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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 4,372 People

    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 18-21, M 7 Responses Dec 14, 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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    mrman77 mrman77 22-25, T 5 Responses Mar 1

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    Having moved on from lingerie/panties I have

    been having an off/off talks with wife regarding this hobby of mine. Despite her not liking it she tries to accomodate it. I have now got some dresses and skirts from many places and have a lovely 50's swing type dress with super 3" heels. and petticoat. Not that keen on the...
    purecotton purecotton 51-55, M 5 Responses Mar 21

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    I'm no longer a boy,

    but a man that crossdresses daily. I very rarely wear any men's clothes. Sweaters, blouses, jeans, pants, skirts, dresses, panties and hosiery are my only wardrobe. I will never go back to men's clothing.
    martiecd martiecd 51-55, M 2 Responses Feb 26

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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 Love Wearing My Dresses

    I've been wearing dresses and skirts for a few years and I've told my friends and they all accept me but my parents will not accept me when I wear my dresses they say it's unnatural for me to like them however I will not let them put down I'm a sissy and I like it
    kiwigirly kiwigirly 22-25, M 10 Responses Jun 4, 2012

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    When i was at a friends I went to the bathroom

    amongst the dirty washing was his sisters skirt, i ******** off and put it on, it felt brilliant i had a little dance in the bathroom before getting dressed again, I went one more time before I left
    mike020200 mike020200 13-15, M 7 Responses Mar 20

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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'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 9 Responses May 3

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    so i have long hair,

    and i love wearing dresses.. so when i get home, i am alone.... so one day i took my clothes off in my room and walked across the hallway naked and went to my sister's room! :P so i choose a dress(pink), i wore my hair in a high ponytail and then curled my high ponytail :D and...
    deleted deleted 26-30 6 Responses Dec 29, 2013

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    A man becoming Herself I haven't

    written anything lately because I've been afraid of something going wrong. I'm far from where I want to be still, but believe I'm finally on the right path to being me. Since my last experience of going out in public dressed as a woman and seeing how great it made me feel about...
    cindy3 cindy3 26-30, F 11 Responses Dec 5, 2013

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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 36 Responses Oct 29, 2010

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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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    Hey everyone I'm looking

    for crossdressers between 15 and 18 to talk to. Message me! Willing to exchange pics
    mrman77 mrman77 22-25, T 2 Responses Feb 26

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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 5 Responses Jul 20

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    I Love Dressing As A Girl

    I was about 15 or 16 years old . I had a party to go AND I did not have any niceclothesto wear my friend dare me to ask my step sister to lend me a outfit for the party .she ask me to wait when she come back holding a mini leather skirt with a white silk blouse .i took...
    maryyork50 maryyork50 18-21, T 5 Responses Mar 10, 2012

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    swagstagram100 swagstagram100 16-17, F 4 Responses Jun 30

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    I love to wear dresses

    and women underwear. i'm searching other people who also likes that and would like to shear experiences
    dannygoemeare dannygoemeare 18-21, M 15 Responses May 24

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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 6 Responses 5 days ago

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    I love dressing up as a schoolgirl,

    pleated miniskirt, blouse, and knee socks!
    schoolgyrlKaren schoolgyrlKaren 41-45 12 Responses Apr 6

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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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    well I am interested to trained the lifestyle

    and willing to have you as one of My sissies and feminization.
    TheSeductressMiss TheSeductressMiss 26-30, F 12 Responses Feb 12

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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 18-21, 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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    ​was thinking of getting another wedding

    dress what do you guys think?
    vjss vjss 22-25, M 14 Responses 3 days ago

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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 10 Responses Jul 23, 2013

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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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    When I started cross dressing it was a winter

    thing, but now own so many summer dresses short and long......
    amber8642 amber8642 51-55 4 Responses Jun 29

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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 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, M 11 Responses Jan 10

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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 10 Responses Jul 22, 2012

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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 5 Responses Jun 18

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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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    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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    Volunteer Day This past Saturday was probably

    the most feminine day of my life. I was wearing my favorite brown plaid jumper with a black turtle neck, black patterned tights and black wedges. This particular jumper is a bit shorter than usual and ties in back . It feels so pretty. My hair and makeup came out very nice, and...
    1SarahAnn 1SarahAnn 46-50, M 4 Responses Feb 18

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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

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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 7 Responses Jun 10

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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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    I'd like to hear what you like about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 2 Responses Feb 9

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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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    i want cross dress as a female like all the

    clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help me out any girl in dubai who would help me and support me
    shifakhan shifakhan 18-21, M 2 Responses Apr 11

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    ptk1113 ptk1113 22-25, M 3 Responses Apr 10

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    mrman77 mrman77 22-25, T 2 Responses Mar 5

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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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    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 19 Responses Oct 8, 2012

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    Ever since I was young I have enjoyed dresses.

    For some reason my eye has always been trained to lock onto a dress or even a skirt. When I was young I would get home and would stay home alone for a coupe hours until one of my parents came home. One day I had tried on a pair of my mother's pantyhose and from there things...
    SissyEJ SissyEJ 36-40 6 Responses Feb 16

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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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    These are just some of my thoughts,

    and this is my first post, so bear with me. I'm a 15 year old boy. But sometimes, I think to myself, what would it be like to be a girl? I hang out with a pretty bad crowd in my school. I don't really participate in the bad activities they do, or approve of them, but they're my...
    Drew0113 Drew0113 36-40, M 6 Responses Feb 26

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    Its more fun when you crossdress in front of

    your hot girlfriend and then you both decide to change roles and she gets her toy and starts to do my hole and makes me the female for the night i loved it and wouldnt say no to doing it again :)
    sissyslave18 sissyslave18 18-21, M 7 Responses Feb 9

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    New Dress Recently I was looking at one of the

    ads that we all get when we are online anymore and it showed a very shiny skin tight little dress at Amazon.com. So I checked it out just for kicks to find out it was only $9.60 with free shipping no less. So I ordered one in gold even though the sizing was listed as fitting S-M...
    hoborob hoborob 51-55, M 4 Responses Feb 27

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    Related Experiences

    I am a business man I am merried my wife is also know about my hobby of wearing female dresses i like to wear saree blouse much. i have few collection of saree blouse bra paticoats...
    surekha57rpandya surekha57rpandya 56-60, M 3 Responses Jul 10

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    I have always liked wearing high heels even when I was a child. As I got older I was told I must not wear them, as they are for girls. I had to wear them secretly. After searching...
    hh4evry1 hh4evry1 36-40, M 5 Responses Jul 14

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