Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

Another Year at St Cat’s Ch. 02

by nightvoice2 on Sep 25, 2017
Novels and Novellas

Discipline and Dilemmas (2) -------------------- Wednesday, 9 October -------------------- The headmaster couldn't sleep. He rolled over in bed and looked at the clock again. Still only ten past five in the morning. He'd been away from the school for way too long for his liking. He'd originally planned to be back on Monday but his mother had been taken i...

Bad Girl Ch. 1

by anneski on Sep 14, 2017
BDSM

She stood with head bowed in front of the Headmaster's desk, flanked by the head girl and her crony of a deputy. Her heart was pounding and she was very scared indeed. Anya had only been at this institution for a short time, but already she was finding that the discipline was like no other she had come across. She had heard of canings, and rumours of more,...

Service Provider Ch. 14-23

by IdeeFixee on Sep 19, 2017
BDSM

Chapter Fourteen — Sunday School When she'd gone to Mass as a teenager on the old Headmaster's orders, Janice had been struck by the appearance of the Father leading the service. He was tall and rough looking, with large, craggy features and recessed but gleaming dark eyes. He had also noted the presence of the gorgeous, sensuous young brunette sitting in t...

Scottish Boarding School Ch. 01

by HollyRed on Sep 13, 2017
BDSM

It was a shock to be packed off to boarding school- especially at the age of eighteen. I thought my school days were over but due to a very damming report card I was not free just yet. I had enjoyed the last two years of my A'levels a bit too much. Party followed party and my results showed this. I may have learnt how to tease a man's cock up to greet me but...

The Party's Ripe for Caning Ch. 03

by lesliejones on Sep 19, 2017
BDSM

[This story takes place in a prep school which prepares pupils for three years after high school for university, from ages 18-20. Previous chapters explored Miss Crawford's introduction to the strict disciplinary regimen as the first female teacher of the boys' school.] Linda Crawford now had completed her second full year as an English teacher at Hamilto...

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...

Schooling Ch. 02

by VGracen on Sep 12, 2017
BDSM

The darkly paneled hallway to the Headmaster's office seemed to grow longer with each step she took that day. Her body moved obediently, never betraying the war going on in her head. "What he is doing to me is abuse! I should report this to somebody, I should just tell him NO! He doesn't have any right to touch me that way or tell me what to do"! Her hand...

Downtime at the Office

by Finansol on Aug 30, 2017
Erotic Couplings

Marissa had some downtime at work and was surfing the Internet trying to find a site to help with sales leads when she noticed that her email had a new message waiting. She checked the inbox and discovered that a friend of hers had sent her a link to an erotic story site. She smiled. It had been a while since she'd had the time to flip through such a site an...

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...

Bringing Her Along Ch. 06

by honourableboy on May 30, 2018
BDSM

- well my dear. We should get dressed and get going. And then to us - You two. Chauffeur uniform. Slave. Just as you are. - And boy, go get the cage in the back of the truck. Tamara and I dashed to our rooms to get into our Chauffeur uniforms. Something we could be seen in the outside world. For me it was shiny black shoes, pressed and tight dress slack...