I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,679 People

    Here is my Jessica Simpson dress with Platino

    tights and my new Mary Janes!
    sensuousPH sensuousPH
    41-45, M
    17 Responses Jan 19, 2015
    KatrinaBoyer41 KatrinaBoyer41
    41-45
    5 Responses Oct 7, 2015

    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

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

    I'm a girl, to be honest with everyone here.

    I love to get on this experience page and read what you all have gone through. This is a truly amazing and inspiring section you all have here. These stories always make me smile. Never be shy to be who you want to be!
    Emilia0659 Emilia0659
    18-21, F
    7 Responses Dec 6, 2014
    Bell1990 Bell1990
    26-30, M
    2 Responses Mar 27

    I wish this was me as a young boy.

    He looks to be very happy to be sitting there is his frilly pink dress.
    mat2Robin43 mat2Robin43
    51-55, M
    5 Responses Mar 24

    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
    32 Responses Oct 29, 2010
    LucyAshley LucyAshley
    18-21, T
    11 Responses Feb 21, 2015

    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

    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
    17 Responses Mar 17, 2015

    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

    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
    5 Responses Nov 1, 2014
    GoddessAlexia GoddessAlexia
    26-30, F
    1 Response Nov 5, 2015

    Just some more new stuff,

    love my new clothes, I need more clothes and sone make up also a wig
    ArejayakaRegina ArejayakaRegina
    26-30
    7 Responses May 18, 2015

    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
    5 Responses Dec 17, 2014
    JadeChoceur JadeChoceur
    22-25, M
    2 Responses Jan 5

    On 23/06/2015 i joined a dance class with help

    my elder sister. the dance class name is suma dance class. the owner of dance class miss suma say ok come and joint tomorrow. 1st on my dance class i see 10 girls only and there no other boys . i ask to my miss that were is boys. she said. that you. are. first boy i was...
    janecool janecool
    16-17, F
    3 Responses Oct 23, 2015

    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
    5 Responses Feb 15, 2015

    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.
    deleted deleted
    26-30
    13 Responses Jun 24, 2014

    once i was alone in home.

    when i removed my mom's skirt from her wardrobe and wore in.after that i went out in streets . people were staring at me .it was very funny and i returned home where my mom saw me .i confessed i like skirts and she bought me new skirts.
    chidhiya chidhiya
    13-15, M
    Apr 4

    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
    4 Responses Dec 3, 2015

    My son has been wearing his sisters underwear

    and dresses now for over a year. Not the same thing everyday. Don't know what to do
    deleted deleted
    26-30
    10 Responses Jan 21

    Headed out on an adventure tonight.

    Next stop is Payless for a new pair of shoes.
    deleted deleted
    26-30
    5 Responses Dec 5, 2014
    JadeChoceur JadeChoceur
    22-25, M
    8 Responses Jan 17

    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
    12 Responses May 3, 2014
    JadeChoceur JadeChoceur
    22-25, M
    10 Responses Dec 23, 2015

    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

    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

    I love these dresses

    and am really wanting one to wear about the house and yard. Big problem is that wifey won't agree to it. I live in hopes of talking her round but it's probably fruitless.
    MarieJosephe MarieJosephe
    66-70, M
    6 Responses Feb 21
    JadeChoceur JadeChoceur
    22-25, M
    3 Responses Dec 7, 2015

    trying to think so something i should buy next

    clothes wise im up for suggestions just nothing to expensive
    JadeChoceur JadeChoceur
    22-25, M
    5 Responses Feb 19

    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
    4 Responses Sep 9, 2014

    Bieng A Girl

    ever since i was 10 i had a dream of bieng a girl so i decided to go into my mums bedroom and toke out a pair of knickers, a pair of tights, a bra and a red dress. then i went into my room and put them on it felt so nice then i heard my mum open the front door and then i quickly...
    skingley skingley
    18-21, T
    18 Responses Oct 22, 2011

    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
    17 Responses Aug 16, 2014

    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
    51-55, M
    Jan 6, 2015

    Any other crossdressers

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

    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

    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.
    deleted deleted
    26-30
    3 Responses Nov 25, 2015

    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
    9 Responses Jan 10, 2014

    I love wearing dresses

    and having gone out to experience
    luvpanties60 luvpanties60
    36-40, T
    19 Responses Sep 16, 2014

    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

    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

    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
    9 Responses Dec 27, 2011

    I love the feeling of wearing a dress.

    It makes me feel super hot and naughty.
    deleted deleted
    26-30
    1 Response Nov 7, 2015

    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
    LucyAshley LucyAshley
    18-21, T
    61 Responses Jan 5, 2015

    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

    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

    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
    31-35
    6 Responses Oct 31, 2015

    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...
    deleted deleted
    26-30
    7 Responses Jun 17, 2011

    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

    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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