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I Was Crossdressed At School

school initiations in high school are a drag 581 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 1 Response May 3, 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    For Halloween . Fall dress,

    tights,and shoes.
    pardax pardax 13-15, M 1 Response May 12, 2014

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    Related Experiences

    I was caught by my landlord we told him we were having problems with the pipes in the bathroom for master bedroom I was home alone so I was crossdressed I did not realize he had...
    Edwardkarter Edwardkarter 36-40, M 2 Responses Feb 2

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    ok so we was at the dinner table eating our dinner in peace, and then we was rudely interrupted by mom's phone. it was the school calling mom to tell her that I skipped school...
    ThatOneSomaliGirl ThatOneSomaliGirl 13-15, F 6 Responses Feb 19

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    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 Feb 1

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    I was at school one day and I was just talking to my favorite teacher (she's 23 and really pretty) at the end of the day. Then I fel the urge to poop, s o I started pushing. She...
    ac18 ac18 13-15, M 1 Response Feb 6

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    I was in 8th grade and me and my friend cheated of each other during a test and our teacher Mr guffy saw us and gave us zeros and I thought that was all of the punishment until he...
    sharakate1234luvbug sharakate1234luvbug 22-25, F Feb 2

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    I'm in a bad position to become a crossdresser or any kind of trans/sissy/ect. I'm 17 and live at home with family and I don't go our much. I do not currently attend school so I...
    ConfusedSecrets ConfusedSecrets 18-21, T 2 Responses Feb 17

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    Well not just but i did this when i was 15. I had been dressing in my mums stuff for years aswell as saving pocket money and buying some of my own items. It was the summer holidays...
    louisetv louisetv 41-45 3 Responses Feb 1

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    Went out fully dressed a few weeks ago. Wore a white and purple striped top, black skirt and black 5 inch pumps. Looked and felt awesome. Left very early in the morning. Went...
    83218tb 83218tb 36-40, M 2 Responses Feb 7

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    Advice to those that do. There was a time when I was dressed enfemme 24/7 for weeks at a time and more people knew me as Amber than as Albert. That was a long time ago and I'm...
    AlbertSAT AlbertSAT 66-70, M 16 Responses Feb 7

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    I am on a mid-winter business trip to a place where it was warm and sunny. So I had to get out and enjoy the sun. I went to Payless and bought a pair of sandals (male style...
    cdsubalice cdsubalice 56-60, M 5 Responses Feb 11

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    My first time out dressed was a number of years ago. Prior to this my dressing was at home, both in the closet. and when I finally came out to my wife. After a period of...
    MandytgAndy MandytgAndy 70+, T 5 Responses Feb 11

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    today for the first time i decided to wear these panties i really like under my clothes n i LOVED it:) so comfy! I've been cross dressing for a good while now don't know why i...
    ivcd101 ivcd101 22-25 Feb 10

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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 1 Response Feb 1

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    So, I'm a Catholic but attended more public schooling than private. My husband is a cradle Catholic. We chose to send our children to a Catholic elementary school (the same one I...
    FindingBetterWay FindingBetterWay 46-50, F 1 Response Feb 17

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    My husband (who we shall call Bug) and I met when I moved to his small town (we're talking less than 2,000 people) halfway through 7th grade. We were in the same year, but it...
    quirkygirl520 quirkygirl520 22-25, F 1 Response 4 days ago

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    so my wife already knows I dress, and I have been doing it openly with her for a few years now. Well a few nights ago my daughter came downstairs and caught me in my wig and no...
    Allyson02 Allyson02 31-35 4 hrs ago

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    You may be shaking your head at this experience. I mean, what the heck would a 13-15 year old know about love? If I were somebody else, I’d brush this story aside into the...
    SugarAndStrawberries SugarAndStrawberries 13-15 6 Responses Feb 3

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    Most of us of a certain age got the cane at school at least once. I was 11 when I got it the first time (and the only time at school), still in junior school. I used a word in...
    alanbt alanbt 61-65, M 2 Responses Feb 9

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    I hate high school, middle, elementary, and I know I will hate college. High school is such a battle for me, socially and academically. Its one of the main causes of my depression...
    LoveLovingElmer LoveLovingElmer 18-21, F 1 Response Feb 12

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    I see all you younger and it makes me think about what I went through. Break ups, he said she said, fake friends and trying to fit in somewhere. Well I never fit in anywhere but...
    TheVirginRapids TheVirginRapids 18-21, F Feb 12

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    Not just high school. I hated school in general. I used to beg to stay home not that it ever did a bit of good. My parents would say you aren't the only person in the world who...
    jamlham jamlham 31-35, F Feb 11

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    In the seventh grade I started at a new school. It was very hard for me to adjust. I didn't make many friends and I kind of just did things on my own. I really wasn't accepted by...
    tourdeforce tourdeforce 18-21, F 7 Responses Feb 19

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    Ok I want to post something. I need to get this off my chest. I want to know why my school singles me out. The reason why I believe this is that I have gone down memory lane at the...
    cloudycarnage cloudycarnage 16-17, M 1 Response 2 days ago

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    Please read my last post before this one. I haven't gotten to writing this post for a few weeks now as I've completely drowned into all my projects and exams at school. So please...
    hopetolive2000 hopetolive2000 13-15, F 1 Response Feb 16

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    My high school looks like a DMV Mental Institution. I went to so many other high schools for matches and you can literally fit my entire school into half of their entire school...
    mightymouse69 mightymouse69 16-17, F 1 Response Feb 8

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    and it was unfair! I am usually a very nice person, I have been in school for a long time and I have NEVER gotten in trouble to where I was sent to the principals office. I just...
    ForeverUninvited ForeverUninvited 22-25, F Feb 10

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    High school really stuck out in my life. I Grew up in P.A. And moved when I was 10. I started middle school and had to sorta shadow some people I met in other classes...
    Nightwheel Nightwheel 16-17, M Feb 15

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    I started to study at an open school years ago,i chose to study there instead of going to normal school because i hated a lot of kids at my old school.i only have to go to this...
    IsmaelAlejandro IsmaelAlejandro 16-17, M a week ago

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    My step dad used to try and 'toughen me up' when he realised I just wasn't like that he started mentally abusing me, he would say I was a girl for not liking fighting and would...
    LeighUK LeighUK 41-45, M 2 Responses 4 hrs ago

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    It was the summer after high school graduation. I was young, dumb and didn't really know what I wanted. I had jumped the gun and held off on having a grad party until close to the...
    Loyaljay Loyaljay 18-21, M Feb 3

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