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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,112 People

    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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    shadowhero92 shadowhero92 22-25, M 1 Response Jan 5

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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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    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 6 Responses Feb 1

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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 16-17, T 35 Responses Oct 29, 2010

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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 15 Responses Dec 6, 2014

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    Headed out on an adventure tonight.

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

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    I begun to dress as a Girl early my 9

    or 10 years but knowing that it was a "sin", always where in secret. When I reached 14 year old, I got my first best friend (a Girl called Marlen) and she was really close to me, in some how she toldme "I can dress you as a cuttie girly-girl", that turned me on, but with some...
    L0yd L0yd 31-35, M 8 Responses Jan 6

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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 4 Responses Jan 6

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    i am going to talk to my wife abut my dress

    today i dont no how to explain her please help me i wont her and gown....
    daya55 daya55 26-30, M 3 Responses Jan 16

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    AshleyNicolee AshleyNicolee 18-21, T 10 Responses Jan 3

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    I went out again today.

    First to a costume party. Since everybody was in some sort of costume it wasn't too bad. After that I went grocery shopping in my dress. I loved doing it. I dropped off the groceries and after a nap I went back out to the local mall. Did anyone else start feeling like it...
    Dora922 Dora922 31-35, T 5 Responses Oct 25, 2014

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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 6 days ago

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    daya55 daya55 26-30, M 11 Responses Jan 16

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    My wife has caught me wearing panties

    so many times I think she has given up on trying to stop me. At least she knows I don't wear hers.
    tgkristenmarie tgkristenmarie 56-60, F 3 Responses Jan 5

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    Got to wear a dress an entire afternoon

    and evening after work on two days this past weekend... It was so nice. Since my family was out for the weekend I didn't have to worry about getting caught, (they don't approve, end of the question.) and it was stress-free relaxing. It was a white knee-length cotton dress with...
    Roccondil Roccondil 22-25, M 8 Responses Aug 7, 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 11 Responses Dec 27, 2011

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    I love wearing them! They are really

    comfortable, and hug your body so well, especially with their interesting fabrics. And of course the lower body freedom. I would not want to wear them out to places, just within the privacy of my own home, for comfort... I am a male who wants to stay a man. (It kind of repulses...
    Roccondil Roccondil 22-25, M 8 Responses Aug 1, 2014

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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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    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?
    Cassandrajoan Cassandrajoan 61-65, M 6 Responses Feb 6

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    Well, i recently split up with my girlfriend

    and decided no more dressing up so got rid of all my girly clothes. It didn't take long tho until i needed some new underwear...while looking round Tesco, it was a choice of 2 pairs of boxers for £7 or 4 pairs of knickers for £5, it was obvious which i chose. Also with it...
    algina algina 36-40 6 Responses Feb 14

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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 11 Responses Jan 2

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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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    AshleyNicolee AshleyNicolee 18-21, T 78 Responses Jan 5

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    This is not really a story

    but I am looking for advice. I have my mind up to come out of the closet. My first time will be Thursday and looking for advice on how far to go or what to wear.
    SylviaJames SylviaJames 56-60 7 Responses Jan 24

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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 7 Responses 4 days ago

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    I know this isn't a dress

    or anything but I loved the support I was getting last night for my dress I had to post this picture for all you lovely people. If you want add me on Snapchat baeevelyn inbox me if u wanna chat! I was surprised you all thought I was so pretty!
    AshleyNicolee AshleyNicolee 18-21, T 4 Responses Jan 6

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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 11 Responses Feb 15

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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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    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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    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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    ok to set things straight I have never ever

    really worn a dress but would love to because I'm trying to get more girl clothes with no success unfortunately but if u think u can help in any way respond to this and I'll get back to u
    StarcraftsSwarm StarcraftsSwarm 13-15, T 4 Responses Jan 23

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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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    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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    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 10 Responses 5 days ago

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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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    is there any better feeling in the world

    than standing outside on a breezy day wearing a dress or even a skirt with wee cute panites on and just letting the wind blow them up to show off your panties to the world?
    Pjstuart Pjstuart 26-30, M 19 Responses Apr 13, 2014

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    Brianhi26 Brianhi26 46-50, M 2 Responses 2 days ago

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    daya55 daya55 26-30, M 5 Responses Jan 25

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    i am gong to remove my night gown now.

    Reding to go to work i am going to wear my my wife panty she prefer for me all her cloth that i can wear to my work....... i love her so much
    daya55 daya55 26-30, M Jan 18

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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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    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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    AshleyNicolee AshleyNicolee 18-21, T 11 Responses a week ago

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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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    I love wearing dresses

    and having gone out to experience
    luvpanties60 luvpanties60 31-35, M 20 Responses Sep 16, 2014

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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 4 Responses Feb 16

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    LIKE THIS PAGE PLEASE

    https://m.facebook.comprofile.php?id=1534157783490006
    daya55 daya55 26-30, M Jan 19

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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 15 Responses Jun 24, 2014

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    what are you wear now.

    ... i have wear my nightgown
    daya55 daya55 26-30, M 6 Responses Jan 25

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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 10 Responses Jun 17, 2011

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    Im a guy who is completely straight

    but i love wearing dresses from time to time.
    2114mike 2114mike 18-21, M 4 Responses Feb 18

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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...