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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 4,844 People

    Lately with a pair of black leggings.

    I must admit my legs look great in them.
    deleted deleted 26-30 1 Response Aug 13

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    Wearing Dresses Is Fantastic

    I am a straight male who loves to wear dresses. I love the feel of a dress against my legs. I love the fact that I do not have something hanging on my hips like pants. The freedom of a dress is so appealing that I want to wear them or a skirt all the time. I like the idea of...
    Adam59 Adam59 56-60, M 11 Responses Jul 22, 2012

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    dressing in public number 3.

    Who else has made this journey- having a single item you obsess about for years (often panties , i believe , but mine was tights) , telling yourself that you aren't interested in cross dressing (although it was probably some early dressing up experience that got you hooked on...
    donnaka donnaka 36-40 9 Responses Nov 4

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    It so happens that there was a long time

    before my opportunity to go out a 4th time. But in the summer my wife was going away for a week-end. I was so excited!! I shopped around the internet where I found , in a city several hours away, a dressing service that didn't just photograph you in a studio, but took you out...
    donnaka donnaka 36-40 3 Responses Nov 27

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    My friend took me dress shopping this morning ,

    it was the happiest I've been in a long time. I got to twirl and try on several dresses. I picked out an awesome blue dress that's thighs on the top and flares on the bottom. I can't wait to wear it on Halloween! I was a little nervous with the other customers and the cashier...
    Hiddensissy69 Hiddensissy69 26-30, M 9 Responses Oct 16

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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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    I have always enjoyed wearing feminine clothes

    and makeup but only to relieve myself. And when I am done with that I usually remove all the makeup and feminine clothes. Now when I wear women's clothes, I don't even feel the need to relieve myself. I have started enjoying wearing makeup and really look forward to putting it...
    sexysissy11 sexysissy11 18-21, M 2 Responses 1 day ago

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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 wear female clothes except at school.

    even when going out, I prefer dressed as girl, than as a boy with long hair.
    charudays charudays 18-21, M 3 Responses Jun 29

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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

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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 7 Responses Dec 5

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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 3 Responses 11 hrs ago

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    Anyone wants to add me feel free also

    if you want to know anything or ask anything just msg me thank you xx
    cutieXtights cutieXtights 22-25, F 3 Responses Sep 29

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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

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    I am a young teenage boy

    who absolutely loves anything girly (frilly dresses, puffy dresses, tights, panties, bras, leotard, makeup) and i would just love love for a group of girls to give me a full girly makeover including bras and panties and full girls clothes and then have a girly day out shipping...
    iloveparkour iloveparkour 13-15, M 10 Responses Dec 21, 2013

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    OK... Google the phrase "shopping tunic",

    then click the "shopping" tab. You'll see that pretty much all the results are for "women's tunic dresses". Then search "gladiator sandals", and you'll see that the vast majority are sold as "women's shoes". Can we agree that these are considered "women's clothes", and a man...
    steve66oh steve66oh 46-50, M 5 Responses Aug 11

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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

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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

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    Prom Dress

    Hello, my name is shay and im 18, last year it was my last year at school and it was a prom, and me and my female friend had a bet, i lost it and she told me to wear a dress to prom, i had no choice but to keep in my word and respect the bet, we went to the mall and we went ti a...
    SHAY8877 SHAY8877 16-17, M 4 Responses Nov 20, 2013

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    Well I did it went to Halloween

    as a girl still in the dress as a matter of fact. Only problem was my friend forgot my makeup and jewelry. But it turned out okay because another let me borrow her makeup. Noone had any issue with me dressing up I even went out and got breakfast in my dress. Ihad a great...
    Hiddensissy69 Hiddensissy69 26-30, M 6 Responses Nov 1

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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

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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 34 Responses Oct 29, 2010

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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

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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

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    on Thursday I wrote about how I was going to go

    out this weekend dressed in my female persona. I just want to say and OH MY GOD! It was so much fun. I didn't want to come back home.at first I was excited but more nervous but now I can't wait for next weekend to do this again. When I do it next weekend it will be at a...
    Dora922 Dora922 31-35, T 10 Responses Oct 18

