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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,367 People

    Do you love wearing dresses

    and skirts and what color are they do you haveLong or really long hair and do you wear plain or fancy hair clips hair barrettes bobby pins flowers and hair bows in your hair
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 7 Responses May 15

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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 that the proprietor is ill. So anyway , I've got the day off , so I've booked in instead for a make-up-and-go somewhere else. That's not not...
    donnaka donnaka 36-40 8 Responses Apr 27

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    Headed out on an adventure tonight.

    Next stop is Payless for a new pair of shoes.
    CDKristiK CDKristiK 51-55, T 11 Responses Dec 5, 2014

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    LucyAshley LucyAshley 18-21, T 13 Responses Feb 21

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    a week from now i'm using a dressing service to

    go out for a day en femme. i've asked for challenges, had some daft replies, but so far one good one, to try on a dress in a department store. i've never done that before. what other challenges , that don't involve using my voice or giving myself away, can anyone think of?
    donnaka donnaka 36-40 3 Responses Feb 16

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    Brianhi26 Brianhi26 51-55, M 7 Responses Feb 26

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    Wearing dresses at home There are only a few

    occasions I'm wearing dresses in public: On halloween or other opportunities where it is "normal" or somehow accepted for men wearing dresses. Usually I'm wearing dresses at home but did not used to do it all the time. I checked if no-one would come over to see me and lowered...
    ToShareStories ToShareStories 22-25, M 12 Responses Jan 14

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    So today I had my makeover.

    It was awesome. I tried on lots of outfits, and we chose a blue skater dress with daisies on it, opaque tights, wedge ankle boots with fur trim , and one of those furry hats with no top, like a big furry polo mint on your head.We went to the museum , then we went for coffee and...
    donnaka donnaka 36-40 12 Responses Feb 23

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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 8 Responses Dec 17, 2014

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    daya55 daya55 31-35, M 5 Responses Jan 25

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    After taking a break two weekends ago I spent

    this past Saturday as a female. I met up with someone for lunch and then went to a BDSM club with my wife. I was so excited to at least go out but to be seen as a female and receive so many compliments made my day. I have come to enjoy doing this on the weekends and can't...
    Dora922 Dora922 31-35, T 4 Responses Nov 10, 2014

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    I finally told someone This is already my 4th

    story in this group but I have to say thank you to all of you! Your comments on my story encouraged me to tell someone about my crossdressing. But let me tell you the whole story: Last week I attended a costume party in celebration of mardi gras. Of course I dressed as a woman...
    ToShareStories ToShareStories 22-25, M 10 Responses Feb 24

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    Went to Sears today and I tried on this dress

    cause I thought that it looked really cute what do you all think? Please ignore the socks
    highkin highkin 36-40, M 13 Responses Mar 25

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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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    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 12 Responses Dec 27, 2011

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    so in 2 weeks i'm going out again.

    i've set myself the following tasks to complete whilst hopefully passing as a woman (i) visiting a particular tourist attraction , and having my photo taken doing the "thing" you do there (ii) visiting a "passage of terror" attraction- like I won't be sh**ing myself enough (iii...
    donnaka donnaka 36-40 6 Responses Apr 15

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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 51-55, T 14 Responses May 3, 2014

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    All your sissy's are too much.

    Girls dont talk about what kind of panties or bra's they are wearing. I think its so funny listening to you all brag about how wonderful it is to wear them. Girls usually talk about not having anything on under their clothes as that is a turn on for most guys. Wearing a dress...
    jennylee911 jennylee911 41-45, F 4 Responses Apr 9

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    ilikepugs ilikepugs 13-15, M 10 Responses Apr 24

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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 20 Responses Mar 17

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    Like many of you I really like wearing dresses.

