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I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 414 People

    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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    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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    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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    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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    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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    Ok

    Perfectly fine as long as he has underwear on
    Articchill32 Articchill32 31-35, M Jan 3, 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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    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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    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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    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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    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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    aqww aqww 13-15, M 3 Responses Jan 27

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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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    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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    Related Experiences

    I also wear dresses & skirts, I'm sat in hotel room, wearing red skirt, stockings and panties. Tomorrow I intend going into town and buying a LBD.
    simonsteane simonsteane 46-50, M 3 Responses 5 days ago

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    omg...... I live at home with my brothers and mum and I like wearing my school dress witch I brought online at home and no one knows I sometimes walk out in public wearing it and...
    imcool2002 imcool2002 13-15, M 2 Responses May 9

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    I just loves every single thing about wearing a dress. Girls grow up wearing dresses as a a formality that turns many women off to wearing a dress, but I can't see how anyone would...
    CDcarly CDcarly 22-25, T 2 Responses 5 days ago

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    Do you love wearing dresses and skirts and what color are they do you haveLong or really long hair and do you wear plain or fancy hair clips hair barrettes bobby pins flowers and...
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 7 Responses a week ago

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    I do like wearing dresses but also shorts now that it's so warm out. Next it's the beach.
    jusleaving jusleaving 18-21, F 2 Responses May 12

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    My first time wearing a dress was when I was 14. I put on a black dress with stockings. I knew then I was different and had a female side. I enjoyed more and more as I started...
    bmg1kel bmg1kel 61-65, T 3 Responses 2 days ago

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    talk to me anyone who likes wearing cute or sexy dresses ;)
    ilikepugs ilikepugs 13-15, M 10 Responses Apr 24

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    Ive never seen a girl whi acctually enjoy teasing guy with there mini skirts and no panties if u line that messege me i wanna hear stories about it
    joeslincer17 joeslincer17 18-21, M May 1

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    Oh how i love Pencil Skirts!! the feeling of the material hugging tight to my body. I love how they make me feel almost trapped in them. i love to wear a tight fitting stretch top...
    deleted deleted 26-30 May 9

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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 Apr 22

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    None of them fit me properly and when I go shopping for dresses it makes me feel terrible about the way I look.
    23fly41 23fly41 16-17, F 1 Response 1 day ago

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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 5 Responses Apr 26

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    I do. Call it old fashioned. Or girly. Or a desire to be just a little sexy, but I like wearing them. I am so glad spring is here!
    pinkcorsetgirl pinkcorsetgirl 41-45, F 17 Responses Apr 30

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    I don't think many are open minded. Sometimes I just want to give it all up. It gets so tiring fighting the pregudices
    beyerswede beyerswede 61-65, M 11 Responses 6 days ago

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    The second my house is empty I put on my gaff, then some sexy lingerie and a dress. I'm at my happiest when I'm walking around in a tight sexy dress. X
    HaileyPenny HaileyPenny 18-21, M 4 Responses 2 days ago

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    So tomorrow was going to be a day out with a dressing service. and like a small child at Christmas , i was counting the sleeps till it happened . And wot? Today I get a message...
    donnaka donnaka 36-40 8 Responses Apr 27

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    So I made myself pretty , and went to the library:- new photos , friends only.
    donnaka donnaka 36-40 1 Response Apr 29

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    If anyone want to give me advice I want to start dressing like a girl
    deleted deleted 26-30 4 Responses May 5

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    for those of you who have noticed I've been asking for cross-dressing challenges, today(i) had coffee and a ciabatta in a cafe(ii) then went to a ticket office , where the "thing...
    donnaka donnaka 36-40 14 Responses May 6

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    Look at my dress 😍😍😍...I'm sorry but when it comes to a cute dress. I will buy it no matter how short it is.
    ANNI3PI3 ANNI3PI3 16-17, F 10 Responses May 8

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    Just some more new stuff, love my new clothes, I need more clothes and sone make up also a wig
    ArejayakaRegina ArejayakaRegina 22-25 6 Responses 4 days ago

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    First warning. Between 1959 and 1967, I attended a boys-only state grammar school, at which corporal punishment was commonplace. This usually involved the miscreant being called to...
    gunner64 gunner64 66-70, M 16 hrs ago

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    First warning. Between 1959 and 1967, I attended a boys-only state grammar school, at which corporal punishment was commonplace. This usually involved the miscreant being called to...
    gunner64 gunner64 66-70, M 1 Response 15 hrs ago

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    When I go out always use dresses or skirts (except for a few days every 28 days haha:c) I love wearing jeans and high heels,but what I love the most is feeling super girly and...
    HappyWife16 HappyWife16 18-21, F 2 Responses May 5

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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 Apr 23

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    A couple months ago i mentioned to my wife that I was curious about expanding my pantyhose wearing to skirts and shoes. She didnt seem to keen on the idea but said ok. A couple...
    curioustxn curioustxn 36-40, M 2 Responses 1 day ago

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    When I am at work I am usually wearing a skirt and a blouse. I love wearing dresses when at work too. I include hose and high heels. When not at work I am very casually...
    mominoffice mominoffice 26-30, F 2 Responses May 3

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    First warning. Between 1959 and 1967, I attended a boys-only state grammar school, at which corporal punishment was commonplace. This usually involved the miscreant being called to...
    gunner64 gunner64 66-70, M 1 Response 1 day ago