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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 171 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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    sexymommy2014 sexymommy2014 31-35, F 1 Response Aug 7, 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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    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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    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 12 Responses May 11, 2011

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    Related Experiences

    Growing up, I HATED dressing up .. Only because I had really bad body image issues. But but now that I'm a lot older, more mature & ALOT more confident.. It's one of my favorite...
    shesdifferent516 shesdifferent516 18-21, F 1 Response a week ago

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    I love dressing up for work, eating out at restaurants, going to movies with my sons, shopping, running errands, and going to other places. I love wearing a nice short dress or...
    singleredheadfemale singleredheadfemale 41-45, F 4 Responses Apr 10

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    OMG! I love dressing up for any occasion! I went out dressed as a hula girl a couple of weeks ago! It was awesome x
    Laurainthepink Laurainthepink 18-21, F 4 Responses Apr 25

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    I love dresses i waer them alot in my boreding school.
    Emogirlriley Emogirlriley 13-15, F 1 Response Apr 10

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    Love this style:) Polo - Dress!!! #boyishtogirly #creative
    RedThatDescribesMe RedThatDescribesMe 18-21, F 9 Responses Apr 14

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    Hey. I am looking for models in the Philadelphia area for a portfolio building photo shoot. Is anyone interested?
    Heellover2222 Heellover2222 26-30 1 Response Apr 17

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    As comfy as I am in jeans and a hoodie, sometimes it's nice to dress up, go somewhere lush and have some classy time and spoil myself.
    Happyindark Happyindark 18-21, F 3 Responses Apr 17

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    Sometimes I dress up as a Disney princess for no reason. (YOLO seems to be thge saying with today's generation of hormonal teens) My wife on a rare occasion will do the same, but...
    ThatGayGirl187 ThatGayGirl187 26-30, F 2 Responses Apr 17

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    you know, just for the fun of it..I love clothes
    StevieOakley14 StevieOakley14 13-15, F 4 days ago

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    dresses make me feel so cute!!
    deleted deleted 26-30 1 Response 19 hrs ago

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    Prom was wonderful!!! Now want to go be with my love<3
    Nottheaveragegirl Nottheaveragegirl 18-21, F 8 hrs ago

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    I like having boyfriend beco'Z I really don't likes rules in the house that's why I choose having a boyfriend than follow rules on these house...
    donita015 donita015 13-15 Apr 23

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    I'm 15, around 6'1, I live in North Yorkshire, and I would like a boyfriend. I don't mind height weight etc., but I would like someone who cares about me. Message me if you're...
    Emporer01 Emporer01 13-15, M 2 Responses Apr 9

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    I feel like it's over between us.... And I really don't want it to be... but I've been crying everyday for the past week and I know that this is an unhealthy sign. Why does he have...
    hiddennlove hiddennlove 18-21, F 4 Responses Apr 21

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    Recently I was kind of wrestling if I was trans or not. I think mostly I felt that I had a gay guy trapped in me but at the same time I was a straight female. I didn't want to say...
    PateFist PateFist 22-25, F 7 Responses Apr 23

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    My Husband came out to more off our friends this past weekend with mixed results. A few of his male friends could not understand her wanting to dress and act like a female and the...
    karenpat karenpat 26-30, F 5 days ago

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    I know what it is , I am a loving and intimate woman . Living in a marriage without the intimacy is like watching myself from above , bleeding to death. Walking in hope everyday...
    heavenlyflower123 heavenlyflower123 36-40, F 51 mins ago

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    This experience made me think of a story that happened 15 years ago. There was a charity all-male beauty pageant at a local Banquet hall. The group of girls we hung out with at...
    Hot4Tgurlz Hot4Tgurlz 31-35, M 3 Responses 6 days ago

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    I have never felt guilt from cross dressing and never will but when a girl gets older we have to cover up those lines blemishes and stuff cause we are woman and stay that way...
    samara11besc samara11besc 51-55 4 Responses Apr 16

