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I Am Dating A Crossdresser

Personal Stories, Advice, and Support 36 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

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    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 41-45, M 1 Response Mar 16, 2012

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    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 Apr 19, 2012

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    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

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    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 2 Responses Feb 17, 2013

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    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 6 Responses Nov 24, 2009

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    Related Experiences

    I love crossdressers... and why. I always saw things from the girl's body, feeling like a boy point of view. It was natural for me to wonder about the other side, if there were any...
    DarkwingGoslyn DarkwingGoslyn 31-35 1 Response Jun 28

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    I've struggled with being a crossdresser all my life, and be Christian crossdresser for the last 21 years. When I was only a crossdresser I just though I was sick and something...
    DawnR59 DawnR59 51-55, T 7 Responses Jun 30

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    I am a crossdresser, add me on snapchat : ghostmanjj
    Elincd Elincd 18-21, M 2 Responses Jun 25

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    I'm a bisexual crossdresser who wants a relationship with a man.
    shawnyboi18 shawnyboi18 18-21, M 1 Response Jun 26

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    Are there any other crossdressers in NEPA looking for friends to dress and socialize with?
    capricorn79 capricorn79 31-35, T 3 Responses Jun 29

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    I'm not a teenage crossdressers but I sure would love to get to know some pretty girls like you're self
    kerw94 kerw94 18-21, M 4 Responses Jul 7

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    Hey crossdressers message me for chat and maybe even RP
    RacerXX2 RacerXX2 13-15, M 2 Responses Jul 10

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    Well I do adore ladies who like crossdressers, but that's like, not the point. What I wanna say is - I'm a mtf trans (15) myself and I'd luv a bf who crossdresses, he may even...
    LindavdB LindavdB 13-15, T 5 Responses Jul 16

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    I am 18 and a crossdresser I love the appearance of being a girl I put on bras and panties and get some of my sisters skinny jeans and put on a tight shirt and get my moms heels...
    Jlmendez15 Jlmendez15 18-21, M 1 Response Jul 17

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    Hi im a pantie boi from nyc and would like to chat or meet up with other crossdresser or pantie bois. Message me or add me
    fromBK718 fromBK718 26-30, M 1 Response 4 days ago

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    Hi! Not one myself, but I was wondering if any drag queens/crossdressers would want to discuss makeup?! <3 I need more tips and I'm willing to give some as well!
    JustCammy JustCammy 16-17, F 14 hrs ago

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    Hi! Not one myself, but I was wondering if any drag queens/crossdressers would want to discuss makeup?! <3 I need more tips and I'm willing to give some as well!
    JustCammy JustCammy 16-17, F 1 Response 14 hrs ago

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    Hi! Not one myself, but I was wondering if any drag queens/crossdressers would want to discuss makeup?! <3 I need more tips and I'm willing to give some as well!
    JustCammy JustCammy 16-17, F 3 Responses 14 hrs ago

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    ARE YOU AN OLDER MAN SEEKING A YOUNG GiRL? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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    ARE YOU AN OLDER MAN SEEKING A YOUNG WOMAN? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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    ARE YOU AN OLDER MAN SEEKING A YOUNG WOMAN? "Datingayounerwoman.com is a newly launched unique dating service, which helps young girls looking for older men or vice-versa...
    datingayoungerwoman datingayoungerwoman 22-25, F Jul 2

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    Well me and my boyfriend have been dating for 2 months and we have been wanting to kiss Eachother but then all of a sudden he didn't want to anymore and I didn't know why and it...
    kdub13 kdub13 13-15, F 1 Response Jul 9

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    I don't use them anymore due to personal, past experiences and from hearing crazy stories about online dating. From all of my experiences, I've learned about 90% percent of people...
    texaschic35 texaschic35 31-35, F 1 Response Jun 30

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    Hello everyone,nice to meet you!Anyone is sugar baby or sugar daddy here ? I would like to recommend a online dating website which is 100% free to you. http://www.findingsugardaddy...
    Saralink Saralink 22-25, F 1 Response Jul 5

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    There is a lot of strange information about dating firefighters online that focuses on firefighters' masculinity, and how a woman should act in order to 'land' one as a boyfriend...
    ameliabedelia63 ameliabedelia63 26-30, F 1 Response 6 days ago

