I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 84 People

    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
    5 Responses Jan 26, 2010

    Im not dating a crossdresser

    but I joined in hopes of finding a woman who would date a crossdresser.
    deleted deleted
    26-30
    Aug 12, 2015

    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

    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

    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
    8 Responses Nov 18, 2013

    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
    1 Response Jun 25, 2015

    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
    8 Responses Dec 5, 2009

    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

    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
    4 Responses Jun 5, 2011

    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
    2 Responses Sep 15, 2013

    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
    4 Responses Apr 17, 2011

    Related Experiences

    I miss crossdressing. I need to own some clothes. Last time I did, it was just borrowed.
    Meow1357 Meow1357
    18-21, M
    1 Response Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    I am alone here at Chennai. searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20
    Just take action to meet your own love! http://www.whiteblackdating.org ‪#‎whiteblackdating‬ ‪#‎datingsites‬ ‪#‎interracialmatch‬ ‪#‎wmbw‬ ‪#‎wwbm
    malibulang malibulang
    31-35, F
    Apr 20
    Just take action to meet your own love! http://whiteblackdating.org ‪#‎whiteblackdating‬ ‪#‎datingsites‬ ‪#‎interracialmatch‬ ‪#‎wmbw‬ ‪#‎wwbm
    malibulang malibulang
    31-35, F
    Apr 20
    Just take action to meet your own love! http://whiteblackdating.org ‪#‎whiteblackdating‬ ‪#‎datingsites‬ ‪#‎interracialmatch‬ ‪#‎wmbw‬ ‪#‎wwbm
    malibulang malibulang
    31-35, F
    Apr 20
    Just take action to meet your own love! http://whiteblackdating.org ‪#‎whiteblackdating‬ ‪#‎datingsites‬ ‪#‎interracialmatch‬ ‪#‎wmbw‬ ‪#‎wwbm
    malibulang malibulang
    31-35, F
    Apr 20
    been cross dresser for a long time now love to have a cross dresser girlfriend any in the uk England in Cambridgeshire
    janetjanet janetjanet
    51-55, T
    Apr 20
    Was caught this morning by my 70year old neighbor he come around the house I was sitting in the patio he coughed I looked up reading paper and drinking coffee .i was wearing a...
    lvrofhose lvrofhose
    56-60, M
    2 Responses Apr 19
    If You want to Date an Interracial/LGBT Lover, Come to Our FREE and SERIOUS Online Dating Sites. With over 14 years experience. Especially designed for interracial / LGBT singles...
    malibulang malibulang
    31-35, F
    Apr 18
    People always need someone cute to accompany in this cruel world. Wish all of you could meet your own #love with our FREE & SERIOUS dating site. http://whiteblackdating.org...
    malibulang malibulang
    31-35, F
    Apr 18
    People always need someone cute to accompany in this cruel world. Wish all of you could meet your own #love with our FREE & SERIOUS dating site. http://whiteblackdating.org...
    malibulang malibulang
    31-35, F
    Apr 18
    May I recommend two free and serious dating sites to you? The links are http://whiteblackdating.org http://interracialgenderlesslove.org ( for pc) http://m...
    malibulang malibulang
    31-35, F
    Apr 15
    If You want to Date an Interracial/LGBT Lover, Come to Our FREE and SERIOUS Online Dating Sites. With over 14 years experience. Especially designed for interracial / LGBT singles...
    malibulang malibulang
    31-35, F
    1 Response Apr 15
    If You want to Date an Interracial/LGBT Lover, Come to Our FREE and SERIOUS Online Dating Sites. http://whiteblackdating.org http://interracialgenderlesslove.org( for pc) http://m...
    malibulang malibulang
    31-35, F
    Apr 14
    I just want to say that our interracial dating sites are FREE & SERIOUS. With over 14 years experience in online dating, we have many successful stories and lovely couples. If you...
    malibulang malibulang
    31-35, F
    Apr 14
    What to cross in tonight? :) something with leather
    leatherx leatherx
    26-30, M
    2 Responses Apr 13
    I started cross-dressing at seven. That is when I bought my first bra and panty set. I was nervous as hell and tried to play it off that it was for my girlfriend. I don't think...
    Thejannettearmet Thejannettearmet
    51-55, T
    Apr 13
    Hi everyone, I'm doing a class project about the experiences of individuals who use online dating websites to meet potential romantic partners, so I'm looking for anyone who has...
    sfylling23 sfylling23
    26-30, F
    1 Response Apr 12
    Hi everyone, I'm doing a class project about the experiences of individuals who use online dating websites to meet potential romantic partners, so I'm looking for anyone who has...
