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I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 399 People

    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 Highland Games festival at Grandfather Mountain in North Carolina. Can't remember the exact year, but think it was about...
    Charlesea Charlesea 70+ 2 Responses Mar 21

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    I was caught By my 14 year old Sister I am 13

    and walked in my sisters room while she was downstairs and I had just seen on tv of a boy in girls clothes and being the only male in the house it just popped in my head to try her clothes on so I took my clothes of and put on her White knickers and bra and stuffed them with...
    02hamster02 02hamster02 18-21, T Mar 11

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    Caught By Sister

    I am 14 and walked in my sisters room while she was downstairs and I had just seen on tv of a boy in girls clothes and being the only male in the house it just popped in my head to try her clothes on so I took my clothes of and put on her White knickers and bra and stuffed them...
    Goatsfortwoweeks Goatsfortwoweeks 36-40, M 1 Response Nov 19, 2011

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    Schoolgirls Band From Wearing Skirts School Uniform

    While more and more GUrls (femminin boys) are being more & more allowed to wear skirts to school, somme girls (GG's) are being band from wearing them again a case in role reversal. I Know for a fact that this is not just the only case like that. There was another case in france...
    annemarielongueuil annemarielongueuil 41-45, F 4 Responses Jan 31, 2013

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    Uk Boy In A Skirt

    Chris Whitehead is a boy who didn't like wearing hot dark pants to school during the summer and shorts were forbidden. He took a stand on it and has been wearing skirts everyday to make a point about comfort. In the UK, it is perfectly acceptable for this to be done. Here in the...
    andreaneejustinfield andreaneejustinfield 41-45, T 20 Responses May 11, 2011

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    UK Schoolboy Dressed As Schoolgirl

    There were reports in the Scottish press at the weekend about Callum McLean, a 16yo schoolboy who went to school in Lanarkshire completely cross-dressed in the girls school uniform complete with long hair girls wig, padded bra, full make-up, mini skirt, bling etc etc. Callum...
    tartanpleats tartanpleats 61-65, M 1 Response Oct 14, 2013

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    Matching His'n'hers

    I noticed this picture (top) on another site but I have no idea what's going on apart from it's obviously an Irish dancing competition/display of some kind.  Perhaps someone here might be able to explain why these little boy and girl dancers are wearing matching yellow...
    tartanpleats tartanpleats 61-65, M 12 Responses Nov 30, 2011

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    Ok

    Perfectly fine as long as he has underwear on
    Articchill32 Articchill32 31-35, M Jan 3, 2013

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    More UK Schoolboys Wearing Skirts

    Another protest about a school dress code which stipulates girls can wear skirts or trousers but boys must wear long trousers only. A group of 17 boys in Year 10 (15yo) at Whitchurch High School in Wales staged a skirted protest about not being allowed to wear short trousers...
    tartanpleats tartanpleats 61-65, M 3 Responses Oct 25, 2013

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    How About Wear A Dresses To School Abd Even Being The Prom Queen

      My son, the prom queen:Transgender student, 16, dressesin drag for big night... and mother does his make-up.. Classmates call him 'Hailee' and one even took him for a twirl on the dancefloor Tom Komrowski looks pretty in pink for his school prom after teachers agreed he...
    annemarielongueuil annemarielongueuil 41-45, F 9 Responses Jan 29, 2013

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    Asked Why?

    So as I go through my journal having written down most of my favorite or what I found funny about people towards my cross dressing was two years ago during February when most of our schools boys were forced into girly dresses or some. Most either are fearful of the jokes thrown...
    babybluenightieboy babybluenightieboy 18-21, M 1 Response Nov 21, 2012

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    First Time Turned Into A Three Day A Week Thing >///<

    So the first time I cross dressed at school was during my schools dress week were a friend of mine brought an Alice in Wonderland, Alice outfit for me. I put it on and came out with my glasses on and my cat ears and nearly got tackled to the ground by three of my friends. When I...
    babybluenightieboy babybluenightieboy 18-21, M 2 Responses Nov 18, 2012

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    South African Teen Banned From School For Not Wearing A Skirt

    Dec 13th 2010 1:26PM What's the link Between this post and the TITLE: "Boys Wearing Dresses and Skirts To School", The answer is simple, we see more and more gender role reversal. As I go along we that girls are Either band from wearing skirts or just don't want to wear them...
    annemarielongueuil annemarielongueuil 41-45, F 8 Responses Jan 31, 2013

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    Lavinias Brown School Knickers

    The girl next door,Lavinia always used to sit so that we could see her navy blue regulation knickers. Tantalizing! One day I went around to the house and in an open drawer in the kitchen sat a pair of brown school knickers. Lavinia had just left Brownies at 11 and her Brownie...
    Jimknickers Jimknickers 61-65, M 2 Responses Jan 2, 2012

