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I Love Crossdressing As A Naughty Schoolgirl

Personal Stories, Advice, and Support 481 People


    just love to dress as naughty schoolgirl!! since i know that i will get punished by havin my panties pulled down and dress up so that i can be spanked on my bum!!! love to dress as a sissy schoolgirl!!!
    mandiejune mandiejune
    51-55, M
    Feb 10, 2010

    Uncle Charlie

    i met a man through a friend of a friend the his name was charlie but he liked me to call him uncle charlie we talked on the phone for about a week and we gradually worked a scinirio out between us the sinario was that i would pretend to be his neice and he was uncle charlie we...
    fcukpanties fcukpanties
    41-45, M
    11 Responses Jul 17, 2011


    I have 3 times dressed as a school girl and guys love it. I have so much fun Being a **** dressed. Makes me so happy and I get really horny too.
    SissyTony SissyTony
    61-65, M
    2 Responses May 18, 2013

    My New School Dress

    it was my birthday about a month ago and with some of the money i recieved as presents i decided that i wanted a new girly dressing leans more towards costumes and age play, so a set out to find a perfect little girl outfit and i found it.i got a custom made pink...
    cdBethany cdBethany
    22-25, M
    3 Responses Jul 27, 2012

    Dressed By A Schoolgirl

    How I became a cross dresser with a fetish for schoolgirl uniform, humiliation, small winkie humiliation... My mother used to work and was not home until 6pm so it was arranged for our neighbor to take me in her house for two hours after school and I could play with her14year...
    rachelusissy rachelusissy
    31-35, M
    2 Responses Jun 4, 2011

    I Would

    I woud, given the chance, and the way my life is going that might not be too far away. Fingers crossed one of my friends has a back to school party.
    Heellover Heellover
    36-40, M
    Nov 25, 2012

    Role Playing

    had a tv friend who shared my taste in clothes. we were both switchable and one evening at her place i changed into a wite blouse, plaid skirt knee socks amd mary janes. i let her spank me , use my mouth , then lead me to the bathroom where i knelt to drink her hot stream as she...
    deleted deleted
    2 Responses Jun 17, 2012

    Bad Girl

    It's such a turn on when my wife talks dirty to me while I'm dressed in my schoolgirl outfit. The nastier she gets, the hotter I get.
    deleted deleted
    1 Response Nov 5, 2009

    Please read my blog on my transgender journey ,

    my life on sex and pleasure! Do comment and text me if you want to continue with me
    IndianZeus IndianZeus
    22-25, T
    Apr 6, 2016

    Gymslips & Knickers!

    For me, the ultimate school uniform is the gymslip or pinafore, worn with a crisp white blouse, school tie and of course matching cotton interlock school knickers underneath. I dream of being a 'schoolgurl', outwardly demure and well behaved in my uniform as I attend lessons, all...
    PrettyPennyM PrettyPennyM
    3 Responses Jul 26, 2011

    New Plaid Skirt

    I'm feeling too gurly to go to bed. Ijust put on a plaid skirt and mary janes to take a walk. I'ts late and the best time, since the neighbors wont be up. too late to arrage a date. : ( i already feel like a bad gurl , so i'll just take a walk, enjoy my drink- maybe wet my skirt...
    deleted deleted
    1 Response Feb 22, 2013

    I Like Dressing As Most Things.

    I like dressing as most things, right now i seem to be in an adult baby girl stage, but who doesnt like dressing as a school girl. Girls do, men do when they get the chance, its alot of fun, brings back school memories.I dont limit myself, i also enjoy dressing as a maid...
    Babyclaireuk Babyclaireuk
    46-50, M
    Jun 8, 2011

    Wearing Naughty Clothing While Crossdressing

    I love wearing slutty or naughty clothing when I crossdress. Panties, pantyhose, bras, bodystockings, lingerie, stockings, garters, tight pants, short skirts, spandex tight fitting pants or skirts are my favorite as they cling to my body and show off what I am wearing underneath...
    pantiescouple pantiescouple
    Dec 13, 2011

    Gym Knickers And Skirt

    Lucinda – it was me who borrowed, well took, your gym knickers and gym skirt from the girls’ changing rooms. I know its more than thirty years ago but I feel better for confessing. I was 17. I was in the early stages of my cross-dressing habit. I was in school late...
    xxlexiexx xxlexiexx
    Mar 28, 2012

