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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,396 People

    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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    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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    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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    ilikepugs ilikepugs 13-15, M 10 Responses Apr 24

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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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    When I was 13 I started to wear my sisters

    clothes and going I really like them and now have been sharing them for four year now. I have been on hormone surpressents and have just started hormone therapy I love my life as a girl
    jenna98jenna jenna98jenna 18-21, T 4 Responses 5 days ago

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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 5 Responses Feb 22

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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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    My 4 year old daughter bursts in with a proud

    twirl "Daddy, do you like my pretty new dress that mummy bought me?" Somehow it feels like she is taunting me. Like 'ner ner, I've got a pretty new dress and you haven't' but she doesn't know, so it can't be. Oh I hate feeling like this, and I hate myself for feeling like this...
    Heellover Heellover 36-40, M 6 Responses 5 days ago

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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 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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    LucyAshley LucyAshley 18-21, T 75 Responses Jan 5

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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 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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    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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    Little girls with long long long hair love to

    wear 2 ponytails any height with hair bows– and they also love to put little boys long long long hair up in 2 ponytails any height with hair bows πŸ‘§πŸΌπŸ‘§πŸΌπŸ‘§πŸΌπŸ‘§πŸΌπŸ˜πŸ˜πŸ˜πŸ˜πŸ‘πŸ‘πŸ‘πŸ‘πŸŽ€πŸŽ€πŸŽ€πŸŽ€
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 5 Responses Apr 21

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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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    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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    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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    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 Β£7 or 4 pairs of knickers for Β£5, it was obvious which i chose. Also with it...
    algina algina 36-40 8 Responses Feb 14

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    LucyAshley LucyAshley 18-21, T 9 Responses Jan 3

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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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    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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    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 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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    I love wearing dresses

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

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    LucyAshley LucyAshley 18-21, T 13 Responses Feb 21

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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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    Brianhi26 Brianhi26 51-55, M 7 Responses Feb 26

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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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    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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    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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    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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    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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    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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    girlyboy83 girlyboy83 31-35, T 6 Responses Apr 3

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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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    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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    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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    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 am cross dresser man i like wear saree blouse

    . my close friend knows my this hobby one day he challenge me to pass in public as lady. At that time i have no time for make up on face but i agreed for the challenge I told him to come with me as my boy friend then i wear saree blouse bra etc &wear dupatta on face (as all...
    surekha57rpandya surekha57rpandya 56-60, M 2 Responses Mar 16

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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 6 Responses May 18

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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

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    for those of you who have noticed I've been

    asking for cross-dressing challenges, today(i) had coffee and a ciabatta in a cafe(ii) then went to a ticket office , where the "thing" was in fact shut , but we were cornered by some-one , and I had to speak! I've discovered that the best tactic is to think of the accent in...
    donnaka donnaka 36-40 15 Responses May 6

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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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    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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