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I Love Crossdressing As A Naughty Schoolgirl

Personal Stories, Advice, and Support 505 People

    Cheerleader

    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 56-60, M 2 Responses May 18, 2013

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    If Not For Detention

    One of my favorite costumes,and allways love the teacher,student scenario.I am a terrable student,with an even worse teacher.You would wonder why i keep going back to learn these painfull lessons i never retain.If not for detention,i would drop out completly.However i have been...
    royalflush70 royalflush70 41-45, M Aug 3, 2012

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    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 5 Responses May 17, 2010

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    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 41-45 6 Responses Jul 26, 2011

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    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 outfit.my 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 4 Responses Jul 27, 2012

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    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(www.experienceproject.com/stories/have-been-dressing-since-childhood/984252) ive worn over 14 different styles,currently own the clothing items...
    cdBethany cdBethany 22-25, M 2 Responses Apr 11, 2010

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    Skoolgurl

    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

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    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

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    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 22-25, T 2 Responses May 10, 2013

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    Being A Naughty Little Girl

    When I was in my early teens I loved to dress up as a "bad" school girl. I would wear a short pleated tartan skirt, white blouse, tartan tie, & a black bra. But rather than socks & school shoes i would wear sheer black stockings & black patent leather 3" high heels. I...
    nanna2 nanna2 56-60, M 7 Responses Jan 7, 2012

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    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 26-30 Nov 5, 2009

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    Ah, My Favorite Outfit

    I had been dressing up in mom's underwear since I was about 12. Just her rubber girdle and tan support stockings, with panties and 3" heels. That is about as far, as I could get, before exploding. And I was content, until, I discovered one of dad's girlie mags. Inside, among all...
    Joyce1951 Joyce1951 56-60, T 6 Responses Sep 9, 2010

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    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 26-30 2 Responses Feb 22, 2013

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    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 51-55 Mar 28, 2012

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    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 26-30 Dec 13, 2011

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    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 26-30 2 Responses Jun 17, 2012

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    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 26-30 Jul 19, 2010

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    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 26-30 Dec 2, 2011

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    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 3 Responses Jun 9, 2010

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    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 4 Responses May 30, 2010

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    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 12 Responses Jul 17, 2011

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    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

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    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

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    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 5 Responses Feb 6, 2011

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    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 41-45, M Jun 8, 2011

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    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

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    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 1 Response Oct 6, 2011

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    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

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    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 4 Responses Jun 4, 2011

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    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 46-50 Aug 2, 2013

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    Related Experiences

    I can't help but dream of just being a naughty schoolgirl. I want to wear an adorable white blouse that exposes the tiny bow in the middle of my pink bra so I can tease the boys...
    cutegirlypanties cutegirlypanties 31-35, T 1 Response Jul 4

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    Someone send me a naughty story ;) make me wet
    sidkyd99 sidkyd99 18-21, F 2 Responses Jul 12

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    detailed erotica! makes me feel all the sensations by reading them.. love them!
    remydodol remydodol 36-40, F 6 Responses Jul 16

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    I love reading stories that turn me on
    mikayla3223 mikayla3223 18-21, F 9 Responses Jul 24

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    I love answering questions. I love answering naughty questions even more! Bring it baby! lol
    Slutteen Slutteen 18-21, F 8 Responses Jul 6

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    I love reading naughty stories. To me there a big turn on. I heard this site is good for dirty type stuff. If any guys are interested give me a shout
    deleted deleted 26-30 9 Responses Jul 12

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    This is about my experience with sexuality. On the inside, I love being naughty and frisky and submissive, but i'm having trouble with that. Lots of people don't like that, and I...
    HarrisonPorterLacy HarrisonPorterLacy 16-17, M 1 Response 4 days ago

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    I have been married for 15 years. The crossdressing came out about 8 years ago. I was really supportive and loving about it. Felt sorry for Husband that he had had to hide it all...
    LadyLana39 LadyLana39 51-55, F 2 Responses 7 hrs ago

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    Hi guys I'm from uk looking for crossdressing friends.
    sarapiper sarapiper 31-35, T 2 Responses 6 hrs ago

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    A couple musings on my philosophy on "passing." I would love to see interesting discussions/debates develop in the comments section, so if you have anything to say, say it! My...
    necxo necxo 18-21, M 9 hrs ago

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    Any women fancy a naughty chat???
    lecitrician lecitrician 41-45, M 14 hrs ago

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    I was 16 and home alone. I was putting things into the was basket when I noticed a tiny pair of black things on the floor. I picked them up and loved the feel. Curious I pulled...
    sarapiper sarapiper 31-35, T 10 Responses 6 hrs ago

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    Hi my name is ben I, live in swansea in wales, and im 17. I have long had fantasies about crossdressing, I would love to meet people on here to explore this aspect of my...
    swansea21 swansea21 18-21, M 3 days ago

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    Cuffed and detained during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
    banannasplitz09 banannasplitz09 22-25, M 1 Response 1 day ago

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    Sometimes people think that crossdressing automatically would make someone seem gay, but that isn't it! Crossdressing is just a thing that some men (or women) like to do! It makes...
    naco26withcheese naco26withcheese 13-15, M 1 Response Jul 19

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    I have been crossdressing for a while now but the first time I was caught was when i was 10. I have a older sister that washed cloths with mine one morning, and she had her pink...
    Fogle3 Fogle3 18-21 1 Response 1 day ago

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    The first time i was caught crossdressing i wad 16 and wearing high heals, fish net stockings, a short skirt, a small skimpy shirt and makeup on. The worst part is my mom caught me...
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

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    Why are females who accept a guys feminine side so hard to find? Looking to chat to females or males who accept crossdressing 💋
    susspender susspender 41-45, M 4 Responses Jul 12

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    Looking for some one to share story's about getting caught wearing girls panties or crossdressing
    ddavis21 ddavis21 18-21, M 1 Response Jul 13

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    I have been crossdressing since I was in my teens .over the years the compulsion to dress as a woman has intensified dramatically .i now dress completely with full make up and am...
    francescalewis1956 francescalewis1956 56-60, M 1 Response Jul 22

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