I Was Crossdressed At School

school initiations in high school are a drag 646 People

    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

    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

    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

    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

    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

    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
    6 Responses May 25, 2010

    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


    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

    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

    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

    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

    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

    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

    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

    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

    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
    pardax pardax
    13-15, M
    1 Response Apr 29, 2015

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