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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,903 People

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings thongs dresses skirts tank tops gowns skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 1 Response Dec 5, 2015

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    LucyAshley LucyAshley 18-21, T 8 Responses Jan 3, 2015

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    JadeChoceur JadeChoceur 22-25, M 4 Responses Dec 7, 2015

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    The more I dressed, Mom didn't have to ask

    if I wanted. She decided to take me shopping. Nervous as I was mom held my hand as we entered the store. Mom notice this pretty dress and told me to try it on. She was right with me and when I looked in the mirror, I knew it was for me. At least I looked smaller then my age, so...
    rlkiner rlkiner 13-15, M 3 Responses Dec 3, 2015

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 30, 2015

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    Oh yes I do, cute mini's

    and long slender gowns with high slits. High heels are a must, just like nice dark nylons or fishnet stockings. Thigh high only of course, although crotchless pantyhose are sometimes ok. A bra full shape, lots of lipstick and perfume. oh yes ********************* You're...
    IrmaNeufrau IrmaNeufrau 56-60, T 5 Responses Nov 11, 2015

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    I've always loved girl's/women's/feminine

    clothing, everything, from dresses, skirts, makeup, shoes, lingerie, jewelry, the works , since I was very young , I only love women, and I am 100% strait, I kind of think of myself as a male lesbian.
    DawnR59 DawnR59 56-60, T 13 Responses May 3, 2014

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    Love to dress up in tights

    and skirt with nice top almost anything girly love been girly wish was more feminine I am in away I guess but don't like the idear of getting older :(
    cutieXtights cutieXtights 22-25, F 5 Responses Sep 9, 2014

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    Just bought my first strapless mini dress

    for Halloween party! Gonna look stunning and sexy! :) <3
    meladylike meladylike 18-21, M 6 Responses Oct 28, 2015

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    Isn't it amazing that a single moment in time

    can flip a switch inside of us and nothing is ever the same? I can think of a hundred things that might have affected me in a significant way, but today they mean nothing more than a simple event in a passing instant in time. I suppose its probably true for everybody. For...
    deleted deleted 26-30 19 Responses Aug 16, 2014

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    deleted deleted 26-30 Sep 18, 2015

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    Mom always wanted a girl.

    they had three boys, I being the youngest. when 7, mom decided to dress me and take me to a party. I just acted myself, with my long hair and being small, was easy to pass. That was my start, seeing girls get more toys and dolls. Summer I would be in dresses a lot. My brothers...
    rlkiner rlkiner 13-15, M 5 Responses Nov 19, 2015

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    No more dresses for me !

    ? Mistress does not want me to wear dresses any more. She wants to be able to see my lingerie, she does like my leather dress, so I am not without a dress. I need to find some very sheer black lace dresses and other sheer fabric dresses to even hope to wear more than 1...
    Plugslave Plugslave 31-35 3 Responses Apr 13, 2015

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    I started dressing when I was 11

    or 12. I would wear my step mom's clothing any chance I could. I still dress every chance I get and love wearing dresses and skirts
    jasminecd5 jasminecd5 36-40, M 6 Responses Nov 1, 2014

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    I am a 15 year old sissy boy

    who wears his 18 year old sisters bra panties bikini gowns dresses leggings skirts pj and I wear her lipstick and eyeliner it's all a secret and I like men tough ones and masculine ones
    deleted deleted 26-30 Sep 17, 2015

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    Thought I would share my experience I'm a boy

    straight not gay me and my mum where out shopping and we walked pass a wedding shop while she told me to wait outside about 20 mins later she brought out a dress and I said who's that for and she said me she said your going to be the bridesmaids at your aunties wedding next...
    Unknown2006 Unknown2006 13-15, M 3 Responses Jan 18

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    There isn't a single week in

    which I don't make it a point to dress up. I love girly clothes and the assortment of possibilities!
    deleted deleted 26-30 4 Responses Dec 19, 2015

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    Just some more new stuff,

    love my new clothes, I need more clothes and sone make up also a wig
    ArejayakaRegina ArejayakaRegina 22-25 7 Responses May 18, 2015

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    I love to experiment with different

    outfits. This is my black/white mod dress with white tights and my favorite Mary Janes!  See more in my album.
    sensuousPH sensuousPH 41-45, M 22 Responses Mar 17, 2015

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 11, 2015

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    can anybody tell me the name of webside

    when i can found boy drssup as girl videos and photos? ???
    deleted deleted 26-30 5 Responses Oct 3, 2015

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    I Like To Wear Girls Dresses

    I have worn dresses since I was about 5. It was at a family members house and I went in to the bath room, I closed the door and I saw it hanging there. A white dress, like a wedding dress. I tried it on and I felt good. Then I...
    Elizabethamber Elizabethamber 18-21, T 35 Responses Oct 29, 2010

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    Musical Theatre Chorus Girl

    I had early feelings about crossdressing and experimented a number of times as I was growing up. But my first real experience dressed as a girl was when I was in my late teens. I did summer musical theatre and I sang and danced in a number of shows. Those were wild times and we...
    jennyla73 jennyla73 36-40, F 11 Responses Dec 27, 2011

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    I love wearing dresses

    and having gone out to experience
    luvpanties60 luvpanties60 31-35, T 22 Responses Sep 16, 2014

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    GoddessAlexia GoddessAlexia 26-30, F 1 Response Nov 5, 2015

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    Headed out on an adventure tonight.

