Inspection Headmaster Stories

12,642 results
Orientation
Length
Source
Infinite Scroll

Arcadia Castle Ch. 01

by Hal1031 on Jan 8, 2018
BDSM

Chapter 1: THE HEADMASTER The taxi driver checked his odometer, sighed, and cranked the A/C as high as the knob would go. The desert was especially unforgiving this time of year. Sweat trickled down my neck and rolled inside the paper-thin, white tank top they'd so generously provided for my trip. No bra, no panties allowed. Just the tank, a pair of cheeky...

The School Prize Giving

by Mrzxcvb on Sep 13, 2017
Exhibitionist & Voyeur

I'm running a little late for the school prize giving ceremony. My nephew is singing in the school choir as part of the entertainment. The event is to be held in the school grounds on a glorious summer's day with blue skies and just a gentle breeze to keep the temperature to a bearable level. As I approach the seating area with a minute or so to spare I no...

School Daze

by Croony on Dec 29, 2017
Fetish

Abbottsford College, situated in the City of London, was a prestigious all boys finishing school that catered for teenagers from the age of sixteen to eighteen. The pupils were mainly from rich and titled families who wanted their sons to experience the strict regime and make them into better adults. David Bryden was the headmaster that dealt with disciplin...

Telling Tales of Sunny and James Ch. 01

by Redgrenadine on Dec 11, 2018
Erotic Couplings

They met two years before, on the other side of the world. Tonight, Sunny and James both thought with bittersweet regret about how they got here - a third floor officetel on the outskirts of Seoul - Sunny, on the tiny kitchen hallway floor, wiped tears from her tightly closed eyes with a corner of her blanket, while James rested with one eye open, on his bed...

Sexy Schoolgirls

by Mag58 on Sep 13, 2017
Exhibitionist & Voyeur

“School Disco!” Friday night, doors open 8.30 FREE ADMITTANCE (Anyone wearing a school uniform.) I read the poster, which was advertising our favourite night-club, again. Immediately, I rang my friend, Shelly. “ We are going to have so much fun on Friday. P.J.s’, night-club, is having a special night, and we will get the chance to dress up as schoolgi...

A Headmaster's Lesson Pt. 01

by LittleKay on Nov 6, 2018
Fetish

Greetings! Thanks for taking the time to read my story. Feedback and Comments are welcome! Please read the disclaimers at the end before leaving negative comments on the themes or content. This *is* a dark, twisted story. Apologies in advance. _________________ The only thing worse than growing up in a wealthy religious family was being sent to boarding...

Naughty School Girl Ch. 02

by Maddisyn on Sep 9, 2019
Erotic Couplings

Report to the Headmaster! In her previous story about Doctor Love's Practice, Natalie shared her concerns about her naughty school girl fantasies and her initial counselling. The charming Doctor Love's proposal of sexual therapy was too tempting for the young teacher. Natalie returns for a follow-up session to fulfil her fantasies and discovers more Practic...

Joys Private Education Ch. 01

by fredricka on Sep 13, 2017
BDSM

She knew she should not have been cheating; she would not have had to except that Bobby had kept her out late last night. They were getting pretty heavy into petting and her mind just forgot about the test. Damn Miss Knead had it out for her, she did not know why but now Miss Kneed had got her. She was sent to the principal's office. Slowly she entered the...

Cane and Cock

by AnnGoode on Sep 17, 2017
BDSM

Lady Dawn was born into a family of wealth and influence. One of the families that had three centuries ago formed a secret society to preserve their status. Only male members of the families could join. In the year 1703 they set out the principles by which they and future generations would continue to prosper. Today those same families having endured wars an...

The Headmaster and the Pupil

by irisheyesgirl on Sep 12, 2017
BDSM

The characters in this story are consenting adults. St. Ann's School exists in the imagination of two creative lovers. If you enjoyed reading these characters as much as I enjoyed writing them, please leave suggestions for what you'd like to see them up to next! ***** -The Headmaster- "WHAT am I going to do with you, Miss Connolly?" I sighed heavily as I...