    Naughty Schoolgirl

    I love to wear a White blouse,Navy and yellow Stripe tie,White Knee length Socks,a Short Pleated Navy blue Skirt,Black Shoes and a Long blonde Wig tied with navy Ribbon into 2 bunches, and underneath a pair of  Thick Cotton regulation Navy blue knickers.I love to Tease and...
    kimknicks1 kimknicks1
    46-50, M
    4 Responses May 17, 2010

    Cross Dressing With Friend

    Well i had known John for over a year i knew he was gay and probly wanted to sleep with me .up this point i had been cross dressing since i was 17. I started out mostly with dance wear leotards tights leg warmers and such. Over the years I grew to enjoy plaid skirts and fastion...
    mical1234 mical1234
    26-30, T
    2 Responses Feb 6, 2011

    I Bought My Schoolgirl Skirts At The Thrift Store For A Dollar

    Currently, my favorite is to get dressed up when my wife is out of the house running errands and I know she will be gone for awhile. I have aquired several very short tartan/plaid schoolgirl skirts from the local thrift store that I can barely get over my hips ($1.00 each from...
    deleted deleted
    Dec 2, 2011

    Love Wearing Lingerie

    I have always been a crossdresser. Weekends alone in full dress, nights of sleeping in a nightie, days of going to work in bra, panties and stockings. Back when I was dating I started to date a beautiful woman and slacked off somewhat with dressing. One day I wore my usual bra...
    pantiescouple pantiescouple
    Jul 19, 2010

    How I Got My Girl Name(a Crossdressed Schoolgirl Sex Story)

    it was about 4 years ago. id got my girlfriend to dress up as a naughty schoolgirl a few times while we had sex(something she still does for me) one night i suggested that i dress up as the schoolgirl and to my amazement she agreed.the uniform was a short black skirt,white...
    cdBethany cdBethany
    22-25, M
    1 Response Apr 13, 2010

    My New Uniform

    finally came yesterday.... my cute new japanese schoolgirl inspired lolitta dress,it feels fantastic on and looks sooo cute hope you like my pics bethany
    cdBethany cdBethany
    22-25, M
    3 Responses May 30, 2010

    Let Me Be The Master -maybe The Headmaster.......

    ....and will mean I can tell the naughty schoolgirl when to give head to the master who is me................
    phildavis15 phildavis15
    51-55, M
    1 Response Sep 6, 2012

    What I Have Always Wanted

    i have alwayd loved being a school girl. it all started when i was playing dress up at a friends house and his sister dressed me as a little school girl so we could pretend she was a teacher and me and my mate were her students and ever since then i have loved role playing as a...
    xdsubamy xdsubamy
    26-30, T
    1 Response May 10, 2013

    Naughty Gurl Yesterday

    always on my day off when im showering and shaving i deside how i will dress this day. sometimes conservative like a housewife, sometimes like a little **** tight short skirt heels ect, somes in my little sissy girl outfit, but this day i desided to be a school girl. i put on...
    stephaniea stephaniea
    46-50, M
    Jan 1, 2012

    Playing With Another Naughty Little School Gurl

    I have been cross dressing for quite a number of years. It wasn't till recently though, that I took steps to become what I had fantasized about for some time............."A Naughty Little Lesbian School Gurl" Through a local dating site, New Zealand Personals, I had met up...
    redbow25 redbow25
    56-60, M
    Oct 6, 2011

    What Can You Do When Crossdressing As A Naughty Schoolgirl?

    Let's see, You can play with the princess. You can help out the neighbor lady. You can escape the boredom with friends while in detention. You can discover why you have so much in common with your aunt when you have nothing in common with your mom. You can bump that "B" in AP...
    sissyskoolgurlatgmailcom sissyskoolgurlatgmailcom
    Aug 2, 2013

    Being A Naughty Schoolgirl

    I love dressing as a naughty school girl in a pair of see through panties, a short pleated skirt, a white blouse & a pair of knee high socks
    xdpaul xdpaul
    56-60, M
    1 Response Jun 12, 2011

    I Love Schoolgirl Uniforms

    ive always loved wearing schoolgirl uniforms infact it was the first thing i ever wore while crossdressing which is in another story( ive worn over 14 different styles,currently own the clothing items...
    cdBethany cdBethany
    22-25, M
    2 Responses Apr 11, 2010
    Garethhyde56cf833le Garethhyde56cf833le
    46-50, M
    1 Response May 18, 2015

    A Day Out In My School Dress

    this past weekend i was in london,spending a full weekend crossdressed.i wouldnt dare do this around my own areabut i dont know anyone in london. on saturday i was meeting up with some people that would be at a club id be at on the evening.i decided to go to this meet in my cute...
    cdBethany cdBethany
    22-25, M
    2 Responses Jun 9, 2010
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