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I Love Crossdressing As A Naughty Schoolgirl

Personal Stories, Advice, and Support 501 People

    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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    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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    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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    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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    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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    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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    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...
    tvkaren tvkaren 51-55, T 2 Responses Feb 22, 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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    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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    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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    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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    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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    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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    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...
    tvkaren tvkaren 51-55, T 2 Responses Jun 17, 2012

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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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    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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    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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    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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    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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    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 1 Response Nov 5, 2009

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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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    Fem Sissy Boy is honestly searching for a masculine and protective boyfriend/husband and treat me as your princess wife! I am TG and would even love to dress for you and if you...
    FemGayBottom FemGayBottom 26-30, T 1 Response Apr 4

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    I'm a crossdresser, I love wearing women's panties anyone girls like that? :)
    natessecret natessecret 18-21, M 2 Responses 5 days ago

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    Push me up against a wall and do dirty thing to me. :x
    TxVANITY TxVANITY 16-17, F 2 Responses Apr 10

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    Attention all guys out there! Soo uh quick question... any of ya'll have any specific things that a girl does to turn you on? Any little tips or tricks that you could give me would...
    syddakidd syddakidd 18-21, F 4 Responses Apr 11

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    I'm not interested in women so if you're a woman no offence but that's just me thought I would let u know so u don't add me thinking I am.
    sfjf sfjf 36-40, F 5 Responses 5 days ago

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    I love playing teacher and having my partner play the role of a teenaged naughty schoolgirl who won't do what she is told. I take her over my knee, lift her skirt, pull down her...
    BaredBottomBill BaredBottomBill 51-55, M 3 Responses Apr 6

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    To Sir With LoveLuluThose schoolgirl days of telling talesAnd biting nails are goneBut in my mind I knowThey still will live on and onBut how do you thank someoneWho has taken you...
    Batboy69 Batboy69 56-60, M 1 Response Apr 10

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    I discoved my love of strap ons and beautiful woman doing it to me. I love being naughty ;) so any woman want to make me there slave ? ;) pm me asap
    akstud akstud 18-21, M Mar 31

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    I love crossdressing for sex with men. I like feeling as much as a girl as possible. I love thongs and bras, and all womens sexy clothing.
    islutmyself54 islutmyself54 26-30, M 1 Response 6 days ago

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    Case #1 Part two: I am lying bound and gagged on a bed in my schoolgirl outfit. I can’t see or hear anything in this quiet room. The cloth tied around my eyes is real tight...
    schoolgyrlKaren schoolgyrlKaren 41-45 2 Responses Apr 14

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    At the fire station day dreaming of having a Beautufull sexy naughty lil girl.. Only in stilettos and nothing else making my humpday.. Having sex inside a fire truck mmmmmmmm on...
    mckddy mckddy 36-40, M 37 mins ago

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    i wish to tell you about an experience i had with my fiance years ago... we had to attend a friend wedding...so i was all dressed up in an indian outfit (lehga..choli)..one of my...
    miistyy miistyy 22-25, F 1 Response 7 hrs ago

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    In any of my assorted schoolgirl outfits. I must be wearing a short skirt or minidress. The feeling of struggling against ropes, being held prisoner, unable to scream, and...
    schoolgyrlKaren schoolgyrlKaren 41-45 Apr 12

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    A night out as Rhonda had me visiting a local establishment where a band was playing that I follow. I was with a friend, and she is very acceptable of my crossdressing. I was...
    SweetRhonda SweetRhonda 51-55, T 5 Responses Apr 8

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    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30

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    I want to know more about crossdressing
    nightfun56 nightfun56 18-21, M 2 Responses Apr 9

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    I like Crossdressing. But I have never told anyone. Do you think I should?
    Pinklovemaddie Pinklovemaddie 13-15 4 Responses Apr 14

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    I want a girlfriend who fully supports me crossdressing but I cant find anyone nearby.
    natessecret natessecret 18-21, M 1 day ago

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    Nothing more beautiful that sweet young asian girl with there schoolgirl uniforms.
    leginspector leginspector 26-30, F 4 Responses Apr 7

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    I love schoolgirl and teacher
    andrew969 andrew969 26-30, M 3 Responses 5 days ago

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    I like reading a lot. Novels, poëtry and philosophy. But also naughty stories, for example at ASSTR.org. Discovered that website in 1998 and visit it often. There is also a...
    MartenBoots MartenBoots 41-45, M 2 Responses Mar 29

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    Who doesn't love to be naughty.. Soo let's get very naughty for Easter soo you can call me thumper!!
    mckddy mckddy 36-40, M 5 days ago

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    I'm a mother to a 4 month old gorgeous perfect baby. Being a mom is the best thing in the world. However, when the baby is asleep I can't help but chat dirty online, and send...
    92youngforever 92youngforever 18-21, F 23 Responses Apr 8

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    I think this young mans voice is simply amazing. I am sure a lot of you have heard it already so enjoy! :) "Ride" Oh, oh, oh, oh yeah Take off those heels, lay on my bed Whisper...
    DoubleyouX DoubleyouX 22-25 Apr 8