Headmaster Stories

774 results
Orientation
Length
Source
Infinite Scroll

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

The Headmaster

by P_V on Sep 13, 2017
Erotic Couplings

Though I must apologize to my wonderful readers who are hungry for more "Orgasm Torture" for not posting any installments lately, I hope that this "early work" of mine will amuse and arouse them. There a hundreds of fantasies that take place in all-female academic settings (and that's just in *my* mind!) but hopefully, you will find this one different enough...

Summer Ch. 15 Gwen's Story 3

by TheTyke on Sep 19, 2017
First Time

The affair quickly gathered pace. They met again the next day and within moments of arriving he was inside her; fingers, tongues, his penis, it didn't matter; he filled her to capacity and then some, they were insatiable. They made love throughout that first day; and the next and the next. She could not wait to be with him, the thought of his hands on her...

Clover Watches Jed fuck Miss Akin

by clovermoffatt on Sep 14, 2017
Erotic Couplings

He was waiting for me with a glint in his eye when I went into his office, and a bowl of ice on his table. 'Clover," he said. "What were you doing in the music store cupboard with Kevin?" "Nothing, Sir." He licked his lips. "I thought I saw him licking your little titties, Clover." "No sir, he was just checking them for... a medical problem." "And the c...

Yes, Headmaster

by Literalist on Sep 16, 2017
Letters & Transcripts

Transcript of Headmaster M*****'s Private Phone call 11/09/2009 1:26 AM (*ringing*) (*Phone is picked up*) Mr. M***** Hello, (Female Student) (Female Student) Why- hello, sir. Mr. M***** I understand you've been misbehaving in your classes again. (Female Student) Uh, yes, sir. I have. Mr. M***** That won't do, Ms. *****. You'll have to be discipl...

Class Rules Ch. 02

by 0131aj on Sep 17, 2017
BDSM

One afternoon during the following week, Mr Gallagher was casually looking out of his window onto the lush green lawns below his study and saw something that took his eye. He rang his bell and his faithful secretary Miss O'Hare entered his room quietly. "You called me Head Master?" The Head nodded. "I have just seen Mrs West crossing the lawn from the gymna...

Morgana's Painful Lesson Ch. 2

by Morganauk on Sep 16, 2017
BDSM

It was Friday afternoon and the last day of the school year. There was an expectant buzz in the air, as everyone's thoughts were concentrated on tonight's leaving party. Morgana was as excited as everyone else – she had big plans for tonight. Headmaster Dave had kindly agreed to hold the yearly event in his large country house. Only the older pupils were in...

Taught a Lesson

by goodnight_sweetheart on Sep 12, 2017
BDSM

The cold December rain was beating hard on the classroom windows. Amber watched it run down the glass; she liked the rain but wished it wasn't accompanied by the chilling wind. The school's heating wasn't working again, so all the halls and classrooms were freezing. Amber glanced over at Dru, her best friend whom she also shared a room with, Dru smiled sligh...

Naughty Kate Ch. 01

by randomspaces on Sep 12, 2017
BDSM

Authors Note: I wrote this for a girl I met on a dating website, with the intention for her to write a small part of it. I don't have any intention to post her response, so you'll just have to make up your own version. All characters are over 18, and they exist in a universe without sexually transmitted diseases, or any real negative consequences to sex. Enj...

The Unwitting Guardian Prequel Ch. 02

by Arraiga on Sep 26, 2017
Sci-Fi & Fantasy

In the months after his defeat at the hands of the headmaster, Naek had trained ridiculously hard with the old man to be able to protect the Academy as its next headmaster. Finally, after months of grueling training, Naek was allowed a leave for two days under the guise of "Survival Training". Naek hustled about, preparing the items he would need for his li...