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I Am Dating a Cross Dresser

Personal Stories, Advice, and Support 75 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 6 Responses Jan 26, 2010

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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 3 Responses Apr 17, 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 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 9 Responses Dec 5, 2009

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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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    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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    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 5 Responses Nov 18, 2013

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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 3 Responses Apr 20, 2012

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    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

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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 6 Responses Mar 27, 2012

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    Related Experiences

    I'm a 17 year old crossdresser in Mississippi. Message me!!
    ChloeGirl15 ChloeGirl15 16-17, M 14 hrs ago

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    Hey girls!! My name is Chloe. I'm a 16 year old crossdresser. Message me!!!
    ChloeGirl15 ChloeGirl15 16-17, M 1 Response Nov 5

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    well I have been cross dressing since I was 6 and I finally just came out of the closet a little bit a little while ago. as I grew up, I stole my sister's clothes and I took...
    CDMichelle16 CDMichelle16 18-21 5 Responses Nov 8

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    Are there any UK based girls on here? I'm looking for crossdressing friends for outings and small get togethers. :) x
    DeliciousDelirious DeliciousDelirious 31-35, T 2 Responses Nov 11

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    I like to talk to people. Especially about cross dressing. But then we can talk about anything you like. Message me if you want to talk.
    Adam59 Adam59 56-60, M 1 Response Nov 19

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    How come society makes us feel bad for thinking out the box when all the time it's made up to control us. Come play at secreterotica . com it's sexy, fun the groups and library are...
    YouKnowItMakesSense YouKnowItMakesSense 31-35, M 1 hr ago

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    I went as a girl on Halloween it was really fun and all my friends loved my costume, no one was rude to me and I'm still wearing the costume haha, here's a picture, I was caught...
    JulieCakes JulieCakes 13-15, M 1 Response Nov 1

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    Well today I found out that my moms coworker, the one we're living with at the moment has a friend that she grew up with and she hadn't talked to him in about 20 years and then she...
    JulieCakes JulieCakes 13-15, M 3 Responses Nov 5

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    Hello gurls! How is everyone feeling today?
    GingerPrissXD GingerPrissXD 31-35, M 3 Responses Nov 7

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    I would love to be made to ware a wedding dress for a women
    pittsfield pittsfield 41-45, T 1 Response Nov 7

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    I enjoy hearing about others experiences and talking about my own so hmu if you want to chat.
    jasminecd5 jasminecd5 36-40, M 5 Responses Nov 10

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    Anyone in the Thames Valley area? I'm near Uxbridge. :)
    DeliciousDelirious DeliciousDelirious 31-35, T Nov 13

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    I'll be a slave. I really like wedg-ies but I'm down for anything
    hangingwedgie23 hangingwedgie23 22-25, M Nov 14

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    Yes I am a cross dresser. Only because I choose to wear the clothes I want. I want the softer clothes and comfortable clothes. So that means I wear clothes that is customarily know...
    Adam59 Adam59 56-60, M 2 Responses Nov 19

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    Looking for other cross dressers. I want to learn from you and talk about everything related to being a cross dresser.
    SamanthaCD5 SamanthaCD5 22-25, T 1 Response 4 days ago

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    So Halloween just passed and it reminds me how hot crossdressers are. Yes, I know most of the guys dressed up like female characters on Halloween aren't normally crossdressers but...
    newasexy newasexy 26-30, F 9 Responses Nov 2

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    That would be great. There are some cross dressers like me who like being a man but love to wear women's clothing. It is cross dressing for a man to wear women's clothing. However...
    Adam59 Adam59 56-60, M 1 Response Nov 12

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    I am a 38 year old male to female cross-dresser. I have been married twice, divorced twice, and have a daughter. I am in a relationship with a loving and kind woman who I have...
    Mich38 Mich38 36-40, M 3 Responses 6 days ago

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    I, like most cross dressers, tried on my first pair of panties in my early teens. What an exciting feeling! I still get that rush of excitement every time I put on! When I go out...
    christine3000 christine3000 46-50, M 5 days ago

