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I Went To School Dressed As A Girl

gone to school dressed as a girl, either secretely or openly 415 People

    I Just Couln't Do It...but I Wanted To!!

    To start with, I have never told anyone- even my wife of 39 years- this story...not sure why I'm telling it now...  I guess after reading some of the stories here on this site I feel like I can get this off my chest.  (even though I do believe some of the stuff I have read is...
    gellis gellis 56-60 6 Responses Jan 7, 2012

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    Band Initiation

    Back when I became a member of my local high school band, all freshmen had to participate in freshman initiation day. We were each assigned to an upper classman who picked the "costume" we had to wear on initiation day. Mostly, for boys at least, it involved coming to school...
    jere51 jere51 51-55, M May 11, 2011

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    My 12th Birthday

    Children can be so cruel and my school days were not happy times. It wasn’t because I’m handicapped because I attended a school for disabled kids. The other boys and some of the girls ridiculed me for a variety of reasons, having big ears was one of them. For some reason I...
    betty3100 betty3100 51-55, T 6 Responses May 30, 2011

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    Senior Year

    I was a Senior in High School, and it was "SPIRIT WEEK", the week before the homecoming football game and dance. There was Powder Puff Football, where the girls played flag football and the players were cheerleaders. Well, I borrowed a letter girl outfit (letter girls were the...
    KandisTX KandisTX 41-45 2 Responses Feb 19, 2012

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    Sixth Grade Graduation Party

    At the time (50's) elementary school went through the sixth grade. The PTA moms wanted to give us a party as we were the first graduating group to spend all six years in the new school. However, there were school district rules that prohibited that. So they came up with a work...
    AlbertSAT AlbertSAT 66-70, M 2 Responses Apr 24, 2013

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    I've done it for Halloween.

    Dress, stockings, panties. Shoes. The whole nine yards.
    pardax pardax 13-15, M 3 Responses Aug 24

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    It Started In Hight School The First Day

    of the year we would ware matching out fits to school that day both me and my wife dressed as twins just to draw out the bullies
    rickibrat2 rickibrat2 61-65, M 1 Response Jan 8, 2012

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    The Worst Thing To Happen To Me...

    Well... It all started about a year ago when me and my sister Amanda (22) started getting along more. We usually talked on facebook about random stuff. Anywho, one day I brought up the topic of crossdressing. She asked me if I wanted to go shopping with her, sooo... nervously I...
    KaylinStrype KaylinStrype 18-21, M 12 Responses Feb 1, 2012

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    There was a story on the news just today about

    two guys at a school in Washington who went to school dressed like girls. This apparently occurred on Monday or Tuesday and the Principal called them in and gave them two choices; either change their clothes or get sent home from school. They chose to go home. But then the...
    tghubby tghubby 51-55, T 3 Responses Oct 17

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    What Fun It Was

    My freshman year at college, was the first time I went to school as a girl. Although I did attend a prom dressed in High School my first real adventure was in college. The fact is that as a very active t girl at 14 and not being able at that time to go to school as a girl...
    MiriamK MiriamK 56-60, T 6 Responses Jun 8, 2012

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    My One Girly Day

    i played football in high school they had a slave auction the girls that got me made me dress as a girl for the day
    spaz2692 spaz2692 46-50 Dec 14, 2011

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    Some Of The Best Times

    I had been wearing my mom and sister's panties since I was eleven and while that was pretty fun to do it soon was too much to wait every day for school to end for the short 45 minutes I'd have to myself before my sister got home. I eventually got brave and started wearing panties...
    chris76 chris76 31-35, T 1 Response Dec 24, 2011

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    I was 14 and auditioned

    for the my (all boys) school's annual play, this year it was Daisy Pulls It off. I thought it would be a fun way to meet new people etc. I auditioned and really thought I'd get a part as everything went well. A week later I went to the Drama notice board to find my name and as...
    BXT97 BXT97 16-17, M 5 Responses Dec 31, 2013

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    Looking Up The Dress part#1

    when i was in highschool i had the chance to look up a girls dress as a dare well i got caught by the teacher well i can tell you my mother was pissed on the way home we made a stop @ her hair salon she goes to have my long hair styled as a girl as they worked on me she left siad...
    maryyork50 maryyork50 18-21, T 8 Responses Nov 2, 2011

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    Related Experiences

    This is a photograph of me in a London hotel room a few minutes before I went out for a walk around Charing Cross Road and Leicester Square, including a visit to a bar in Lisle...
    clairemeredith clairemeredith 46-50, T 3 Responses 4 days ago

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    Cool Teen HairstylesA lot of options can be purchased there, with regards to haircut styles and ideas for girls. All of these hairstyles can't be practiced if you are in college...
    Ethan019p4koi Ethan019p4koi 31-35, M Nov 28

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    My only grammar school caning. I was a well behaved boy at grammar school but even the best behaved pupils could get the cane as I found out. I was in the fifth year and it was...
    LuckyPete LuckyPete 61-65, M 1 Response 1 day ago

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    And unfortunately I lost a best friend because of that. I was best friends with a very smart and mesmerizingly beautiful Korean girl in all of my middle school years and we were...
    CursedWithABlessing CursedWithABlessing 18-21, F 2 Responses Dec 2

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    I need the opinion of a girly girl. I have been debating for some time about getting some tattoos and maybe and eyebrow piercing for a while. I have always been more attracted to...
    DahliaSun123 DahliaSun123 18-21, M 2 Responses 18 mins ago

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    I do this at least once every year, where I go to school barefoot.In my kindergarten year it was fun. We had a pajama day, and that's the day I chose to go barefoot. So, that...
    Barefoot1999 Barefoot1999 13-15, M 4 days ago

