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I Boys Wearing Dresses And Skirts To School

Personal Stories, Advice, and Support 397 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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    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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    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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    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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    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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    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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    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 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 6 Responses Jan 31, 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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    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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    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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    Related Experiences

    Wearing dresses make me feel more feminine
    KinkyKatieLouise KinkyKatieLouise 46-50 6 Responses Aug 13

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    OK... Google the phrase "shopping tunic", then click the "shopping" tab. You'll see that pretty much all the results are for "women's tunic dresses". Then search "gladiator sandals...
    steve66oh steve66oh 46-50, M 6 Responses Aug 11

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    I have worn dresses or skirts since i was 6 but i would love to live in a world where a boy can wear them openly instead of having to be called a cross dresser. i hope that day...
    jamie172 jamie172 46-50, T 9 Responses Aug 4

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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 8 Responses 4 days ago

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    I can't wait to get home from work and get out of my work clothes. I take a shower and shave all my body hair. I then get out and lotion all my body. Then I pick out panties and...
    Michelle1976 Michelle1976 36-40, T 6 Responses Aug 16

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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 10 Responses Aug 1

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    Got to wear a dress an entire afternoon and evening after work on two days this past weekend... It was so nice. Since my family was out for the weekend I didn't have to worry about...
    Roccondil Roccondil 22-25, M 9 Responses Aug 7

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    I wear a dress as often as possible. It's such a free feeling. You don't have to wear underwear if it's not see thru. I love the way they look, especially the long ones that are...
    jaylow13 jaylow13 36-40, F 2 Responses Aug 18

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    When I was a teenager I loved wearing miniskirts. In fact I used to wear them as much as possible in preference to jeans, etc. to show off my legs. My mum used to let us wear...
    Jilly53 Jilly53 56-60, F 1 Response Aug 14

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    Isn't it amazing that a single moment in time can flip a switch inside of us and nothing is ever the same? I can think of a hundred things that might have affected me in a...
    kayleew2000 kayleew2000 18-21 14 Responses Aug 16

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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 6 days ago

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    I have several mini's. Love them all. This one I wore yesterday when I went to town. Did some shopping and visited the doctors office.
    Brandie1960 Brandie1960 41-45, M 6 Responses Aug 13

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    I wish I could be Abby all the time
    abbyseaney abbyseaney 16-17, T 7 Responses Aug 5

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    I'm going to be posting and sending nude pics or will be on Skype so add me kik: missjazzmin Skype: misscrossdresser
    missjazzmin missjazzmin 18-21 2 Responses Aug 11

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    Lately with a pair of black leggings. I must admit my legs look great in them.
    deleted deleted 26-30 2 Responses Aug 13

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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 3 Responses 2 days 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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    I'm Pentecostal so I have my reasons. Besides my religion, I enjoy wearing dresses and skirts instead of pants. Pants are so uncomfortable.
    PeaceBatman PeaceBatman 22-25, F 5 Responses Aug 16

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    I was on holiday last year at Morfa Dyffryn near Harlech and staying at the campsite near the beach. One afternoon, myself and my family (mum, dad and older brother) were on the...
    xemmaammex xemmaammex 18-21, F 5 Responses Aug 6

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    A little conversation with my 3 year old daughter the other day. She was wearing a pretty little dress, spinning round so the skirts puffed out. She looked so cute. She turned to...
    Heellover Heellover 36-40, M 9 Responses Aug 8

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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 4 Responses Aug 1

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    Dressed my best friend in a dress today and he did not look gay he looked quite nice to be honest I hope he wears it more and more and I don't know why guys can't wear skirts or...
    honeypettle honeypettle 36-40, F 3 Responses Aug 3

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    I loved wearing miniskirts as a teenager and a young woman. I wore them in preference to jeans or trousers where possible. However, they did have their own hazard! One day, when we...
    Jilly53 Jilly53 56-60, F 5 Responses Aug 16

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    I love to dress up and wear short dresses and skirts with a nice looking blouse or top. Also, I love to wear shorts and swimwear with hose and four inch high heels on.
    tammylynne tammylynne 41-45, F 8 Responses Aug 10

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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 6 Responses 6 days ago

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    I really do! They're so comfy and a great substitute to dresses and skirts for me who isn't really the girly type! Perfect for summer
    Sasha0827 Sasha0827 16-17, F 3 Responses Aug 2

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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 a week ago

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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 3 days ago

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    Back in high school I would wear shorts on the winter but I'm excited for this winter to stop wearing shorts and start wearing skirts! Also I usually hate winter and the snow but I...
    Alexis117 Alexis117 18-21, T 1 Response Aug 6

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    Back in June I had written my first story in this group about how my skirt experiences got started. I mentioned how my wife reacted when I told her about this. I had not expected...
    Myotheridentity Myotheridentity 46-50 2 Responses Aug 7

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    I attended a mixed gender school and discipline was strictly enforced at our school, especially with regard to the uniform. The compulsory uniform for all boys until Grade 10 (age...
    Bintobox Bintobox 46-50, M 4 Responses Aug 13

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    Wearing some sexy lacy panties underwear my trousers at work today. Shh. No one knows!
    LoveWearingTights LoveWearingTights 22-25, M 4 Responses 5 hrs ago

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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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