I Was Crossdressed At School

school initiations in high school are a drag 634 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
    61-65, T
    2 Responses May 3, 2013

    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

    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...
    deleted deleted
    1 Response May 5, 2013

    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...
    deleted deleted
    4 Responses Jul 26, 2012

    My love of crossdressing started at school

    when I was dared to go with twom of the girls from the convent school on a bus ride with them in their school uniform. I found it an amazingly uplifting experienvce to be dressed in a rather plain gymslip but with quite sexy lingerie underneath
    deleted deleted
    Nov 5, 2015

    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
    7 Responses Nov 3, 2012

    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
    1 Response May 3, 2015

    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
    5 Responses May 25, 2010


    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
    pardax pardax
    16-17, M
    1 Response Apr 29, 2015

    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

    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
    Jun 22, 2014

    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
    7 Responses Jan 25, 2013

    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
    May 1, 2015

    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
    2 Responses Aug 30, 2011

    In the seventh grade I was starting to be more

    openly feminine and had confided to a couple of the girls in my class that I cross-dressed. So they started inviting me over to their houses after school to hang out with them. Their parents were really cool about it I guess because of me acting feminine. I got invited to a...
    Jena1976 Jena1976
    36-40, T
    1 Response Jan 1

    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

    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
    61-65, M
    Nov 8, 2012

    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

    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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