Gay Gay Punishment Stories

22,838 results
Orientation
Length
Source
Infinite Scroll

Punished Asian Shoplifter Ch. 12

by asianspankee on Sep 19, 2017
Gay Male

After my oral submission to you, I'm left quietly in the corner to reflect on everything that's happened so far till now. Mrs. Jones leaves satisfied, having "conquered" yet another sissy boy with her obscene weapon. After ten minutes you call me back to your side and announces that next week will be my final punishment session. I feel both relieved and sad...

My Awakening Ch. 01

by FaggotCumDump91 on Aug 18, 2017
Gay Male

It was my first year of university. Never had I lived away from home, and now I'm in a residence building surrounded by people my age with the same interests. I was in heaven. Every week that went by seemed to facilitate the transition. Everyone was getting along, I had found my groove academically and the parties were great. It was the night of November 2...

Beach Bros

by peachmangopie123 on Jul 6, 2020
Gay Male

This is the story of the beginning of a very wonderful summer. ;) The place we rented was amazing. It was one of those cheap places you could find at airBnB. It was a shabby little beach house owned by a blogger couple who travel around the world all the time. The house was not the most amazing aspect of the place. In fact, the house itself looked a bit wo...

Beginning Latin

by Turbidus on Feb 13, 2018
Gay Male

A quick one about the college of my dreams. Thanks to LarryInSeattle. ============ "Mr. Goyette, please read us your translation." "I'm sorry Professor but I haven't completed the assignment." "Indeed? I hope you have an excellent excuse. You must be aware that I have a very strict policy regarding the timely completion of assigned work. Latin is not a...

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...

The Highland Festival Ch. 03: The Rules

by BareBearsFan on Apr 3, 2019
Gay Male

***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 professional novel, I'm not going to take time to explain every little change in a scene. If you're looking for 100% a...

Yes Sir - Lecturer and Student

by boxerj on Oct 11, 2017
Gay Male

My names Joe and I'm a student at university that always thought I was straight. I've had sex with several women and even had serious long term relationships, so I never thought that I was interested in men at all. I didn't think there was anything different about me. I was always a keen masturbator, sometimes spending whole evenings wanking myself off. It...

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...

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...

Defeated Jock Ch. 05

by maxpotter on Mar 3, 2020
Gay Male

Kam left Taylor out tied to the tree. He got a cup of coffee and sat watching the defeated jock. Taylor finally stirred and looked morose, barely lifting his head except a few longing glances to the cabin. Taylor's shoulders were slumped. Kam watched from a vantage point that prevented Taylor from seeing Kam's observation. Kam kept an eye out through a long...