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I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 387 People

    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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    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 Dec 15

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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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    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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    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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    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 10 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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    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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    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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    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 1 Response Nov 21, 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+ 2 Responses Mar 21

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    Related Experiences

    As a transgendered Catholic boy who was forced to grow up male, I remember my first communion and wanting so desperately be one of the girls dressed in a beautiful communion dress...
    tessoconn tessoconn 18-21, F 2 Responses Dec 2

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    Yes I love wearing dresses. They are so liberating. My feminine side can be herself. Not shoved into pants. Rather being the classy lady that she is.
    Adam59 Adam59 56-60, M 2 Responses Nov 26

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    I have always enjoyed wearing feminine clothes and makeup but only to relieve myself. And when I am done with that I usually remove all the makeup and feminine clothes. Now when I...
    sexysissy11 sexysissy11 18-21, M 4 Responses Dec 16

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    My style has become progressively more feminine over the last few years. In some ways at odds with that is my continued disinterest in the sort of embellishments I loved as a teen...
    morea morea 22-25, F 2 Responses Dec 1

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    I hate wearing skirts ever since my step dad started touching me so no I don't like them
    cattie1283 cattie1283 18-21, F 3 Responses Dec 8

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    I am a 14 boy that likes to wear skirts and dresses and all girl clothes I'm not going to tell anyone. Well I've told a few really close friends and one of them gave me a skirt. I...
    smallfry14ify smallfry14ify 13-15, M 2 Responses 4 hrs ago

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    I've been wearing this one all afternoon.I dared myself and ventured out, TWICE!It was my first time out dressed in the day time.I went to the local RedBox outside the local...
    JosetteLaRoc JosetteLaRoc 36-40 5 Responses Dec 9

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    I try my best not to dress like a woman. I can can keep it under control for a month maybe two. But there isn't a day that goes by that I don't think about it. Eventually the...
    chrissyk48 chrissyk48 46-50, M 9 Responses Dec 13

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    Just put in an order for this amazing dress from the Ashley Roberts Key collection.. I cant wait for it to come. You gen girls are so lucky to be able to buy these dresses and wear...
    cdlovingguy cdlovingguy 31-35, M 6 Responses Nov 30

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    I just had a once-in-a-blue-moon opportunity... I recently visited a local thrift shop and to my excitement I discovered on the dress rack a figure skating dress just about my size...
    Roccondil Roccondil 22-25, M 6 Responses Dec 17

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    I have long legs and have always loved wearing miniskirts! With or without anything on underneath ;)
    BlazerFan BlazerFan 36-40, F 17 Responses Nov 29

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    I've been wearing this one all afternoon.I dared myself and ventured out, TWICE! Once was through a drive-thru to get a bite to eat. The other was to the RedBox outside the local...
    JosetteLaRoc JosetteLaRoc 36-40 7 Responses Dec 9

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    i love to go out fully dressed as a woman with heels, wig, makeup and whatever dress or skirt I fancy that day.
    nikkitran nikkitran 51-55, T 8 Responses Dec 9

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    Christmas day...The 1st dressed as Amber now the truth is out, New leather dress black stockings and high heels, but stillcooking the Christmas dinner, Dress so good you can clean...
    amber8642 amber8642 51-55 3 Responses 19 hrs ago

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    I love dressing up as a girl when I go out
    TheGrandPoobah TheGrandPoobah 13-15, M 2 Responses 1 day ago

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    It so happens that there was a long time before my opportunity to go out a 4th time. But in the summer my wife was going away for a week-end. I was so excited!! I shopped around...
    donnaka donnaka 36-40 3 Responses Nov 27

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    Found this pretty dress at goodwill.
    jazz2013 jazz2013 56-60, M Nov 30

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    Panties, hose, bra, eye makeup and lipstick and off shopping. Pretty dress at home.
    jazz2013 jazz2013 56-60, M 3 Responses Nov 30

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    Headed out on an adventure tonight. Next stop is Payless for a new pair of shoes.
    CDKristiK CDKristiK 51-55, M 8 Responses Dec 5

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    I'm a girl, to be honest with everyone here. I love to get on this experience page and read what you all have gone through. This is a truly amazing and inspiring section you all...
    Emilia0659 Emilia0659 18-21, F 14 Responses Dec 6

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    I love wearing dresses and skirts. I feel like I'm expressing the real me when I do.
    Nyssa59 Nyssa59 51-55, T 9 Responses 2 days ago

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    Some learners at Centennial Substantial School have shaved vertical traces into their eyebrows inside a trend a short while ago designed common by hip-hop star Soulja Boy. School...
    Anthony6913uep8 Anthony6913uep8 31-35, M 1 Response Dec 14

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    This may sound cliche but I hated high school because of a boy.I thought I loved him,but I was completely wrong.It all started my freshman year.He was a sophomore who was second...
    Katherine27 Katherine27 22-25, F 1 Response Nov 27

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    To this day I still think of the horrors that happened in middle school. I hated how I was the only one people picked on because I suffer traumatically from it. I understand that...
    WeirdOtaku WeirdOtaku 18-21, F 41 mins ago

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    ...some days I feel very self-conscious about going out in mini-skirt and tights. (See my photos), but I have noticed a great difference between the attitude of the French compared...
    dambust3r dambust3r 46-50, M 1 Response 5 days ago

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    Yes it is time for men and boys dresses and skirts. At the least have them in the men's clothing section. That won't happen until more and more men appear in public wearing them...
    Adam59 Adam59 56-60, M 1 Response Nov 26

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    When i was at school cane was frequently used in school. If it is carried inside our class we girls have to lift our skirts after bending over teachers desk ,for...
    mellisa222 mellisa222 51-55, F 1 Response 2 days ago

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    In my prep school the headmistress decided that all the pupils must wear the girls' regulation school uniform and p e kit . There were only a few boys in each class . They all...
    nickycherub nickycherub 46-50, F 4 Responses a week ago

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    When the headmistress at my prep school had the boys and girls wearing the same uniforms,she had knicker inspections in the morning and afternoon. We had to stand up a row at a...
    nickycherub nickycherub 46-50, F 1 Response 4 days ago

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    ... I've got a couple of minutes to tell you a little more about my 'public wear'... as i was saying in my last post - i wear mini-skirts and tights every day, out and about. I'm...
    dambust3r dambust3r 46-50, M 1 Response Dec 16

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    Im a 18 year old boy who has just finished high school. Ive always loved the idea of wearing girly clothes as they are often really cute and nice.. im always checking girls out but...
    Giles2142 Giles2142 16-17, M 1 Response 1 day ago

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    Hi let me share my story on high heels. I love wearing high heels from my teens. I'm addicted to the height power and dominating authority i feel on top of two ultra skinny steel...
    sajeesmiles sajeesmiles 31-35, F 7 Responses Nov 30

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    I've always wondered why. Ever since I was a small child I was told that it was okay for a girl to wear "boys" clothing but that it was completely and utterly wrong for a boy to...
    Unapologeticallybrilliant Unapologeticallybrilliant 13-15, F 1 Response 2 days ago