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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 3 days ago

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    I went to the same school with this girl and we had always been acquaintances but not friends. when we were in 8th grade, we became super super close and she's now one of my best...
    unknownthoughts unknownthoughts 13-15, F 3 Responses Nov 29

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    Last year I was absoluty crazy about a girl (I still am). She is the most beautiful girl I've ever laid eyes on. She has these beautiful eyes that pierce into your soul. She is...
    Jessica4729 Jessica4729 13-15, F 2 Responses Nov 28

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    Not me as caning isn’t allowed in school now but my aunty Vi was telling me in the kitchen the first time she got the cane in school when she was about 13. She said that she and...
    Susanna96 Susanna96 16-17, F 4 Responses Nov 30

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    i hated going to school, i liked learning and i was a fantastic student but through most of my schooling i was made fun of because of my weight. i didn't really take care of...
    jbm1984 jbm1984 31-35, F 4 Responses Nov 30

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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...
    deleted deleted 26-30 2 Responses 4 days ago

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    I am a 14 year old white girl and for the past several weeks there has been this 14 year old black girl at school who has had her eye on me and has been checking me out almost...
    downbutnotout1 downbutnotout1 13-15, F 1 Response Dec 9

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    The Paddling Queue The other week we met another couple through a school engagement. I invited the lady, Marsha, who's a bit younger than me to have coffee with me. During the...
    Tina303 Tina303 41-45, F 3 Responses Dec 14

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    Trendy Hairstyles For Every Girl Out ThereHairstyles in the Rich and Famous don't only will be their identity signatures. These may also signal cultural shifts and trends. A...
    Daniel702i5hei Daniel702i5hei 31-35, M Dec 7

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    I'm 24 years old and I'm just now experience what it's like to fall in love for the first time. I've never been the type of girl to just say that I love someone for the sake of...
    atheGAYlouise atheGAYlouise 22-25, F 4 Responses Dec 10

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    On Monday, some of our classmates got punished very severely. However, i'll tell it from my perspective. It all started with an extreme stinging pain in the ear. "Sophie, haven...
    hopetolive2000 hopetolive2000 13-15, F 1 Response Dec 11

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    Today I wore another dress and white pantyhose to school and once again that black girl in my 3rd period history class who has had her eye on me for quite a while was wearing a t...
    downbutnotout1 downbutnotout1 13-15, F 2 Responses Dec 11

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    I do want to be dressed up like a girl. So I dress like a girl every day. I enjoy wearing the clothes they can wear.
    Adam59 Adam59 56-60, M 1 Response Nov 29

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    I was standing at the bus stop with some other students, when I suddenly realized I was standing so far away from everyone else. They were all gathered in a group, chatting...
    JustBlueEyes JustBlueEyes 16-17, F 1 Response Dec 4

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    Random song or story/poem I made. Tied to a chair was where I was woken, Only to find I wished I was broken, "She's just so cute they said and mocked." As I sat there feeling the...
    Timelord47 Timelord47 18-21 1 Response 5 days ago

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    Long Distance Relationships. They suck. But they can be the most amazing things in they're own way... There's this man. This absolutely amazing man that I'm head over heels in love...
    AirmansPrincess112113 AirmansPrincess112113 18-21, F Dec 7

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    So I go to middle school and I was gone for like 3 weeks because I hurt myself (don't worry, I'm OK now :-) ) but as soon as I came back, this girl that I guess I sorta liked keeps...
    krw2 krw2 18-21, M Dec 11

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    My cousin dressed me as a girl and my mum thought it was cute,
    nannysboy nannysboy 46-50, M 1 Response Nov 29

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    One time at work, my gorgeous lesbian co worker was giving me a hard time by suggesting I might be gay in front if 2 other female co workers. My reply was "if I was gay I would...
    chrissyk48 chrissyk48 46-50, M 3 Responses Dec 3

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    It is so exasperating. It just sucks the life out of me. Monday morning, I drag myself out of bed with a "Oh no, not again! WTH! It's Monday once more...ughh!” and get myself...
    EvanescentIridescent EvanescentIridescent 16-17, F 1 Response Dec 8

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    Part 2 So now I am stood at the headmasters desk in front of a class of 10 senior boys. Two lads from my class, three prefects, Ms Perry and the headmaster. "Last chance son" Mr...
    ojexpress ojexpress 51-55 3 days ago

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    These past few days were amazing. I finally got to see my boyfriend on Wednesday (26th). I'm so proud of him and glad that BT hasn't changed him one bit. He's still the caring...
    ac9914 ac9914 18-21, F 1 Response Dec 1

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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 Dec 18

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    I am a fairly weak and feminine white girl who wears dresses and white pantyhose to school every day. I am not very popular at school and don't have many friends. I am a straight A...
    samhorst17 samhorst17 16-17, F 7 Responses Nov 28

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    Have been since I was in middle school. I dated a few guys, just couldn't find anything in them that caught my interest. Never did anything sexual with them either. When I...
    WanderingNotQuiteLost WanderingNotQuiteLost 18-21, F 2 Responses Nov 29

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    I was eating on a fast food chain yesterday and I saw this pretty girl staring at me. I dunno if there's something wrong with how I look that time or is it the way I chew or eat...
    NadineIsBi NadineIsBi 16-17, F 2 Responses Dec 4

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    My boyfriend of a year went to Basic Training for the marines on 10/27. We had such a magical love. We spent every day we could together. We both worked so even if it was just for...
    Stephlisette Stephlisette 18-21, F 6 Responses Dec 16

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