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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 186 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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    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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    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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    Related Experiences

    For those of you who are emotionally burned out, let me paint you a picture: Pick a setting and imagine yourself there, holding hands with 'your' MM. Once you've got that mental...
    ashadams244 ashadams244 26-30, F 2 Responses 1 hr ago

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    I'm an auntie for the third time!! My little brother and his wife had their first baby on Monday night at 9:31. My third nephew. This kid has more hair than me I swear. On top...
    AvaLennon AvaLennon 31-35, F 1 hr ago

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    This is a dumb dilemma but just wondering what to do... MM leaves for work around 9:50am and we usually talk until that point. We talk later too but he's driving until 10...
    AvaLennon AvaLennon 31-35, F 2 Responses 1 hr ago

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    I like what is called a mesomorphic female, with full thighs, and a lot of hip (having even somewhat wide child-bearing hips) and shoulder development, but fairly tight in the...
    silmarilion123 silmarilion123 41-45, M 6 hrs ago

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    I´ve never had a boyfriend and so I made the badest mistake in my life: I´ve married immediately when I fell in love and this was really the biggest mistake in my life because I...
    Loretta78 Loretta78 36-40, F 2 Responses 7 hrs ago

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    i lost another bet and have to wear a dress for a hole week and i am doing it i had take my wife to work and she said we nead milk at home i said ok i went to the store and got the...
    dragqueenpa dragqueenpa 51-55, M 4 Responses 7 hrs ago

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    An ugly man walks into a bar and a beautiful woman approaches him... ... the woman asks the man, "How would you like to get out of here?" and the man is stunned. He never thought...
    getitdonelove getitdonelove 22-25, M 8 hrs ago

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    Its not you, its me....I like both men and woman...And im starting to like you...A woman...You would be my first girlfriend if it ever came to that point...I see you more as a...
    Hon3yD3w Hon3yD3w 13-15, F 3 Responses 1 day ago

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    For the last three weeks, I’ve worn panties with napkins to hold me tucked, a bra, and nylons continuously. When I go to bed I put on pj’s and my you know what, it seems like...
    joanw joanw 61-65, M 1 Response 2 days ago

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    I love dressing up in skirts and dresses. Which I do 7 days a week. I never wear pants or shorts...ever, never have in my entire life, never will. I celebrated my birthday tonight...
    SweetJane45 SweetJane45 41-45, F 3 days ago

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    Newly divorced after leaving a very abusive relationship, I moved back to my hometown and was able to get a job through an old friend from school. During my first week there, I...
    kitkat0216 kitkat0216 31-35, F 2 Responses 4 days ago

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        I started dressing in my mothers clothes when I was 10. To this day I'm not sure why I did it, but one afternoon in the summer I was home alone for a couple of...
    MichelleTiedup MichelleTiedup 56-60, M 2 Responses 5 days ago

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    One of My Fake Mother's boyfriends and his entire family use some sort of drug to give me bodily itching, especially through fecal excrement. The only thing I could think up of...
    ONESTARRYSTARRYNIGHT ONESTARRYSTARRYNIGHT 26-30, F 5 days ago

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    Wearing a bombshell bra and panties, black pullover, red plaid mini skirt, fishnet stockings and MaryJane shoes, foundation, black eye shadow, red lipstick and my Cleopatra wig. It...
    Foxanne Foxanne 22-25, T 4 Responses 5 days ago

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    I find a women that are Voluptuous with the right clothing can look very sex and very appealing. A woman which excepts the body that she has can out power a lot of women in our...
    chuck152 chuck152 46-50, M 6 days ago

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    Dressing up can be the best thing ever. I never get bored because I love dressing up and it occupies me a lot. From makeup, clothing, accessories and shoes it's amazing. I love...
    Pinkygir Pinkygir 16-17, M 2 Responses Aug 25