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    Are their any cross dressers that want to talk
    TheGamer101 TheGamer101 13-15, M 4 Responses Nov 2

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    I have been married to a cross dresser for over 20 years. He told me very early on in our relationship to give me a chance to back away from him. The main question I asked him was...
    vilewart vilewart 66-70, F 8 Responses Nov 12

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    I have been dating a widower for two and a half years. She passed away seven years ago. We go out once a week. We have a good time. I think I love him. He just told me that he...
    mecati mecati 56-60, F 5 hrs ago

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    Me and my cross dressing bae! Yes, the one that's prettier than me! Love him to death! Not dating, but best friends since 2nd grade. And even then I was happy to apply his makeup!
    JustCammy JustCammy 16-17, F 1 Response Nov 9

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    If I could compare my online dating experience to anything, I'd compare it the IPhone game "Flappy Bird". You see, when I first downloaded that game, I thought: "This game looks...
    DeathstalkerScorpion DeathstalkerScorpion 22-25, M 1 Response Nov 13

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    Middle-aged men and teenagers don’t really want to get that tag of a committed relationship and fall into a long-term relationship at an early age. However, women in today’s...
    CougarsWoo CougarsWoo 36-40, F Nov 19

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    Hey, You know age gap dating? I’d like to recommend a current popular dating site ~~? – AgeMeet.com — It is the best, largest and most successful age gap dating site for...
    sadecc11 sadecc11 26-30, F 1 Response Nov 10

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    Okay, so this is actually old news that I'm experiencing strong emotions about again. My mother died when I was 13, after about 8 months of battling cancer. That in itself was...
    jaclynhampson jaclynhampson 18-21 17 hrs ago

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    It all started when I got a job at McDonald's on feb 22 2014. I immediately had a crush on this guy named Oscar. Keep in mind I am 17 and he is 16. I liked him from day one...
    Alliforevers Alliforevers 16-17, F 6 Responses Nov 2

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    I'm not doing it again, I had many trust problems with that. I'm not telling who they are, It's my business. But I would tell yall that I dated on here and it was a wreck for me...
    YoungSwagTheRapper YoungSwagTheRapper 16-17, M 5 days ago

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    It seems that 95% of all crossdressers are male to female, unless it is just that females are less likely to come out about crossdressing. But regardless it is pretty rare for me...
    LexyCD LexyCD 18-21, M 2 Responses Nov 20

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    I don't see a problem with cross dressing. I am a male and I wear dresses and skirts. I also wear other women's clothing. If your happy with what you wear then your more relaxed...
    Adam59 Adam59 56-60, M 4 Responses 3 days ago

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    MixedSingle.com is an interracial dating and personals site that brings together singles of all races, ethnicity and cultures seeking an interracial partner for friendship, dating...
    latrineantesa latrineantesa 26-30, F Oct 30

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    Our 29 Year Age Difference! Hello, I am 21 and my boyfriend is 50. We meet on AgeMeet.com.We were friends for a couple years before we got together, we have been together 3 amazing...
    danacc11 danacc11 26-30, F 1 Response Nov 12

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    I know I'm not attractive. In certain angles I look a hell lot better. That's why I use those photos online. They have not been edited and I wear no makeup. But my skin is always...
    1lonelydaisy 1lonelydaisy 41-45 2 Responses Nov 16

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    CrossPlay is amazing. I just got done with it at the latest comicon. I'm a bit surprised that so few people seem to enjoy Crossplay on here... It's really fun, I'm fem 15, the pic...
    SaikoTersuga SaikoTersuga 18-21, F Nov 12

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    I don't get to do it much, I mean, when I was younger it was fine. Get in a boyish outfit or if you felt fancy a suit. My wardrobe used to be guy clothes because well I wanted to...
    SaikoTersuga SaikoTersuga 18-21, F 4 Responses Nov 12

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    Im done crossdressing now i need to get my life in order but i still care about my friends in my circle that crossdress also i don't like guys anymore i don't know if i will ever...
    TheGamer101 TheGamer101 13-15, M Nov 19

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