Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

Perchance to Dom Ch. 03

by DiscipleN on Sep 15, 2017
BDSM

As has already been established in Chapters 1 and 2, all characters in this story are 18 years or older. ***** I called off my date with Gina. I told her in person. "Too bad. I was considering buying black fishnets for the occasion." "On you, they might have turned into a fetish for me." "Instead, you turned into a shit." Her shaking head underscored di...

Den of Iniquity Ch. 09

by Sir_Nathan on Sep 17, 2017
BDSM

My eyes were closed and Annie's silky hair caressed my face. With her back to me, and my arms around her, we were recovering from our fun with the remote-controlled egg. My fingertips trailed lightly up and down her side, and I enjoyed listening to Annie's pleasurable cooing noises. The minutes ticked by. We had a big night ahead, but we weren't in a ru...

Jane Marwood, Governess Ch. 03

by harrietmarwood on Sep 25, 2017
BDSM

This story contains aspects of female domination and male humiliation. If you're not one of those (Grown up) boys who would like to have their little bottoms bared and spanked, I advice you NOT to read it. If you want me to continue with the story, please leave a lovely little comment, and rate it generously. All characters are over 18. ----------------...

Aphrodite's Curse Ch. 097

by Gaius8666 on Sep 25, 2017
BDSM

Deep inside Vesuvius, Archimedes smiled in complete bliss as his body spasmed once again. Under the soothing pulsing ministrations of the milk of Cerberus teasing his cock the poor denied and frustrated boy Genius was able to obtain a slight modicum of relief as he exhaled deeply. Although still locked in his "spirit cage", Hephaestus had helped out immensel...

The Ladies' Man

by Hellball on Sep 25, 2017
BDSM

For the first time in years, Randy actually paid attention in class. It wasn't just because he was afraid of getting kicked out of yet another high school; well, he was, but the last time had been for pulling the fire alarm before an exam, not for bad grades. It also wasn't because he had suddenly discovered a passion for learning; Randy had seen little in h...

TXR-92U-2280 – Call Name: Sara Pt. 03

by epexia on Sep 14, 2017
BDSM

TXR-92U-2280 -- Call Name: Sara -- Part III In a society that otherwise resembles our own, mass slavery has persisted into the 21st Century. It is a common and accepted feature of public and private life. Males and females of all ethnic backgrounds are held thrall, without status or legal rights. They are quite literally living property, and may be bought,...

Subject Line: Rope-Fun NSFW

by sirsemega on Sep 14, 2017
BDSM

"Are you going to book the tickets" she replied through email. He had sent her a link, Subject Line: Rope-Fun NSFW. The body cryptically said: "I think this might be interesting..." a link was provided and when she surreptitiously clicked it, she discovered that he was suggesting a live bondage stage show. The image and the thought of attended it excited he...

Hunting for a Master

by JohnsMom69 on Sep 12, 2017
BDSM

Claire sat at her desk day dreaming. It had been two weeks since she had gotten laid. It was all she could think about. It wasn't the longest she had ever gone without sex either but it was just that she needed sex. As a nineteen year old college student Claire had come into her sexual awakening during her freshman year. She hit the ground running and didn't...

Disciplining the Milkmaid

by Sylvana_Thornton on Mar 13, 2018
BDSM

Finn followed the road to the large dairy farm on the outskirts of Ellatar. With everyone busy with the preparations, he had offered to run a few errands for Hilda after lunch. He didn't mind, really, since it gave him a chance to escape the chaos. And would be one less thing Hilda would have to worry about. Owned and operated by the same family for many g...

Explorations Ch. 11

by Reardon1 on Sep 15, 2017
BDSM

Part 1 As Jessica pulled up to the two-story townhouse, parking in one of the visitor spaces, she could feel her heart begin to race as a moment of apprehension and panic momentarily overtook her. For the last few days, she wondered if she had perhaps lost her mind. The previous day, she had read and co-signed a contract that, while not legally binding, sig...