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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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    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...
    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...
    annemarielongueuil annemarielongueuil 41-45, F 2 Responses Jan 31, 2013

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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 longย trousers only. A group of...
    tartanpleats tartanpleats 61-65, M 3 Responses Oct 25, 2013

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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...
    Charlesea Charlesea 70+ 2 Responses Mar 21

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    Matching His'n'hers - I noticed this picture (top)ย on another site but I have no idea what's going on apart from it's obviously an Irish dancing competition/display of some...
    tartanpleats tartanpleats 61-65, M 12 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...
    annemarielongueuil annemarielongueuil 41-45, F 8 Responses Jan 31, 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...
    Goatsfortwoweeks Goatsfortwoweeks 36-40, M 2 Responses 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...
    Jimknickers Jimknickers 61-65, M 2 Responses Jan 2, 2012

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    How About Wear A Dresses To School Abd Even Being The Prom Queen - ย  My son, the prom queen:Transgender student, 16, dressesin drag for big night... and mother does his make-up...
    annemarielongueuil annemarielongueuil 41-45, F 9 Responses Jan 29, 2013

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    Related Experiences

    One Sunday I wore a purple dress to church. It was nothing special but it looked nice. After church we went into the Commissary to get a few groceries. We were checking out when I...
    SweetMae SweetMae 56-60, F 27 Responses Mar 21

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    Love dresses! ๐Ÿ’œ I grew up in a family mostly of ladies. I was 6 when I was put in my first dress by my cousins. I was embarrassed then but I really liked that experience. Since...
    sissyyumi sissyyumi 22-25, M 5 Responses a week ago

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    I'm loving the short skater style skirts at the moment. I have several in different colours. They are lovely to wear but also a little risque, especially when it's a bit breezy and...
    karenhobbs karenhobbs 26-30, T 4 Responses Apr 1

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    I love dressing up as a schoolgirl, pleated miniskirt, blouse, and knee socks!
    schoolgyrlKaren schoolgyrlKaren 41-45 8 Responses Apr 6

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    is there any better feeling in the world than standing outside on a breezy day wearing a dress or even a skirt with wee cute panites on and just letting the wind blow them up to...
    Pjstuart Pjstuart 26-30, M 8 Responses 4 days ago

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    When i was at a friends I went to the bathroom amongst the dirty washing was his sisters skirt, i ******** off and put it on, it felt brilliant i had a little dance in the bathroom...
    mike020200 mike020200 16-17, M 5 Responses Mar 20

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    I love the way they feel when they hang off of me and swish around as I'm walking. But I also love the way a short skirt shows off my round buns when I bend over. My wife knows I...
    SamanthaLei SamanthaLei 46-50, M 2 Responses a week ago

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    When i was at a friends I went to the bathroom amongst the dirty washing was his sisters skirt, i ******** off and put it on, it felt brilliant i had a little dance in the bathroom...
    mike020200 mike020200 16-17, M 5 Responses Mar 20

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    Good I wear women's underwear pantyhose dress heels I love it
    astroboy4545 astroboy4545 61-65, M 4 Responses Mar 21

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 1 Response 6 days ago

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    I believe fathers, uncles, etc. of male appearance will have to start wearing dresses/skirts before boys will be able to. I hear the argument girls/women can wear pants, neckties...
    CdKimmi CdKimmi 61-65, M 3 Responses Apr 10

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    First off I am a girl. When I was 13 and getting ready for my confirmation my mom bought me my first pantyhose. My older sister showed me how to put them on. I wore pantyhose...
    trojan83 trojan83 26-30, F 4 Responses Apr 2

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    Every since I was in 4th grade I'd occasionally go into my sister's (who's 3.5 years older than me) bathroom to wear her underwear and (training) bras. Then when I was older in...
    BlackHedgehog24 BlackHedgehog24 16-17, M 2 Responses Apr 5

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    Of Petticoats and Parking Lots When I got married in 1987 the retro fashion of crinoline petticoats had just come into style. I loved the look and comfort of wearing three white...
    BadPam BadPam 51-55, F 3 Responses 1 day ago

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    So when I was very young, I knew I was meant to be a girl. Some say that when you are 2-3 years old, you are to young to tell what you are and many pass it off as a phase or like...
    Soontobegirl Soontobegirl 16-17 3 Responses Apr 8

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    Going green Using Olive Maid-matron of Beach Wedding Dresses honour Dresses-short environmentally friendly prom gowns A lot of practices concerning the classic bridal gowns have...
    flowydresses flowydresses 18-21, M Apr 9

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    Effeminate Sissy Boi who was always bullied and called names by jealous girls and mean boys. Sigh.
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 3 hrs ago

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    Since I was 12 I started dressing up, i stole some of my sister's dresses and heels I love how femenine and girly they make me feel but I can't tell anyone. My fantasy would be to...
    Girlyprincess1401 Girlyprincess1401 18-21, M 1 Response Mar 31

