Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

Wild Cat

by Katiecat on Sep 12, 2017
BDSM

Cat squirmed on the hard wooden chair and watched the seconds tick by on the clock. 4:55 on Friday afternoon. Five minutes until doomsday. She worried at an almost non-existent hangnail, nibbling it smooth. Was she a glutton for punishment? Had a death wish, perhaps? She smiled ruefully to herself. Why, oh why, was it so hard to get kicked out of school? T...

Detention Pt. 03

by Croony on Sep 15, 2017
Mature

Toby Johnson had a fitful sleep recalling all the things that had happened that afternoon. How he'd been seduced, sucked and fucked by Mr Gayson, his music teacher, while his mother had been used and abused by his headmaster, Adam Jones and Mrs Smith, the school secretary who when Mr Grayson left came to the bedroom he was in and sucked and fucked him for t...

Naughty School Girl Ch. 03

by Maddisyn on Aug 27, 2019
Erotic Couplings

Natalie's in trouble again! A coincidence introduced Natalie to the Practice and a new doctor in her first story. She sought assistance for her concerns about a long-held intimate secret effecting her teaching career and personal relationships. Doctor Love's sexual therapy was too tempting for the young teacher, fulfilling her favourite fantasies in her s...

My Boyfriend Likes to Expose Me Ch. 08

by VanessaEvans on Sep 11, 2017
Exhibitionist & Voyeur

All characters involved in any sexual activities in this story were over the legal age of consent when the events took place. Part 08 - House Sitting – Week 3+ part 2 ============================ DAY 20 --------- I woke up to the sun shining through the window and wondered where the hell I was. There was a clock on a table and I saw that it was nearly 12 o...

Back to School

by AaronWebster on Sep 18, 2006
Swinging

The train clatters through the English countryside, past nameless farms and villages. You clutch the letter from the school to your chest, in case anybody recognises it. For one bizarre and irrational moment, you imagine yourself on the way to Hogwarts or some other school of juvenile literature. Cautiously, you slide the prospectus for St Mabyn’s out of its...

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West Valley High Day 124: Cattle Prod

by homeboundboy on Oct 6, 2020
NonHuman

"Good morning, Miss Mitchell," West Valley headmaster Stephen Krutz said as he approached his prize student. Susan Mitchell was standing in one of the faculty restrooms, her legs spread wide with ropes tied to the plumbing fixtures. Her arms were tied outstretched with rope around her wrists. Kylie had brought her here earlier in the morning and bound her be...

Six of the Best Ch. 03

by KinoKe on Sep 17, 2017
BDSM

'NO RUNNING IN THE CORRIDOOR.' The Headmaster's voice rang out loud and clear. For a brief moment the three miscreants halted in their tracks and cast a guilty glance in the direction from which the edict had come. 'How many times do you boys need to be told?' The ringleader muttered something appropriately apologetic, and then all three walked, cautiousl...

Yes Please, Headmaster

by Stripemoff on Dec 21, 2017
Mature

Charles, my husband, hadn't left me much to do when he left for the U.S.A. on a business trip. That was because he was such a brilliant organiser. He planned everything down to the last detail covering the weeks he was away. But, he did leave me one thing to do. "Just make sure that William's entry form to St. Leonard's school gets there before the 20th of...

Six of the Best

by KinoKe on Sep 17, 2017
BDSM

'Ah. Mrs Preston. Do come in.' The Headmaster rose slightly from behind his large desk but the late-afternoon light flooding in through the windows behind him made it difficult for Mrs Preston to see him properly. There was, however, no mistaking his rich authoritative voice. 'It's Dale, isn't it?' 'Delia,' Mrs Preston said. The Headmaster turned his he...

Sarah Has Another Bad Day

by 0131aj on Sep 13, 2017
Exhibitionist & Voyeur

Ever since her calamitous last day at school the previous year, Sarah's wardrobe had changed significantly. Throughout the summer she had been preparing for the new term and now she owned contained several elegant and professional trouser suits. She liked the look of them, the feel of them, the protection they offered and the unspoken message they sent to he...