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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 168 People

    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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    Give him this for a gift.

    http://www.amazon.com/Feminizing-Men-Achieve-Maximum-Feminization/dp/1502959674/
    AaronFel AaronFel 36-40 Nov 28, 2014

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    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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    sexymommy2014 sexymommy2014 31-35, F 2 Responses Aug 7, 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 11 Responses Dec 11, 2013

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    Related Experiences

    I dress up mainly for my man because it's fun and he always compliments me even when I don't dress up :) my man goes crazy when I put on a cute dress and straighten my hair and put...
    Mizpoppy Mizpoppy 26-30, F 1 Response 9 hrs ago

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    Thinking about changing my hair debating on going blonde or a purple to pink hombre
    AshleyNicolee AshleyNicolee 18-21, T 4 Responses Jan 14

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    i am wearing panty for my work its so soft and so comfortable..........
    daya55 daya55 26-30, M 1 Response Jan 15

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    i am going to buy a new nightgown tody....
    daya55 daya55 26-30, M 1 Response Jan 16

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    I'm always excited when I have the opportunity to dress up. In August my uncle is getting married and I"m already looking at dresses to buy. I own five pairs of heels!
    Kayleehere Kayleehere 18-21, F 2 Responses Jan 8

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    there's something lovely about the feeling when a girl starts choosing clothes to put on you and makes you go along with it :P
    charkzilla20 charkzilla20 16-17, M 5 days ago

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    i am gong to remove my night gown now. Reding to go to work i am going to wear my my wife panty she prefer for me all her cloth that i can wear to my work....... i love her so much...
    daya55 daya55 26-30, M 6 days ago

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    “A WOMAN SHOULD HAVE …. enough money within her control to move out and rent a place of her own even if she never wants to or needs to… A WOMAN SHOULD HAVE …. something...
    abrokenlittlegirl abrokenlittlegirl 46-50, F 1 Response Dec 28, 2014

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    Hi there I have a YouTube channel that I upload a video on every week! I like to do top ten videos like this video; top ten weirdest Holiday traditions! It includes things like...
    TheBellaBubbles TheBellaBubbles 16-17, F 1 Response Dec 31, 2014

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    i like dressing uop as a girl i like how it feels to wear a dress and i want to look more like a girl
    guyinadress guyinadress 22-25, F 1 Response Jan 11

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    so my mom was sitting next to me on the couch - and I was surfing the internet - and we stumbled upon an article that said "7 signs you're dating the wrong man" and my mom was like...
    BananaSmoothiee BananaSmoothiee 18-21, F 2 Responses Jan 11

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    I have an amazing boyfriend ! he is the best thing has ever happened to me ! he forgave me for cheating on him and he has helped me better myself so much. he saved my life from the...
    psychedeliica psychedeliica 18-21, F 1 Response 3 days ago

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    My name is Joseph and I live in the north-East of England. I am gay but I'm not out and I am straight-acting. I would like a boyfriend from England who is interested in most of the...
    EqualityinAges EqualityinAges 16-17, M 2 Responses Dec 25, 2014

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    I am 16 and living in England. I'm not out yet, have admitted that I am Bi. I would like a boyfriend 15-17, in England if possible, would like to take things slowly. Message me if...
    vipers2816 vipers2816 16-17, M Dec 26, 2014

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    Well I'm not gay I'm bi and would like a boyfriend and a girlfriend.
    bornfem bornfem 56-60 2 Responses Dec 31, 2014

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    I feel like my boyfriend is losing feelings for me for some odd reason... We talked s few days ago and it was great. I told him he was stuck with me forever and he said he was...
    tiffanygetchell tiffanygetchell 16-17, F 1 Response Jan 11

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    Not all of it. But if the opportunity comes I'm always up for flashing anyone who wants it. Or more than flashing. Sometimes I ***** for strangers online just for fun. It turns me...
    maddiegraddie maddiegraddie 18-21, F 6 Responses Dec 28, 2014

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    I really do. Every girl does. There is just something magnetic about him. He makes you feel like the only woman in the world at the moment. He sweeps you off your feet without even...
    bossvixen bossvixen 26-30, F 1 Response Dec 29, 2014

