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I Went To School Dressed As A Girl

gone to school dressed as a girl, either secretely or openly 416 People

    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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    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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    I college I was doing group work

    and I was the only guy in the group. for the presentation I agreed to wear a skirt suit.
    Therealjason Therealjason 31-35, F 1 Response Jan 16

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    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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    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 4 Responses Aug 24, 2014

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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, 2014

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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 11 Responses Feb 1, 2012

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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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    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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    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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    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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    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 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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    Related Experiences

    I went out the other day dressed in a black skirt, yellow sweater top, black 5 inch pumps and full makeup with big hoop earings on. Felt very pretty and passable. Went to Dress...
    83218tb 83218tb 36-40, M 2 Responses Jan 18

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    I grew up alone my life. Lived my life, most of it alone. About 99% of my life I been single and alone. Girls always rejected me, and turned me down. It hurt me back then, still...
    Niko864 Niko864 41-45, M Jan 17

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    Omg yes this happened to me at a school camp in about year 3. It was shower time so I walked down to the bathroom blocks and they'd shown us earlier which was which but I was sure...
    Peelover94 Peelover94 18-21, M 42 mins ago

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    My boyfriend is in the Air Force. We started dating a week after we graduated from high school, broke up two years later. I went to college three hours away and he stayed in our...
    sunnycheer sunnycheer 22-25, F 19 mins ago

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    I cross dressed and got caught many time by my mother. She said no way I could be a girl. I was a boy so start acting like one. Like that helped. My life took a big turn when I...
    bpb62 bpb62 61-65, T 4 Responses 5 days ago

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    New Years Eve 2014 My wife and I have spent the three previous New Year’s Eve nights out of town at small hotels. Each of these hotels had a small lounge and a party to bring in...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Jan 6

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    It started with a visit to my girlfriends house with my son who was 7 yrs old. He wanted to play under a water rose with my friends daughter, but had no bathers and because he was...
    katherine36 katherine36 46-50, F 3 Responses Jan 22

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    I was often bullied a lot in school, because of the way I acted and dressed. One high school day, it was the end of school, and I was packing up my things to head home. I normally...
    HipsterEagle HipsterEagle 18-21, F 1 Response a week ago

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    Okay sooo...there's this dude. lol I don't know how else to start this! alright. so yeah. I met this guy named Antonio, who's in my supervision room, he's also in my gym class...
    Gabsters05 Gabsters05 16-17, F 3 Responses Jan 7

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    More Haste Less Speed! When my friend Katie and me were about 15 we were running to a class because we were late. we weren’t supposed to run in the corridors but most teachers...
    Jilly53 Jilly53 61-65, F 5 Responses Jan 16

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    More Haste Less Speed! When my friend Katie and me were about 15 we were running to a class because we were late. we weren’t supposed to run in the corridors but most teachers...
    Jilly53 Jilly53 61-65, F 2 Responses Jan 16

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    2014 Review 2014 was a year of firsts in my crossdressing adventures, as I was able to go out dressed for a new record number of hours. Some of those extra hours were those that I...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Jan 4

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    The Baby Sitter. I love a woman a gut! Ever since I was a kid I've felt this way and there's a story behind it. I'll try to type it out as I remember it to the best of my ability...
    iloveflabbiness iloveflabbiness 18-21, M 1 Response 2 days ago

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    I went to high school in South Africa in the 80s where corporal punishment was used extensively. Nearly every teacher had a cane in the class and could give up to six strokes...
    johnabagnail johnabagnail 41-45, M 6 Responses Jan 19

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    Although getting spanked at school was certainly no fun, we always found it fun when someone else was spanked - as long as it wasn't us! But it didn't do too much to let it show...
    Jilly53 Jilly53 61-65, F 1 Response a week ago

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    PE Slippering I think I was 13 when this happened. It was the third time I had forgotten my kit. In my school, it was if you had forgotten your kit for three times in a row, you...
    lauraAd lauraAd 31-35, F 4 Responses Jan 9

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    Remember one time with this chick just walking out of school (yay skipping woodwork) and just walking on the field opposite the school and up the roads from the school. We sat down...
    1lonelydaisy 1lonelydaisy 41-45 Jan 2

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    Yes, it is true. I have, and if my memory serves me right, it was my first physical experience. I think I was about 13, maybe 14, but most likely 13. There was this girl in my...
    kinkysexybabe kinkysexybabe 36-40, F 5 Responses Jan 20

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    An untimely sneeze! When we got into the fifth form at school we thought we were getting a bit above the rules. Hence we did things like sneaking into the sneaking into the...
    Jilly53 Jilly53 61-65, F 1 Response Jan 2

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    An untimely sneeze! When we got into the fifth form at school we thought we were getting a bit above the rules. Hence we did things like sneaking into the sneaking into the...
    Jilly53 Jilly53 61-65, F 1 Response Jan 2

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    My girlfriend and I have been dating for a almost a year and had always been really skinny until we started dating. She used to work out and diet but once we started dating that...
    Bbg145 Bbg145 16-17, M Jan 11

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    Some may dream of a return to childhood, and for some the role of school child or expressly schoolgirl is very much apart of it. Like PrincessAlicia, I to love dressing up as a...
    Joanne0chan Joanne0chan 31-35 3 Responses Jan 15

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    Just after high school finished my then girlfriend told her mother to get ----- well her mum just snapped she pulled my girlfriend over her knee lifted up her skirt pulled down her...
    sissy1972 sissy1972 22-25, T 4 Responses Dec 31, 2014

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    I am tall but weak. I was always quite weak also as a child. My first experience was at school. I was 16 and a girl from the neighborhood who was swimming a lot once teased me by...
    lagavulin lagavulin 31-35, M 2 Responses Jan 5

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    I have a really good friend that I went to high school with. She was a grade above me but we knew each other since middle school. we were on the track and field team together, we...
    RunDMC7 RunDMC7 18-21, M 1 Response Jan 5

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    I hate school so much... And when you have Emetophobia, it gets worse for you. I have never puked at school before, but I did have some close calls in the past. Once in...
    Erenjaegertitans Erenjaegertitans 13-15, F Jan 6

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    I try to get out at leasy weekly. Lately i have toned it down a bit, age appropriate clothing & makeup. I seem to get fewer looks this way. I'll be heading out in a few minutes. I...
    ta61 ta61 51-55, T 3 Responses Jan 7

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    in Jr high my cousin would do this to me. She was a little older and this went on for a while...Her mom, my aunt, caught us a few times. I had some good times with this cousin.
    Therealjason Therealjason 31-35, F 1 Response Jan 8

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    I have been very lucky through the years and have taken a number of my gfs for fully clothed swims. my fiance and I love to swim and have done so many times. the first time was...
    kerrmit84 kerrmit84 31-35, M Jan 12

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    hi ladys, im a 23 yo boy from germany, and i really love tenn girls feet... a lady out there who wanna show hers? :)
    lureebel lureebel 22-25, M 10 mins ago

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    My first experience was with an older woman. I was young and she was in her 30s. She was my mom's friend. She has a daughter who has special needs so I used to help her out all...
    purpleangel98 purpleangel98 16-17, F 2 Responses Jan 9

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    Hey guys... It's been some months since i last came online here. There had been several mock tests at school and that had been consuming nearly all my time. Anyways, its holiday...
    hopetolive2000 hopetolive2000 13-15, F 1 Response Jan 19

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