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I 'm A Boy Who Likes Wearing Dresses

We as boys 10 and above want to wear dresses 4,003 People

    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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    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...
    Adam59 Adam59 56-60, M 9 Responses Jul 22, 2012

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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...
    Elizabethamber Elizabethamber 16-17, T 36 Responses Oct 29, 2010

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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...
    hairy96 hairy96 18-21, M 7 Responses Jan 8

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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...
    MiriamK MiriamK 56-60, T 10 Responses Jun 12, 2012

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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...
    Cade14 Cade14 13-15, M 3 Responses Dec 19, 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...
    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...
    cindy3 cindy3 26-30, F 11 Responses Dec 5, 2013

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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...
    b65milligan b65milligan 18-21, M 8 Responses Aug 14, 2011

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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...
    Sissygirlieboy Sissygirlieboy 36-40, T 3 Responses Nov 6, 2013

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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...
    shifakhan shifakhan 18-21, M 1 Response 6 days ago

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    Just uploaded a couple of pics check them out!
    mrman77 mrman77 22-25, M 5 Responses Mar 1

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    I'm interested in getting a sex change.
    Demintor1 Demintor1 31-35, M Jan 3

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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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    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...
    beautifulOwendi beautifulOwendi 18-21, M 2 Responses Sep 22, 2012

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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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    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...
    iloveparkour iloveparkour 13-15, M 11 Responses Dec 21, 2013

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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...
    hoborob hoborob 51-55, M 3 Responses Feb 27

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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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    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...
    corneliousrodriguez corneliousrodriguez 22-25 3 Responses Feb 3

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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...
    SissyEJ SissyEJ 36-40 6 Responses Feb 16

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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...
    CharleeneA CharleeneA 18-21, M 4 Responses Dec 29, 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...
    Cade14 Cade14 13-15, M 6 Responses Dec 20, 2013

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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...
    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...
    skingley skingley 18-21, T 24 Responses Oct 22, 2011

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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...
    jennyla73 jennyla73 36-40, F 12 Responses Dec 27, 2011

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    I like sucking **** geting ****** n the *** till i cant take it nomo
    andrew1234sp andrew1234sp 22-25, M 1 Response Dec 20, 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).
    jadesissy jadesissy 18-21, M 10 Responses Jan 10

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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...
    sissyslave18 sissyslave18 18-21, M 7 Responses Feb 9

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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...
    theBillyandBudBear theBillyandBudBear 66-70, M 17 Responses Jan 5, 2011

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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 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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    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...
    kinkyboy6969 kinkyboy6969 36-40, M 4 Responses Jan 5

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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...
    RobinLeade RobinLeade 22-25 4 Responses Aug 19, 2011

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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...
    1SarahAnn 1SarahAnn 46-50, M 4 Responses Feb 18

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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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    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...
    sissyyumi sissyyumi 22-25, M 5 Responses 6 days ago

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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...
    Kylec12 Kylec12 13-15, M 18 Responses Oct 8, 2012

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    Good I wear women's underwear pantyhose dress heels I love it
    astroboy4545 astroboy4545 61-65, M 4 Responses Mar 21

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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...
    deleted deleted 26-30 8 Responses Jan 7

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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...
    ao159 ao159 18-21, T 3 Responses Dec 26, 2013

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    Uploaded more pics go check them out!
    mrman77 mrman77 22-25, M 3 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...
    SHAY8877 SHAY8877 16-17, M 3 Responses Nov 20, 2013

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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...
    MsLettle MsLettle 56-60 14 Responses Jun 17, 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...
    Pjstuart Pjstuart 26-30, M 8 Responses 4 days ago

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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...
    Drew0113 Drew0113 13-15, M 6 Responses Feb 26

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    Hey any guys wearing panties message me liked to talk with you :)
    TheGrandPoobah TheGrandPoobah 13-15, M 1 Response 3 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 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 a week ago

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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