    sfylling23 sfylling23
    26-30, F
    Apr 12
    Hi everyone, I'm doing a class project about the experiences of individuals who use online dating websites to meet potential romantic partners, so I'm looking for anyone who has...
    sfylling23 sfylling23
    26-30, F
    Apr 12
    Today I went to the thrift store to find some new clothes (well, old clothes i guess) and I almost got seen by a coworker that happened to be there with her boyfriend. Lucky I...
    CDMichelle16 CDMichelle16
    18-21
    Apr 12
    hi everyone.. I'm knew here.. crossing my fingers I meet some people who understand my taste.. I have always liked older men. my age frame is usually 10-15 years older.. I'm...
    muddinGirlXxx muddinGirlXxx
    22-25, F
    3 Responses Apr 11
    Hello world. . . My name is Paul, and i'm currently in a long-term relationship with a male-to-female transsexual. 6 month ago, I most likely wouldn't think twice about dating a...
    introvertedrunner introvertedrunner
    26-30, M
    2 Responses Apr 11
    This is embarrassing My name is Damien I am a male teen crossdresser It was a school day and I forgot that I had painted my nails last night red so it was no problem really. I...
    EvaMarie1406 EvaMarie1406
    22-25, F
    3 Responses Apr 11
    I don't "crossdress"! I femulate I express in the feminine I wear clothing that suits my expressions Q: Why don't we say tomboys are crossdressers? A: Crossdressing is a...
    JoanieNewHampshire JoanieNewHampshire
    61-65, T
    6 Responses Apr 10
    wouldn't mind dating someone 21 and under, London uk
    YourSecret1982 YourSecret1982
    31-35, M
    Apr 10
    I m 21 and been Secretly cross dressing from 16, I m out for months nw ,lost old my old friends here, nw I m here , msg me ??
    elena4 elena4
    18-21, T
    1 Response Apr 8
    I am 16 years old and I adore crossdressing! Unfortunately, that means I have to wear my mom's clothing, which is a little awkward, but I can't help myself! I haven't worn panties...
    zmlmbnlfh zmlmbnlfh
    18-21, M
    1 Response Apr 8
    If You want to Date an Interracial/LGBT Lover,Come to Our FREE and SERIOUS Online Dating Sites.http://whiteblackdating.orghttp://interracialgenderlesslove.org
    malibulang malibulang
    31-35, F
    Apr 8
    I'm 14 years old in the UK. Looking for someone who is also interested in cross dressing and bondage. Pansexual.
    zappsty zappsty
    13-15
    Apr 7
    If all the crossdressers could pick up the underwear and toys on their way out. That would be great. -shakes head- We'll never get the deposit back....
    JessicaMarie35 JessicaMarie35
    36-40, T
    3 Responses Apr 7
    For me to say that I like to crossdress would be understating it. I absolutely love cross-dressing. I hope to get my life in order so I can become as feminine as possible. Females...
    Thejannettearmet Thejannettearmet
    51-55, T
    3 Responses Apr 6
    I am a fiftyfour year young crossdresser. I have been cross-dressing since I have been seven. I can think of many things that I would enjoy discussing with other crossdressers...
    Thejannettearmet Thejannettearmet
    51-55, T
    Apr 6
    A doctor of mine and me finally went out on a date. I knew she was bisexual and she had broken up with her girlfriend of several years. She knew that I often wore panties if not...
    Thejannettearmet Thejannettearmet
    51-55, T
    Apr 6
    My first time really getting caught I was 11 or so. I had been cross dressing for a while, but don't think that I had been caught. One night when I thought everyone was out, I...
    lauratdc lauratdc
    46-50, T
    Apr 6
    were not dating but u make me flutter
    Regkid Regkid
    16-17, F
    Apr 6
    So far I have no luck with any of these dating sites I been on for quite some time now; POF, Zoosk, eharmony, hotflings, and now been using okcupid as well. I'm a 23 yr old male...
    JLR555 JLR555
    22-25, M
    Apr 5
    Last weekend a young male teenager who was a crossdresser was assaulted and ran over and is in critical condition. The newspaper,La Times, had this has their lead paragraph, Young...
    lvrofhose lvrofhose
    56-60, M
    1 Response Apr 5
    I love crossdressers because it takes courage. The further you go the more courage you have. I really hope I can get good enough to go out on a date as a woman.
    Thejannettearmet Thejannettearmet
    51-55, T
    1 Response Apr 5
    I like dating younger women. I like listening to there point of view. Women have changed so much and are more open about there sexual needs. Older women I've sleep with never tell...
    equinereiki equinereiki
    61-65, M
    Apr 5
    One time I was caught by my dad when I was crossdressed. I had been laid off the day before from my job. I spent the morning in the macho mood. I had gotten up early to put in job...
    Thejannettearmet Thejannettearmet
    51-55, T
    2 Responses Apr 3
More Stories