Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

Helping Jess Pt. 03

by mski on Sep 18, 2017
BDSM

Sometime in the morning I woke up with Jess on top of me giving me a good morning kiss. 'Wakey wakey sleepy head!' she said with a huge smile. I grinned back, it was a nice way to be woken and she looked as gorgeous as ever in her red silk chemise. I started to get aroused but my penis was always going to lose the fight against the chastity belt. I grimac...

Dark Horse: Tales from the Ranch Ch. 02

by AwkwardMD on Sep 17, 2017
BDSM

"A little farther," Ms. Winters called, hands cupped around her mouth. Peep looked over at Belle, and they each dragged their barrels back a few more feet. The indoor arena had been divided in half, and all of Ms. Winters normally-disused gymkhana equipment had been pulled out of the storage shed. It was pouring outside and so, instead of their normal routin...

Masters Ch. 02

by masterslilgirl on Sep 11, 2017
BDSM

Hi everyone thank you for the kind words and critiques. I've been writing stories for my Master for a couple years after first reading stories on Literotica. The stories I write are for him and most of them are in my point of view to him. I hope this clears up some of the confusion from the first story and I'm so happy that he pushed me to post them. Please...

Love in Chains Ch. 03

by Nephylim on Sep 16, 2017
BDSM

I was very disturbed when I left Adam and Nye. It wasn't just what I had seen in the dungeon. It was the way Nye was. He had changed so much I hardly recognised him. Apart from the fact that he had lost weight... he also seemed to have lost his spark, his soul. He was lost and empty and he didn't even know it. Adam was a bad man. I knew that with absolute c...

Chianti's Counseling

by justincbenedict on Feb 25, 2019
BDSM

Chianti squatted happily over Jocelyn's perspiring face as the older woman strained to fully get her tongue in Chianti's asshole. "Faster, that's right, Jocelyn. You have to rim me in and out, up and down, there you go, and now to my cunt, hon." Jocelyn groaned and Chianti looked down, wincing slightly. Jocelyn was perhaps not Chianti's most enticing clien...

The Real Gabi Pt. 04

by mjar65 on Oct 30, 2018
BDSM

After the night together in the hotel, Simon decided to step things up. He had several reasons for that. First was the fact that Gabi was progressing so well. He was curious to see how far she could be pushed. She was young and malleable and responding well to her "training". The second reason was that he knew this could not last. Being so young, it was cer...

Golden Girl Ch. 13

by Case21 on Oct 16, 2018
BDSM

Chapter 13: The Golden Lady It was a warm summer morning, already promising to be a hot day, and Dorée sat ensconced in comfort, sipping her tea. She could hardly believe how things had changed since she passed through what the Duc called "the turn." He had turned her with a single word from girl to Lady, from slave to Mistress, and turned her world upside...

The Edged Lexicon Ch. 01: Discovery

by raunchyandpaunchy on Sep 12, 2018
Celebrities & Fan Fiction

This is the first installment in a multi-chapter series, which explores the adventures of original character Nadine Rielle as she delves deeper into her own sexual discovery. It features themes of BDSM/kink, voyeurism/exhibitionism and group sex throughout, and any other relevant stuff will be tagged per chapter. Massive thanks to PastMaster for editing this...

Dominica

by Emirus on Dec 3, 2018
BDSM

I would like to thank a special friend for her proof reading skills and for her advice generally which have made this story better than it would otherwise have been. WARNING: This story contains a scene of "golden showers," female on male consensual urination. If this is not for you then I would suggest that you proceed no further as I have no wish to offen...

Going Home

by Lili on Sep 17, 2017
BDSM

She'd done it. She'd left her husband and her old life far behind, miles beneath on the ground. She soared through the skies, heading west, into the sun, feeling weightless and exhilarated, with that scary trembling in her gut that told her things were changing rapidly, perhaps too rapidly. As the plane broke through the low, gray clouds, the orange sun bla...