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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 164 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 1 Response Feb 3

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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 8 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 8 Responses May 11, 2011

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    Related Experiences

    I don't know why but I'm beginning to like dressing like a girl and feeling like one..the only thing is I like doing it sometimes not all the time and I'm straight..what's wrong...
    Heaven21 Heaven21 18-21, M 7 Responses 5 days ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 1 Response 6 days ago

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    I like to dress up. I than have a moment where I actually feel beautiful
    thatgirlluvsred thatgirlluvsred 13-15, F 4 Responses 5 days ago

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    A plane passed through a severe storm. The turbulence was awful, and things went from bad to worse when one wing was struck by lightning. One woman lost it completely. She stood...
    ScotsQueen ScotsQueen 51-55, F 1 Response Jul 10

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    I enjoy the hair and makeup, perfume, people looking at my chest. I enjoy it all. I do it because I like it.
    giggles78758 giggles78758 36-40, F 3 Responses Jul 16

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    Why the **** did I get into this relationship?
    BarelyAdulterated BarelyAdulterated 18-21, F 1 Response Jul 18

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    I had a relationship for 2 months & this guy was just smothering me, I couldn't take it anymore so ya I dislike clingy guys
    xJamix xJamix 18-21, F 1 Response Jul 18

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    I love having my belly button poked! I have packed on some weight, resulting in a pot belly and sometimes when I bloat, it looks pregnant! One time I ate so much, my belly button...
    MJ123321 MJ123321 22-25, F 2 Responses Jul 21

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    I've been single for a year now. It was hard to get over my ex but I feel that now I am over him. I do still have some feelings for him but not like they used to be. I wish I had a...
    estefany1994 estefany1994 18-21, F 2 Responses 1 day ago

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    Today was a rare treat, I got a text from MM, our usual one letter text so the other person knows it's ok to call if they can. He asked if I could find a sitter for the kids and...
    ynoTme83 ynoTme83 26-30, F 1 Response 2 days ago

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    Ever since I was 12 or 13 I've been cross dressing in secret. My mother caught me once when I was about 13 or 14. She was okay with it and asked me if I liked cross dressing. I...
    masspink masspink 18-21, M 3 Responses Jul 2

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    I'm so happy that times have changed and it's possible for transgender children to become their true gender at such a younger age than I was able to. I am a girl. I've always...
    SaharaSands SaharaSands 46-50, T 1 Response Jul 7

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    I so badly crave my friends boyfriend he's hot and possessive and dominant and I love everything about him and my friend is a ***** to me anyways and they have only been dating for...
    cootyboo cootyboo 22-25, F 4 hrs ago

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    Wish I had a gorgeous woman, riding my face like a rocking horse right now.
    Jackem82 Jackem82 31-35, M 2 Responses 6 hrs ago

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    Let my start off by saying that I'm a Christian and I am gay. I live with both my parents and my younger brother and I have a dog. I've been dating a guy for the past 2 months. We...
    jowaymedina jowaymedina 13-15, M 3 Responses Jul 3

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    I can not stand the sight of my boyfriends mother. She's a very manipulative, judgmental, selfish, lying, narcissistic ***! She has a long history of drug and alcohol abuse. She's...
    SilentNynja SilentNynja 22-25, F Jul 15

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    Some wives like to dress their husbands in womens clothes when their boyfriends are visiting. In this way both are available for the boyfriends pleasure!
    longskirts longskirts 70+, M 1 Response Jul 15

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    This is about my MM, but not particularly about the A itself. We work together - he came after me and pushed and pushed trying to get me to give him/us a chance while I was M. I...
    Arubagal Arubagal 51-55, F 4 Responses Jul 21

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    Just call me your modern day Audrey Hepburn. I love perfume, putting on lipstick, and eyeliner. From the little black dress to floral flowing dresses. I love to loose for the...
    MissingBoston MissingBoston 26-30, F 5 Responses 1 day ago

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    It is a crazy story. Sometimes it feels because I am female, I must be the competing enemy to some. Ever since I have moved to London, I just find the women who work here are...
    EstuaryRivers EstuaryRivers 26-30, F 2 Responses 1 day ago

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    Everyday, I am defined by my gender. Not by my personality, my interests, my voice, my actions. By my gender. Everyone is. All the time. Just as many people are defined by their...
    EyeOfLight EyeOfLight 18-21 49 mins ago

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    I didn't plan to be, but it found me! I am such a driven vibrant sort of person that anything I touched was going to take off. I've now got to the top in my career as a director of...
    terridactyl terridactyl 26-30, F 24 mins ago

