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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,671 People

    well , i've just had a work trip away to a

    faraway city. Knowing i'd be at a loose end one night, and this was a big city with anonymity on offer, i took some lady clothes , and , for the first time , bought my own make-up. Dermablend , to cover my beard. Concealer , round the eyes. Foundation , and powder. Lip liner...
    donnaka donnaka 36-40 8 Responses Jun 7

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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 May 27

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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, T 9 Responses Feb 24

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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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    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 19 Responses Aug 16, 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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    I am a 15 year old girlyboy

    who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all a secret
    deleted deleted 26-30 1 Response Aug 20

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    I don't know why but one day like 5 years ago I

    started stealing my sister's and step mother's clothes and I kept them for a couple months and they found out then they gave me some and those kept me busy for 5 months and then I stole more when I was home alone and it was pretty cool and then 4 months later they caught me...
    te214696 te214696 16-17, M 5 Responses Aug 16

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    This past Saturday my wife

    and i went to a gaming convention. It was like a comic con but with different games you could play or buy. As with other conventions like these you could go in "costumes." Well for me it wasn't just a chance to go in a costumr but a chance to be myself. I was pleased to be...
    Dora922 Dora922 31-35, T 6 Responses Aug 3

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    LucyAshley LucyAshley 18-21, T 12 Responses Feb 21

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    ilikepugs ilikepugs 13-15, M 8 Responses Apr 24

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    LucyAshley LucyAshley 18-21, T 70 Responses Jan 5

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    There are some in this group

    who are looking for tips and tricks. Here are some I found or discovered with trial and error. Starting from top to bottom. Hair - I use a wig. A good quality wig will cost money but in the long run it is worth it if you take good care of it. I use shampoo and conditioner...
    Dora922 Dora922 31-35, T 5 Responses Aug 7

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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 have never done it before,

    but I really want to try. **** gender roles! Clothes have no gender!
    Madobsession Madobsession 16-17, M 5 Responses May 25

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    Bought a new dress today,

    and it is a hit ! I love this little dress ! 
    Plugslave Plugslave 31-35 6 hrs ago

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    Mistress left me my clothes

    for the day, a pair of silky sheer nude pantihose, a little black body-con dress and platform sling back pumps. I love wearing so little, and looking so good.
    Plugslave Plugslave 31-35 3 Responses Aug 24

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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 14 Responses May 3, 2014

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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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    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 6 Responses May 28

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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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    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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    jman0105 jman0105 13-15, M 3 Responses Aug 20

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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, T 12 Responses Jan 14

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    I love wearing dresses

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

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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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    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 11 Responses May 15

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    As you all know I love my skater dresses.

    So what could be more natural than making my next outing en femme to the skating rink.but I'm not sure what to wear. So I've decided to put it to the vote . I'd like everyone who views this to vote on what I should wear.(1) black skater dress with flower pattern(2) shorts and...
    donnaka donnaka 36-40 5 Responses 1 day ago

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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

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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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    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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    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 11 Responses Jan 10, 2014

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    I'm almost done for the week.

    Since my weekend is almost here I get to make a decision. What to wear? I love these kind of decisions.
    Dora922 Dora922 31-35, T 5 Responses Aug 7

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    Mistress was pleasantly surprised

    when I served lunch dressed in a corset dress, full fashion back-seam stockings and platform sling back heels. She could tell I was enjoying being able to wear a dress over my lingerie.
    Plugslave Plugslave 31-35 3 Responses Aug 16

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    LucyAshley LucyAshley 18-21, T 9 Responses Jan 3

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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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    Dressing up time again.

    I had a few hours today in a resort town known for it odd ways , shall we say. I put on a navy skater dress with white polka dots and red braid (lovely , sort of 50s , goes with bright red lips) , navy tights (that was a bit hot) , converse, and a denim jacket to cover the hairy...
    donnaka donnaka 36-40 7 Responses Aug 8

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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 23 Responses Mar 17

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    I'm selling tons of adult baby clothes

    and a adult baby crib message me if your interested
    feedeeforyou feedeeforyou 18-21, F 7 Responses Jul 15

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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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    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, T 8 Responses Nov 14, 2014

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    im selling tons of adult baby girl dresses

    message me if your interested
    feedeeforyou feedeeforyou 18-21, F 1 Response Jul 17

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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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    Here is my Jessica Simpson dress with Platino

    tights and my new Mary Janes!
    sensuousPH sensuousPH 41-45, M 23 Responses Jan 19

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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 am a 15 year old sissy boy

    who wears his 18 year old sisters panties bra lingerie and dresses and tights and gowns and make ups secretly and Im attracted to tough guys lol??????????????
    deleted deleted 26-30 2 Responses Aug 16