Gay Punishment Stories

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Infinite Scroll

The Vicar of St. Dunstan's Guide

by Nigel Debonnaire on Sep 19, 2017
Novels and Novellas

To be obvious: this isn't a story, but a guide to the series. Since the series covers 24 episodes, I thought this list would help in keeping track of the major characters, especially their descriptions and basic history. It may not be comprehensive guide, but I hope it's helpful. If there's something that should be here and isn't, please let me know; I would...

First Time Nude Beach Blowjob

by speedodave on Sep 17, 2018
Group Sex

My server admin Kip runs all the important tech stuff for all of my blogs and sites. He is brilliant and I wouldn't have a business if it wasn't for him. WE met years ago through my previous server administrator who was given a job at one of the mega tech companies and he suggested Kip. The role doesn't require that someone has a speedo fetish or are even g...

Liam's Submission Tested Pt. 01

by PupTracer on Sep 28, 2020
BDSM

The insides of the car shook as we pulled into the dark and gravel laden parking lot. I looked around at our surroundings, trying my absolute best to not appear nervous to the man on my left driving. I saw several plain cars as well as a run down looking bus. One of the cars was illuminated by the light of a phone, though the windshields were too foggy from...

Big Dick Fucks Blonde Girlfriend Pt. 06

by EroticDelights on Sep 26, 2017
Fetish

When I got home Jess was in bed, alone. I crept in and slid under the covers as quietly as I could. "Hope you enjoyed yourself," she said. I froze. "Because tomorrow your punishment starts." I waited expectantly. I wanted to know what was in store for me, but too afraid to ask. I was deathly afraid that it would involve Pete. I laid awake a long time,...

Scat Lessons Pt. 02

by Gamahooch on Jul 4, 2018
BDSM

The day had finally arrived. Sam Gates was up early, preparing for his first session with Mistress Andrea. As instructed, he gave himself an enema and took a soapy bath to scrub his own asshole completely. At the same time he desperately hoped that Mistress Andrea was not doing the same thing. One thing Sam loved was the taste of nasty female asshole. Sam d...

Brian's Sleepwalking Adventure Pt. 07

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

The Pledge Mistress Ch. 30

by caligula97236 on Sep 14, 2017
Novels and Novellas

Chapter 30 -- Two days in the forest Thursday and Friday passed uneventfully as the pledges went to class, did their chores, and attended their evening training seminars. Lisa continued to wear her thong on campus, but by Friday the novelty was wearing off. The stares and whistling had from her onlookers had diminished considerably. By the following week sh...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...

Tito's Torment

by justincbenedict on Dec 10, 2019
BDSM

Randa rubbed Tito's cock as it bobbed between his legs. "I've never seen anything like that before." There was a piercing, a little silver loop looping through the head of Tito's penis, and then there was another little circle behind his scrotum, and the two hooks were conjoined by a tiny padlock. Randa was quite amused by this. She took her hand away from...

The Engagement Ch. 05

by Compliant1 on Sep 26, 2017
BDSM

I had a lot to think about as I made the long drive home from Stephie's. I always enjoy spending time with her, but the past week was exceptionally interesting. I'd met Steph's boyfriend Ron, several times. Ron is tall, dark and handsome enough to make a living as a model for high end retail catalogues. We spent a wonderful week together, enjoying the beach...