Gay Punishment Stories

1,311 results
Orientation
Length
Source
Infinite Scroll

The Slave and His Master Ch. 08

by loveandlust28 on Nov 11, 2019
Gay Male

Day 6, Afternoon, After Aiden survives the beast: There were rumors in the servant's quarters. There were rumors in the kitchen. There were rumors in the corridors and rooms. There were rumors among the houses of all the great lord's. There were rumors in the streets and in the marketplaces. There were rumors in the whole of Arodasa. All of them featured a...

Don't Look Back

by ShelleyRunyon on Sep 14, 2017
Gay Male

"Stop running and face me, boy." The words sent chills skittering along Marshall's spine. He was torn between the desire to obey and the need to provoke punishment. Giving in and turning was his first instinct, but the idea of being stretched out across the other man's lap, his ass exposed, bared to receive those glorious swipes of his firm hand was too str...

My Hairy Brother-in-Law, the Cop

by MajorDick on Aug 30, 2017
Gay Male

Although I'm way back in the closet, I like hairy, masculine men. And my brother-in-law is fits my type to a "T": tall, early 30's, good looking, olive complexion, clean-shaven but with a dark heavy beard, black short hair with a slightly receding hairline, sexy brown twinkling eyes, an infectious laugh and a furry chest that makes my dick woody just think...

The Apprentice

by briboy2008 on Aug 18, 2017
Gay Male

Chapter 1 I could not believe it; my application for an apprenticeship had been granted. I was to start next week at the oil refinery. OK, sheet metal work was not the most romantic of professions but at least it paid well for an apprentice and that was all that mattered to me. I could learn a trade and get paid well for it in the process. I had just turne...

Winners and Losers Ch. 02

by bawdybloke on Sep 15, 2017
Gay Male

We trained a lot that following week; the humiliation the Woodford Wanderers suffered in giving blowjobs to the victors of our friendly match burnt into every aspect of our waking moments, and even as I was fucking my girlfriend, the vivid memories of the swell of his cock and the tickle of his pubic hair on the end of my nose, was innermost in my mind. In...

Jeff's Dirty Arcade Adventures Ch. 02

by occurious on Jun 1, 2020
Gay Male

This is a continuation of my first story, you don't have to read that one to enjoy this one but I encourage you to do so. * Driving home from the arcade I was praying that nobody would be home, I really looked worked over and even though I'm sure it was my imagination I could swear I smelled the cum leaking from my ass. Thankfully my prayers were answered...

The Highland Festival - The Hotel

by BareBearsFan on May 15, 2019
Gay Male

Chapter 7 -- The Hotel ***Hello Readers Quick note, my stories tend to progress a bit slower, if you're looking for quick paced sex scenes try another story. Also some past people have nitpicked about small consistency details in my stories. I'm not writing a classic novel, I'm not going to take time to explain every little change in a scene. If you're...

Holiday

by callis on Aug 18, 2017
Gay Male

The candy cane trails across my lips and I open them eagerly, sucking the tip into my mouth. "Ready for this, puppy?" "Yes Sir!" I answer, grinning up at him. "Good boy," he murmurs. "Gonna make you all pretty, puppy." "Really?" "Oh yes. Close your eyes." I obey immediately, shivering as I feel him peel off my clothes. "Lift your arms," he says, pullin...

The Adventures of slave sal

by maxpotter on Jan 16, 2019
Gay Male

Author's Note: This story is inspired by/for slave sal of Florida. It is a fantasy of what his perfect slave life would be, and who knows, maybe it will come true. Of course, I couldn't help but put myself in it as well :) . I'm also conforming to some of his slave voice style of writing. There will be some "inspired by actual events" parts as well. Enjoy!...

Frontier

by wickedwicker10 on May 11, 2020
Gay Male

He left the ruins of Georgia in the summer of 1874, another orphan of the War of Rebellion and one step ahead of the lynch mobs and night riders. Headed west into the territories seeking out the promise of fortune on the far frontiers, but he was broke and hungry in the slums of St. Louis Missouri before the month was out. A young man without promise or pro...