Inspection Headmaster Stories

12,642 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Finishing School Handbook

by brewster926 on Sep 16, 2017
Humor & Satire

Please note: this is an official copy of the handbook actually used at Dr. Deucel's famous finishing school which was in existence in Wayward on the Tool in Lower Suckexx during the latter part of the Nineteenth Century. Dr. Deucel's school was known for taking ladies in their twenties and older that everyone else had given up on and helping them become happ...

Yes Please, Headmaster

by Stripemoff on Dec 21, 2017
Mature

Charles, my husband, hadn't left me much to do when he left for the U.S.A. on a business trip. That was because he was such a brilliant organiser. He planned everything down to the last detail covering the weeks he was away. But, he did leave me one thing to do. "Just make sure that William's entry form to St. Leonard's school gets there before the 20th of...

Six of the Best Ch. 03

by KinoKe on Sep 17, 2017
BDSM

'NO RUNNING IN THE CORRIDOOR.' The Headmaster's voice rang out loud and clear. For a brief moment the three miscreants halted in their tracks and cast a guilty glance in the direction from which the edict had come. 'How many times do you boys need to be told?' The ringleader muttered something appropriately apologetic, and then all three walked, cautiousl...

Sex School: Induction

by vixenoftheNorth on Sep 17, 2017
BDSM

Tori applied one last coat of bright red lipstick to her lips before stepping out of her parked car and crunching up the gravel pathway towards the imposing stone porch of the old school house. Her 6 inch platform heels sunk slightly with each step, and the gentle breeze sent a shiver round her toned thighs, which were barely covered by the short micro bodyc...

Drug Check

by MALIBUMAN666 on Jan 8, 2019
Fetish

This is another very old story, probably from the early 00s. ALL CHARACTERS ARE OVER 18. ***** Mr Shaw twirled his pen through his fingers impatiently. Why did he ever become a teacher? Drugs were becoming such a problem these days and as ever the responsibility for protecting the children fell on him. And as if that wasn't bad enough, now he had the job...

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...

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...

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...

The Headmaster's Indiscretion Pt. 01

by emeraldangel on Sep 12, 2017
BDSM

Day One -- Journal entry Starting my new undercover assignment today. This one is going to be interesting, I expect. I will be posing as a 18 year old girl at Miss Priscilla's Boarding School. The chief says there have been some disappearances of girls from there and although the girls show up eventually, claiming to have run away...he thinks there is somet...

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...