Headmaster Stories

774 results
Orientation
Length
Source
Infinite Scroll

The Girls of St Catherine's Ch. 01

by nightvoice2 on Sep 16, 2017
Novels and Novellas

The Headmaster Ritual (1) Prologue: Friday, 26 April Portia danced sinuously in the half-light of the dimly lit study, closing her eyes and losing herself in the thumping beats and intricate rhythms of the Latin music. She reached up and ran her hands around the brim of her straw hat, the fingers brushing against the silky pink ribbon. She watched him tapp...

A Very Naughty Girl Indeed!

by Jonathan Phillips on Sep 11, 2017
BDSM

The PE teacher had buzzed ahead telling me to expect you. She had not however, prepared me for exactly what I was to be punishing you. I could easily have lost my job for the punishment I chose for you. Christ, I really should lose my job for the punishment I chose for you. *** There was a knock at the door... "Come!" I shouted. You stepped inside. You...

My Friend Sophie Ch. 02

by LeanneSinclair on Sep 17, 2017
BDSM

In the previous story I introduced you to my lovely friend Sophie and told you about an evening when she and I got very drunk and she told me, in great and explicit detail, about her submissive fantasies and desires, which were focused on her male boss. I'll pick up the story again on the morning after that, briefly, although I'll probably then gloss over so...

Shaman Chronicles Ch. 03

by worldwarwalther on Sep 15, 2017
Sci-Fi & Fantasy

Well hello dear reader! The pre-exams are over and right now I am a free man ( or boy ) again. I hope the wait was worth it and I present you very proudly the third installment of the "Shaman Chronicles". Sincerely WorldWarWalther P.S. I really want to thank you guys for the awesome feedback you gave me and I hope your mind doesn't screem "HARRY POTTER" a...

Journey of Submission

by msterrilynn on Sep 12, 2017
BDSM

Chapter 1: Phone Call The phone rang as she came in the door with her hands full of groceries. Amelia set them down and reached for the phone. "Hello?" she said. "You have been accepted into The Academy. A packet will soon arrive with instructions on how to proceed", a voice said. Amelia collapsed into a nearby chair and slowly smiled. She has been accepted...

Tales from the Guilds Ch. 05

by voluptuary_manque on Mar 5, 2018
Sci-Fi & Fantasy

In his capacity as Master of Assassins, Lord Downy was accustomed to receiving mail on the very finest of paper emblazoned with ancient sigil rings. He treated them with respect but never felt any exceptional need to treat them with expediency. However, in today's post came a letter emblazoned with a simple 'V' on black wax and that he opened at once. Though...

The Slow Bowler

by mangrove jack on Sep 13, 2017
First Time

Christine Morgan jumped in fright and turned when she heard her name. To her surprise a tall blonde young lad wearing a grocer's apron stood staring at her in supermarket aisle. "Were you speaking to me," she asked as the boy licked his lips and stared. "Yes Mrs. Morgan, I'm Craig Smith you don't know me but I'm in your daughters class at school. I'm sorry...

The Program Ch. 01-06

by IdeeFixee on Sep 19, 2017
BDSM

Chapter 1: How the Program works - exam, selection, installation, observation and accessories The Headmaster of exclusive Ansonia Academy was sitting by the fireplace in the Faculty Lounge with his younger colleague from a sister prep school in New England. They were drinking sherry at tea time, alone. In his mid-forties, the Headmaster was wiry, with stiff...

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,...

Teaching Professor Mahoney Ch. 05

by JubeCube on Sep 13, 2017
Erotic Couplings

The weather had turned cold over the week and everyone suited up in pants and jumper. Snow started to fall the day before last. Scarves, gloves and beanies were also present. I had even seen a few earmuffs. As the class entered the room they seemed to sit closer together for warmth. I noticed Lara wore grey track pants and a grey zip up jumper. A rainbow sca...