Post

I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 398 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Ok

    Perfectly fine as long as he has underwear on
    Articchill32 Articchill32 31-35, M Jan 3, 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 3 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 8 Responses Jul 14

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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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    When I was young the miniskirt was all the rage and we loved wearing them. We used to get into trouble at school if our skirts were too short but mum was very good about our desire...
    Jilly53 Jilly53 56-60, F 1 day ago

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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...
    Roccondil Roccondil 22-25, M 7 Responses 11 hrs ago

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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 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 6 Responses Jul 20

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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 6 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 Jul 19

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 5 Responses 5 days ago

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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 5 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 3 Responses Jul 10

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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...
    zoey764 zoey764 18-21 6 Responses Jul 23

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    ​was thinking of getting another wedding dress what do you guys think?
    vjss vjss 22-25, M 15 Responses a week ago

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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 2 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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    When I grew up I did at least in private and sometimes not so private wear short pleated skirts and the occasional pinafore style dress. This was not a punishment and indeed I am...
    littlegreyshorts littlegreyshorts 51-55, M 2 Responses 22 hrs ago

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    Skirts are so comfortable - especially when your most sensitive parts hang outside your body! And, really, skirts are as "feminine" as the Roman Army - badass lion fighting...
    steve66oh steve66oh 41-45, M 2 Responses 4 days ago

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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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    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 2 Responses Jul 23

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    Likes to dress me beautiful. Already as a little girl I liked it, to wear lovely dresses and skirts and that's still the same. Of course I have pants, leggings and sweater but I'd...
    prettysybill prettysybill 22-25, F 5 Responses Jul 24

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    When I was in Junior High I was not the most popular kid. I was picked on a lot and the subject of a lot of embarrassing things. One day I was taking a shower after PE and someone...
    Soccer127 Soccer127 18-21, M 1 Response 3 days ago

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    I have such fond memories of childhood. I was the last of four children, 14 years behind my oldest sister and the only boy in the family. I have only scant memories of a father...
    Varience Varience 70+, M 1 Response Jul 9

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    I really don't like to wear them and sometimes I just wear short dresses or skirts without underwear it's more comfortable
    AshleyYoung98 AshleyYoung98 16-17, F 4 Responses 6 days ago

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    Yesterday I decided I would change into my skirt at work. I just happened to have one in my briefcase, well, you do, don't you?! So I walked through the office and out into the car...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 4 Responses Jul 19

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    Am I the only one who feels like someone should be able to do whatever they want to? Why can men not wear make up, dresses, pink etc without being told they are gay? Which makes...
    AnomalousEarthling AnomalousEarthling 22-25, F 13 Responses Jul 19

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    I love shirts and dresses. There just awesome. I mainly posted this so I could get opinion from people with fashion lol Pink skater skirt or Aztec skirt?
    LovelyDeadly LovelyDeadly 16-17, F 7 Responses Jul 20

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    I think men should wear whatever they want to wear. Skirts are cooler in hot weather. As long as the clothes are well fitting and look nice what does it matter what any one wears...
    renah64 renah64 61-65, T 2 Responses Jul 20

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