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I Went To School Dressed As A Girl

gone to school dressed as a girl, either secretely or openly 420 People

    I used to be home schooled

    so every morning my step mom would dress me up like a 9 yr ols school girl my father died so I was raised by 3 dominant women i haven't worn any male clothing since my dad died and that was 15 yrs ago
    subsissy1989 subsissy1989 26-30, M Feb 14

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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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    Well I am over East and just fully dressed myself as Natasha and went for a stroll in the CBD. What a feeling of freedom. The best bit was a couple of young girls passing comment...
    motokini motokini 56-60, M 2 Responses 4 days ago

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    I had seen a pair of cute flats at a shoe store a few weeks back and had been dying to go back and buy them. Last week I got dressed en femme and went shopping. I headed to the...
    Bellringer2c Bellringer2c 56-60, T 13 Responses Feb 15

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    My mom made me go with her and i brought 10 pink dresses all of different length the shortest barely covers my little penis and the longest goes to my ankles...
    subsissy1989 subsissy1989 26-30, M 3 Responses Feb 14

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    So, my boyfriend is my first serious relationship and I lost my virginity to him and he knows that I lost it to him, but he still accuses me of lying about being a virgin and...
    marinadelmonroe marinadelmonroe 18-21, F a week ago

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    So, my boyfriend is my first serious relationship and I lost my virginity to him and he knows that I lost it to him, but he still accuses me of cheating and lying about being a...
    marinadelmonroe marinadelmonroe 18-21, F 2 Responses a week ago

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    There was an incident in Middle school. there was a girl that came up to me and started asking me questions. She told me stuff like "you smell bad," "That jacket looks old why are...
    awsome2 awsome2 18-21, M 17 hrs ago

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    Many years ago I worked hard to get my *** into a top design school, but while I was there everything in my life went to crumbles. I ended up dropping out after having an early...
    emmunster emmunster 26-30, F 8 hrs ago

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    There have been a rash of suicide attempts lately. One of then succeeded. Its a small school so I've basically grown up with these kids. And about a month before prom a really...
    shootdownthestars shootdownthestars 16-17, F 5 hrs ago

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    Finally home from China. NY looks great even as cold and snowy as it is. Met a few girl friends and went to dinner. At the restaurant I saw a girl I went to high school with, and...
    MiriamK MiriamK 56-60, T 5 Responses Feb 15

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    I know my experience pales in comparison to many ones on here. But here it goes... Some background info: So I've been pressured ever since I was little (yes I know... crazy) to go...
    Paigeypoo101 Paigeypoo101 16-17, F 8 hrs ago

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    What I'm about to tell you is a true story and happened a few times. it was a Monday and I had just for ready for school putting on my blue top black and red jumper along with my...
    XxChloexXx XxChloexXx 16-17, F 8 Responses Feb 14

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    It was in either in pre-k or kindergarten that I only had one friend that would hangout with me. We had a good time together. After he left I turned into a loner. I would try to...
    awsome2 awsome2 18-21, M 1 Response 17 hrs ago

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    My husband (who we shall call Bug) and I met when I moved to his small town (we're talking less than 2,000 people) halfway through 7th grade. We were in the same year, but it...
    quirkygirl520 quirkygirl520 22-25, F 3 days ago

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    My sister was beautiful and I was so attracted to her I went through her laundry a lot. One I overheard her downstairs say she had and accident and I rushed to her room found it...
    G677 G677 41-45, T 6 hrs ago

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    There were five of us; my mom, my dad, my brother, my sister and me. My dad was obsessed with his work, he left home before I was awake and came home in time for a late dinner...
    GirlInABottle GirlInABottle 13-15, F 1 Response Feb 2

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    My mom has always asked me why do I hate school so much? well I wish I could be honest but sadly my mother doesn't seem to comprehend anything I say. It's not because she's...
    bunnypop bunnypop 18-21, F 2 Responses Jan 31

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    Just warning, this might get slightly long. So, I am a 13 year old girl. (Please don't judge me by my age). I have always been kind of "boyish" or however you want to call it. I...
    Wildheart919 Wildheart919 13-15, F 7 Responses Feb 6

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    Just warning, this might get slightly long. So, I am a 13 year old girl. (Please don't judge me by my age). I have always been kind of "boyish" or however you want to call it. I...
    Wildheart919 Wildheart919 13-15, F 3 Responses Feb 6

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    I was at a school that was based on the English system of discipline - and I am grateful that I did attend that school. I also think that family values were instilled n you both...
    Brian1953 Brian1953 61-65, M 23 hrs ago

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    wooooow! we meet online, fall in love, am in high school his in the marines. He goes on missions we talk some times during his missions and wnen he comes back, I love him, he...
    kanny11 kanny11 13-15, F 7 hrs ago

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    So I've been married to my husband for almost four years now. We met when I was 18, still in high school, and I fell so hard for him so so fast. He was 21, and was spending one...
    marinesprincess93 marinesprincess93 18-21, F 2 Responses 3 hrs ago

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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 Jan 28

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    I cant really recall while at junior school, but definitely at senior school it was a case of being punished as the infraction was discovered. Eventually when I discovered i...
    Brian1953 Brian1953 61-65, M 21 hrs ago

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    Today. Today I hate school. I don't hate it that much, but I still have to get this off my chest. I can't adjust to the regime. In my natural state I'd sleep long and then fill my...
    dahilia dahilia 18-21, F 17 hrs ago

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    My dad force me to play basketball. My coach was hard on me because I was the weakest on the team. My last year in middle school we lost badly so in the locker room my team mates...
    BEARNDN BEARNDN 22-25, M 1 Response Feb 10

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    I once love this girl in school, i know that i am neither "handsome" or pretty. But we start to went out but it was my first time falling in love, so things was not going smoothly...
    alexisskylar1234 alexisskylar1234 26-30, F 4 Responses 6 days ago

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    last week i straightened my hair and used clutcher to pin my hair at back. I completely dressed as girl with blue salwar kameez with padded bra. feeling amazing really. I dressed...
    SowmyaWhore SowmyaWhore 22-25, M 1 Response 4 days ago

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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 Jan 31

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    I love my boyfriend. We have been dating for over a year and a half. About 6 months into our relationship, he confided in me that he used to cross dress. He said it was in the...
    honestsleep honestsleep 22-25, F 2 Responses Feb 8

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    As far back as I can remember I have always showed an interest in doing female things. It all started when I was really young (about 3rd or 4th grade, he was a grade older than me...
    katielove43 katielove43 18-21, T 1 Response Feb 18

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    I see all you younger and it makes me think about what I went through. Break ups, he said she said, fake friends and trying to fit in somewhere. Well I never fit in anywhere but...
    TheVirginRapids TheVirginRapids 18-21, F Feb 12

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