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    I need to send this to my mm. I am in a place where I don't know what he wants. He went on vacation from work and I found out he proposed to his gf. I was broken when I found out...
    Livesforme Livesforme 26-30, F 7 Responses Jul 12

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    I have just come back from a long weekend away camping it was the first time I gave been away with my new boyfriend. We had a lovely time I can't wait to spend more like it we...
    thefox71 thefox71 41-45, M 1 Response 2 days ago

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    I am a 21 year old woman I work full time and live with my partner who is 23 and just finished a business degree, problem is I want to have a baby but I am so scared of being...
    TheEmpress14 TheEmpress14 18-21, F 3 Responses 5 hrs ago

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    I would love to find a girl that would support my cross dressing! Please message me!
    wjk1849 wjk1849 46-50, M Jul 16

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    I have always been fascinated by the way they speak, look and treat others. Personally I love how calm they look and how confident they are looking straight at a woman’s eyes...
    AlexandraWard AlexandraWard 22-25, F 11 Responses Jul 21

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 1 Response 3 days ago

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    I have been with my fiancé for tree years now and have been dealing with his ex for three years now I honestly have had enough she drives me crazy and makes me soooooo angry she...
    kelseyt26 kelseyt26 26-30, F 2 Responses Jul 21

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    I've thought about it for years, and it all makes sense; no use denying it now. She hates me. I've known her since I was eight years old and dating my father, and everything was...
    NotNicole NotNicole 18-21, F Jul 19

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    I have been over the years having stronger feelings towards dressing and becoming more fem. Lately though it has gotten stronger and I am wanting to do other things to help me...
    Cristine3030 Cristine3030 41-45, T 2 Responses 1 day ago

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    I am new here. I found EP and it has been just in time. You women are so strong and brave for posting your experiences. Not many understand the emotional trauma of being the other...
    lostanddistraught lostanddistraught 22-25, F 4 Responses Jul 7

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    I turn 22 next month and I've never had a boyfriend, never been on a date that was considered a date by the guy, and never had my first kiss. I never really worried about it until...
    janicefromkansas janicefromkansas 18-21, F 1 Response Jul 14

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    24 year old woman-child. she comes home to visit and its a nightmare. She doesnt take care of things. like physical 'stuff', material things. She smashed her iPhone, then got drunk...
    milkynine milkynine 18-21, F 2 Responses Jul 16

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    So I've noticed I've been dressing grunge and idk why. I don't mind it I love it but I'm just wondering what happened and why the change. It was just one day I'm dressing sweet and...
    starktonya03 starktonya03 13-15, F Jul 17

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    I think I first realized my like for other girls when I watched lesbian **** for the first time. When I found myself getting turned on and intrigued, I turned it off and refused to...
    kittybabe100 kittybabe100 16-17, F 5 Responses 1 day ago

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    In 3 days I meet my man at the airport and he's staying with me for 3 days. Then he's flying back for 5 days at the end of the month. We met online via mutual interests 2 years ago...
    CosmicGirlA CosmicGirlA 26-30, F Jul 3

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    Today is 3 months since I found out that I was dating a taken man. We had been talking and going out since October of last year, and things were great. We have so much in common...
    Epea24 Epea24 22-25, F 2 Responses Jul 4

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    So ladies... An update... Starts off bad but ends soo soo good!!! So after I broke up with him I realized that I was putting all of it on him... I was using him not calling me and...
    Jlynn1424 Jlynn1424 22-25, F Jul 4

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    Ever since I started school I felt I was never a 'pretty' girl for different reasons the main reason being I had really bad and noticeable eczema( a skin condition that makes ur...
    lavabug01 lavabug01 13-15, F 1 Response Jul 7

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    I am so disgusted with myself. Instead of just having no contact with my MM and leaving with my self-respect and head held high, I blew it. I did have a conversation with him on...
    lavc lavc 46-50, F 3 Responses Jul 21

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    not sure where else to post . Need some guidance here. Some of you saw I have my son's friend living with me now. It was suppose to be just till the weekend and his dad was going...
    lilred101 lilred101 41-45, F 3 Responses Jun 30

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    I don't know what to do. I live with my boyfriend, we've been together since February. I don't have the means to secure housing if I leave. I love my boyfriend very much, he's like...
    pandess pandess 22-25, F 1 Response Jul 21

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    Here's the task. My boyfriend put this all together and planned it out for me. It starts off quite easier and gets more challenging as it progresses. Firstly, I must wait until...
    OliviaBabe OliviaBabe 18-21, F 9 Responses Jul 6

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