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    The common clothes i love to wear, i literally have a walk in closet full of skirts and dresses. My reason for loving to wear dresses is that it not tight on the body like jeans...
    NymNin NymNin 18-21, F 3 Responses Mar 19

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    My favorite thing in the world used to be wearing my sisters clothes whenever I was home alone. She was in college when I was in high school so you could imagine she had a lot of...
    isabellavegara isabellavegara 18-21, M 5 Responses a week ago

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    I love women that wear dresses and skirts. I love them because women look sexy and it excites me. I love how the dresses fit on their body, plus it is easy access.
    2014lover1 2014lover1 22-25, M 1 Response Mar 22

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    Spring is almost here! I want to go shopping for spring / summer dresses and skirts. What will be the best styles to buy this year, I wonder.......
    karenhobbs karenhobbs 26-30, T Mar 28

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    I thought a guy who was 24 years old would be more mature than the boys my age. I'm so tired of all talk and no action. I thought you were different, but I was wrong. There's a...
    Rachellie Rachellie 18-21, F 1 Response 3 hrs ago

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    I do in summer! I was wearing shorts under my dress in case I wanted to mess myself. I was walking my dog and I had the big urge. While my dog was owing, I stood there and messed...
    loveylaura loveylaura 26-30, F 2 Responses 3 days ago

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    My favorite skirts are my schoolgyrl plaid skirts. I have a red, pink, green, and kaki.
    schoolgyrlKaren schoolgyrlKaren 41-45 2 Responses 6 days ago

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    I love to wear a skirt when I get the chance, it's such a welcome change from wearing trousers all the time. When I'm at home on my own I love putting on one of my short pleated...
    Julie957 Julie957 51-55, M 10 hrs ago

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    I want to try wearing skirts but I cant :(
    lostgirlboy lostgirlboy 22-25, M 1 Response Apr 5

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    Yes I do.. Very much so. I love to show off my long sexy legs in short skirts. I do have some long skirts but don't wear them all that much. Most of the time I'm wearing a short...
    TiffanyMarieLeggs TiffanyMarieLeggs 51-55, T 2 Responses 4 days ago

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    Springtime is almost here! I love warm weather and a short or mid length skirt is the perfect thing to wear on a warm breezy spring day. I love having my legs un-covered after...
    shygirl214 shygirl214 18-21, F 5 Responses Mar 24

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    Do u ever wish u could go back to school and re-create for real your fantasies? How many of u have sat in a class admiring the teacher more than the subject ? I had a crush on my...
    Sandyshaw13 Sandyshaw13 36-40, F 2 Responses Mar 21

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    I never knew my father. My mother and her sister lived together in a two bedroom home. Her sister had a daughter a few months older than myself. She and I shared a bed from as...
    burkaboy burkaboy 26-30, M 1 Response 5 days ago

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    I love wearing any colour dresses. My fav colour for dresses is Pink.xxx๐Ÿ‘—๐Ÿ‘—๐Ÿ‘—๐Ÿ‘ง๐Ÿ‘ง๐Ÿ‘ง๐Ÿ˜Š๐Ÿ˜Š๐Ÿ˜Š
    babyannie57 babyannie57 56-60, M 4 days ago

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    as a former pediatrician, i see the genuine need for the united states FDA to approve Androcour, also known as cyprotone acetate, or siterone, for it's wonderful testosterone...
    drlucy2 drlucy2 56-60, M 2 Responses 1 day ago

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    When I was about 7, my brother and I received one gold chain each as a gift from a close family friend. Our parents thought that we were too young to wear something so valuable so...
    deleted deleted 26-30 6 days ago

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    I wear it almost like muslim women wear theirs. I'm not muslim but, I have read the Quran before and think that its a great piece of clothing. I wear it for the same reasons in a...
    reeree2012 reeree2012 22-25, F Mar 24

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    Today I was able to get off work early and wear my skirt and boots. I wore the skirt in my truck and hid it when running errands. Still skittish about being open with a skirt...
    shadowplt shadowplt 46-50, M 3 Responses Mar 26

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    The other day I was wearing some nice work clothes, hose and scrub shoes. My wife commented that the shoes were too casual for my attire. Went to breakfast then looked at what I...
    shadowplt shadowplt 46-50, M 1 Response Apr 8

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     There are a lot of various clothes especially the long sleeve dresses emerged in the market. Long sleeve dresses are popular with an ocean of females at present, and I...
    cabrielking cabrielking 18-21, F Apr 9

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    The shorter the better. I have a collection of schoolgirl skirts, and I wear them mostly with kneesocks, and tights at times.
    schoolgyrlKaren schoolgyrlKaren 41-45 4 Responses 6 days ago

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    Been wearing my flat boots and skirt to work in the past week or so. No one has said anything. Of course I have on guy pants and shirt, but the boots are definitely not "male...
    shadowplt shadowplt 46-50, M 13 hrs ago

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    Today I'm wearing a tight red dress, it is such a great fit and look lovely. I really like the tight clingy look and look forward to seeing my friends reactions :) My only worry...