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I Love Schoolroom Roleplay

Personal Stories, Advice, and Support 339 People

    A Visit To The Headmaster

    Last week i reported to a new headmaster for the first time. On arrival i was sent to change into school clothes. this consisted of white vest and underpants grey long school socks white shirt small grey school shorts school sweater and tie shiny black school shoes. Once...
    deleted deleted
    26-30
    11 Responses Dec 18, 2012

    Visiting My Headmistress

    This account is of my first visit to my ‘Headmistress’. I had been reported for misbehaviour and instructed to report to the her study. On entering, I was initially berated for having picked on Amanda (a girl in my form) to such an extent that she was desperately upset, and...
    AllanBurns AllanBurns
    61-65, M
    4 Responses Dec 31, 2010

    I'm in the position where I can be put into

    traditional uniform, bent over for a paddling or the cane, skirt raised and knickers lowered for just being cheeky, not doing my work or lying. It'll learn me, I guess.
    deleted deleted
    26-30
    3 Responses Jul 30, 2015

    Sent To The Headmistress

    This is some roleplay from recently:   I had an email stating “COME TO MY OFFICE AT 12 NOON SHARP” it contained instructions on how to get there, and instructions on what to wear, and how to present myself.   I got to the property just outside Wrexham it...
    madeager madeager
    31-35, M
    2 Responses Feb 4, 2010

    U Like Younger?

    I´m yours at yahoo IM: Adelina_ger
    deleted deleted
    26-30
    Dec 17, 2012

    Caned By The Biology Master

    A friend and I carried out this Schoolroom Roleplay scenario with me as a 14 year old pupil at an English Grammar School and he the Biology Master. I was very cheeky about the Biology Master, saying to another boy that he had a lovely pert bottom I would love to smack...
    deleted deleted
    26-30
    Jul 11, 2012
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