Headmaster Punishment Bdsm Stories

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Length
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Infinite Scroll

Class Rules Ch. 03

by 0131aj on Sep 17, 2017
Fetish

Shirley thought that the Headmaster would now agree to retaining both her husband, Julian, and herself in their teaching posts at the all girls school. She had allowed him to spank her over his lap, had held his large cock (much larger than Julian's) in her hand and had not tried to escape when he started to shoot his spunk all over her face. Julian had neve...

Tabatha's Taboo

by MisterRe on Sep 13, 2017
BDSM

Tabatha sat at her desk as bored as usual, she chewed on her pink bubblegum and blew out a big bubble letting it burst before gathering it all back in and starting again. She was, as usual, oblivious to what her teacher was saying choosing instead to spend her time writing "Tabatha 4 Jack" and various other schoolgirl notes on her book, her minded drifted...

Reunion

by LaurelAspen on Jul 4, 2018
BDSM

Penny's footsteps echo down the long corridor, early evening sunlight filters through windows set with leaded glass, splashing rainbow colours onto plain stark walls. Penny, more properly Penelope, stops for a moment; a knot of anxiety twists in her stomach, apprehension lines her face. Pushing back her shoulders resolutely she continues, carefully checking...

Spank Me

by Goldeniangel on Apr 3, 2019
Fetish

Authors' Note: This is a rough spanking story involving anal sex. Enjoy! ---------------------------- Hannah shivered as she walked down the hallway to the Headmaster's office. She was a horny little slut and she often got in trouble... ever since the very first day that she'd arrived at the all girl's school at the tender age of 18. That day she'd gotten...

Painful School Reunion

by djt_one on Sep 19, 2017
BDSM

It had been over 6 months since John and Sue had first been introduced to the painful pleasures of caning by the fraudulent Dr Hay. Whilst they realised that his methods would not help their chances of conceiving their first child, they had found another dimension to their sex life. John very much enjoyed caning his wife, and Sue enjoyed the sex afterwards!...

The Headmaster's Room Ch. 01

by Mag58 on Sep 12, 2017
Fetish

This story is in three parts and begins in 1985 when I was 18 and finally ends last year. "Miss Simpson! Go straight to the Headmaster's room now!" Mr. Flanders shouted as he pointed to the Religious Knowledge classroom door. I shrugged my shoulders and slowly made my way to see Mr. Skinner for the third time that week. With hindsight, at that time of my l...

A Headmaster's Lesson Pt. 01

by LittleKay on Nov 6, 2018
Fetish

Greetings! Thanks for taking the time to read my story. Feedback and Comments are welcome! Please read the disclaimers at the end before leaving negative comments on the themes or content. This *is* a dark, twisted story. Apologies in advance. _________________ The only thing worse than growing up in a wealthy religious family was being sent to boarding...

The Headmaster

by PaulieCelt on Mar 11, 2019
BDSM

Fiona sat in her car for long moments, her head leaning toward the open window and exhaling puffs of smoke as she readied herself for the situation ahead of her. She glanced back and forth at the little gold-bracelet style watch on her wrist, shaking her head, and sighing through her nostrils each time. As her lips wrapped around the butt for the last time...

Morgana's Painful Lesson Ch. 3

by Morganauk on Sep 16, 2017
BDSM

Morgana lay in bed on Monday evening and wondered what the next morning would bring. Her mind had been filled with thoughts of nothing other than last Friday's party. She slipped her fingers inside her pussy and smiled as she remembered the events of that evening. The time with Headmaster Dave had been wonderful even though she still felt ashamed of her ba...

The Headmaster

by P_V on Sep 13, 2017
Erotic Couplings

Though I must apologize to my wonderful readers who are hungry for more "Orgasm Torture" for not posting any installments lately, I hope that this "early work" of mine will amuse and arouse them. There a hundreds of fantasies that take place in all-female academic settings (and that's just in *my* mind!) but hopefully, you will find this one different enough...