    My favorite is an a-line bodice with short sleeves and having a full skirt. I cherish the task of having to zip up the back of my dress and clasp the hook and eye. However, my body style is not conducive to wearing dresses. I rarely wear them but, when I do I'm all WOMAN!!
    deleted deleted 26-30 9 Responses Apr 5

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    i'm booked in with a dressing service ,

    for a whole day, in a few weeks. they'll take me out. anyone got any dares for me , while i'm out and trying to pass?
    donnaka donnaka 36-40 2 Responses Feb 11

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    I love wearing dresses

    and having gone out to experience
    luvpanties60 luvpanties60 31-35, M 23 Responses Sep 16, 2014

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    send me pics of boys in dress

    or girl clothes or if they are Male to Female any age under 18
    raileymathins raileymathins 18-21, T 4 Responses Mar 17

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    I love the way dresses

    or pleated skirts twirl around my stockinged legs when I walk in them.
    nikkitran nikkitran 51-55, T 13 Responses Jan 2

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    If anyone want to give me advice I want to

    start dressing like a girl
    deleted deleted 26-30 4 Responses May 5

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    Why I like wearing girls clothes?

    Those who read my story "My first time" (http://www.experienceproject.com/stories/When-I-First-Dressed-As-A-Girl/2768800) know that I was five years old when I wore a dress for the first time. My mom begged me to try a dress because she wanted to check if the dress would fit my...
    ToShareStories ToShareStories 22-25, M 7 Responses Feb 1

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    Dressed as girl for Halloween To Halloween I

    attended a costume party. A good opportunity to jump into a dress a be a girl some ours. I tried to find a dress on the internet, it should not be that expensive. I found a denim dress, made of elastic material. I bought it, it came with a matching red belt. I also bought pumps...
    ToShareStories ToShareStories 22-25, M 8 Responses Nov 14, 2014

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    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 11 Responses Dec 6, 2014

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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).
    ChanelleCD ChanelleCD 18-21, T 11 Responses Jan 10, 2014

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    LucyAshley LucyAshley 18-21, T 75 Responses Jan 5

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    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 19 Responses Oct 22, 2011

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    Yes, its true! I love wearing dresses; short,

    to my knee's or way above them, or anywhere below my knees. Guess what? I'm a man and I've always felt comfortable and at ease wearing a dress. Why don't more men wear dresses?
    deleted deleted 26-30 7 Responses Feb 6

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    As I wrote in my first story (found in I

    Dressing Boys as Girls), sometimes all we know is what others have told us. As you also know, even though I was a boy baby, my mother dressed me up as her little girl until my father stopped it. During the time I was my mother’s girl, she told me about herself as a girl and...
    SylviaJames SylviaJames 56-60 4 Responses Feb 22

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    girlyboy83 girlyboy83 31-35, T 6 Responses Apr 3

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    So I made myself pretty ,

    and went to the library:- new photos , friends only.
    donnaka donnaka 36-40 1 Response Apr 29

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    LucyAshley LucyAshley 18-21, T 9 Responses Jan 3

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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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    Been a long, long time

    since i was a 'boy' but I remember how much I loved to play after school with the girls in my neighborhood wearing the play dresses my mom made for me. I was around nine years old when I decided I wanted to be more like the boys at school. No more dresses. No more wearing...
    AlbertSAT AlbertSAT 66-70, M 4 Responses Apr 12

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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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    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

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    Here is my Jessica Simpson dress with Platino

    tights and my new Mary Janes!
    sensuousPH sensuousPH 41-45, M 21 Responses Jan 19

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    I do not just like to wear them I love it

    and do as often as possible
    jamie172 jamie172 46-50, T 9 Responses May 26, 2014

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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...
    kayleew2000 kayleew2000 18-21 23 Responses Aug 16, 2014

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    I'd describe myself as a straight,

    in the closet , cross dresser. For years I used fancy dress parties as an excuse to dress up, and , to be honest , i've always had a thing about tights. I love black tights. But in the last few years I've felt more and more driven to go out and try and pass as a female. Let's be...
    donnaka donnaka 36-40 5 Responses Oct 26, 2014

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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 10 Responses Feb 15

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