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I Was Crossdressed At School

school initiations in high school are a drag 572 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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    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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    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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    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 9 Responses May 25, 2010

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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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    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

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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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    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 May 3, 2013

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    At School Concerts

    This is a summary of two stories I posted in other groups.The first incident was in the 2nd grade, when I had to play a girl role in the class play. At that time I had long hair, and my mum took the whole thing very seriously and prepared me for my role by dressing me up at home...
    shalinigirl shalinigirl 31-35 6 Responses Aug 17, 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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    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 11 Responses Nov 3, 2012

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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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    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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    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 6 Responses Jan 25, 2013

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    Crossdressed For Gym Class

    This isnt a long story, just the basic facts. In 1985 i was at my upper school (Senior or high school). I rarely did PE or Gym as i hated it. I wasnt very sporty and used every excuse in the book to get out of it. The day came when i was pulled aside by the PE teacher and told i...
    Babyclaireuk Babyclaireuk 41-45, M 3 Responses May 25, 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 1 Response Aug 30, 2011

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    For Halloween . Fall dress,

    tights,and shoes.
    pardax pardax 13-15, M May 12

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    Related Experiences

    I was at school in ENgland in the 1960s and 70s, when corporal punishment was still widespread. At primary school I went through a "difficult" period, possibly related to my...
    preaparvum preaparvum 46-50, M 1 Response Jun 26

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    There was a report by the Human Rights people regarding the disciplining of school children when misbehaving in class. In particular the practice of using a "naughty corner" which...
    aussieman01 aussieman01 51-55, M 1 Response Jul 10

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    Ok, so this happened to me in the past. A boy at school held my right arm and told his friend to hold my left arm and told his other friend '' To rape me and hold my private''. I...
    Rafeerahman Rafeerahman 13-15, M 1 Response Jul 11

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    Yup.. not worried at all, since I am all sexy *feels cocky* :P No, actually it is not about being sexy, I just think that I look younger than my age anyway, so it will take longer...
    MissGaga MissGaga 22-25, F 2 Responses Jul 4

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    Ok, so this happened to me in the past. A boy at school held my right arm and told his friend to hold my left arm and told his other friend '' To rape me and hold my private''. I...
    Rafeerahman Rafeerahman 13-15, M 1 Response Jul 11

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    Ok, so this happened to me in the past. A boy at school held my right arm and told his friend to hold my left arm and told his other friend '' To rape me and hold my private''. I...
    Rafeerahman Rafeerahman 13-15, M Jul 13

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    I was 10 yrs old. This was in school too lol. I didnt know it was wine i just dont listen. I attended a Church of England primary school for years five and six. It was nearly...
    ssaaraahh ssaaraahh 18-21, F 1 Response 3 days ago

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    When I was at school, getting licks was a regular hazard, especially if, like me, you were mischievous and tended to get caught.
    Tina303 Tina303 41-45, F Jul 1

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    I am currently in highschool and try to fight bullying as much as I can. But I can never escape the fact that I once was a bully. Being a socially awkward person I had trouble...
    SalemKat SalemKat 13-15, F Jul 3

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    Only once, and I was in grade one. I don't even remember being that desperate. I walked into the bathroom and when I was about to pee I started wetting my Pants. I hid in a stall...
    Robotboy100 Robotboy100 13-15, M 1 Response 4 hrs ago

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    Well I can honestly say that I don't remember what was the first item I wore . I suspect that it was my moms knee highs . I was maybe 6 or 7 . As I got older , I began to explore...
    Mindi3107 Mindi3107 26-30 1 Response Jun 28

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    I love to drive around crossdressed and being seen. Seeing the look on women's faces. Have u had the same experience?
    sexipants sexipants 41-45 1 Response Jul 14

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    So in school, I'm doing my year ten choices, this is basically were I choose lessons that I want to specialise in for my GCSES exams in year eleven (my future depends on those...
    ellienottingham ellienottingham 13-15, F 1 Response 3 hrs ago

