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I Was Crossdressed At School

school initiations in high school are a drag 573 People

    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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    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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    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 8 Responses May 25, 2010

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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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    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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    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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    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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    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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    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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    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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    For Halloween . Fall dress,

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

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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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    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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    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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    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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    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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    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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    Related Experiences

    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 16-17, 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 16-17, M 2 Responses 3 days ago

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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 16-17, M 1 Response 3 days ago

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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 1 Response 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 16-17, 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 16-17, M 1 Response 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 2 Responses Jul 20

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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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    I have had morphea since 1965 at the age of 14. Back then it was extremely rare to find a doctor who even knew what morphea was. My morphea started as a round spot on my wrist...
    Muffygirl Muffygirl 61-65, F 2 hrs ago

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    In 4th grade I wrote this , it was the first time I got rejected by a boy: I cried , I died , My heart is scattered , my love really mattered , but got shot, by this boy who...
    bela5562 bela5562 13-15, F 1 Response 4 hrs ago

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    But I still LOVE school so much!!! School is love school is life ( for me )
    bela5562 bela5562 13-15, F 4 hrs ago

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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 2 Responses Jul 14

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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 Jul 15

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    Yesterday I got out of the shower and put on a white push-up T-shirt bra, my short shorts, a white "Wife Beater" style T-shirt, sandals, strawberry blonde wig and headed for the...
    davis36a davis36a 61-65 2 Responses 5 days ago

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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 Jul 22

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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 Jul 22

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    I have just got out of bed. I was wearing a thong and animal print shortie nightie. Now I am dressed in a red bra, a very short blue vest and a pair of see through blue knickers...
    deleted deleted 26-30 3 Responses 4 days ago

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    I haven't gone out fully dressed in years. Went through a big purge and haven't had the money to buy new clothes. The last time I did went to the mall and no one ever suspected. I...
    AmandaM02 AmandaM02 36-40 2 Responses 14 hrs ago

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    When I was 17, my friend had convinced me to go with her to this guy's house. There was four of us: me, my friend, and the two guys. I was 27, my friend was 18, and the guys were...
    Becca831 Becca831 16-17, F 4 hrs ago

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    Lately I've been questioning myself a lot lately, "How was I not worth it?" Or "Was I not worth it for him to fight on my side?" I would replay our time together and all the...
    stella517 stella517 26-30, F 1 Response 3 hrs ago

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    This could be super long, so I'll try to sum it up. (: Preschool, kindergarten, & 1st grade were fine. In the middle of 2nd grade I moved to this sorta ghetto town because my mom...
    girlinNJ girlinNJ 16-17, F 6 days ago

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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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    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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    I am a very recent high school graduate. In the speeches at graduation, they were talking about starting the "new chapter in your lives." I have strong ideas about where, who...
    jpk29 jpk29 18-21, F a week ago

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    10 years. I got bullied for 10 years while in Primary School and High School, from grade 2 till grade 12, the year I graduated. So it all started in grade 2 when my best friend...
    darkbladeangel darkbladeangel 18-21, M 6 days ago

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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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