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    Related Experiences

    So I love dressing up in my/and my wifes dresses. I love trying on her dresses. Wished I could do it with her knowing I would love to be fully out of the closet, I hate having to...
    Laurie1960 Laurie1960 51-55 7 Responses Jul 14

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    I love my Leather and PVC skirts and Dresses, it make me feel so sexy.......
    amber8642 amber8642 51-55 3 Responses Jun 29

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    I love crisp tailored clothes- I try to wear nice jackets, pencil skirts or shift dresses for work. Usually in neutral colors like white, black gray or navy. Sometimes I might...
    theyrereal theyrereal 31-35, F 4 Responses Jun 25

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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...
    sissypantyhosekiss sissypantyhosekiss 18-21, T 16 Responses Jun 24

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    Check out this maker of skirts for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 2 Responses Jul 15

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    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 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'm a jeans-and-T-shirt kind of girl, but I just love dresses. My dream is to find the perfect dress to wear with Chucks.
    cece930 cece930 18-21, F Jun 25

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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 3 Responses Jun 29

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T Jul 4

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T Jul 4

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T 1 Response Jul 4

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T Jul 4

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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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    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 3 days ago

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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...
    jmallon764 jmallon764 18-21, M 6 Responses 15 hrs ago

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    I woke up yesterday and went to help my wife make her lunch. I had on the blue floral nightie I had slept in. When my wife left for work I went and toke a quick shower and then put...
    mat2Robin43 mat2Robin43 51-55, M 4 Responses Jul 8

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    I'm going to dress up sexy and walk around at Milford lake park
    harley80cu harley80cu 41-45, M 1 Response Jul 14

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    Last weekend I wore a skirt everywhere I went and it was a lot of fun and I really enjoyed myself and so did my fiancé. We both had a lot of fun with it and going to do it again...
    highkin highkin 31-35, M 6 Responses 4 days ago

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    They're cute, but I can't pull them off :p
    cotygal123 cotygal123 13-15, F 1 Response Jun 23

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    O yes, they are an absolute pleasure to wear as they show off my slender legs and with heels, they are gorgeous. I love the way guys stare at my butt.
    annieka annieka 22-25, F 4 Responses Jul 7

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    I consider it fun attire! Not just for special occasions or going out for drinks, but quite often I do this. Love going out in the summer.
    chrissy1979 chrissy1979 31-35, F 2 Responses Jul 10

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    I just took a good look at my favorite house dress, and realized I'll have to replace it. It is threadbare! I like it so much that I've worn it out. It is a yellow cotton...
    aprilrose aprilrose 61-65, T 4 Responses Jun 26

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    I bought 2 today. And shoes. Did I need them? Not a bit. But I always feel prettier in a dress.
    pinkcorsetgirl pinkcorsetgirl 41-45, F 2 Responses Jun 28

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    Yeah guys sorry , (I'm not really)
    swagstagram100 swagstagram100 16-17, F 4 Responses Jun 30

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    Even though I'm quite masculine looking, I love wearing dresses and skirts. I only wish I had been allowed to do so as a child.
    quearme quearme 56-60, M 3 Responses Jul 15

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    Cleaning Out the Closet I have been cross dressing for many many years and have acquired a collection big enough to fill a walk in closet. Some of the items I have date all the way...
    jamie50 jamie50 51-55 5 Responses Jul 3

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    I love wearing dresses, but changing into sweat pants and a hoodie is so much more comfortable! 😍
    TheSongPlaysWithin TheSongPlaysWithin 16-17, F 2 Responses Jun 25

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    Almost all of my female attire is second hand! I go to Garage sales a great deal. I have purchased; second hand panties, bras, slips, pantyhose, skirts, blouses dresses, and...
    OhioSissy OhioSissy 51-55, M 6 hrs ago

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    Had to see a Dr today so I can see another Dr tomorrow. I have cancer for the third time. It's a form of skin cancer that's very treatable. Caught early it's not a problem. Does...
    shadowplt shadowplt 46-50, M 1 Response 2 hrs ago

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    Our religion (we are a Christian denomination that requires women to wear skirts and dresses, never pants) believes that pants are for men and skirts and dresses are for women. Our...
    IAmLovingLife1234 IAmLovingLife1234 41-45 3 Responses Jun 23

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    In the late 60's I was a teen boy who discovered and wore for the first time MASCARA, I was hooked. My girlfriend, future wife, was delighted that I was ok with more makeup and on...
    CdKimmi CdKimmi 61-65, M 3 Responses Jun 29

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    Check out this maker of skirts for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M Jul 15

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    I have just discovered this maker of skirts for men http://www.skirtcraft.com Check it out!
    Prettyjennifer2004 Prettyjennifer2004 51-55, M Jul 15

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