    Next stop is Payless for a new pair of shoes.
    CDKristiK CDKristiK 56-60, M 9 Responses Dec 5, 2014

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    i am 18 years boy. i feel attraction on girls

    cloths when i was 15 and i love nailpolish.then i started wearing my sister's cloths when i was 16 but no one know this at my home. when i was feel alone at home i dressup as girl. i also wear makeup. i love to doing this things. i like all girls cloths.
    deleted deleted 26-30 4 Responses Sep 21, 2015

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    I'm not a boy anymore

    but I do remember as a boy being dressed by my sisters in their clothes. I didn't mind the attention at all and felt very special at the time. If I'm home alone I will still try on things.
    deleted deleted 26-30 5 Responses Oct 27, 2015

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    I started to like wearing girls clothing

    when I was about 9 years old. I wore whatever I could get my hands on. From sleeping dresses all the way to panties. I especially loved wearing an empire-waist sleep dress. I wore it a lot. But it was my sister's. Later on, I was able to secretly buy a girl's uniform for my...
    ConfusedGirlWannabe ConfusedGirlWannabe 26-30 6 Responses Oct 31, 2015

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    I am a 15 year old sissy boy

    who wears his 18 year old sisters bra panties bikini gowns dresses leggings skirts pj and I wear her lipstick and eyeliner it's all a secret and I like men tough ones and masculine ones
    deleted deleted 26-30 Sep 18, 2015

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    I really like to wear dresses

    because of the shapes it gives to your body. And it is really exiting as well to wear a dress when you are a teenboy (crossdresser).
    deleted deleted 26-30 10 Responses Jan 10, 2014

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    I especially like to wear short dresses over my

    corset and stockings, always with sexy high heels.
    Plugslave Plugslave 31-35 1 Response Dec 11, 2015

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    I just love wearing short babydolls

    and fit and flare dresses. It has to be short, it is all about the legs !
    Plugslave Plugslave 31-35 9 Responses Feb 15, 2015

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    Any other crossdressers

    that would like to chat or any females?
    Eriborn Eriborn 18-21, M 3 Responses Oct 13, 2015

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    I wish i could wear dresses

    and skirts 24/7. I want to wake up in a nighty every morning. Finish my morning rutines then change to a short dress/skirt and slip in to some nice pantyhose, some heels would be lovely too. At night I would then take everything off and get in to the nighty again.
    sissypantyhosekiss sissypantyhosekiss 18-21, T 16 Responses Jun 24, 2014

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    KatrinaBoyer41 KatrinaBoyer41 41-45 7 Responses Oct 7, 2015

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    LucyAshley LucyAshley 18-21, T 12 Responses Feb 21, 2015

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    JadeChoceur JadeChoceur 22-25, M 14 Responses Dec 23, 2015

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    None of my friends or family have any idea

    but when I get home at night and if I have no prior plans the first thing I do is shower shave or wax if I need it then spend a glorious hour or two choosing what sexy little outfit I am going to wear and what make up, underwear etc will go with it. I love the feel of a wearing...
    Jimhes Jimhes 31-35, M 5 Responses Sep 30, 2014

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    Hi I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Oct 14, 2015

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    Teachers Pet

    When I was 11 (1963) I picked up the rubbish at a local school to earn pocket money.I would always wear my sisters panties after school as I loved how it made me feel.One day while I was getting the rubbish from one of the rooms the teacher (an older man, retired but had come...
    MsLettle MsLettle 56-60 8 Responses Jun 17, 2011

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    I have started to crossdress at the beginning

    of the month and will be till new year. After that i'll still dress up from time to time when ever I fell like it. Me and my mom decided that during the summer I will dress up when we go on vacation.
    EmBlaze EmBlaze 18-21, M 4 Responses Nov 25, 2015

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    New Years Eve 2014 My wife

    and I have spent the three previous New Year’s Eve nights out of town at small hotels. Each of these hotels had a small lounge and a party to bring in the New Year. All of these were small affairs, and each one helped me gain confidence to go out in public dressed as a woman...
    1SarahAnn 1SarahAnn 46-50, M 5 Responses Jan 6, 2015

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    I just love wearing a short flared dress over

    my corset and stockings, usually with no panties. ; )
    Plugslave Plugslave 31-35 3 Responses Nov 24, 2015

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    I just had a once-in-a-blue-moon opportunity.

    .. I recently visited a local thrift shop and to my excitement I discovered on the dress rack a figure skating dress just about my size! It is a plain sky-blue leotard with a knee-length skirt. I had to have it immediately. I tried it on almost immediately after getting in my car...
    Roccondil Roccondil 22-25, M 7 Responses Dec 17, 2014