Headmaster Stories

774 results
Orientation
Length
Source
Infinite Scroll

Another Year at St Cat’s Ch. 03

by nightvoice2 on Sep 25, 2017
Novels and Novellas

Winter Sunshine (1) ------------------ Friday, 18 October ------------------ The old Jaguar sped along the main road, the harsh noise of its engine echoing off the stone walls of the row of cottages on the edge of Eastbrook. It quickly climbed the steep slope of the hill, its headlights cutting through the early morning mist. Past the neat rows of new ho...

Naughty School Girl Ch. 01

by Maddisyn on Aug 27, 2019
Erotic Couplings

Natalie's naughty school girl Natalie brought more than her teaching dreams and aspirations with her when she secured a position at a prestigious college for ladies. Concerns about a long-held intimate secret effecting her teaching career and personal relationships prompted her to seek assistance. A surprising coincidence lead her to the Practice and Doctor...

Jack and Mary Nobbled Pt. 03

by Clare_Ca_2 on Sep 15, 2017
Exhibitionist & Voyeur

Chapter 48. It was around 2 O'clock in the AM: Shift work coupled with snow made Jack later than usual getting home - not to mention the blisters on his ass-hole that caused walking to pose a real bind to his getting around lately. Mary was sleeping: Zonked-out on pills and booze. They hadn't talked that much since the incident, and there was a large, cold,...

The Adventures of Clover Ch. 02

by clovermoffatt on Sep 16, 2017
First Time

I was eighteen and I had never been fucked, and it was really playing on my mind. I think the boys just thought i was a prude. I was due to leave school that summer, when my sexual life was suddenly launched, like a galleon on a raging sea. The day that changed my life was probably about two days after Henry Jones had sucked my nipples. It was the day that...

Discovering my True Self

by Monalott on Sep 18, 2017
Transsexual

"Billy Soton. You are to report to the headmasters office immediately." Mrs Hollinhoe, my teacher announces to the class as the school receptionist, Miss Copelyn, waits patiently beside her. The class immediately jeers and I hear more than a couple of faggot insults thrown my way under the cover of the noise. Normally their insults would stab into...

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New Teacher Bad Boy

by braindump on Sep 12, 2017
First Time

The Teacher Sally Williamson had been the star pupil at her university and despite the wishes of her family had been determined to push forward with a teaching career. Her life had been one of plenty, and she told herself she needed to do something on her own. She had many brief flings at University building up a broad sexual knowledge from the men she dat...

Fantasies Revisited Ch. 03

by BrightCatsEyes on Sep 14, 2017
Erotic Couplings

John Wilson cursed himself roundly as he walked along the corridor towards the Dormitories. He had wrestled with his conscious all through the drive back to school but the impressive hard-on he had had for days now had proved more powerful than his sense of self-preservation. So here he was, skulking along a school corridor at midnight going to find Jenny. H...

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!...

A Costume for Every Trick

by Bethyboo on Aug 31, 2017
Group Sex

There's a brisk rain falling, I can hear it hitting the window pane, tappity tap. The accompanying wind is stripping the leaves from the trees creating a colorful carpet on the ground. A lazy stretch as I realize my bladder is done lying in bed, warm feet hit the cold floor and with a full body shiver I hurry to the bathroom. Just before the flush of the toi...

The Program Ch. 06-11

by IdeeFixee on Sep 19, 2017
BDSM

Chapter 6: like mother like daughter, big-titted mother visits, office discipline In September, at the beginning of Janice's junior semester, she informed me that her mother, Janine, was intent on visiting during Thanksgiving. I was dismayed, since a parent's visit meant lots of preparation and inconveniences. Janice assured me that her mother would not be...