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I Was Crossdressed At School

school initiations in high school are a drag 593 People

    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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    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 May 3

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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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    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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    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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    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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    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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    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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    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 1 Response May 3, 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, F 5 Responses Jul 26, 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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    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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    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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    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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    pardax pardax 13-15, M 1 Response Apr 29

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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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    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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    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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    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

    i probably am. it all started a few years ago. a fire had burned down my house and the only thing that had survived it was a doll i made. naturally i took it with me to my new...
    selselsky selselsky 13-15, F 54 mins ago

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    I was mugged walking home alone. I had been drinking so I can't even remember everything. I feel ashamed like its my fault and don't know how to get over it. There were a few guys...
    dennison4 dennison4 22-25, M 2 hrs ago

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    I can respect people who had a good experience at NAU. More power to you guys. Also, congratulations to the new graduates. You guys definitely deserve it. However, my experience...
    LyraAlluse LyraAlluse 26-30, F 2 hrs ago

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    Anyone who lives in Arizona is aware of the cruddy job market. There aren't enough jobs to go around in the first place, and when you do find a job, you are likely to be abused in...
    LyraAlluse LyraAlluse 26-30, F 3 hrs ago

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    I had been having a very rough time in the weeks leading up to that day. I was still recovering from my break up with the high school girlfriend but I also moved on enough to...
    oncemoreuntothebreech oncemoreuntothebreech 36-40, M 3 hrs ago

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    I wish these was Made in my size would love to wear them again :(
    XxChloexXx XxChloexXx 16-17, F 1 Response 3 hrs ago

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    all my friends used to freak out when someone was getting a spanking. I always thought it was kind of amusing and fun to watch (as long as it wasn't me getting it haha)
    angela82 angela82 31-35, F 5 Responses 3 hrs ago

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    I wish these was in my size would love to wear them again :(
    XxChloexXx XxChloexXx 16-17, F 3 Responses 3 hrs ago

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    so many of you know I have PTSD. I didn't develop it until I was being molested but my story doesn't start there. it starts in the second grade. I had a lot of guy friends simply...
    alantae14 alantae14 13-15, F 4 hrs ago

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    Not long after the group sleepover at my friend’s house, the next installment of “Nude with friends” (friend) happened. My friend’s parents were going away over the...
    auau71 auau71 36-40, M 7 hrs ago

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    I was always being called either shrimp or midget when I was in school
    Rosalindaj Rosalindaj 26-30, F 14 hrs ago

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    I look back at my experience in high school and am so glad it lasted for only 4 years. I know a childhood creates (having a rough/ abused) and shapes you for the rest of your life...
    Vacationings Vacationings 36-40, M 1 Response 15 hrs ago

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    I had bright orange hair way back in 9th grade. I used to get called highlighter head and construction cone. Kids used to make fun of my clothes and my eyebrows also. Back then I'd...
    SphiDaSledgehammer SphiDaSledgehammer 18-21, F 1 Response 1 day ago

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    Now I've started dressing as a woman about 90% of the time at home and my wife just looks at me as her wife. She told me she's equally attracted to her wife and her husband! She...
    tgheather tgheather 26-30, T 2 days ago

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    When I was 18 and into the early months of my 19th year I volunteered to help at the same elementary school I went to up until lunch period. I really noticed how strict school is...
    TheEnduringSunrise TheEnduringSunrise 18-21, F 2 Responses 2 days ago

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    When I first began school in pre-school, I loved it. School was exciting to me. I got to meet new friends, play fun games and learn in fun ways. This persisted throughout most of...
    PinkMellow PinkMellow 18-21, F 1 Response 4 days ago

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    I am a white girl and when I was 10 years old and in the 5th grade I wore dresses, white pantyhose, and a blue jean jacket to school every day. Almost every day during that school...
    beatendownbylife47 beatendownbylife47 13-15, F 4 days ago

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    In the fifth grade I was called fat, worthless,ugly and stupid. Everyday of my fifth, sixth and seventh grade life I wouldn't speak to anyone until I got home. I felt like if I did...
    ThatOneGirlOnTheMoon ThatOneGirlOnTheMoon 13-15, F 5 days ago

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    It was so hot and miserable today, I took off my red blouse and black skirt and had to jump into a cool shower wearing a pair of tan pantyhose, red bra and full slip. I took off...
    CrossdresserLauren CrossdresserLauren 46-50, T 1 Response 6 days ago

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    Being home schooled has advantages and disadvantages. In my opinion, being home schooled out weighs going to public school. My mother was my mentor and a great teacher. She was...
    collegecomputerwiz collegecomputerwiz 22-25, F 1 Response Jun 21

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    At the end of January I went on this amazing program where high school students went to a different country and studied there for 4 months together, while traveling around. I don't...
    TheEverythingFan TheEverythingFan 18-21, F Jun 20

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    I was very ugly and awkward in the middle school. No guy liked me. Then my best friend Liz got a new neighbor. He was our age but he went to another school. He convinced us to...
    coolestdweebyahknow coolestdweebyahknow 22-25, F 1 Response Jun 20

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    Confused? Who am I? I am a man who should have been born a girl. As a child I did not like boy play. I preferred girl’s styles. I believe that I was more mature at an early...
    jbamberg jbamberg 46-50, M 6 Responses Jun 19

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    I have been utilizing my privilage at my new dressing studio to really go for it as it relates to "crossdressing". My latest outing resulted in a very strange sensation of a...
    JessicaDale JessicaDale 51-55 6 Responses Jun 19

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