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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 176 People

    So I'm very new to this.

    I tried on my mom's bra/panties/pantyhose/dress for a dare and it felt pretty good. Don't misunderstand me, I'm not a crossdresser, but I am male. I posted a pic anon online (without my face) and had many guys over me. Some problems: hands not slender, shoulders too broad, hips...
    corneliousrodriguez corneliousrodriguez 22-25 Feb 3, 2014

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    Give him this for a gift.

    http://www.amazon.com/Feminizing-Men-Achieve-Maximum-Feminization/dp/1502959674/
    AaronFel AaronFel 41-45 Nov 28, 2014

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    sexymommy2014 sexymommy2014 31-35, F 2 Responses Aug 7, 2014

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    My Best Friend

    Confessed to me that he likes to dress up, but never really had. He slept over one night and I set up the spare bedroom as a dressing room. I hung up at least 30 outfits and undergarments. And a makeup area and we wear the same shoe size so he walked in heels all night. When I...
    Beth4u Beth4u 36-40, F 11 Responses May 11, 2011

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    I'm damn jealous coz he is more ******* prettier

    and sexier than me. lol thank u for making my day.
    sexymommy2014 sexymommy2014 31-35, F 1 Response Aug 4, 2014

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    My cross dressing boyfriend

    and I are thinking about camming. I know there is a large audience for shemales, but I'm curious if there is an audience for crossdresser and female. What's your opinion?
    Lalalauli Lalalauli 31-35, F 10 Responses Dec 11, 2013

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    And a woman's mind can be a thing of pure beauty.. ..I've always had a thing for art!☺️
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    I ran into W at the gym yesterday. Haven't seen her since the birthday fiasco back in May. I originally ignored her but decided to say 'hey' because I knew that MM would hear about...
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    I just want a woman to talk with to get to know and see if there's a connection why is it so hard
    LadyAnnebella LadyAnnebella 18-21, F 1 Response 8 hrs ago

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    and im just thinking out loud. im NOT using this site as a dating site or anything, but i need a REAL boyfriend.
    ThatOneSomaliGirl ThatOneSomaliGirl 13-15, F 2 Responses 9 hrs ago

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    anyone want a boyfriend? Just let me know I live in Arizona.
    marksaiga marksaiga 22-25, M 9 hrs ago

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    l would love to share the experience with someone else it would make it much more fun
    dresscross dresscross 51-55, M 4 Responses 19 hrs ago

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    I absolutely love it I cannot get enough of it love the under wear so must to try on it is never ending love it love it
    dresscross dresscross 51-55, M 1 Response 1 day ago

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    Every night before I go to bed I act like I'm being forced into a sex change that I choose it to stop... I like doing that for some reason and I wish I was a female. I love doing...
    Crossdress4life Crossdress4life 18-21, M 1 day ago

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    I am a man and I do not have any clothes to go to a wedding. I do , however, have the clothes to go as a woman. I have a few choices, I could go as a bride, bridesmaid, mother of...
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    I would like a boyfriend in the USA someone near Colorado springs Colorado
    eman2012 eman2012 31-35, M 2 days ago

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    I've always had thoughts about being with another woman. Something about the way their bodies look and how gentle they move. And I cannot explain just how hot and arousing it is...
    Sensualfeelsxo Sensualfeelsxo 18-21, F 6 Responses 2 days ago

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    its the highlight of my day. :)
    littlejoey4190 littlejoey4190 22-25, T 3 Responses 3 days ago

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    I guess it makes sense, since I want to be an actress, but I still dress up all the time. I'll put on bracelets and use a barbie phone and act out scenes from movies or musicals...
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    For me.. Uh lets see. I'm not picky, but I'll do this anyways. *Looks* -Brunette -Latina or Asian -Blue eyes -Thick/Curvy -Good style when dressing *Personality* -Down to...
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    A taboo topic that would be hard to talk about with friends, I feel alone. So, my dad has been with this woman for 8 years. I've known this kid since he was 7 and I was 10, we've...
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    I just ********** watching Jodie mash finger her self. I think next door saw me. I do look hot tho.
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    I love my boyfriend and we're in a really great relationship. But lately I've realized that I find his older brother (Let's call him B) attractive and I behave a bit flirtatiously...
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    I came home and found my boyfriend on the bed with a lingerie and him in his birthday suit. 😏
    RageComics RageComics 18-21, F 1 Response Jun 23

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    10 years ago after years of my wife using toys on me, she asked me if I ever wanted to experience the real thing, I confessed that I did. she was very open minded and understood...
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    iam a beautiful girl in mens body ....I will comeout when I want by dressing as a girl I have a wide range of dress collection. ..happy to be a girl
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    I love to dress up for my husband and then he tells me I look so sexy and he grabs me and kisses me I love it
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    hi I like dressing as Tiffany
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    I have been with my boyfriend for 2 years, he has a 13 years daughter, I feel more like a conviniente spare woman for me, as his daughter doesn't have enough time for him. His...
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    Last week I was shopping with my friend. I had to pee so bad, I thought I might burst. This was after we had been shopping for awhile. The urge had been building for a long time...
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    I like see through shirts, especially. I try one bras underneath them and have a mini fashion show.
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