Gay Jail Spanking Stories

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A Kid And A Cop Ch. 01

by DomQuiote on Aug 22, 2017
Gay Male

Chapter one "OOOOOWWWWWW! YOU'RE KILLING ME! NO MORE! PLEASE!" The boy lying naked over the cop's lap screamed, tears streaming down his cheeks as the cop spanked his bright red butt with the lexan paddle. "NO MORE, NO MORE, PLEASE." About an hour before, the cop had stopped the boy as he was leaving the store where he had just shoplifted 4 DVD's. He qu...

Jason's Trip to Mexico Ch. 04

by beefylatn on Sep 25, 2017
Gay Male

Jason was pushed into the jail cell by the two officers causing him to stumble and fall, landing on top of a large snoring drunk inmate as the cell door clanged shut. "OOOOFFFFF!" the large hairy sweaty inmate exclaimed as his eyes flew open and he glared at the naked blond stud that landed on his belly. "I'm so sorry, the cops threw me in here and I trippe...

Jason's Trip to Mexico Ch. 05

by beefylatn on Sep 25, 2017
Gay Male

Jason's revenge Jason eventually heard keys jangling and the cell door opening as he sat up to see El Capitán opening the door and Juan standing there with a concerned look on his face. "Dios Mio, Señor Jason are you all right?!" exclaimed Juan as he rushed over to help Jason stand from the cot. Jason was never so happy to see anyone in his life as he follo...

Man Fucked by Mannequins

by buttcheeks777 on Sep 16, 2017
Gay Male

I'm traveling again, in western Canada this time. On the way there I stopped at a little "pioneer village" sort of thing in a small town and it was totally deserted except for me walking around by myself. And, as usual, I started to get horny. It never fails; I always start fantasizing when I'm alone outside like this, thinking and hoping that something migh...

The Doggie Door

by Kent100 on Aug 28, 2017
Gay Male

Hey, I'm Mark and this is my story. I'm gonna explain who I am now, who I am was before, and how I got here. My story is gonna start kind of slow but I want a good foundation to explain how I got in the spot I'm in now. It wasn't my fault I ended up this way. Physically, I'm almost 5'8"s tall, very slim, smooth, no facial hair, and a face my mother calls an...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Prison Story

by Mysteria27 on Mar 27, 2018
Gay Male

Life can be sweet until you fuck up. Life was going great for Michael Brand. He was living the high life. He had beautiful girls following him around. Nice cars and a cool house. He wore fancy sneakers and all the cool hoodies any guy would want. He loved designer clothes and living the high life. Michael had the greatest parties. Everybody who was anybody w...

Getting Used in the Windy City

by buttcheeks777 on Sep 14, 2017
Gay Male

This is a fantasy that involves male-on-male action and forced sex. If you're not into that please move on. It isn't meant to be a great work of literature, it's meant to be a silly fantasy of mine. I think I have a problem. I'm always horny and wanting to fuck someone or to be fucked by someone. Is that normal? I sometimes wonder about my life; is it getti...

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...

My Evolution into Gay Sex

by Magda_Sorensen on Aug 18, 2017
Gay Male

I had never thought I was gay. I've always been crazy about girls, always attracted to them, obsessed with porn involving women. The only time men turned me on was in the pictures with the women, but it was always the female bodies that made me hard. Nobody who knows me would ever think I was anything but very heterosexual. Since I was a kid I always had a...