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    When I was younger I used to steal my older

    sisters' clothes one was ten years older the other six years older than me. Until I was caught and got the belt and made ashamed by my parents for even thinking about wearing girls clothes. My dad used to threaten to let the neighbors see me dressed up. I haven't wore a dress or...
    Hiddensissy69 Hiddensissy69 26-30, M 3 Responses Oct 1

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    Cdallaslover99 Cdallaslover99 13-15, M 6 Responses Sep 3

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    Here is me in a skirt

    and a top and also tights
    Cdallaslover99 Cdallaslover99 13-15, M 3 Responses Nov 10

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    I'm transgender, but gender doesn't matter on

    what you like to wear. I mean.. sometimes I'll feel like I'm less of a boy when I wear "girl" clothing, but w/e. I love wearing those dresses that flow so easily and have that sort of Roman feel to it. Aah yes. Dresses.
    SleepyGamers SleepyGamers 13-15, T 5 Responses Nov 10

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    I'm going to be posting

    and sending nude pics or will be on Skype so add me kik: missjazzmin Skype: misscrossdresser
    missjazzmin missjazzmin 18-21 3 Responses Aug 11

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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

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    I have just started writing a new blog

    chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the writing down of any kind of fantasy scenario. The contents are a true and accurate representation of the day-to-day life of an adult couple...
    deleted deleted 26-30 2 Responses Sep 5

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    I first started experimenting

    when I was 6 years old with wearing female clothing. As I reach puberty I started experimenting more with bras and panties and occasionally address.now I wear dresses in other female attire around the house but this weekend is going to be my first time going out in public well...
    Dora922 Dora922 31-35, T 11 Responses Oct 16

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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

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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

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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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    ok , so here goes for the second time.

    if you've read my first post, you'll know what a rush I got from being out in the street and passing , for all of 5 minutes. i attribute the success of this to several things (i) lots of mirror practice- including videoing myself trying to walk like a girl (ii) the magic of...
    donnaka donnaka 36-40 1 Response Nov 4

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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 14 Responses Dec 6

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    One amazing spectacular day my life changed.

    I wore a dress thanks to some friends help. I loved the feel the look the sparkle... Hehe. I wanted to make all the boys stare... If only they thought I was a girl but not a boy. I love blue dresses, they match my eyes. I have shard legs, a wig I do everything clothes wise, and...
    Cade14 Cade14 13-15, M 3 Responses Dec 19, 2013

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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 14 Responses Jun 24

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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 21 Responses Aug 16

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    I love wearing dresses

    and having gone out to experience
    luvpanties60 luvpanties60 31-35, M 17 Responses Sep 16

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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

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    I've been wearing this one all afternoon.

    I dared myself and ventured out, TWICE! Once was through a drive-thru to get a bite to eat. The other was to the RedBox outside the local Walgreen's.The guy at the drive-thru was very professional.
    JosetteLaRoc JosetteLaRoc 36-40 7 Responses Dec 9

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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

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    I started dressing when I was 11

    or 12. I would wear my step mom's clothing any chance I could. I still dress every chance I get and love wearing dresses and skirts
    jasminecd5 jasminecd5 36-40, M 4 Responses Nov 1

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    Related Experiences

    I love wearing black pantyhose so come on boys let's have a bit of fun and msg me X
    tights1111 tights1111 26-30, M 18 hrs ago

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    Joanne0chan Joanne0chan 31-35 2 days ago

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    As a transgendered Catholic boy who was forced to grow up male, I remember my first communion and wanting so desperately be one of the girls dressed in a beautiful communion dress...
    tessoconn tessoconn 18-21, F 2 Responses Dec 2

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    Yes I love wearing dresses. They are so liberating. My feminine side can be herself. Not shoved into pants. Rather being the classy lady that she is.
    Adam59 Adam59 56-60, M 2 Responses Nov 26

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    Ok so I'm new but I need advice.......there's this guy I like and he's sorta a bad boy he likes to skip class and cut school he once asked me if I wanted to tag along I wanted to...
    DaggerPaw DaggerPaw 13-15, M Dec 2