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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 5,667 People

    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 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 Aug 20

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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 2 Responses Aug 16

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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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    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

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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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    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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    Headed out on an adventure tonight.

    Next stop is Payless for a new pair of shoes.
    CDKristiK CDKristiK 51-55, M 10 Responses Dec 5, 2014

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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 2 Responses Aug 24

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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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    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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    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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    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 4 Responses Apr 21

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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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    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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    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'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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    jman0105 jman0105 13-15, M 2 Responses Aug 20

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    And skirts, bras and panties!

    Just in private, but I look forward to my mornings when I get some alone time. (With pics) I feel so relaxed... My wife knows but doesn't want to see unfortunately.I don't shave because I'm too hairy and my wife loves my hairy chest. So this is a happy compromise :-)
    SamandLynda SamandLynda 46-50, M 10 Responses Jul 25

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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'm a boy that likes putting on my sisters

    makeup πŸ’„ bra panties and high heels πŸ‘‘ lipstick πŸ’„ dresses skirts
    tmccom123450 tmccom123450 13-15, M 3 Responses Jun 22

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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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    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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    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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    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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    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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    LucyAshley LucyAshley 18-21, T 12 Responses Feb 21

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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 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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    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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    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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    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 13 Responses Feb 23

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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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    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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    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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    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 7 Responses Jun 7

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    LucyAshley LucyAshley 18-21, T 9 Responses Jan 3

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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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    So I made myself pretty ,

    and went to the library:- new photos , friends only.
    donnaka donnaka 36-40 3 Responses Apr 29

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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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    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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    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 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'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'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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    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