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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 168 People

    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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    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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    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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    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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    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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    Related Experiences

    I like dressing up whether its wearing casual clothing to a full Tail-Coat Tuxedo, dressing up can be pretty fun (not an everyday thing). But its ok to dress up once in a while...
    PatrykM PatrykM 18-21, M 3 Responses a week ago

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    This probably sounds weird, but I like dressing jot only fancy, but just in a fantasy way. in a way you'd see in a movie such as Lord of the Rings. I know, I'm weird.
    SarmiraKitti SarmiraKitti 18-21, F 1 Response Feb 2

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    This probably sounds weird, but I like dressing jot only fancy, but just in a fantasy way. in a way you'd see in a movie such as Lord of the Rings. I know, I'm weird.
    SarmiraKitti SarmiraKitti 18-21, F 2 Responses Feb 2

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    If I type 'clingy' in the search box, all the experiences that come up are negative; "I don't like clingy boyfriends", "I hate clingy people", etc. And honestly, I don't understand...
    LanniLette LanniLette 13-15, F 3 Responses Feb 2

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    She has the same routine every morning, She wakes up, sits on the edge of her bed and looks out the window to see what the weather is like. She believes she can always judge how a...
    majesticalbree majesticalbree 16-17, F 1 Response Feb 18

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    Whether it's a simple collared shirt or a whole suit and tie, dressing up is awesome. There's no feeling like being dapper!
    Blue707 Blue707 16-17, M 1 Response 1 day ago

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    For the majority of the time..... I was sick earlier this week because of an allergic reaction that turned into a fever and chills and loss of appetite. Then loss of energy and...
    xxblasianxx xxblasianxx 18-21, F 3 days ago

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    Yep I also want to be a girl so I mean that's why haha
    AshleyNicolee AshleyNicolee 18-21, T 4 Responses Feb 3

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    I'm bored what you guys think??
    AshleyNicolee AshleyNicolee 18-21, T 9 Responses Feb 4

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    I wish it was summer I wanna go swimming! How do I even look in this anyway?
    AshleyNicolee AshleyNicolee 18-21, T 4 Responses Feb 17

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    What do u guys think some of u wanted to see more! Here it is!
    AshleyNicolee AshleyNicolee 18-21, T 2 Responses Feb 18

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    You guys asked for other pictures so here you go ❤️
    AshleyNicolee AshleyNicolee 18-21, T 3 Responses Feb 18

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    I'm a Neko (Cat Girl) now! Nya! =^_^=
    AshleyNicolee AshleyNicolee 18-21, T 2 Responses 2 days ago

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    I'm sure crossdressing counts rightp
    hunters25 hunters25 13-15, M Feb 2

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    I am seriously addicted to lingerie!!(; I love to dress up(; I've thought about trying out to be part of a maxim magazine!!(;
    ashley35189 ashley35189 18-21, F 6 Responses Feb 2

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    I believe I am the queen of impractical shoes.
    littlefox2 littlefox2 26-30, F 3 Responses Feb 2

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    i am a scenester always will be die hard try hard scene kid
    lovelyxalice lovelyxalice 18-21, F Feb 12

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    A friend once told me "Always dress as if you have some place better to go afterwards". I love creating new looks and seeing how many different looks I can match with different...
    LegStyles LegStyles 26-30, M 3 Responses Feb 17

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    I need some input on how to move forward. I am married and I have a single OM. He was in a serious dating relationship when we first started but eventually they didn't work out. We...
    myheart99 myheart99 36-40, F 10 Responses 6 days ago

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    I wish I had a boyfriend I can sit down and he actual hold me like a boyfriend should. Instead my boyfriends tell me "to get off" or sit beside them. I'm single right now I'm...
    lorrena19 lorrena19 18-21, F Feb 17

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    I was an ordinary woman today. It was lunch time, so I put on a 38C bra with breast forms, a reddish/beige patterned shirt, a camel colored leather skirt and a pair of leather...
    Robertredlips Robertredlips 56-60, M 2 Responses Feb 4

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    I love to go to the local mall, buy a slice of pizza or some coffee, and watch all the people just wandering around. Occasionally I find someone I am interested in and casually...
    Sxculent Sxculent 18-21, F 5 Responses Feb 4

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    I love my boyfriend. We have been dating for over a year and a half. About 6 months into our relationship, he confided in me that he used to cross dress. He said it was in the...
    honestsleep honestsleep 22-25, F 2 Responses Feb 8

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    My first experience of sleeping in nighties on a regular basis was after my sons had left home to go to university. I had wanted to wear nighties to bed for a number of years and...
    MandytgAndy MandytgAndy 70+, T 3 Responses 10 hrs ago

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    It's been a really long time since I was with another woman... She was one of my best friends at the time and it was kind of an accident the first time it happened between us but...
    bbfeels bbfeels 18-21, F 1 Response 4 hrs ago

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    Please excuse my stories being posted under the same heading . I wrote down my feelings for you my wonderful woman in November. The words express how I feel. I don't intend to...
    JohnCrighton JohnCrighton 51-55, M 2 Responses 12 hrs ago

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    when I was 12 my mother drank a lot. she started dressing me as a girl. I did not think anything about it. As I got older I started liking it. I am 56 love cross dressing love to...
    charlett charlett 56-60, M 1 Response Feb 4

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    I have a crush on my boyfriends friend. I just wanna kiss him and make out and then **** him.
    Emmalee410 Emmalee410 18-21, F 14 hrs ago

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    He now wants me back, we've been dating for a month his leaving for university. Well he changed on me and started acting strange said he doesn't trust me and what not. He kept on...
    NamzyZizi NamzyZizi 16-17, F 2 hrs ago

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    So this is going to be somewhat of a long story.. But I need to share with someone. Maybe sharing it will help me figure out where my heart lies. My ex an I broke up about 2 years...
    StephanieLynne1125 StephanieLynne1125 22-25, F Feb 6

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    I love and hate being single. I like being single because I have freedom. I don't have to hear a guy telling me "come to my house, or its my birthday where my gift".. I can spent...
    lorrena19 lorrena19 18-21, F 1 Response 9 hrs ago

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    I hate when my bf lies to me, when he gets mad he checks out other girls and I don't like to feel like I need to worry about him. is It wrong for it to bother me so much.. I've...
    SierraV15 SierraV15 18-21, F 1 Response 4 hrs ago

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    I want to find a woman who loves strait men willing to do anything for her I love dressing like a woman and want to be a bestie girlfriend with another woman
    pantyhose4me4life pantyhose4me4life 31-35, M Feb 17

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    It feels good to type everything down here.. I have been keeping everything to myself and it is getting harder to manage but I am sure that I can seek advises from other persons...
    Zenalia Zenalia 18-21, F 6 days ago

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    How Do You Resolve conflicts? Sitting in my office with a woozy head, a massive headache, sore throat and jolts of lightening in my lower back and knees... Yup! this is how...
    warriormama warriormama 41-45, F 9 Responses 7 hrs ago

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    ''Hey people, I'd like to know where the good women at? I am fed up repeatedly being hit on by un-symmetrical, obese, low life girls. I mean c'mon get employed, get a spacious...
    WinterSunShine WinterSunShine 18-21, M 9 hrs ago

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