Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

David's Tall Girls' School Ch. 03

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I was 20 years old and was following my hobby of bird watching. I had unfortunately been captured by Amelia Wiff-Naseford, headmistress, for apparently being a Peeping Tom in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. I had decided not to get the police involved by agreeing to submit m...

Lady Burglar and Her Painful Error

by 123z on Mar 12, 2019
BDSM

Jessica Robinson blamed it all on Brexit of course. The twenty two year old had never known hardship in her young life until this wretched saga of the UK leaving the European Union changed everything. Brought up the daughter of an electric car dealer, the slim blonde had been spoiled rotten by her loving parents. Schooled at the exclusive Burgess Hill Boardi...

Birds of Prey: Twisted Desire

by Ryswell on Jul 10, 2019
Celebrities & Fan Fiction

Hello, Readers. I am happy you decided to check out my little story here. This is not my first crack at writing an erotic story, but it is my first time writing one within a world created by someone else - or in this case, created by a great number of someone elses. I've always been a fan of DC Comics - and comics in general - but the Birds of Prey have alw...

Agatha Allbut & The Bimbo Squad Ch. 07: Reunions

by Salacious_Scribe on May 11, 2020
Erotic Couplings

© 2012 Sal De Klerk, All Rights Reserved Authors Note: This is a long story, containing 10 chapters a prologue and epilogue. All chapters have been submitted and should be posted within a few days of each other. The idea for this story came from a story idea forum. Thank you janetsexy77! Warning: This story contains lesbian sex. If this is not your kind...

My Highschool Monster Girl Harem

by viewer67 on Apr 7, 2017
Amateur

Name: Haji Hino Height: 5'2 Build: Average, kinda scrawny Hair: Short, brown, spiky Eyes: Blue Haji isn't really someone you could call a jock. He's never really worked out much, he's always picked last in games, and he didn't really have that many friends. What he did have was smarts. He managed to skip a grade though with all the bullying he went through h...

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Unexpected Perquisites Ch. 02

by Lady_S on Oct 12, 2017
BDSM

The joy and ecstasy of that incredulous tongue fucking by Mr. Williams had brought about a chain of orgasms that I lost count of. Fortunately, he had gagged me when, earlier, he had put on the cuffs and tied my thighs. Or else, my endless screams would have reverberated through the entire mansion that housed my boss's residence and office. And yet, I hadn't...

Serafina and The Milking Machine

by Pastel_Comma on Sep 25, 2017
Sci-Fi & Fantasy

Serafina sat with her hands in her lap, waiting alone in the nurse's office. She squirmed. No place for her to rest her eyes. They were everywhere, the mirrors. One on the wall. Another on the nurse's desk. All gleaming from the sunlight, all sneering at her inhuman traits. They were like eyes, human ones, but far worse. Never blinking. Never relenting. Th...

A King's Touch Ch. 06

by dragontatto on Sep 19, 2017
Sci-Fi & Fantasy

Philip eased Sara into the couch before he was attacked by a whirlwind of flying fists. "Son of a bitch!" Turning he expected to see an unknown assailant instead he saw a young boy with golden hair. He was shocked by the fury -- even rage the boy directed at him. His heart nearly broke as he saw the replica of his twin-brother as a child. There was no doub...

Return to "Weekend School" Ch. 05

by cynthiablaine7 on Sep 14, 2017
BDSM

[This story involves bodily functions as well as discipline, so anyone offended by either should read no further. All characters are over 18.] * It was time for the final assembly at the weekend school. As Melody Haynes and Anne Smithers supervised the pupils, they filed into the large hall where Laura Franklin stood at the lectern on the stage. Laura was...

Infernal

by Sabledrake on Sep 13, 2017
Novels and Novellas

Chapter One – Abigail did not quite run, knowing that if she did one of the other girls might see and wonder what was the matter. She did not run, but she hurried at as fast a walk as she dared, her pulse hammering and a hot flush awash on her face. A repulsive, slippery-warm feeling had taken up residence inside of her, making her skin tingle and her n...