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I Was Crossdressed At School

school initiations in high school are a drag 658 People

    First Day Dresses In School

    I came out to my friend Marissa after she caught me in make up. I then asked her to help me get ready for dressing up as a girl for the first day. She did my make up and she French braided my hair. I then wore a jean miniskirt with a sparkly pink thong under I also had a pink bra...
    gcd4life gcd4life 18-21, T 5 Responses Feb 18, 2013

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    The first instance I can remember was

    when I was in the fourth grade. We had our traditional new year festival. It was a only boys school and I was one of those in my class chosen to dress as a girl for the festival. I wore a print skirt and a blouse, with a bead necklace, and had my face make up. I also wore a long...
    Nilooshi Nilooshi 26-30 May 1, 2015

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    I Was Crossdressed At School

    when i was at secondary school i use to hate games (PT) so every time i could get away with it i use to miss it and just hide untill it was over, one time i was hiding in the main hall behind the stage and was caught i was taken to the gym and presented to the gym master when he...
    paul1953 paul1953 56-60, M 1 Response Jun 20, 2011

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    pardax pardax 13-15, M 1 Response Apr 29, 2015

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    As I told in the other story I was slim

    and small and had longish hair, so I always got caught to play girl parts in school plays. In one I was in a girls dancing group (all boys dressed), another a school teacher, and one the daughter visited by a broker and a boy to fix a marriage. Earlier I didn't like because...
    Nilooshi Nilooshi 26-30 1 Response May 3, 2015

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    Going To School Crossdresssed

    it was on friday me and my friends had talked about the plan, it was for a class deal i made with teacher that i had first period, but the plan was i was gonna stay like that for the day. on fridays we had language arts, spanish, and P.E. they were about 3 hours each class, i was...
    archangle909 archangle909 18-21 7 Responses Nov 3, 2012

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    Found Out At School

    This story starts for me some time prior to the events that I am reciting here. The world seems full of people who question that these events happened to some of us, well I am here to tell you that to some they did! Cutting a long story short that I may upload in the future, my...
    cathy0516 cathy0516 41-45 2 Responses Aug 30, 2011

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    Crossdressed At School

    Its funny what a person will do on a dare. My best friend dared me to wear girls clothes and makeup to school for a week. I was going to become a freshman at the time and had been crossdressing as long as I could remember. ( he had caught me crossdressed after my sister moved...
    christinexxy christinexxy 61-65, T 2 Responses May 3, 2013

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    Shopping

    this past weekend i went shopping with my niece/ nephew we got a total make over she had a a pink silk skirt white slik blouse4 inch heels he got a new garter belt stocking pantie with a matching bra i got panties bras i found a mother daughter outfit we will be wearing...
    maryyork50 maryyork50 18-21, T 1 Response Nov 20, 2011

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    My Perfect Dare

    This is a true account of what happened to me at my junior school in the early 80s. One day a group of us boys were looking at the girls playing in the playground in their new summer dresses. They had changed them from a dark grey colour to a new summery gingham pattern in a sky...
    skidrep2013 skidrep2013 41-45, M 1 Response May 5, 2013

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    The Initiation

    It was the start of junior high school in september of 1962.   I had a very good summer and looked forward to it.  I walked to school that morning as we were not bussed during that period.  It was only about 3 miles, so it was a long walk.   I...
    bobbie13 bobbie13 56-60, T 7 Responses May 25, 2010

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    My love of crossdressing started at school

    when I was dared to go with twom of the girls from the convent school on a bus ride with them in their school uniform. I found it an amazingly uplifting experienvce to be dressed in a rather plain gymslip but with quite sexy lingerie underneath
    deleted deleted 26-30 1 Response Nov 5, 2015

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    Destiny With Femininity

      Vincent Laundree a 9 year boy in the forth grade at Saint Mercy School a hang over from the days of being a Catholic school back in the 50’s and becoming a public school in the late 80’s. The Catholic Church because of the tremendous drop in students adding to and already...
    stylishned stylishned 61-65, M 4 Responses Jan 27, 2011

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    I Was Crossed Dress At School As Well

    It was part of our ritual at the high school I went too in my younger years that the new class coming in had a orientation week. Well part of that week we had to be dressed as a girl. In some ways that was my coming out but others didn't realize it. As I had been dressing for...
    deleted deleted 26-30 7 Responses Jan 25, 2013

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    Caution: This Is True

    Sometimes you read stories about a persons life and you might think that was just a made up story to get instant group appeal but that's not true of mine. The high school I went to was a boarding school and I was lucky in that a few people were in on my 'being a girl' and my...
    deleted deleted 26-30 5 Responses Jul 26, 2012

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    Going To School Crossdressed

    I remember going to scholl underdressed.  It was fun wearing my bra and panties under my clothes.  I only did it a few times but it was thrilling to know I was.
    jml2000 jml2000 61-65, M Nov 8, 2012