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    if someone can burn down my school i will bring you cake and doughnuts...
    xmonsterx xmonsterx 13-15, F 1 Response 2 hrs ago

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    Drama,yelling,fighting! It's too much! people don't know that there is a lot more going on in school then learning
    hellokitti hellokitti 13-15, F 40 mins ago

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    Last night I went to a gay bar which has a t girl night regularly. I had a fantastic night, I wore a black dress with black tights and heels. It felt wonderful being out. There was...
    LisaTG LisaTG 26-30, T 10 Responses Jun 26

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    Finally! I had a chance to get into something "more comfortable" last night for a few hours. God, how I miss crossdressing if I have not done it in a few weeks (or more...
    chantelletv2 chantelletv2 41-45, T 4 Responses a week ago

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    today I was forzed to wear corset, anal gag and extreme skinny corset with a tied dress and high heels sometimes I don't want to I am tired
    sashaching sashaching 16-17, T Jun 23

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    I wore a matching black lace bra and thong, black garter belt with red back-seamed stockings, red knit mini-dress, black high heel pumps, blond curly wig, make-up and a pearl...
    Chefsteve69 Chefsteve69 51-55, M 4 Responses Jun 25

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    Instead of the word want I have to say I already do cosplay as the 'opposite gender', at least the opposite gender to how I was born anyway, but I'm not talking about that here...
    JaimeSparkles JaimeSparkles 13-15, T Jul 8

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    ​Last weekend {7/18-20/14) my wife allowed me to dress for her. It was so much fun waking in the morning with my makeup and everything still on.7-18-147-19-14
    stefiecdtv stefiecdtv 51-55, T 10 Responses 21 hrs ago

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    I go out cross dressed regularly. I am very comfortable as my feminine self. I have the opportunity to go out as I travel regularly. One of the special times I have had lately...
    RandiHill RandiHill 51-55 2 Responses 9 hrs ago

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    After leaving the Indian reservation where my father was the government surgeon he was transferred to a job as Zone Director of India Health Services in a small white bush town...
    amiklake amiklake 56-60 Jun 24

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    7 years ago, my life went downhill. I'm turning 17 next week. I sound a little young for this and you may think i'm posting this just because my hormones are busting up and down...
    roberteezy roberteezy 18-21, M Jul 14

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    Junior School Embarrassment When I was in the top year of Junior school I got into trouble in the playground. It wasn't my fault, I still insist after all those years! We had a...
    Jilly53 Jilly53 56-60, F 1 Response Jun 27

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    I was being bullied at High School for "being different". Nobody ever seemed to bat an eye when I walked out of classes for fresh air back in Primary School. I was diagnosed with...
    KMargatroid KMargatroid 16-17, F 2 Responses Jul 5

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    From the beginning of this year I knew I had my work cut out for me. But I didn't know how hard it would truly be. I go to a Private school, we have a small amount of students at...
    rachelharperr rachelharperr 13-15, F Jul 6

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    A quick reminder... this is a true story. None of it is made up. This is PART 4 of the experience I first wrote on July 1st 2014. I would like to suggest you to read that one first...
    hopetolive2000 hopetolive2000 13-15, F 3 Responses Jul 9

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    First of all, I know how lucky I am to have the opportunity to go to college and the option to graduate. But here are my honest thoughts about the whole thing. Some of these...
    LEMONkinks LEMONkinks 18-21, F 1 Response Jul 11

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    A quick reminder... this is a true story. None of it is made up. This is a new topic and has very few links to my previous experiences. None of the things in this story is made up...
    hopetolive2000 hopetolive2000 13-15, F 3 Responses Jul 1

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    What is the best kept secret Karate school in Sacramento and Elk Grove?School of the Tiger Martial Arts!! The school has amazing quality at a lower cost by instructing it's...
    JudyRaderchak JudyRaderchak 26-30, F Jul 1

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