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    Best Older Men Younger Women Dating Site - AgeMeet.com AgeMeet.com a website specifically designed for older man and younger woman relationships and older woman and younger man...
    cindytongcc11 cindytongcc11 26-30, F 4 days ago

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    Not all men and women have the same romantic needs in life. Some prefer the member of the opposite sex to be of the same age, some prefer individuals older to them, while some...
    janecc11 janecc11 26-30, F 1 Response 4 days ago

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    Not all men and women have the same romantic needs in life. Some prefer the member of the opposite sex to be of the same age, some prefer individuals older to them, while some...
    janecc11 janecc11 26-30, F 1 Response 4 days ago

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    Not all men and women have the same romantic needs in life. Some prefer the member of the opposite sex to be of the same age, some prefer individuals older to them, while some...
    janecc11 janecc11 26-30, F 1 Response 4 days ago

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    I’m a 46 years old single, also can call “cougar”, I am a SWF, never married, no children, and quite content with that. I also had thought find a person to marry, then plain...
    vivian420 vivian420 36-40, F 1 Response Jun 25

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    Hi,I'm simon,come from California,25 years old and like cougar. Recently,I met my true love,share my love story and happiness to everyone,hope you can find your love. I finally met...
    janleif janleif 26-30, M Jun 25

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    Are you bold when it comes to telling someone you like them? ☺️Do you walk right up to them, or are you more reserved with it? Should a woman tell a guy, or wait for him to...
    AEHeroine AEHeroine 18-21, F 1 Response Jun 26

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    I have Aspergers, and am not dating anyone. I just wanted to say a heartfelt thanks to all those women and men who express such love and appreciation for those with Aspergers they...
    jollygoat jollygoat 22-25, M 1 Response Jun 27

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    I'm too young have a boyfriend and also I don't think I want to use a dating site to find someone to love or to love me back. I want to have someone find me or me find him in real...
    FighterWolf FighterWolf 13-15, F 1 Response Jun 30

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    Hi, I am new to this MPD so, I may not know much about it. I am currently dating a woman who has it and it has been a little rocky ever since we dated 4 months ago. Our love for...
    Junchew Junchew 18-21, M 1 Response Jun 30

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    If you are a very rich or a younger men yet very lonely woman, it's time for you to get online and start dating too! There are just too many good men out there on the market that...
    tanglelau tanglelau 31-35, F Jul 5

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    So I have been casually dating this guy since early May and things have been pretty awesome. 2 weeks ago we went to the beach and on the way back I was talking about something and...
    karabeara123 karabeara123 26-30, F 3 Responses Jul 6

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    I’m a 46 years old single, also can call “cougar”, I am a SWF, never married, no children, and quite content with that. I also had thought find a person to marry, then plain...
    avenlence avenlence 31-35, F 1 Response Jul 7

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    LONG READ BUT ID APPRECIATE SOME FEEDBACK PLZ Hey so i tried match.com for about a month before i got sick of it and cancelled my acc. Im 26 year old guy considered handsome by...
    braster25 braster25 22-25, M 3 Responses Jul 9

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    I Am Dating My High School Sweetheart I Am dating my highschool sweetheart and me and her have both fallen in love <3 and I am planning to propose to her this September...
    ECrierie ECrierie 16-17, M Jul 9

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    I have a hard time time dating cause I have a disability carabal palsy and that turns people off I love who I am but not dating sucks
    footballfan2121 footballfan2121 26-30, M Jul 10

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    I am 23 years old and have essentially had no dating experience whatsoever. I have recently trying to venture into online dating with no avail. I just don't seem to know how to...
    aha55555 aha55555 22-25, M Jul 10

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    Online dating sucks, but what other options are there? I'm not a bar or club person, I hate sports, and I work with only one other person so meeting a guy through a coworker is...
    dolceharajuku dolceharajuku 26-30, F 3 Responses Jul 14

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    Man! I cannot stand online dating sites, these people nuckin futs man! Seriously. I've been online dating for several months and it has been a nightmare, chicks crawling around in...
    2Blueiiz 2Blueiiz 41-45, M 1 Response 5 days ago

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    Younger Women Looking for Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F 4 days ago

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    Younger Women Looking For Older Men is because Older Men are more confident and generally more wise and intelligent, qualities ,Older men know how treat a woman better than younger...
    SkyCC11 SkyCC11 26-30, F 4 days ago

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