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I Was Crossdressed At School

school initiations in high school are a drag 615 People

    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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    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

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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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    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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    pardax pardax 13-15, M 1 Response Apr 29

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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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    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

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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 61-65, M 4 Responses May 16, 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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    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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    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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    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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    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 56-60, M Nov 8, 2012

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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...
    Joanne0chan Joanne0chan 31-35, F 5 Responses Jul 26, 2012

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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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    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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    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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    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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    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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    Related Experiences

    I hate school , the education system is corrupt, everyone attending knows it and nobody is speaking up about it
    Brookeross521 Brookeross521 13-15 1 Response 50 mins ago

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    I was at school the other day and look what I saw😂😂 and I agree with this.
    kidLeftInTheDark kidLeftInTheDark 13-15, F 3 Responses 1 day ago

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    The new school year has nearly begun and I really just want switch schools so I can be with my primary school friends again! I've already went through a year of the high school I'm...
    Eninferno Eninferno 13-15, F 1 Response 1 day ago

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    So i'm in my second year of highschool and a Teacher that I had in 9th grade and I had a special type of relationship. First of all, we are both girls. There's never been any type...
    HazyNightmares HazyNightmares 18-21, F 1 Response 2 days ago

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    Most kids would say In school, other kids bullied/teased/edc them. Not me. The teachers, the staff for me. It was forth grade. I went to a special ED class because I have traumatic...
    itsCassidyG itsCassidyG 13-15, F 2 Responses 2 days ago

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    When i was 13...i don't know if anyone will read this i just feel i need to get this in writing because i have told only my therapist and my dad. My therapist didn't help much, and...
    Sawke Sawke 22-25, F 1 Response 2 days ago

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    I didn't really have any friends in high school. It was awful being an easy target for people. I have friends but they don't go to my school. I'd rather be with them then the...
    Fairylover32 Fairylover32 13-15, F 4 days ago

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    I went out for the first time at Fryday night to see if I am ready for Saturday night. On Saturday night my wife did my make and we went ti the KitKat club in Berlin. It was a...
    IsraeliCD IsraeliCD 36-40 2 Responses 4 days ago

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    I went out for the first time at Fryday night to see if I am ready for Saturday night. On Saturday night my wife did my make and we went ti the KitKat club in Berlin. It was a...
    IsraeliCD IsraeliCD 36-40 4 days ago

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    when I was born my mother couldn't except me ... I still don't know why. However my dad loved me to bits and took really good care of me while my mum couldn't even look into my...
    kstra38 kstra38 13-15, F 1 Response 4 days ago

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    Last Friday I was followed home from school by this group of boys. There were four of them and they all appeared to be following me as I walked home from school. It seemed as if...
    allisonhashope allisonhashope 13-15, F 1 Response 5 days ago

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    Another step forward today! I spoke to my boss, my immediate line manager, told him I want to come to work in a skirt, this is the bit I was dreading. His reply: "That is...
    janrichards2015 janrichards2015 56-60, T 2 Responses 5 days ago

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    I am a senior in high school this year, and I am fed up with the whole damn system. Most years, toward the end of summer, I would look to the next school year with some...
    Isayoldchap Isayoldchap 18-21, M 6 days ago

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    I've had quite a few number of friends in my life so far and sadly I am no longer friends with most of them. To the reader reading this that sounds pretty bad, but honestly...
    agathashelly agathashelly 26-30, F 6 days ago

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    I decided to do sort of a crossdress dare to go in public without the possibility to chicken out. If you've read my previous story, I explained how I got caught and had to dress up...
    DCYDDON DCYDDON 18-21 7 Responses 6 days ago

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    Hi my name is Valarie Montoya and I have a big butt. In fact, I have the largest butt in my entire school (including teachers). At my school I'm known as the "popular" kid and the...
    ValarieMontoya ValarieMontoya 13-15, F 1 Response a week ago

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    Between Kindergarten and 5th grade I was enrolled at St. Peter School in Kirkwood, Missouri. Although it has been eight years since I have set foot on that campus, I cannot say...
    Livenka007 Livenka007 18-21, F 1 Response Aug 22

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    Big step forward!! I got this message from the HR department at work after telling them that I want to come to work wearing skirts and dresses. "You are fully protected by the...
    janrichards2015 janrichards2015 56-60, T 3 Responses Aug 21

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    I'm always told that I am brave for what I have been through and what I am going through with my operations... that I am so much stronger than they are or they couldn't imagine...
    Gemz2411 Gemz2411 18-21, F Aug 21

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    I was bullied throughout most of my schooling. The hardest part about it was nobody really believed me since i was always tall for my age the principle would tell me why would...
    TheMidNightCrow TheMidNightCrow 26-30, M 1 Response Aug 20

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    Today 8/20/15, Was a stressful day at school. First of all, the schedule has changed and now it's all confusing. In my 2nd hour class, I have Metal Works which is a class that you...
    Jgummy123 Jgummy123 13-15, F 2 Responses Aug 20

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    I grew up in the north of England in the 60s, early 70s. Unlike today, when corporal punishment is often regarded as inappropriate punishment for children, in my youth it was very...
    billjacko billjacko 61-65, M 2 Responses Aug 19

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    Man oh man still with a babysitter. Well here's what happened I was playing a video game after school while I wasnot done with school well answer my babysitter came in and said...
    ginny1q1q ginny1q1q 13-15, F 2 Responses Aug 18

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