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I Was Crossdressed At School

school initiations in high school are a drag 586 People

    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 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 2 Responses 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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    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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    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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    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 4 Responses Feb 18, 2013

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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 56-60, T 1 Response 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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    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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    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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    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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    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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    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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    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 5 Responses May 16, 2011

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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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    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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    Related Experiences

    When I was of school age I went to a private boys boarding school run on a army style regime where corporal punishment was the norm and using nudity as a punishment or just cause...
    nakednudist nakednudist 46-50, M Apr 7

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    Ahhhh! It's coming up for my last official week at Academy/Highschool. I can't believe that 13 years have gone so quickly! (7 years in Primary, 6 in Academy) I haven't loved every...
    HandsomePrince1 HandsomePrince1 16-17, M 1 Response Apr 18

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    I was in school pre-k I remember heading out with my class. We were heading out outside. I didn't know but today I do lol. My teacher rushed us out the room. If you didn't have...
    lorrena19 lorrena19 18-21, F 3 Responses 4 days ago

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    One aspect of these discussions is seldom if ever considered. I was a school teacher for many years and I defy anybody, of any age or gender, to deny the feeling of satisfaction...
    Marjory35 Marjory35 70+, F 13 Responses Apr 13

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    I wrote my first experience in EP just a few days ago and was surprised by the positive response. I was a school teacher and I both slippered and caned, boys and girls.
    Marjory35 Marjory35 70+, F 3 Responses Apr 15

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    Well, four years really, of being depressed and moody, thar was a waste. That was high school though, lots of poop happening there :/ I've realized I was just really stressed...
    Justjonathan Justjonathan 16-17, M 2 Responses Apr 3

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    When I was in school I was at the top of every class, aced all my exams and I was classed as 'gifted'. I'm now stuck in a dead end office job and I feel like I'm not going anywhere...
    cyanide88 cyanide88 26-30, M 1 Response Apr 4

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    i was showering at school naked and my friend and i was whipping each other with towels lol and well i accidentally pushed him out of the door into the gym with all the girls...
    gdent16 gdent16 13-15, M 3 hrs ago

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    I think the only thing that really changed is that I'm not a kid and I have a slightly better understanding of how to explain stuff to people. Well for one I'm extremely anti...
    BleedingOrchids BleedingOrchids 13-15, F 5 hrs ago

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    (*see previous story of mine*) So as I said in my previous story, there was a boy that i helped during a fight with another boy who verbally bullied him; the bullied boy got...
    imJboy2001 imJboy2001 13-15, M 18 hrs ago

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    I'm excited for school this week.I found out my friend in hospital goes to my school and she is in the same classes as me.I can't wait for school for once I'm excited to go to...
    MusicLover4Eternity MusicLover4Eternity 13-15, F 1 Response 18 hrs ago

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    High school was hell for me and I'm glad I don't have to deal with it anymore. Reunion is just a time to relive the horrific memories I suffered.
    JK7448 JK7448 18-21, F 14 hrs ago

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    I was just on Facebook when I got a friend request from this childhood friend I have not seen or heard from in 30 years. I went over to his profile to say hi. When I asked...
    littlecreekgirl littlecreekgirl 41-45, F 1 Response 11 hrs ago

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    I know from my own experience that married men don't always leave the wife. I am the wife. I found out two years ago my husband had an affair with some married woman that he met...
    Truthbetold81 Truthbetold81 31-35, F 2 Responses 16 hrs ago

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    I was 14 at the time and was going to be home alone all day. My mother had this beautiful red nightgown hanging in the bathroom. It was soft and silky. I tried it on and it felt so...
    Stephaniegirl226 Stephaniegirl226 36-40, M 2 Responses Apr 1

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    I went to a friends fancy dressed birthday party.i was wearing my blond wig pvc skirt hose and knee boots she did my make up.i was the hit of the party i had my legs rubbed and my...
    Brandie9 Brandie9 31-35, M 1 Response Apr 4

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    A tight, blue dress, a long brown wig with caramel highlights, large silver hoop earrings, black tights, padded underwear, a red lacy bra, two inch heels, liquid eyeliner, gold...
    jessicavamp jessicavamp 41-45, M 2 Responses Apr 14

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    I was dressed in my new matching gown with my wife, with blue mascara, purple eye shadow, light red blush, making love all night into this morning
    Melissa11520 Melissa11520 41-45 Apr 14

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    I bought some of these. Real schoolboy shorts for big boys ?? http://m.ebay.com/itm/120571281530?_mwBanner=1
    poshkid poshkid 41-45, T 6 hrs ago

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    I was teased a lot in my childhood and teenage years. Anyone who knows me knows that I have never been a feminine girl or woman. I got a lot of negative attention from my peers...
    SapphicMinion SapphicMinion 26-30, F 10 Responses Mar 31

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    Many people say hate is a strong word, but when I say I hate school, I mean it. I hate it from the bottom of my heart. I hate it to the core. Today was my first day back to school...
    moose73630 moose73630 16-17, M 2 Responses Apr 6

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    I have a long story so .. Hope you stick around. As far as I can remember, I loved school. I enjoyed the feeling of seeing my friends and learning something new everyday. Was it...
    Jclove1 Jclove1 18-21, F 2 Responses 3 days ago

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    I never had any luck with getting away with anything, throughout my life, especially not when I was younger. I should have known better, but a few of us decided that it would be a...
    Mick672 Mick672 41-45, M 4 Responses Mar 30

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    I was bullied from the age of 2 till I was 11. During my two years at nursery I never made any friends which made me vulnerable. The other children physically bullied me, but if I...
    Englishgirl98 Englishgirl98 16-17, F 2 Responses 4 days ago

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    I haven't been paddled in the four years I've been in high school, but when I was in middle school, I went to a special private religious school that paddled. I'd been bullied all...
    brianonthebeach brianonthebeach 16-17, M Apr 11

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    I had been considering dropping out since my freshman year, and inevitably decided to leave my senior year... 5 months before graduation. I know this sounds completely nonsensical...
    hippiesugar hippiesugar 18-21, F 1 Response Apr 13

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    Every so often we had a crackdown on being late at my school, which would not be announced in advance. Normally, depending on your class teacher, being late did not matter very...
    Cheryl1953 Cheryl1953 61-65, F 2 Responses Apr 18