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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 4,666 People

    I love dressing up as a schoolgirl,

    pleated miniskirt, blouse, and knee socks!
    schoolgyrlKaren schoolgyrlKaren 41-45 11 Responses Apr 6

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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 3 Responses Sep 5

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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 Don't Like Wearing Dresses, I Love Wearing Dresses

    My oh my the way it feels when that air rushes up under you dress,. Wow what a feeling. My first real dressy dress was the one I got to wear for my very own Sweet 16 birthday party. It was a white halter dress, with a flaired bottom and short, 3 inches above the knee. I wore it...
    MiriamK MiriamK 56-60, T 10 Responses Jun 12, 2012

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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 10 Responses Aug 1

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    I love ******* dresses.

    Heels. Panties. Lipstick. All in red and I  Wish I had a brunette wig. But I have so pics to post and a story to tell. Here I go. One day my friend and I were fooling around, chatting on Facebook. She was talking about dresses and how she was a princess (joking) and how I would...
    Cade14 Cade14 13-15, M 6 Responses Dec 20, 2013

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    I'm a young teenage boy,

    who wants to experience the life a young teenage girl has. that's why I like to wear dresses, and stuff
    CharleeneA CharleeneA 13-15, M 7 Responses Dec 14, 2013

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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

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    I shared this somewhere else on EP before,

    thought I could put it in this group too. SO this is an actual true story, not like the stories on many TG sights and what, this actually happened a few weeks ago ^_^ (I'm a 17-year-old guy) So for the last couple of years I have had a curiosity (less of a curiosity and more of...
    hairy96 hairy96 18-21, M 7 Responses Jan 8

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    swagstagram100 swagstagram100 16-17, F 4 Responses Jun 30

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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 2 Responses Aug 11

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    Today, I'm wearing my new favorite from Old

    Navy with my new favorite Liz Claiborne sandals.I'm just wearing the outfit around home. I haven't worked up to going out and about dressed other than late, late at night; which I am seriously contemplating since it has been so nice lately.
    JosetteLaRoc JosetteLaRoc 36-40 6 Responses Jun 10

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    I have gone out in public in a dress

    and boy do I like it. as a boy I never felt like anybody was looking at me ,but as a girl not only to I feel looked at , I also get attention and love and kindness
    CharleeneA CharleeneA 13-15, M 7 Responses Dec 29, 2013

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    I wish I could wear dresses twenty four hours a

    day. I have started a small collection of them an am buying more as I can. I will most likely never have enough of them.
    Jessica1967 Jessica1967 41-45, T 7 Responses Jul 10

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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 8 Responses 5 days ago

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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 13 Responses Jun 17, 2011

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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 a week ago

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    Lately with a pair of black leggings.

    I must admit my legs look great in them.
    deleted deleted 26-30 2 Responses Aug 13

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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 10 Responses a week ago

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    ​was thinking of getting another wedding

    dress what do you guys think?
    vjss vjss 22-25, M 15 Responses Jul 25

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    i love to wear my mothers

    and sisters clothes now i feel better wearing them than i do my own but what happens if i get caught
    glovesam glovesam 26-30, M 8 Responses Jul 20

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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'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 13 Responses May 3

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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 3 Responses Nov 20, 2013

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    Wearing Dresses

    I love wearing dresses. I started when I was about 14 trying on things from my mothers wardrobe. I never had any thoughts of them belonging to my mother I just liked seeing myself dressed like a girl in front of a mirror. I later had a girlfriend whowas very turned on seeing me...
    Sissygirlieboy Sissygirlieboy 36-40, T 3 Responses Nov 6, 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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    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 6 Responses Sep 30

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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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    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 6 Responses Aug 11

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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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    Teenage Crossdresser!

    Im a 14 year old boy and ive been crossdressing for almost a year. Ive never told anyone about this. When theres noone else home i go up to my sisters room and try on different dresses and outfits. Im not gay or anything i just love wearing dresses, skirts and anything else girly...
    Kylec12 Kylec12 13-15, M 21 Responses Oct 8, 2012

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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 10 Responses Aug 7

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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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    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 11 Responses Dec 21, 2013

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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 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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    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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    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 23 Responses Oct 22, 2011

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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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    When I started cross dressing it was a winter

    thing, but now own so many summer dresses short and long......
    amber8642 amber8642 51-55 5 Responses Jun 29

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    About a week ago i dressed up in a black mini

    dress and thong and bra. I went out and walked around the Meade co lake.
    harley80cu harley80cu 41-45, M 7 Responses Jun 18

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    abbyseaney abbyseaney 16-17, T 7 Responses Aug 5

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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 4 Responses Oct 1

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    Dresses Became My Obsession.Or - My Courage Is Increasing

    Back in March my class in school had a trail in which I was found guilty, what I did is no longer important, but what is important is the sentence I was given. I was sentenced to one month attending school as a girl, in a dress , makeup all that stuff. At first it was...
    littlelindsay littlelindsay 18-21, M 12 Responses Jul 23, 2013

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    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764 18-21, T 7 Responses Jul 23

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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 12 Responses Jul 22, 2012

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    Cdallaslover99 Cdallaslover99 13-15, M 6 Responses Sep 3

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    Related Experiences

    I first started experimenting with wearing dresses when I was about 6 years old.at first I wasn't sure why I did it fight at the time I enjoyed the experience. When I got older...
    Dora922 Dora922 31-35, T a week ago

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    I just love to wear my high heels. The way they shape my calfs and lift my butt
    cdden4 cdden4 51-55, M 5 Responses Oct 5

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    It's just this simple folks, enjoying the way pantyhose feel does NOT instantly turn or make you gay. This is just more social stigma ingrained into our society which makes us, the...
    nyloncrush nyloncrush 41-45, M 2 Responses 5 days ago

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    I'm a girl who likes girls and I can't help it people have judged me for it but I say if your gay embrace it don't be judged by anyone and don't let pepole control who you love...
    andiloveyou andiloveyou 16-17, F 6 Responses Oct 6

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    Im a Muslim girl who likes girls... Its really suffocating to be me.. Help! I tried to b straight again but i just keep falling for girls...... I want to be with a girl :'(
    lonerBI lonerBI 36-40, F 7 Responses Oct 13