Gay Gay Punishment Stories

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The Punishment Suits the Crime

by L R on Aug 18, 2017
Gay Male

"Steve sit down." My boss said to me as I walked into his office. I sat facing his desk. I worked in a small private school in the inner city. It was a charter school which was trying different educational methods to get the students to learn more. I had gone a bit too far with one of the girl students so I was very nervous right now. The situation had com...

First Punishment

by kinkfiction on Jan 16, 2019
Gay Male

"You disappointed me, baby boy. I know you didn't mean to, and I'll forgive you. But first I need to show you the true extent of my unhappiness. You've been such a good boy up till now but I can't let you think that you can get away with this behavior. You disobeyed me when you went against my instructions. I get that you don't understand why it's such a big...

Double Punishment

by Guy521 on Oct 8, 2019
Gay Male

Adam and Charlie sat silently outside the headmasters office, contemplating what was about to happen. Both young men had been caught fighting yet again, leaving Adam with a split lip and ripped shirt, and Charlie with a bruised eye. The sound of the headmaster's door opening signalled for the boys to enter. The Headmaster stood behind his desk looking less...

Let the Punishment Fit the Crime

by iluvitall on Aug 18, 2017
Gay Male

Jon gradually woke up. His head was woozy and the room was dark, so he couldn't tell where he was. The only thing he could tell was that he was tied down with his arms above him and his feet spread wide apart, and that he was naked. As his head cleared, he tried to remember how he got into this predicament. He remembered talking to some guy at a bar. They ta...

Punishment or Pleasure

by Ewriter111 on Dec 10, 2018
Gay Male

I walked out of the county jail where I was in a holding cell for two and a half days very slowly and slightly bow legged. I had just turned 18 and made the mistake of mouthing off to a police officer during a traffic stop. It was early Friday evening and I didn't have a court hearing until Monday morning. I was put in a remote holding cell with three older,...

Shawn's Punishment

by Guy521 on May 15, 2019
Gay Male

Shawn stood in fear as his master examined his body. Master had shown up unannounced at his dorm room for an impromptu inspection of his boy. They didn't see each other much anymore, as both their lives had become so incredibly busy but Master would always show up at some point to keep Shawn in check. Master ran his calloused fingers over Shawn's rippling ab...

Shawn's Punishment Pt. 02

by Guy521 on Jul 31, 2019
Gay Male

Master led Shawn to the basement, a very familiar place to Shawn. It was here that he had been trained by his master, worshipped his master and been used countless times. Tonight he was here to be disciplined. He had been disciplined before, but Master had was incredibly angry. He was tired with Shawn's insolence and was ready to teach the young man his righ...

Punished Asian Shoplifter Ch. 04

by asianspankee on Sep 15, 2017
Gay Male

A few days after my second punishment session, I decide to return to your store for some much-needed shopping. While I am inside I spot the two college-aged employees doing some stocking and price-tagging work. They must have recognized me because I see them whispering to each other and snickering while looking at my direction. I feel so embarrassed I quickl...

Progression Ch. 09: Punishment

by klapperz on May 1, 2018
Gay Male

Once again Nathan found himself lying awake beside Kevin, who was sound asleep. All that was running through Nathan's mind was having Kevin's cock thrust into his ass. Unable to sleep, Nathan sat up and turned on his laptop to watch some porn. He logged into Ryan and Jacks porn channel and watched the videos. Each one made his cock fill the cage more each t...

Daddy's Boy Ch. 06: Punishment

by ashlaurchamp on Jul 13, 2020
Gay Male

*Again- I do not condone non-consent or reluctance in real life, no exceptions. This is strictly fantasy! Don't like, don't read please. Thank you all.* *Content Warning: Themes of Non-consent/Reluctance* *Content Warning: Themes of Incest* I struggled to keep up with Daddy's aggressive handling of the collars around my neck. He had dug his fingers betwee...