I Am Dating A Crossdresser

Personal Stories, Advice, and Support 53 People

    Pantyhose Run!

    Unfortunately the pantyhose from Hooters didn't hold up as well as expected so I was asked to make another run last night.  No problem there, I don't mind one bit, but it was a bit funny this time around.  Last time I went there was a very busy dinner crowd so I...
    loudamy loudamy
    26-30, F
    8 Responses Dec 2, 2009

    It's Been Awhile...

    Sorry, ya'll. It's been quite a while since I've been on EP. Goodness!! So much has happened. I'm sorry to say that I and the crossdresser did not work out. Nothing to do with his enjoyment of dressing in woman's clothing. We just were not compatible as people. Still good...
    loudamy loudamy
    26-30, F
    3 Responses Feb 29, 2012

    It's Time To Get Dressed Up!!!

    So we are planning a trip to Jacksonville, FL (only a two hour trip from us!) to go to The Metro, from what I hear, a pretty cool gay bar.  They have drag shows on the weekends and I think it will be a lot of fun.  But I really feel like this will give...
    loudamy loudamy
    26-30, F
    5 Responses Nov 24, 2009

    Dating A Crossdresser

    The other day my boyfriend of a year and eight months revealed to me that he occasionally crossdresses. He assured me it was NOT because he is actually gay, NOT for the sexual aspect of it, BUT because it gives him a chance to escape the stress in his life. When he told me, I...
    BFisaCD BFisaCD
    18-21, F
    2 Responses Apr 19, 2012

    I recently found out my guy is a crossdresser.

    It took me completely by surprise, lots of crying and confusion. Because I love him I chose to stay. He only wears womens bra and underwear and occasionally corsets. He said he doesn't feel feminine or want to have a full female persona or wordrobe and he also doesn't consider...
    georgetta1994 georgetta1994
    18-21, F
    4 Responses Apr 7, 2015

    My Wife Is Married To One, Me. Does That Count?

    My wife is married to one, me. Does that count?  She's not active on this site, but I am. I'd be happy to share with others in similar situations, but I'll keep this brief, since I'm not sure how active this group is?
    PStJBR PStJBR
    36-40, M
    1 Response Mar 16, 2012

    A Completely Unexpected Beginning

    I just went on my first date with a wonderful man. I've never had so much fun, or met anyone who gave me butterflies as quickly as he did. I went into the first date knowing that he was a part time crossdresser. I don't know if I was in shock, or simply didn't care, but the news...
    ashfay ashfay
    22-25, F
    4 Responses Feb 17, 2013

