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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 4,006 People

    mrman77 mrman77 22-25, M 5 Responses Mar 1

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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 14 Responses Jun 17, 2011

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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 1 Response a week ago

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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, M 1 Response Feb 26

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    Im A Boy Who Likes Wearing Dresses

    i love wearing dresses balirena dresses every dresses one day i told my mom she said shes ok with it but she wont give me any cloths my dad found me in the back yard wearing a ballirena dresses he asked if mom made me do it i seed nobut i still wear them last night i walked down...
    b65milligan b65milligan 18-21, M 8 Responses Aug 14, 2011

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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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    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 16-17, M 5 Responses Mar 20

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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 24 Responses Oct 22, 2011

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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 4 Responses Dec 29, 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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    Demintor1 Demintor1 31-35, M 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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    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 8 Responses 5 days ago

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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 ******* 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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    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 love dressing up as a schoolgirl,

    pleated miniskirt, blouse, and knee socks!
    schoolgyrlKaren schoolgyrlKaren 41-45 8 Responses Apr 6

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    Im only 14 years old right now

    and Im putting on moms dresses and clothing because I like it . I thought I was the only one but this website really helped me get through but I also need some advice and I do not want to tell my mother (yet). Like how do I dress a little like a girl during school and stuff so I...
    deleted deleted 26-30 8 Responses Jan 7

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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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    Hi im a teen crossdresser from hertfordshire i

    am hoping for somebody to give me a sexy makeover a girl preferred however if a cd can come along would be great to get to know you Hope theres somebody
    ao159 ao159 18-21, T 3 Responses Dec 26, 2013

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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 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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    As A Young Boy I Loved Wearing Panties, Slips, Dresses, Anklets....

    As a young boy I loved wearing panties, slips, dresses, anklets, all clothing labeled as "little girls" cept for tights. (I hated tights, cus, well, I had great looking widdle legs that was meant to be seen and not hidden). Here's my story, or as I called them, 'ventures...
    theBillyandBudBear theBillyandBudBear 66-70, M 17 Responses Jan 5, 2011

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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).
    jadesissy jadesissy 18-21, M 10 Responses Jan 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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    Soccer Updates

    Well, I can say I have good and bad news about being humiliated wearing a dress at soccer practise. The dress was okay, it was a short style dress ,above the knees and light green in color I enjoyed wearing it and of course made a fuss of NOT liking it The coach was too...
    beautifulOwendi beautifulOwendi 18-21, M 2 Responses Sep 22, 2012

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    Kik me: missjazzmin i want to talk to other

    crossdressers and I don't mind trading pics :)
    missjazzmin missjazzmin 18-21 3 Responses Jan 14

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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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    Love dresses! 💜 I grew up in a family mostly

    of ladies. I was 6 when I was put in my first dress by my cousins. I was embarrassed then but I really liked that experience. Since then I have always envied girls because they got to wear such pretty dresses and make up. But whenever my cousins would put me in a dress for fun I...
    sissyyumi sissyyumi 22-25, M 5 Responses a week ago

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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'm a man who loves to wear dresses latex

    plastic or PVC is my thing I just wanted to share my stories with you all. I have many different outfits my favorite has to be my black PVC skater dress with pink fluff round. it its gorgeous I love it I will put some pics up of me in it and also my red PVC nurse outfit I'll top...
    kinkyboy6969 kinkyboy6969 36-40, M 4 Responses Jan 5

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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 18-21, M 6 Responses Dec 14, 2013

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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 9 Responses Jul 22, 2012

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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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    andrew1234sp andrew1234sp 22-25, M 1 Response Dec 20, 2013

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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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    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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    So I'm very new to this.

    I tried on my mom's bra/panties/pantyhose/dress for a dare and it felt pretty good. Don't misunderstand me, I'm not a crossdresser, but I am male. I posted a pic anon online (without my face) and had many guys over me. Some problems: hands not slender, shoulders too broad, hips...
    corneliousrodriguez corneliousrodriguez 22-25 3 Responses Feb 3

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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 11 Responses Feb 12

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    I Just Love Dresses

    I started wearing a dress for a halloween party when I was 13. Several dresses were bought to see which one I looked good in. The other were put aside and i wore them up until halloween to get use to wearing a dress. I was embrarassed at first to be wearing a dress around the...
    RobinLeade RobinLeade 22-25 4 Responses Aug 19, 2011

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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 13-15, M 6 Responses Feb 26

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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 18 Responses Oct 8, 2012

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    mrman77 mrman77 22-25, M 3 Responses Mar 5

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    I like to but on my wife's dress.

    but i want to have a dress of my own. how do you convert guy size to girl size?
    dragtess dragtess 26-30, M 2 Responses Feb 1

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    astroboy4545 astroboy4545 61-65, M 4 Responses Mar 21

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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 3 Responses Feb 27

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    Related Experiences

    Hey any guys wearing panties message me liked to talk with you :)
    TheGrandPoobah TheGrandPoobah 13-15, M 4 days ago

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Mainly I wanted to say that the first picture on this page, the one of both a boy and a girl wearing identical yellow dress costumes was taken by me several years ago at the annual...
    Charlesea Charlesea 70+ 2 Responses Mar 21

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    I love woman in uniforms and would like to find woman who enjoy wearing uniforms
    kevefc kevefc 46-50, M 12 hrs ago

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    I believe fathers, uncles, etc. of male appearance will have to start wearing dresses/skirts before boys will be able to. I hear the argument girls/women can wear pants, neckties...
    CdKimmi CdKimmi 61-65, M 3 Responses Apr 10

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    My name is Marshall and I'm a 16 year old gay teen. I want to find a boyfriend who could love me for who I am. I like to cuddle, watch movies play games. Am really nice but am not...
    PureMale PureMale 16-17, M 1 Response Mar 23

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    i was 17. i told my step mom i wanted to be a model and enter the beauty pageant. she said we would see. the next week was my sister party. she was having a party and her and her...
    loverboy758 loverboy758 18-21, M 2 Responses 3 days ago

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    One Sunday I wore a purple dress to church. It was nothing special but it looked nice. After church we went into the Commissary to get a few groceries. We were checking out when I...
    SweetMae SweetMae 56-60, F 27 Responses Mar 21

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    Every since I was in 4th grade I'd occasionally go into my sister's (who's 3.5 years older than me) bathroom to wear her underwear and (training) bras. Then when I was older in...
    BlackHedgehog24 BlackHedgehog24 16-17, M 2 Responses Apr 5

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    I do in summer! I was wearing shorts under my dress in case I wanted to mess myself. I was walking my dog and I had the big urge. While my dog was owing, I stood there and messed...
    loveylaura loveylaura 26-30, F 2 Responses 3 days ago