a car in the mad Bangalore traffic...
    laaquila laaquila 31-35, M 1 Response Aug 30

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    I've been wanting to cross dress in public but I don't know much about make up or looks. I just started getting into dresses and want to know more. I'd like to meet a few female...
    Eriborn Eriborn 18-21, M 10 Responses Aug 28

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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 6 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 Aug 19

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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 Aug 23

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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 Aug 25

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    Any cross dressers in Hobbs nm around my age 13-16
    coleirleee coleirleee 13-15, M Aug 28

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    Looking For Light Friendly Chat, Or To Lend An Ear. Hey girls! I'm a young adult, bigendered and part time cross dresser. Just extending my hand to other like minded ladies who are...
    ViewtifulMe ViewtifulMe 26-30, T Sep 3

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    Hi Everyone , I wanted to explain a little bit on how I've been feeling lately towards a few different things. First I've kinda come out as a Cross-Dresser , I love wearing women's...
    ThinkDiff ThinkDiff 18-21, M 4 Responses a week ago

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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 Aug 27

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    The idea of senior dating is completely different than dating in current generation times. Usually, when people who have crossed the near fifty years mark engage themselves I...
    sophiescanlan1 sophiescanlan1 26-30, F Sep 3

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    When I was 14 I started crossdressing. My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties...
    Stephaniegirl226 Stephaniegirl226 36-40, M 5 Responses 3 days ago

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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 8 Responses Aug 22

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    I can say nice things without it being a come-on. Take the other day for example. An incident happened at work, and one of the accounts ladies got all upset about a nagging...
    ConcreteSleeper ConcreteSleeper 31-35, M 1 Response 5 days ago

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    Before responding consider what I am saying. Overwhelmingly dating is the way in which people start relationships and it's not that dating is the only way, but dating is so popular...
    idkanswer2014 idkanswer2014 26-30, M 1 Response Sep 7

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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 Aug 20

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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 3 Responses Aug 24

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    Dating online may be an interesting experience with everything dealt with properly.If not, it will surely be rather boring.That's why dating online should be made carefully rather...
    Tink0624 Tink0624 26-30, F Sep 2

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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 4 Responses Aug 23

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    Why does dating suck. Im so sick of letting myself getting hurt. I knew better and I still let it happen. Why do i always pick the emotionally unavailable men! **** Dating!
    Sabr3na Sabr3na 36-40, F 1 Response Aug 18

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    Dating a married man is hard. He whips out his wallet to pay for something and I look down and see a photo of his wife tucked into his wallet. You can imagine how that feels...
    hankpalmer hankpalmer 18-21, F 77 Responses 6 days ago

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    Hello everyone I am a 19 Year old Male who previously got addicted to crossdressing. I am strait but for some reason love to wear females clothing, I have tried on several of my...
    MsLexi MsLexi 18-21, F 1 Response Aug 18

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    I am crossdresser want to have a date with another crossdresser. This is that I am desired all my life but it very dificult to have it because many CD have fear or do not acept it...
    kamilatv kamilatv 46-50, M 9 Responses Aug 19

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    I have my very first cross country practice tomorrow morning I have never run cross country before, but l am in pretty good shape. What's should I expect? and how should I impress...
    WindowAngle WindowAngle 13-15, F 1 Response Aug 24

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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 5 Responses Aug 27

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    Hi. I'm new to this site so is thought I would post! I'm 25 and in a committed relationship with a woman. I consider myself bisexual and have had encounters with both genders...
    Nikki1988x Nikki1988x 22-25, T 7 Responses Aug 31

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    I have now lost nearly fifty pounds just this year and needed smaller clothing. I went back to the Layne Bryant store and fond the same sales lady, Ruth< and she so willingly...
    Varience Varience 70+, M Sep 1

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    I would really like to have a crossdresser friend to spend girl time with, but I am about to move out of the country soon. I don't want to start a friendship with someone local...
    Freja14 Freja14 31-35, T 1 Response Sep 5

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    I am a straight guy who secretly crossdresses and would like to make friends with other crossdressers between the age of 18-25 who lives in around Craigavon, Co.Armagh. If...
    blackdresser101 blackdresser101 18-21, M Sep 8

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