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    I have always loved dressing like a woman but my parents always told me it was bad. Ever since I was young I would hide and dress as a girl and would try to be alone to dress as...
    deleted deleted 26-30 2 Responses Apr 23

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    Aside from dressing, I'm an otherwise normal guy. I want so badly to find an amazing attractive woman that loves, appreciates, and supports all parts of me. Words cannot describe...
    Machiavellian Machiavellian 26-30, M 4 Responses a week ago

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    I love to see a woman dressing this way. To me, the belly is one of the sexiest parts of the body. I prefer a nice jiggly muffintop over a flat tummy! I love when a girl squeezes...
    ShowMeYourBellyPlease ShowMeYourBellyPlease 18-21, M 1 Response Apr 9

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    I have kept it a secret for a long time. Dressing only behind closed doors. The problem is that I wanted to step out into real world and be the girl I was hiding. Where I loved...
    rlt171720 rlt171720 61-65, T 1 Response Apr 22

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    I am a firm believer in signs. I have always believed that life has a way of guiding you and letting you know you were on the right path. My boyfriend and I are both avid runners...
    Randomgirl1122 Randomgirl1122 31-35, F 10 Responses Apr 4

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    There are exceptions for a woman hitting a man, and exceptions for a man hitting a woman. Like self defense. Obviously you should hit someone who's endangering you. Whether it's a...
    PsychGirl94 PsychGirl94 18-21, F 1 Response Apr 4

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    AMEN. Everything you said made me sick to hear because its exactly how I feel and Ive never admitted it. I am a gay woman, dating another woman who has two beautiful, fun, kind and...
    caferacer123 caferacer123 31-35 1 Response Apr 7

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    The next time a married man or woman glances your way, you might think twice before acting on impulse and frolicking between satin sheets. The scorned spouse could sue you. Yes...
    Lezsoccermom75 Lezsoccermom75 36-40, F 22 Responses Apr 16

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    Okay so I've always been a skinny girl my whole life. When I was 14, I was 117 pounds. Then when I got to 16 I've gained 27 pounds and developed curves. I was 144 pounds. I'm 5'4...
    SlimChick101 SlimChick101 18-21, F 5 Responses Apr 17

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    I've been cross dressing for many years & would love to meet other cross dressers, and chat with other dressers possibly in the uk or female. admirers of cross dressing males
    mick69x mick69x 51-55, M Apr 18

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    I had been with my boyfriend for 3 years. He's a head coach for a traveling softball team & one of his assistant coaches (who has a daughter on the team) is female. Apparently they...
    jahill1721 jahill1721 18-21, F 2 Responses Apr 20

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    I love dressing up but I always save makeup for last and it seems to be my favorite part. I love makeup! Especially liquid eyeliner, eye shadows and lipstick! I even love...
    jessicavamp jessicavamp 41-45, M 3 Responses Apr 16

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    Very emotional phone call last night. My boyfriend likes me to talk dirty to him on the phone sometimes, I'm not really into it but i do it anyway because he loves it. So we were...
    hillaryalexis hillaryalexis 18-21, F Apr 14

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    i currently have an alcoholic boyfriend that i can take no longer.. its time for me to finally run........what i should have done years ago. its just tough and hard when you love...
    Latinheat123 Latinheat123 26-30 4 Responses Apr 16

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    I love going to the local beauty shop to have my hair done, and have a manicure and pedicure as well. I do my own make up and eyes. When dressing up, to go out alone or with...
    joan1976 joan1976 36-40, F 2 Responses Apr 19

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    So tomorrow was going to be a day out with a dressing service. and like a small child at Christmas , i was counting the sleeps till it happened . And wot? Today I get a message...
    donnaka donnaka 36-40 8 Responses 5 days ago

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    Name four favorite books you would recommend to others and tell why: - Love Inc. by Sandy Rideout and Yvonne Collins ... about three different girls who attend the same school but...
    blankcheck4urhart blankcheck4urhart 36-40, F