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I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 407 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+ 3 Responses Mar 21, 2014

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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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    This is another example of how a restrictive EP

    entry style followed by the removal of maintained groups with icons has made things worse over the years. Really the style should read "I support boys wearing dresses and skirts to school" as that's really what it's about. You know, the right to present in the attire that best...
    Joanne0chan Joanne0chan 31-35, F Dec 15, 2014

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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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    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 2 Responses 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 6 Responses Jan 31, 2013

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    aqww aqww 13-15, M 3 Responses Jan 27

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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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    Ok

    Perfectly fine as long as he has underwear on
    Articchill32 Articchill32 31-35, M Jan 3, 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 2 Responses Nov 21, 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 7 Responses Jan 31, 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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    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 10 Responses Nov 30, 2011

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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, F Mar 11, 2014

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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 1 Response Nov 18, 2012

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    Related Experiences

    Like many of you I really like wearing dresses. My favorite is an a-line bodice with short sleeves and having a full skirt. I cherish the task of having to zip up the back of my...
    deleted deleted 26-30 9 Responses Apr 5

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    Been a long, long time since i was a 'boy' but I remember how much I loved to play after school with the girls in my neighborhood wearing the play dresses my mom made for me. I was...
    AlbertSAT AlbertSAT 66-70, M 3 Responses Apr 12

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    So tonight my parents went out of town so it was a total girls night for me. I've been trying to wear panties everyday for about a week now, so today I was already in my cute...
    CDcarly CDcarly 22-25, M 6 Responses Mar 29

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    No more dresses for me !? Mistress does not want me to wear dresses any more. She wants to be able to see my lingerie, she does like my leather dress, so I am not without a...
    Plugslave Plugslave 31-35 3 Responses Apr 13

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    Little girls with long long long hair love to wear 2 ponytails any height with hair bows– and they also love to put little boys long long long hair up in 2 ponytails any height...
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 5 Responses 5 days ago

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    talk to me anyone who likes wearing cute or sexy dresses ;)
    ilikepugs ilikepugs 13-15, M 2 Responses 2 days ago

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    I LOVE dressess. l'm a little dress obsessed :P
    NightOwlGirl NightOwlGirl 18-21, F 4 Responses Mar 28

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    All your sissy's are too much. Girls dont talk about what kind of panties or bra's they are wearing. I think its so funny listening to you all brag about how wonderful it is to...
    jennylee911 jennylee911 41-45, F 4 Responses Apr 9

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    Not always. But sometimes I'd like to dress sexy. Tight short dresses are my favorite, some of them reveal my lingeries. (as you can see below) So I enjoy to see how peoples' react...
    Canaria Canaria 22-25, F 19 Responses Apr 12

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    I'm a guy but I like to wear dresses they are comfortable and nice tell me what you think
    changegender changegender 16-17, M 1 Response 4 days ago

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    I am thinking about wearing a blue jean pencil skirt on a road trip from SD to DEGA in 2weeks it takes us 18 hrs to do the trip. It would be three of us my 40 year old son and his...
    jerbare jerbare 56-60, M 3 Responses 6 days ago

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    Just been out for a lovely meal on holiday wearing a dress and heels that cost next to nothing and lots of people wanted to know which designer shop I bought my dress in I haven't...
    girlynicole girlynicole 36-40, F 1 Response Mar 27

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    I'm a 52 year old man and have been crossdressing since I was about 7. I would much rather wear a dress that pants and a belt. Like most men my age I've got a bit of a "belly" and...
    hotgarters hotgarters 46-50, M 2 Responses 13 hrs ago

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    Love them so much!! Love the free feeling especially with no panties on 😊
    Sweetheart126 Sweetheart126 16-17, F 8 Responses Mar 31

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    Today I went out in a short black pleated skirt, thigh highs, black thong and my black high heel boots. I love the feeling when the wind lifts it up a little. Walking through the...
    chase6069 chase6069 36-40, T 5 Responses Apr 2

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    today is my off I am enjoying my short skirt at home
    girlyboy83 girlyboy83 31-35, T 6 Responses Apr 3

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    The poor country pastor was livid when he confronted his wife with the receipt for a $250 dress she had bought. "How could you do this!" he exclaimed. "I don't know," she wailed...
    jml2000 jml2000 56-60, M 3 Responses Apr 3

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    so in 2 weeks i'm going out again. i've set myself the following tasks to complete whilst hopefully passing as a woman (i) visiting a particular tourist attraction , and having my...
    donnaka donnaka 36-40 6 Responses Apr 15

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    Ok. I don't mind if boys wear summer skirts. Good luck to them! I like summer skirts because they are so cool. I am wearing one tonight.
    deleted deleted 26-30 3 Responses 3 days ago

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    Is it just me or do the ladies at church wearing dresses look very gorgeous!? Call me old fashion but I think women should dress like that all the time- None of this sweatpants to...
    EngineerGuy777 EngineerGuy777 26-30, M Apr 6

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    My mom is a single parent raising my sister and I. There were times I needed some underwear and my sister give me hers to wear. After couple times I feel attach to the feeling of...
    Sissycolleen Sissycolleen 36-40, T 1 Response 6 days ago

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    I love that the weather is getting warmer and I get to see more women wearing skirts and dresses, showing off their beautiful legs. Makes a man's mind rage with questions and...
    avgjoe71 avgjoe71 41-45, M Apr 6

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    On the whole, I prefer a skirt and blouse. I think it's more fun to undress someone you are seducing when there are more garments. I also love the half-dressed look, whether top or...
    tyrihans45 tyrihans45 66-70, M 7 Responses Apr 14

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    I Boys dressing nicely in all types of girls shorts pants skirts tops and dresses
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 2 Responses a week ago

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    I prefer wearing skirts! I am having trouble finding a dress and bras my size
    ChessiSometimes72 ChessiSometimes72 51-55, M 2 Responses 4 days ago

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    I love dressing up and wearing either a short dress or a short skirt and a beautiful blouse. I love wearing hose and high heel shoes.
    singleredheadfemale singleredheadfemale 41-45, F 4 Responses Apr 10

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    I once heard of a boy who wore a skirt to school. He was in trouble at school but good luck to him. We have to wear skirts except if it is very cold.
    deleted deleted 26-30 2 Responses 3 days ago

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    Hey there :) I'm a 27 years old guy who would like to talk to girls about crossdressing. I like to wear dresses and skirts when nobody is around. But I also need some advice in how...
    johnthomas12 johnthomas12 26-30, M