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    Aretha Franklin - (You Make Me Feel Like) A Natural Woman (1967)
    Maverick1962 Maverick1962 51-55, M 3 Responses Jan 12

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 1 Response 3 days ago

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 1 Response 3 days ago

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    I'm independent but I'm not a woman. I joined this group to write a post about my lover. While it's true I'm independent, she, I believe is more so. We seldom are different from...
    Bound2You Bound2You 18-21, M 10 hrs ago

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    I have a LOT to reveal about my relationship with my long distance boyfriend. I need ADVICE!!! So if you can, please read this. Thank you for your time. My boyfriend gave me the...
    kamilleredd kamilleredd 22-25, F 3 Responses Jan 16

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 3 days ago

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    My boyfriend and I have been together for the better part of four years. We were highschool sweethearts and after 3 years of being and living together things were stressful. We...
    notjustthegirlnextdoor notjustthegirlnextdoor 22-25, F 4 hrs ago

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    I loved re-dressing my boyfriend after we made love
    toasty420 toasty420 18-21, F 1 Response Dec 30, 2014

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    When I got home from Charlotte's salon I carefully went about my home fearing I would damage or break a nail. They were beautiful. For a long time I sat on the couch in total...
    phylisst phylisst 70+, M 1 Response Jan 15

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    I Don't like Saying that. I derive No Pleasure in calling Men to task. What is to Be Said, though, When MEN see Women running around "Dressed as Men" AND THEY SAY NOTHING ?? It's...
    desireindisguise desireindisguise 56-60 Jan 11

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    I hate - hate hate hate - I can't stress to you enough about how much I just hate his father. I have pure hatred for that person. I don't even say "man" - because he is not a man...
    BananaSmoothiee BananaSmoothiee 18-21, F 1 Response Jan 12

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    I hate him he's always bitchn like a girl complaining about everything I try to talk to him I can never have a good conversation with him he's so immature I've Been with him over 2...
    Emilyc1992 Emilyc1992 22-25 9 hrs ago

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    My boyfriend just can't be happy unless he's stoned or drunk. I hate him for that. I'll get totally disgusted with him eventually and kick him out. Until then, I'm supposed to be...
    yppirt yppirt 31-35, F 2 Responses 14 hrs ago

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    Looking for a boyfriend. In California and is a very good conversationalist. I'm 15. Preferably 15-17.
    mjcig mjcig 13-15, M 13 hrs ago

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    I guess it's a good thing I cleaned my room today... I just got a call from my boyfriend, saying he will be here in 30 minutes to give me a new desk for my room. :D he's so sweet...
    BananaSmoothiee BananaSmoothiee 18-21, F 1 Response 1 hr ago

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    I have long thought about cross dressing. Only recently have I seriously tried it and it sure is exciting. I bought one sexy negligee and G-string. I took some pic's of me and...
    SunsetBreeze SunsetBreeze 56-60, M Dec 28, 2014

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    I let him live with me is more like it. He was couch surfing for years prior to that. I ask for $100 bucks a week, so I don't feel like his sugar Momma. But I still feel that way...
    yppirt yppirt 31-35, F 14 hrs ago

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    1. I am very quiet and always love to be with someone who does the talking for us. 2. I hate to be alone with very loud people who can't stop talking. 3. I am super skinny and...
    interstellartraveler interstellartraveler 22-25, F 11 hrs ago

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    He irks my whole soul. I swear he gets under my skin like no other. We have a 2yr old together, but have only been dating a year. We got along so well before we started dating, now...
    KayBeeElle KayBeeElle 26-30, F 5 hrs ago

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    We had another morning together and it was trully amazing. I wanted it to be special and memorable. Got myself ready early: red lingerie, hair done, body lotion all over my body...
    Chicadelcaribe Chicadelcaribe 31-35, F 2 Responses Jan 14

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    I want find a woman who likes the idea of getting pregnant over and over because she likes being pregnant and likes breastfeeding her partner.
    gamer9857 gamer9857 18-21, M 1 hr ago

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    I am actively feminizing myself and adopting the habits and lifestyle of a woman. I have always felt this way but like many fought my impulses for years. However, finally accepting...
    BiSexElleTgirl BiSexElleTgirl 31-35, T Dec 25, 2014

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