    Related Experiences

    There are three moments in my very short dating history still to this day I'm not proud of. My first and only real girlfriend once really upset me after I offered to take her out...
    niceguycursed niceguycursed
    31-35, M
    a week ago
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    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
    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
    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
    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
    wouldn't mind dating someone 21 and under, London uk
    YourSecret1982 YourSecret1982
    31-35, M
    Apr 10
    I'm a 15 year old sissy boy who secretly wears his 18 year old sisters bikini bra panties lingerie tights leggings panty house yoga pants dresses gowns tank top skirts and lipstick...
    deleted deleted
    26-30
    1 Response Apr 8
    I'm a 15 year old sissy boy who secretly wears his 18 year old sisters bikini bra panties lingerie tights leggings panty house yoga pants dresses gowns tank top skirts and lipstick...
    deleted deleted
    26-30
    2 Responses Apr 8
    I'm a 15 year old sissy boy who secretly wears his 18 year old sisters bikini bra panties lingerie tights leggings panty house yoga pants dresses gowns tank top skirts and lipstick...
    deleted deleted
    26-30
    2 Responses 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
    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
    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
    Please do read my blog on my transgender experience and please do comment https://girlyindianboy.wordpress.com
    IndianZeus IndianZeus
    22-25, T
    2 Responses Apr 6
    Please do read my blog on my transgender experience and please do comment https://girlyindianboy.wordpress.com
    IndianZeus IndianZeus
    22-25, T
    Apr 6
    Nice view? Let me know ;) 
    DamnDanielle DamnDanielle
    18-21
    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
    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 wanna love money and sex
    rehana4 rehana4
    26-30, T
    2 Responses Apr 5
    Hi! It's more some kind of question... I've started wearing girl clothes when I was about... 10/11 years old, and I'm 15 years old now. I always loved wearing them.... As soon as...
    deleted deleted
    26-30
    2 Responses 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
    my new Facebook account name is Smrita Roy ... profile pic is a girl in red saree...
    Smrita36 Smrita36
    18-21, M
    Apr 4
    PLEASE!! Does anybody, ANYBODY at all, know an easy way to put on a garter belt? tried multiple times, back right strap keeps coming undone or not doing up at all :( but a side...
    DamnDanielle DamnDanielle
    18-21
    1 Response Apr 4
    I want to be a male with no testostrone and a estrogen driven driven male. I still want to identify as male, but i want to be as feminine as possible physically. No artificial...
    Strivexwolf Strivexwolf
    18-21, M
    Apr 4
    I am a sissy cd and would like to find someone local to play with. Either a guy or another sissy. I'm in Georgia south of Atlanta. hmu and we can chat.
    SissySubAlyssa SissySubAlyssa
    36-40, T
    Apr 2
    hi, anyone from my area like to chat, I am a bibottom CD, I like to chat with anyone, just like to know a few from my area
    Hotcdbottom Hotcdbottom
    41-45, M
    5 Responses Apr 2
    not a problem for me, i am not prejudice, i like who i like and that's that. i like dating white guys for no specific reason other than i do. i love men black white asian but i...
    deejaygirl deejaygirl
    26-30, F
    4 Responses Apr 2
    I am a boy who like to wear women's underwear and clothes and I like to f****** my a****** and eat my own c** does this make me a cross dresser or Gay!
    Nikkithefag Nikkithefag
    22-25, T
    4 Responses Apr 2
    I love to meet up with more cross dresser in Cambridgeshire uk England
    janetjanet janetjanet
    51-55, T
    3 Responses Apr 2
    So I'm curious as my" girlfriend" and I haven't been out in public together, abd with all the tg issues atm, how do you all handle the bathroom in public?
    Kolisnjor Kolisnjor
    26-30, F
    4 Responses Apr 1
    I'm a cd and I'm hoping to find a man that near me to become friends with and maybe more. I'm in Georgia south of Atlanta.
    sexyalyssagurl sexyalyssagurl
    36-40, T
    1 Response Apr 1
    I've been wearing thongs for past 2 days...
    chrisjay2k16 chrisjay2k16
    26-30, T
    Apr 1
    Leggings too short but you still love to wear them? Pull them up a bit from the bottom and they make great capris :) (You all probably knew that :P ) 
    DamnDanielle DamnDanielle
    18-21
    1 Response Apr 1
    If you're interested, there will be plenty more to come :) 
    DamnDanielle DamnDanielle
    18-21
    1 Response Mar 31
    So I heard Experience is shutting down 😕 so if any awesome cross dressers wanna keep in touch drop me a message :)
    Rosyrose19 Rosyrose19
    18-21, M
    4 Responses Mar 31
    Ah, now you've happened upon my 'foible'. Not a vice. Just nice.
    TValentine TValentine
    56-60, M
    Mar 31
    Add me up, like/comment on my pics and Ill give you more ;)
    DamnDanielle DamnDanielle
    18-21
    1 Response Mar 31
    Back again :) I need to build credit so you can all see my pics again!!
    DamnDanielle DamnDanielle
    18-21
    Mar 31
    So sad to see EP go. Its helped me through some difficult and confusing times, its helped me accept who i am, and I've met tons of amazing people who support me. I really want to...
    HollyTG HollyTG
    18-21, T
    Mar 30
    I love driving around at night wearing bra, lacy panties, stocking and a sexy lacy bra/slip and driving through McDonnell's and teasing the night staff
    pinklacyslip pinklacyslip
    36-40
    Mar 30
    So sad to see EP go. Its helped me through some difficult and confusing times, its helped me accept who i am, and I've met tons of amazing people who support me. I really want to...
    HollyTG HollyTG
    18-21, T
    Mar 30
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