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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 69 People

    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...
    pinglasgow pinglasgow 41-45 6 Responses Jun 5, 2011

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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...
    confusedinw confusedinw 56-60, F 8 Responses Dec 5, 2009

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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...
    fashionablylostinga fashionablylostinga 41-45, F 3 Responses Apr 17, 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...
    bldbeauty bldbeauty 22-25, F 3 Responses Apr 20, 2012

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    My boyfriend, whom I've told you about on my last post, told me he cross-dresses. He was very afraid and insecure to the point where he believed if he told me, I'd leave him. But I...
    takethispain takethispain 18-21, F 1 Response Mar 7

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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...
    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...
    confusedheretoo confusedheretoo 31-35, F 4 Responses Nov 18, 2013

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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...
    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...
    MG1023 MG1023 46-50, F 5 Responses Mar 27, 2012

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    Related Experiences

    Hi(: I'm a cross dresser but you could call me transgender. I'm looking for a mistress or a fem dom...(; message me on here and we can talk(:
    blazin0cd blazin0cd 18-21 Mar 22

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    Below are videos of cross dressers being arrested . LEt me know what you think. http://www.youtube.com/watch?v=EqGplR3x9LE http://www.youtube.com/watch?v=nHi8TUZabTo http://www...
    bobbylee111 bobbylee111 26-30, T Apr 7

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 4 days ago

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    I just started cross dressing. Any one else new that wants to chat?
    nightfun56 nightfun56 18-21, M 6 days ago

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 4 days ago

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 4 days ago

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 4 days ago

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 4 days ago

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 4 days ago

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    and I live in the Port Huron area. Write if you'd like to talk!!
    deleted deleted 26-30 Mar 31

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    Look at mycrox-d.com Lingerie for men
    fercrox fercrox 46-50, M Apr 6

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    My boyfriend and I have been dating for over a year now, and I am completely in love with him. He' my best friend and the love of my life. I can't imagine life without him. He...
    lithium123 lithium123 22-25 6 Responses Mar 30

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    I'm a cross dresser and I'm looking to chat with other cross dressers and females
    Dizy132 Dizy132 18-21, M 7 Responses Mar 24

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 1 Response Apr 5

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    After stumbling across a cross-dresser in p**n, all I think about when I'm in public out of my feminine personality is that I wish I was wearing more than just my sisters tight...
    Peatrie2000 Peatrie2000 18-21, M 4 Responses Apr 7

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    Most people mistake me as one and cross dresser's want me to be one. I think they want to be like me, they have an obsession for my kind.
    Maurelle Maurelle 22-25 Apr 8

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    Some say the shield I carry is because I have experienced pain but the pain I have had I have let go...I carry my on cross now. The pain one see in others is the reflection of...
    bellaluce bellaluce 51-55, F 1 Response 10 hrs ago

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    So today's fun filled event with the wife was a 7 hour complaint fest with 2 hours of arguing in there. Just wouldn't end. I had to walk out of the room after 3 hours which...
    j21043 j21043 31-35, M Apr 5

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    I've always loved the idea of dating a crossdresser. I'm what some people might call a "tomboy" and I just always found the juxtaposition ( I that's the right word I'm not really...
    BrahmaDonna BrahmaDonna 22-25, F 16 Responses Mar 22

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    Some of my girlfriends and I have tried online dating with disastrous results 10 to 13 years ago. Ninety-nine percent of the males we met for a date were creeps because...
    ebonynbill ebonynbill 26-30, F 1 Response 14 hrs ago

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    I love crossdressing for sex with men. I like feeling as much as a girl as possible. I love thongs and bras, and all womens sexy clothing.
    islutmyself54 islutmyself54 26-30, M 1 Response 1 hr ago

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    I am falling for a crossdresser. I love him and who he is and I would never change him. I told my family, which consist of my mother and sister. Mom was accepting, my sister was...
    bbsw1963 bbsw1963 46-50, F 2 Responses Mar 24

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    I was online dating on the Polyamory subsidiary of AFF and was looking for someone older by a few years, someone who could treat me like a woman instead of a replacement mother...
    coconutgirl27 coconutgirl27 22-25, F Mar 18

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    Inside Big Penis Dating Site “Seven or Better” Take a look inside 7orbetter.com—before you let one inside you. Yesterday, I took my first trip around the big penis dating...
    RaceCarrington RaceCarrington 51-55, M 3 Responses Mar 16

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    Insights on Swift Plans of Younger Women Dating Sites It doesn’t constantly adhere to that the women in their twenties will necessarily be interested in a person her very own...
    GarthPasche GarthPasche 26-30, F Mar 24

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    Older Men Like Younger Women as they are more vibrant, spontaneous and full of life. A survey of 2000 adults showed that only one percent of women preferred a relationship with a...
    likeyoungerwomen likeyoungerwomen 31-35, F Mar 31

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    Older Men Like Younger Women as they are more vibrant, spontaneous and full of life. A survey of 2000 adults showed that only one percent of women preferred a relationship with a...
    likeyoungerwomen likeyoungerwomen 31-35, F 1 Response Mar 31

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    Couples have a higher chance of reaching divorce if they are having deep financial trouble, and for this reason, finding a wealthy mate is not something that a person should be...
    lookingforrichmen lookingforrichmen 26-30, F 6 days ago

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    Older Men Younger Women Dating Site - AgeMeet.com AgeMeet.com is the # 1 dating for Older Men Younger Women Dating Site, it offers a meeting place where younger women seeking older...
    sallycc17 sallycc17 26-30, F 1 Response Apr 3

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