Headmaster Stories

774 results
Orientation
Length
Source
Infinite Scroll

The Weekend at the Lake

by erotiquill on Sep 13, 2017
Erotic Couplings

It was two weeks ago that Ray and Emma first told us about Jon. He was someone they had known for a little over two years and felt that our relationship had reached the point where they could tell us about him. My wife, Gwen, and I have had a sexual relationship with Ray and Emma for almost a year and have become very good friends during that time. "We have...

Tales from the Guilds Ch. 02

by voluptuary_manque on Nov 14, 2017
Sci-Fi & Fantasy

"Really, Sinestra, you have to get over this obsession with young Woodbead's class," Arachna, Lady Lacrodecta of Cob Priory chided her daughter as she changed the cast on the girl's arm. "Have you bothered to actually read Twerp's Peerage, especially the early entries on each family? The Nobility weren't created by the gods, after all. All of us were 'common...

Schoolgirl's Punishment

by mybaby on Sep 16, 2017
Novels and Novellas

Sandy was having a bad day, could it get worse? Simple answer? Yes! Much worse, much, much worse. Sandy was in the top form in her final year, A level study was going OK, and all things being equal University next year should be on the cards. On the other hand, her love life was just the opposite. Sandy had convinced herself she had not reached the age yet w...

One for the Team Ch. 05

by MicheleNylons on Jun 1, 2020
Transgender & Crossdressers

Chapter Five - The Cottage May 1986 Detective Sergeant Archie Sanders and his partner Detective Constable Sandra Tingle had stopped at a layby on the A12 near Mountnessing and were drinking tea purchased from the take away food van and smoking cigarettes. "This is the worst cup of tea I think I've ever had," Archie Sanders poured most of his drink onto th...

Bad Girls Go to Heaven

by SizeQueenSupreme on May 15, 2019
Fetish

(Hey all, here's a little Justine prequel that I wrote a while back. My publisher is closing up shop and I'm not fully certain how it will effect my work here and elsewhere, but I'll try to keep you all posted as I learn more. As always, your questions and comments are welcome via the e-mail in my contact page. Enjoy!)) *** You can see sin in the hips, the...

Super Magic School RPG

by conkers024 on May 28, 2016
Fan Fiction

It's the first day of Autumn and the official start of the fall semester at Ash Forest Academy of Magic. The school is located deep within a dense forest of Crow trees, trees covered in black colored bark with leaves that fade from white in the summer to grey in the fall. The trees reach up to twenty meters in height and afford a great deal of privacy to the...

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Telling Tales of Sunny and James Ch. 02

by Redgrenadine on Dec 11, 2018
Erotic Couplings

James left his house at 6:00 am for his daily run, but he had been up since 4:00, and this was Sunday - his supposed day off. His mind was as clear as the cloudless April sky. Morning prayers, a bowl of oatmeal, meditation and yoga, all before a run around the duck pond at the local park. This had been his routine, more or less, for the past five years and...

Jennifer at St. Ciels Ch. 6

by anbk on Sep 12, 2017
Exhibitionist & Voyeur

Jennifer sat dejectly in the cafeteria eating her breakfast. It had been a week since Prof. Gilbert had told her that he was going to recommend her for the Benefactor's Dinner, but as yet she had not heard if she was selected. All week she had played with herself, jerking off to the image of Mr. Lewis slowly fucking her in the ass. Even now, as she thought o...

Service Provider Ch. 01-13

by IdeeFixee on Sep 19, 2017
BDSM

Part 2 — Service Provider Before beginning, please read Part 1: Mother's Helper, The Black Diary. In Part 1, Janice, a hot and sexually frustrated single MILF, is riddled with guilt over her poor parenting of her hot son Matthew, a high school senior. Matt discovers his voluptuous mother's unquenchable penchant for sex and punishment, and quickly increases...

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...