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    okay I love dressing up almost every day, wearing my makeup , wearing skirts and a nice top or sometimes even dresses , I'm not much of a fan wearing jeans I barely have 6. I dress...
    bloodyzombie19 bloodyzombie19 16-17, F 1 Response Aug 25

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    I have never ever come across a woman who accepts, loves or forces their man to cross dress and be a female. If I ever come across a woman like that I'd love her until death. I'm...
    Pinkygir Pinkygir 16-17, M 1 Response Aug 25

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    When i'm alone i feel pretty
    ayeshadenji ayeshadenji 16-17, T 1 Response Aug 23

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    I love all types of clothing - Traditional, Dresses, Jeans, Party wear, skirts and Office. Various dresses but same person and loving girl underneath. What type of clothing do you...
    angelsndemons angelsndemons 22-25, F 5 Responses Aug 22

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 1 Response Aug 20

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    Just a selfie in my favourite pair of leggings
    DildoSniper DildoSniper 22-25, M Aug 19

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    i have a boyfriend and we are on our 2nd month. we are now on a long distance relationship. he is on los angeles, california and i am on the philippines. when he left philippines i...
    magebricks magebricks 18-21, F 1 Response Aug 18

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    The Babysitter Murders Chapter Forty-Six Although I liked Ellen immensely, it was a relief to know Mommy trusted me enough to go with her and my brother and sister shopping. I...
    MaryJanine MaryJanine 56-60, F Aug 18

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    My wife has told me today that if I don't get help for me to stop crossdressing she WILL leave me. She said she doesn't like me . She does love me but just can't live with me after...
    babyannie57 babyannie57 56-60, T 19 Responses Aug 17

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    I mean, I don't like you as like a boyfriend...maybe not yet 😌 but you seem like a cool dude an you like black girls. I'm not trying I show off but I feel like I'm a chill...
    Chilllfam Chilllfam 13-15, F 5 Responses Aug 16

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    Not love but like. I really like my boyfriend. He really caught my attention. There's just something that he has and I can't stop staring at him into his eyes. When he holds my...
    VasquezM VasquezM 16-17, F Aug 16

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    Don't worry, it happens no more but for the longest time I did. The guy is dead to me. We were together for a grand total of 6 months and from the beginning it was attacks so yeah...
    buffalobaby2016 buffalobaby2016 26-30, F 1 Response Aug 16

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    It's so therapeutic! My girls and I like dressing up for a night out every weekend
    DTFgurl DTFgurl 22-25, F 2 Responses Aug 15

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    I love dressing up and going to opera play or consert
    Averageguy41011 Averageguy41011 41-45, M Aug 15

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    It took me a moment to realize I qualify for this one. You see, I began dressing as a girl the day I was born because my mom had been sure I'd be a girl so that's all that was...
    AlbertSAT AlbertSAT 66-70, M 2 Responses Aug 15

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    So I've started rebuilding my clothes and make up once again. I went through another spell of not wanting to do this anymore and feeling as though I was wrong in dressing up the...
    RubyGirll RubyGirll 36-40, T 11 Responses Aug 15

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    I wear a suit almost daily for work... and nothing turns me on more than when I can take a beautiful curvy woman out ina sexy dress.... with lots of shoulder.. cleavage esp... on...
    Rickncali Rickncali 36-40, M 2 Responses Aug 15

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    My exes always surprised me with sexy lingerie when I came home from work sometimes. I knew after a pegging seession was entailed , But I desire to have a woman to help shop and...
    Averageguy41011 Averageguy41011 41-45, M Aug 14

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    Sometimes I feel like my boyfriend doesn't love me as much as I do, or at all. He pretty much hates anything to do with romance and sharing feelings (the feelings I can live with...
    YoungOne1901 YoungOne1901 22-25, M Aug 14

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    I like tall and non petite ones as well, but I think small and petite is more graceful. I've always wanted to be that way myself as well.
    mickitg mickitg 41-45, T Aug 13

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