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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 86 People

    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 7 Responses Nov 18, 2013

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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 11 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 2 Responses Jun 25, 2015

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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 5 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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    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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    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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    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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    Im not dating a crossdresser

    but I joined in hopes of finding a woman who would date a crossdresser.
    Michelle41011 Michelle41011 41-45, T Aug 12, 2015

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    Related Experiences

    I wanna meet a girl that'd like a crossdresser life partner on any terms
    sissyslaveofladies sissyslaveofladies 22-25, M 4 hrs ago

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    The problem that I see with it, "it's inaccurate as a noun!" Might be a decent adverb verb if there were crosses that needed dressing! The only reason it is a word at all is...
    JoanieNewHampshire JoanieNewHampshire 61-65, T 2 Responses 3 days ago

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    Its true I do like the cross-dressing me. Well I do now that I am open about it not just with other people but also with myself. In the past I have tried to suppress who I really...
    TrannyHannah TrannyHannah 41-45, T 7 Responses 3 days ago

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    There are many aspects to the initial dating universe that has become more of a nuisance than good for men with good intentions for a relationship. One in particular that really...
    niceguycursed niceguycursed 31-35, M 4 days ago

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    I will admit it openly one of the pet peeves I have for the dating universe is when a woman is no longer in her physical prime been through every horrifying relationship imaginable...
    niceguycursed niceguycursed 31-35, M 4 Responses 4 days ago

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    I AM NOT HERE FOR DATING OR FLIRTING OR FLIRTING OR DATING! THE END.
    Kornisone Kornisone 26-30, F 4 days ago

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    I am going to try and target 3 caught crossdressing stories by the weekend Here's story no1 they do come in parts. The bridesmaids story.... Hi my name Eric I am 17 and this is...
    EvaMarie1406 EvaMarie1406 22-25, M 3 Responses 5 days ago

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    well 2 years ago for Halloween right before a party I had no costume ideas, with my girlfriend knowing im a crossdressing fanatic her and her friend suggested I dress as a classy...
    crossdresserfun crossdresserfun 22-25, T 3 Responses 5 days ago

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    I always felt like when I cross-dressed it brought me joy because I was expressing the inner me my femme self. I started feeling a tingle when younger but I didn't understand it...
    bcsissy bcsissy 61-65, T 3 Responses Feb 2

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    I love to chat to any cross dresser and make friends and may be have some fun
    janetjanet janetjanet 51-55, T 6 Responses Jan 31

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    Being the man in the relationship or being the play toy sissy in her life. Crossdressing in front of your girlfriend can be the end of your relationship or life time of being...
    KatrinaBoyer41 KatrinaBoyer41 41-45 6 Responses Jan 29

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    I've got a fantastic girlfriend who has supported me when I told her about me being a cross dresser I feel it's brought our relationship together. In fact we've been spending a lot...
    Crazy3282 Crazy3282 22-25 10 Responses Jan 29

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    This is somewhat of a different way of getting caught. I buy my cosmetics at my local drug store. It is nice because they have a self checkout line, and for a closet crossdresser...
    andreatcial andreatcial 26-30, M 3 Responses Jan 28

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    Does anyone know other websites or app where cross dressers can talk?
    Lovebrittany Lovebrittany 18-21, M 5 Responses Jan 28

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    For ***** ‘n giggles of it, I compiled only ‘some’ of the dating questions I would now ask at this point in my life. These questions are rhetorical here. I could come up with...
    OlivePhire OlivePhire 41-45, F 1 Response Jan 27

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    Crossdressers have always facinated me. So I enjoyed seekng them out in chat rooms hoping to find one showing off on a webcam. One particular night the chat room was dead. No...
    chrissyk48 chrissyk48 46-50, M 6 Responses Jan 27

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    Hey, interested in chatting, any cross dressers out there? ;)
    AAroN3rr AAroN3rr 18-21, M 7 Responses Jan 27

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    Love Tuesdays, sale dats at the thrift stores... Honey, heart be still!! Absolutely a gurl's cheapest thrill in town!!! Mmmmm one of my favorite things about being gurl is the...
    imacd4me imacd4me 51-55, M 1 Response Jan 26

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    Oh yeah, I tried it alright. I've had a gut I figured out the demographics and income level. It almost in desperation for survival. I met more single fathers that were granted...
    laceset34 laceset34 36-40, F 3 Responses Jan 26

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    Tinder,Skout,POF..are similar. (I still have keep Okcupid cos at least i've met two guys on this site in a six months.ZERO on other sites) In my case,i couldn't find a guy who...
    babyblueeee babyblueeee 31-35, F 10 Responses Jan 24

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    Me. I'm a crossdresser. Still not fully out. Some know some don't ,it's hard but I persist. Always be true to you, do what you can when you can, I know I'm a girl and I accept that...
    krissy79 krissy79 36-40, M 2 Responses Jan 23

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    I love to cross dress and would like to have a girl friend to share this with and enjoy our self in every way possible so it any cross dresser in Cambridgeshire interested send me...
    janetjanet janetjanet 51-55, T 2 Responses Jan 22

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    It was a day I will never forget, I was 16 years old & my parents went out, I didn't think they would be home for at least 4 hours. I went upstairs & got changed, black bra...
    Joanneforever Joanneforever 56-60, T 1 Response Jan 22

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    This is so true for me. I have tried to resist crossdressing numerous times and I have always failed. There was one time where I have stopped for a period of about 5 years or so...
    12rak38 12rak38 36-40, M 13 Responses Jan 21

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    visit our website outcast-all.com for cross dressers topic related posts
    serious2468 serious2468 22-25, M Jan 21

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    Exciting day! Two new skirts and a new blouse, plus earrings (which I have never had before). All fit perfectly, one skirt is v short (leopard print), the other longer (wet look...
    morro70 morro70 51-55, M 3 Responses Jan 21

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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...
    kimcc11aa kimcc11aa 26-30, F Jan 19

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    I would love to have a cross dresser friend to have lots of fun time and do everything possible and enjoy every second of it I'm in Cambridgeshire uk
    janetjanet janetjanet 51-55, T 2 Responses Jan 19

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    http://www.crossdreamers.com/2016/01/the-life-of-crossdresser.html
    ashwinib ashwinib 26-30, M 2 Responses Jan 19

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    I used to suck at dating till I started dating this older guy. What came with his age was maturity, and a lifetime of experience. He was well into psychology. I think I ended up...
    herdinstinct herdinstinct 36-40, F 1 Response Jan 19

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