Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

Island Discipline Ch. 07

by Cyberdiva68 on Sep 14, 2017
BDSM

As she drove home, the blouse rubbed against her sensitised nipples causing them to stand out proud. The tightness of her skirt kept the butt plug securely in place and the movement of the car over the road's surface caused it to vibrate the butt plug up and down inside her back passage. The combination of the two different sensations had her pussy dripping...

Erin Ch. 01

by DMaster_14 on Sep 12, 2017
BDSM

Jerry sat in the straight backed chair completely immobilized and watched as his boarder, Erin, worked through her Tai Chi movements on the pool deck in the back yard. Her lithe and sensual figure moved gracefully from one combination to the next. Her torso covered only barely by the white dance skin she wore. At 19 she was tall at 5' 5", 118 lbs, had black...

Pool Shark

by Gaius8666 on Sep 15, 2017
BDSM

"I want revenge!" Marie screamed as the front door slammed behind her. "What happened" Lynette, her roommate asked. "I have just been totally humiliated! I was down at Sam's (a local bar), and, Oh I am just so stupid!" "Well, what is it!" Lynette asked, becoming increasingly annoyed by Marie's hesitance to give details. "I somehow got involved in a strip...

Senpai and Kitten: Diving Deeper

by obiyuki_otp on Dec 25, 2019
BDSM

"José Says, remove your clothing." Jackie and José had decided to start exploring domination and submission. It was something that required trust, so it made sense to ease into it with a game. She was standing at the foot of her bed while he instructed her from his position propped up in bed, already naked. "José Says, grab both breasts and play with your...

Lessons in Composition

by Seattle Zack on Dec 25, 2019
BDSM

For the fifth time, Tina signed on the dorm room computer and checked her e-mail. "They don't send out the finals results 'til after five," Maureen reminded her. Tina sighed. "I know. But I'm sure I blew it. The test was too goddamn hard. If I fail this class, my grade point will fall below a two! They'll kick me out for sure." "Should have studied ..." St...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Lukey-Boy Pt. 01

by Tyrnavos on Sep 21, 2020
BDSM

Part 1: The girls next door Lucas took his engorged penis in his right hand and persuaded it into his swimming trunks. He'd had the trunks since the summer before last, and now that he was eighteen he was taller and much sturdier. They fitted low and too snugly, and he had to arrange his sexual organ on an upward diagonal to avoid giving it an uncomfortable...

Wife Gets Blackmailed Ch. 01

by jdrew2001 on Sep 12, 2017
Novels and Novellas

WARNING-- This story depicts group sex, bdsm, humiliation and forced sexual activities, extramarital sex, and several fetishes such as spanking all engaged in by a slut wife. The wife does not make love to the other men nor do they make love to her. They fuck, pure and simple. If you are looking for the monogamous couple spicing things up with each other typ...

Mating Rituals Ch. 11

by Scorpius1945 on Sep 19, 2017
BDSM

Author's notes: 1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk. 2. All characters are fictional and any likeness to any living person is purely coincidental. The story is pur...

Spice Plantation Ch. 08

by professorjames on Sep 14, 2017
BDSM

We brought some lunch back in by the fireplace and ate with me sitting on the floor and Judy sitting on my lap. Of course we were both still naked. I was coming to find - and I think Judy was also - that spending the weekend naked was great. Neither of us had ever spent a long time at a stretch in the nude, but now we hadn't worn anything since Friday aftern...