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I Like Dressing My Boyfriend As A Woman

Personal Stories, Advice, and Support 163 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 8 Responses May 11, 2011

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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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    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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    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 4 Responses 1 day ago

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    In my younger days there was some occasions I wore a dress or girls clothes (see my other stories) but until I lived at home with my parents I never really wore dresses on a...
    ToShareStories ToShareStories 22-25, M Jun 26

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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...
    jmallon764 jmallon764 18-21 1 Response 3 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 3 Responses 1 day 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 a week ago

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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 a week ago

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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 5 days ago

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    I dont normaly have a huge foot fettish,some gross me out, but i like my boyfriends and he brang up even though he doesn't like feet he likes mine,and he also wondered if i loved...
    SummerBerry218 SummerBerry218 18-21, F Jun 27

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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 was with my wife recently companying her to the hair salon. I always find this experience wonderful. Whilst sitting there I was observing two women ( who where obviously friends...
    stefaniesixx stefaniesixx 46-50, M 4 Responses 8 hrs ago

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    I am NOT the other woman any longer but then again I never did feel that way…..For those that know my story already know that my relationship was an open book for all including...
    daisydew1973 daisydew1973 41-45, F 1 Response 8 hrs ago

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    You know that feeling when you want a boyfriend but you don't? Iv had those feelings a lot but now I'm tired of being alone and single and have been for ages, I still have feelings...
    AnotherTomboyGamer AnotherTomboyGamer 13-15, F 7 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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    Efforts for My Spiritual Education along with Works for God Towards Humanities Benefit on Hearing Truths Never Taught in the Religions of Man Worldwide. http://timesofroubles.webs...
    timesoftrouble timesoftrouble 56-60, M 1 hr ago

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    Going to be a rough morning. Having to clean up a problem that H created between me and my inlaws. He through me under the bus with lies cause he couldnt be a man and admit what...
    blue963 blue963 46-50, F 8 Responses 1 hr ago

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    Unknowingly I was the other woman. He lied and said he was divorced. It was strictly an internet affair. When we made to plans to meet he disappeared. It wasn't until I went...
    cutsy cutsy 36-40, F 1 hr ago

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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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    About 2 years ago, I was doing some modeling for a local company. One of the scenes my photographer wanted me to do was was with another girl. Neither one of us had ever been...
    SexyNThick SexyNThick 18-21, F 2 hrs ago

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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 5 days ago

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    I mean I don't like guys because we cooties but I would make an exception if he were like Shawn Mendes or something!!!!!! I am not asking for too much just Shawn Mendes lol
    amyrobbyy amyrobbyy 16-17, F 1 Response 8 hrs ago

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    Does anybody else get jealous of their boyfriend/ girlfriends ex? Lol please tell me I'm not alone.
    BellyBoo5 BellyBoo5 16-17, F 1 Response 7 hrs ago

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    I don't have a boyfriend but if I did I would love to call him daddy in that deep sexy voice..daddy come get some..Daddy I have missed you..Or just call him daddy out of nowhere
    CurvyandChic CurvyandChic 22-25, F 1 Response 4 hrs 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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    My boyfriend and I don't get in fights often, but when we do it's awkward. He and I just got in a little fight and idk what to do? Can someone help me?
    BellyBoo5 BellyBoo5 16-17, F 7 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 9 Responses 4 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 5 days ago

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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 6 days 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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    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 4 days ago

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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 4 days ago

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    Seriously went to bed sad last night and woke up pissed off... He has absolutely no clue what is going on in my head... He thinks we are fine... So tell me why I got totally played...
    Jlynn1424 Jlynn1424 22-25, F 5 Responses Jun 27

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