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I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 396 People

    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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    Ok

    Perfectly fine as long as he has underwear on
    Articchill32 Articchill32 31-35, M Jan 3, 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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    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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    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 3 Responses Jan 2, 2012

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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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    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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    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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    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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    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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    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 2 Responses Nov 18, 2012

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    Related Experiences

    I love wearing dresses and skirts.
    Cdallaslover99 Cdallaslover99 13-15, M 5 Responses Sep 3

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    I love wearing dresses and having gone out to experience
    luvpanties60 luvpanties60 31-35, M 14 Responses 3 days ago

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    I wish constantly I was female so I could wear dresses and skirts all the time. I wear them as a C D every chance I get and just love how I look and they feel.
    Janae60 Janae60 51-55, M 5 Responses Sep 6

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    Just the other day I saw a lovely little lady in Walmart. It was a hot day and she was wearing a floaty mini dress with a low back, down to her waist and very thin straps over her...
    MarieJosephe MarieJosephe 66-70, M 10 Responses Aug 27

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    I always wear dresses cuz I'm to lazy to match my pants and shirts lol
    lovelypoison44 lovelypoison44 16-17, F 4 Responses 19 hrs ago

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    My time, I add panties ,. nylons or hose wearing a dress is totally for comfort. Not to pass as female (as I never could) the FEELING of women clothes don't hurt skin as I have...
    squeekers2 squeekers2 56-60, M 2 Responses 2 days ago

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    All the time now, except at work. My favorite dress ATM, is floral, tight around the bust, with spaghetti straps, and flowing at the bottom. So comfortable!
    deleted deleted 26-30 7 Responses Aug 26

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    I have just started writing a new blog chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the...
    deleted deleted 26-30 Sep 5

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    My first dress that I ever wore is still my absolute favorite dress! I was 12 years old and went into my parents room and into my mom's closet. There it was a beautiful white Mrs...
    allgirlallthetime allgirlallthetime 56-60, T 4 Responses Aug 29

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    I have just started writing a new blog chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the...
    deleted deleted 26-30 3 Responses Sep 5

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    Love to dress up in tights and skirt with nice top almost anything girly love been girly wish was more feminine I am in away I guess but don't like the idear of getting older :(
    boytightslover boytightslover 22-25, M 5 Responses Sep 9

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    Irán a Daymond Vaše želanie sa splnilo v južnej Kalifornii! Nebolo suchého oka u všetci pozvaní na Irán a Daymond obradu. http://www.zhdresses.org Bolo krásne slnečn...
    orologiomegarepliche orologiomegarepliche 22-25, M a week ago

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    Apart from shorts, I have only been wearing dresses or skirts since I was 8 or something. And apart from the fact that my husband does not want to see me in trousers, I like...
    Susanna3 Susanna3 31-35, F 7 Responses Aug 21

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    My parents buy me dresses skirts tights pantyhose makeup bows for my long hair and heels
    tomgirl7499 tomgirl7499 18-21, T 2 Responses Sep 3

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    I just got my first skirt! Right now I'm sitting in my room doing homework wearing a skirt and panties, with my legs freshly shaven and a nice new coat of a royal purple nail...
    jjthom jjthom 22-25, M 1 Response 2 hrs ago

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    Why I Love Fullslips Every woman's body is different. Some have the perfect shape for skirt and sweaters, others are better served by dresses. I am one of the latter. As much...
    slipgirl274 slipgirl274 61-65, F 1 Response Sep 2

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    i love skirts and dresses but in high school people call you easy and the pervs try and get behind you on the stairs
    kkkeeennnzzz kkkeeennnzzz 13-15, F 3 Responses Sep 4

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    My school friends areYazmin (Monkey)Shannon (Nemo)Jack (Chad)Katelyn (Dillo)MaggieThere not all like my friends...But i think theyd be considered my friends.Yazmin is my neighbor...
    KovusShame KovusShame 13-15, F 1 Response Sep 8

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    I like to wear dresses or skirts - and preferably short ones - as often as I can. Partly because I like to feel - and look - feminine - and because my husbands loves to see me that...
    Susanna3 Susanna3 31-35, F 4 Responses Aug 20

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    This has to be one of the worst and unchallenged stereotypes ever. Just because a boy is feminine, it has nothing to do with his sexuality. It's been my privilege to know many...
    MrsJoanieBNH MrsJoanieBNH 56-60, T 5 Responses Aug 25

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    Yes, It happened again. Yesterday night, the temperature was good and I proceeded to go roller skating wearing nothing else than one of my skating dresses. I choosed my very small...
    Nadia1977 Nadia1977 36-40, M Aug 24

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    Went to Lane Bryant today looking for a skirt. Found two long skirts: one in black and one in navy. It was the pre Labor Day sale and the skirts were 60% off. Had to buy both...
    jml2000 jml2000 56-60, M 3 Responses Aug 28

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    I agree my sister dresses me before school every one thinks im a girl and i even use the lady's room and i like being a girl
    tomgirl7499 tomgirl7499 18-21, T 2 Responses Sep 3

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    When I was 12 I used to attend karate practice for a couple of hours every Tuesday night. Practice would normally last for a couple of hours, I would attend with my friend Gary...
    tbar147 tbar147 22-25 a week ago

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    I had been working this summer at the rental office of an apartment site owned by my aunt. I always dress nicely for work (as well as school!) and this day I was in my newest white...
    lookingmybest lookingmybest 16-17, F 1 Response Sep 3

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    It's Becoming More & More About Humiliation http://news.nationalpost.com/2014/05/30/quebec-teen-shamed-for-jean-shorts-becomes-latest-in-wave-of-students-protesting-dress-code...
    deadmoon deadmoon 18-21, F Sep 4

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    I think I do..... For about a year or so, with the exception of my school uniform, that's all I've worn.... I'm so used to them now that it feels strange not wearing one...
    SarahTheHooker SarahTheHooker 18-21, F Aug 20

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    So, to day was my last picture day, and I decided to wear a pretty white dress it's so cute, and perfect for summer! I never wear dresses but, I love them I really want more.
    Vannarose Vannarose 16-17, F 1 Response Aug 20

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    I luv women wearing pantyhose...especially when she wears a pair of sheer tan/nude pantyhose that aren't of the control top variety! If you're lucky your wife or gf will wear...
    booyah73 booyah73 41-45, M 55 mins ago

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    It may sound silly but I'm scared of wearing a two piece swimming suit.It started last summer when I went to the pool with my friend Carla.At the time I was wearing a two piece...
    AnaKona AnaKona 13-15, F Aug 24

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    I was in the locker room after school, just playing around and stuff. This senior boy was really good looking. He came in to shower after practice, and left all his clothes sitting...
    RomanNZolanski16 RomanNZolanski16 26-30, M 4 Responses Aug 26

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    Im only 5'5 and my sister is to when ever she doesn't like her clothes i get them and get really cute dresses
    tomgirl7499 tomgirl7499 18-21, T Sep 3

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    While I like the feel and comfort of wearing a skirt, I like watching American football even more. I may be a guy in women's clothing, but I'm still a football guy Tomorrow...
    shadowplt shadowplt 46-50, M 3 Responses Sep 4

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    I just find them so comforting and exhilarating. As you can read in some of my other stories, it began with bras as a pre-teen and grew slowly over the years. Now that I live on...
    LockedDarius LockedDarius 26-30, M 2 Responses Aug 21

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