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    Best day of the whole school year:P me

    and my friend Mia were hands down the cutest gay couple ever, teachers didn't appreciate it too much though;D
    deleted deleted 26-30 Jun 22, 2014

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    Looking Up The Dress Part 4

    when we got back from shopping we did get some nice dresses matching shoesi got his hair and nails done his own did not know him i was so proud of my work after a month living together we were married we had a big house Nancy my husband brother is now our maid she enjoys her...
    maryyork50 maryyork50 18-21, T 1 Response Nov 23, 2011

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    Me Too

    I know some people will tell you that this NEVER happens-----I'm here to tell you it Does!! I went to a Catholic Grammer School, at that time, taught by Nun's only, no lay teachers. Gotta say, when the Nuns spoke---you better obey---this was coming from God! We wore uniforms...
    carolannP carolannP 51-55, M 4 Responses May 16, 2011

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    In the seventh grade I was starting to be more

    openly feminine and had confided to a couple of the girls in my class that I cross-dressed. So they started inviting me over to their houses after school to hang out with them. Their parents were really cool about it I guess because of me acting feminine. I got invited to a...
    Jena1976 Jena1976 36-40, T 2 Responses Jan 1

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    Everyday of my life since.

    ..a while. Gotta question, do you still have to take a swimming unit in High School?
    DarkOnTheInside13 DarkOnTheInside13 13-15, F Dec 10, 2014

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    Agree.The cane was stopped in the schools but not at my home.My 13 year old is still caned .I use the same method that was used in the school when I was you with a few...
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    In 7th grade, when puberty was in full regalia, I was an awkward, very shy girl who was desperate for a little bit of attention from my peers. I devised my plan for acceptance in...
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    I Reflect On Life I was a victim of molestation at a young age. Homeless and had a Druggie parent. I never told anyone about this until a few months ago because I always felt...
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    I was bullied all the time when I was at school.. For being small, pretty thin and because I had mostly friends who were girls. It all got pretty bad and I was glad to finally...
    ZachOrZasha ZachOrZasha 26-30, T 2 days ago

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    Well my first high school. I could tell you many stories of my horrible two years of high school before I transferred to another school. But one I will tell you is my first high...
    Cutiepeachpie Cutiepeachpie 22-25, F 3 days ago

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    I feel like im always on the wrong end of the conversation t=when the topic of school comes up, because i actually really enjoyed school. No it wasnt just because thats where all...
    firesoul07 firesoul07 22-25, F 1 Response 3 days ago

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    School was over at 2:10pm, and exactly at 2pm, the principal announced something horrible had just happened to the entire school. He was referring to Sandy Hook. I was in biology...
    ACMJC ACMJC 18-21, M 3 days ago

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    I've been upset many times in my life. But during and recently after high school I would have episodes a few times per year. The most recent one was back in 2015. It was close to...
    ACMJC ACMJC 18-21, M 3 days ago

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    When I was in middle school, people made fun of me back then just because they can. I was weak and sensitive. I realised that humans especially love to pick on those. Everyday, I...
    tobiii12 tobiii12 13-15, F 2 Responses 3 days ago

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    My life has been quite unusual; starting from the fact that my parents were separated even before I was born. I was the eccentric boy in school, who got sent to a military school...
    Kurecca Kurecca 22-25, M 4 days ago

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    Well actually I was a pre-teen smoker! It all started when I went to secondary school. It quickly became apparent that there were other students in the school who lit up a...
    TrannyHannah TrannyHannah 41-45, T 1 Response 4 days ago

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    Yesterday like I said in a few posts before I got suspended from school for a whole week. I had hit a girl right in the faceeventhough I defend a friend of mine. They told my...
    Countryroad15 Countryroad15 16-17, F 5 Responses 5 days ago

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    Let's discuss the difference between being punished by a teacher versus being sent to the principal (or headmaster in the UK and elsewhere) for punishment. The one and only time...
    julietx julietx 36-40, F 1 Response 6 days ago

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    Let's discuss the difference between being punished by a teacher versus being sent to the principal (or headmaster in the UK and elsewhere) for punishment. The one and only time...
    julietx julietx 36-40, F 3 Responses 6 days ago

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    I'm in 10th grade.I want to explain my school though. It's a small charter school. I only go there 2 times a week. At home I work on these packets and turn them in on the days I go...
    EnigmaticPerson EnigmaticPerson 13-15, F Feb 3

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    WASH DAY!!!! It was that time of the week again. oh i hate this day, this the day when the popular girls at school target someone less popular then them and decide to clean her up...
    sasahsworld sasahsworld 26-30, F 3 Responses Feb 3

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    when I was in first grade I would have a accident in my seat cuz I was afraid to use the school toilets and when everyone would leave (for something I can't remember) I would stay...
    someone2017 someone2017 16-17, F Feb 2

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