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I Was Crossdressed At School

school initiations in high school are a drag 579 People

    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 4 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 56-60, T 2 Responses May 3, 2013

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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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    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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    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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    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
    alpaqqa alpaqqa 16-17, F Jun 22, 2014

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    For Halloween . Fall dress,

    tights,and shoes.
    pardax pardax 13-15, M 1 Response May 12, 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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    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 8 Responses Nov 3, 2012

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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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    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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    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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    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 2 Responses Jun 20, 2011

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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 1 Response Dec 10, 2014

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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

    Many of the reasons I have cited in my post regarding why I think spanking should come back apply but it is the fact that school truancy and bullying have become so widespread...
    skanda2 skanda2 56-60, M 1 Response 10 hrs ago

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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 1 Response 1 day 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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    I was in school and I was really young but I knew that it was a act of terrorism
    Hottim101 Hottim101 18-21, M Jan 4

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    Well not work, It was the school - at an excursion
    ann1993 ann1993 22-25, F 3 days ago

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    I find it hard to believe that I just now got around to looking on the interweb to find others that have had similar situations....lol. I have never really shared anything to...
    ACMekanik ACMekanik 41-45, M 10 hrs ago

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    Interesting Holiday Story My wife and I were able to get out for a couple of weekends of Holiday fun recently, and had some very interesting experiences while I was dressed as...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jan 4

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    Jan 6 I was 15 and betting on the turn of a card. I was sober and it seemed a good idea. It always did in the early years. The card was red and low. I wanted black and high...
    Rant58 Rant58 56-60, M 1 hr ago

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    Last time crossdressed - right now sitting in my car at a ***** mall enjoying my coffee and adoring all the beautiful women as they shop. White long sleeve turtleneck, blue print...
    debbienc debbienc 61-65, M 7 Responses Jan 22

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    I read a story. And dear god kill these children now! I mean, look. This girl Jennifer in the UK I'm guessing, is evil. EVIL! Just search Jennifer's revenge is sweet and Jennifer's...
    Timelord47 Timelord47 18-21 2 hrs ago

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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 Jan 4

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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 5 Responses Jan 6

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    I remember one time when I was on the streets. I had met this guy with a speak inpetiment problem while sitting at a bus stop. I started talking to him just about various stuff. He...
    Jasminej235 Jasminej235 41-45, F 1 day ago

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    So I was asked to take some pictures the other night to show off my new shoes. I have a pair of patent leather 4 inch stiletto pumps with locking ankle straps. I was told to get...
    Photogeek47 Photogeek47 26-30, M Jan 1

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    Happy New Year everyone :) I had a fantastic New Years Eve, I went to a party as Lisa which was just fabulous. The women were so accepting and asked so many questions which I...
    GirlyLisaTG GirlyLisaTG 26-30, T 12 Responses Jan 1

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    It has been a while since I went out. I was in a long purple dress, black 4 inch heels and blonde hair. I lost my brooch and wished I replaced it with a slender red belt. That...
    priebecl priebecl 61-65, M 2 Responses Jan 5

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    so a few weeks ago I got busted, my activities found out by my wife. I was compelled to execute a purge and trash a lot of my wardrobe in the middle of the night under her...
    AliciaHalfcat AliciaHalfcat 36-40, T 2 Responses 15 hrs ago

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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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    A few simple of experiences of why I have cried in school: Kindergarten: I called a boy in my class stupid, then later when I saw a police car park in front of the school I started...
    SparkleSwirl SparkleSwirl 18-21, F 6 days ago

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    We live in a complex, diverse democracy whose independence is maintained to a great extent through an educated electorate. Ignorance is not democracy's friend. That's why the U.S...
    peytwatson025 peytwatson025 18-21, F 1 day ago

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    I lived with my mom and her mom from birth till I was about 6. she was 16 raising me. I didn't know any different, it was the way I was raised, how I was influenced, the life I...
    summerwinterfallspring summerwinterfallspring 18-21, F 2 Responses Jan 11

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    My experience started the end of summer starting my sophomore year. My family moved as we just lost our house. The house my parents rented had a guy living next door that was a bit...
    princesskimber princesskimber 18-21, F 3 Responses Jan 18

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    I loved my time at school like a hole in the head . I was talking to one of my students about the this very subject . Was it like Tom Browns School Days ? No my school days were a...
    JohnCrighton JohnCrighton 51-55, M 1 Response 16 hrs ago

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    Yes it's true i was in special ed in not only kindergarten but all through middle school and high school. Go ahead laugh all you want but im serious. I've got a TBI cause i was...
    harlemwildcatbaby harlemwildcatbaby 18-21, M 1 Response Jan 2

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    Well...it all happened in May 2010. This was my sophomore year. Little background though. My freshman year, I was big into sports. I played soccer, tennis, and I wrestled. I...
    SocialFlutterBy SocialFlutterBy 18-21, M 2 Responses Jan 4

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    I was bullied from elementary school to middle school. It was horrible. They just bashed me because i was asian. They called me names (ex: chinky eye, idiot, stupid) made racist...
    Horse10202 Horse10202 18-21, F 3 Responses Jan 4

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    I think the reason why I'm such a ****** person now has to do with how I was treated as a kid. Sometimes I tell people of my past and they tell me, "It was just elementary school...
    TryingToLiveLife TryingToLiveLife 16-17, F 1 Response Jan 6

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    My family is rich ok there I said it. In 8th grade we moved and I went to a new school, nobody knew me. Somehow some kid in my class found out where I lived and told people about...
    DemonicPenguin DemonicPenguin 16-17, M 1 Response Jan 11

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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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    It wasn't for a long time, and we're actually friends now, but just thinking about it makes me feel like crap anyway. I was very mean to this girl. I was bullied from the end of...
    Boulier Boulier 18-21, F Jan 21

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