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I Was Crossdressed At School

school initiations in high school are a drag 594 People

    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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    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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    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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    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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    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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    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 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 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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    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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    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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    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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    pardax pardax 13-15, M 1 Response Apr 29

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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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    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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    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 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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    Related Experiences

    pt 2 , from the other experience i posted this is more up to date , this part is basically what my life is like at a new school as a transgender for 1 week. 2 weeks ago i was at...
    louisenufc louisenufc 13-15, T 2 Responses May 6

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    I love learning. Learning gives me a sense of fulfillment. But when I was in school, I didn't learn anything. Well, that's not entirely true. I learned how cruel and judgmental...
    dontyouunderstand dontyouunderstand 18-21 May 18

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    I was at home sick. My mom was a dispatcher and she got 5 calls from in the tower. She came home crying. Apparently one collapsed she was talking to them. She said the women in the...
    takethat69 takethat69 26-30, F 3 Responses a week ago

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    The reason for me coming to this app is to share my life experience n my mother expired when I was in school days n my father married again n my father had sex with me from the...
    bindu2605 bindu2605 22-25, F 5 Responses May 3

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    when i was in middle school i have been bullied a lot, i just afraid if one day i met them again
    sweetberry88 sweetberry88 26-30, F 11 mins ago

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    This happened about a year and a half ago when my Aunt came to stay with my wife and I from out of town so she could attend a high school reunion. She was due to arrive at our...
    hotgarters hotgarters 46-50, M Apr 29

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    A year ago we entered to highschool and so I entered to a school team, after I committed an error in it, the other kids of the team started to call me with an awful nickname, so I...
    ThompsonX ThompsonX 18-21, M 1 Response 3 hrs ago

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    I've had countless "crossdressed while driving" experiences, including being stopped by the police...(I'll get round to posting about that sometime).... but this one hasn't...
    AmandaCarrington AmandaCarrington 56-60, T 2 Responses May 11

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    It was the third grade we had just got done with play practice and I noticed this blue velvet hoodie with a jewled butterfly on the back. Now I love to wear girls clothing but know...
    John681 John681 18-21, T 3 days ago

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    I went to work crossdressed on halloween .after i dint go home i just crused around the town
    Jazonx Jazonx 36-40 5 Responses May 10

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    It was shortly after I started going out dressed enfemme in public and I was wearing a modest blue dress and heels like I had just gotten out of work. Walking into a department...
    Elizabethanne253 Elizabethanne253 61-65, T 9 Responses Apr 29

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    My first time ever going out in public crossdresser. I was with my sister's friend, Tori who knew about my dressing before my sister and mom did. I had asked Tori for her phone...
    CDcarly CDcarly 22-25, T 4 Responses May 17

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    Part 2; Oh what a night that was!!!!! Due to EP censoring this is the Disney version of events. lol I drove the garage courtesy car to my wife's work's customer's car park with 2...
    AmandaCarrington AmandaCarrington 56-60, T 3 Responses May 19

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    My most memorable time going out cross-dressed was the time I had to drive 200 miles for an appointment. I decided I would do it as a women and get changed for my appointment...
    bmg1kel bmg1kel 61-65, T 2 Responses May 7

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    I had such a brilliant night out as Lisa last night, had a lot of fun with my girlfriends. We did a lot dancing and quite a bit of drinking :) It was fantastic being out as Lisa...
    GirlyLisaTG GirlyLisaTG 26-30, T 16 Responses May 10

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    Hi everybody, hope all you agree with me how difficult to hide feminism being male. This is a real incident how I was caught unaware by my wife with my anklets on. After my...
    gm2707 gm2707 22-25, M 3 hrs ago

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    Hi I go by Fruity punch on here.I would like to share a personal story from my experience with my mother.Let me start back when I was younger for you to understand the emotional...
    Fruitypunch15 Fruitypunch15 31-35 1 Response May 13

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    I should have dropped out of school. I remember how happy I was when I was a young kid. I was very carefree and joyfully excited with life. Then school came along and has damaged...
    AnonymousGuineaPig AnonymousGuineaPig 22-25, M 6 days ago

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    I was bullied for 12/13 years of my life. It still hurts me a lot. 4 of those years in particular which I experienced at high school. This was from teachers and students and even...
    1lonelydaisy 1lonelydaisy 41-45 4 Responses 2 days ago

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    Many discussions arise as to whether or not spanking should be allowed in schools. You hear so many anecdotal accounts that it is often hard to where or not anything “good...
    Emily1945 Emily1945 66-70, F 6 Responses 4 days ago

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    I read a quote from Albert Einstein, and we have something huge in common, our distaste for school. It seems like all they do is prepare us for tests and exams. Once we take that...
    moose73630 moose73630 16-17, M 2 Responses Apr 29

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    Over the knee in assembly. I was a normal boy at school and got my fair share of punishments from teachers. The first time I got punished I was 7 years old and at junior school...
    PJL2015 PJL2015 61-65, M 4 Responses May 19

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    First grammar school caning. I went to a grammar school in the 1960’s and the cane was used by all teachers. I was very careful after my experiences with Mrs Brown at junior...
    PJL2015 PJL2015 61-65, M 4 Responses May 19

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    About 7 years ago I had the task of house sitting at my friend's house while they enjoyed a family holiday. Paul and Anita were two of our best friends, and amongst the first...
    AmandaCarrington AmandaCarrington 56-60, T 2 Responses Apr 28

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