Headmaster Punishment Bdsm Stories

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Orientation
Length
Source
Infinite Scroll

Detention Pt. 03

by Croony on Sep 15, 2017
Mature

Toby Johnson had a fitful sleep recalling all the things that had happened that afternoon. How he'd been seduced, sucked and fucked by Mr Gayson, his music teacher, while his mother had been used and abused by his headmaster, Adam Jones and Mrs Smith, the school secretary who when Mr Grayson left came to the bedroom he was in and sucked and fucked him for t...

Naughty School Girl Ch. 03

by Maddisyn on Aug 27, 2019
Erotic Couplings

Natalie's in trouble again! A coincidence introduced Natalie to the Practice and a new doctor in her first story. She sought assistance for her concerns about a long-held intimate secret effecting her teaching career and personal relationships. Doctor Love's sexual therapy was too tempting for the young teacher, fulfilling her favourite fantasies in her s...

My Boyfriend Likes to Expose Me Ch. 08

by VanessaEvans on Sep 11, 2017
Exhibitionist & Voyeur

All characters involved in any sexual activities in this story were over the legal age of consent when the events took place. Part 08 - House Sitting – Week 3+ part 2 ============================ DAY 20 --------- I woke up to the sun shining through the window and wondered where the hell I was. There was a clock on a table and I saw that it was nearly 12 o...

Back to School

by AaronWebster on Sep 18, 2006
Swinging

The train clatters through the English countryside, past nameless farms and villages. You clutch the letter from the school to your chest, in case anybody recognises it. For one bizarre and irrational moment, you imagine yourself on the way to Hogwarts or some other school of juvenile literature. Cautiously, you slide the prospectus for St Mabyn’s out of its...

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West Valley High Day 124: Cattle Prod

by homeboundboy on Oct 6, 2020
NonHuman

"Good morning, Miss Mitchell," West Valley headmaster Stephen Krutz said as he approached his prize student. Susan Mitchell was standing in one of the faculty restrooms, her legs spread wide with ropes tied to the plumbing fixtures. Her arms were tied outstretched with rope around her wrists. Kylie had brought her here earlier in the morning and bound her be...

Daisy's Retraining Pt. 01

by MissTeachers on Dec 11, 2018
BDSM

Daisy could not believe she was standing here; it was bad enough that she had spent the last ten weeks confined in the Punishment and Retraining Institution for professional women as a result of poor performance at work and her desire to keep her job in the longer term. Somehow though she had managed to maintain her discipline despite the deprivations and hu...

Owned by my Mother-in-Law Ch. 16

by Sputnik57 on Sep 13, 2017
BDSM

As the morning of fourteenth day arrived, I cowered at Blanche's feet and kissed them again and again. In just two weeks the women had seized the element of my submissive nature and trained and broken my will completely. I was on the point of begging Blanche to allow me to see the noose again; I would rather have been despatched than go back to Cherie, her m...

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...

Sarah Has Another Bad Day

by 0131aj on Sep 13, 2017
Exhibitionist & Voyeur

Ever since her calamitous last day at school the previous year, Sarah's wardrobe had changed significantly. Throughout the summer she had been preparing for the new term and now she owned contained several elegant and professional trouser suits. She liked the look of them, the feel of them, the protection they offered and the unspoken message they sent to he...

The Girls of St Catherine's Ch. 02

by nightvoice2 on Sep 25, 2017
Novels and Novellas

The Headmaster Ritual (2) Friday, 24 May Portia hunted through her drawers frantically. "Hey, have either of you taken any of my clothes?" she snapped, addressing the other two girls in her dorm. Tara and Lizzy both shook their heads as they got dressed. "Why, what's wrong?" Tara asked, a concerned look clouding her pretty face as she brushed her hair....