Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

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...

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...

Paying Rent

by JailBird Dreamer on Sep 16, 2017
Gay Male

The sound of the gavel rang through my ears and all I heard was the judge say, "I sentence you to 1 year in the county jail." One Year? Why had I been so stupid and put myself in this situation? Will my friends or what family I have left even visit me while I was in jail, or better yet even want to know me when I got out? All of these questions ran through...

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...

Hip Hop Sex

by BlaqJm18 on Aug 18, 2017
Gay Male

Locked up in jail once again for the third time with more felony charges added to his record, 50 Cent lies there in his hot, humid cell room bed with his shirt of, thinking about why he did it. His career was starting blowing up after releasing his second album "The Massacre" a year ago. Now he was in jail, once again but for an agonizing 5 – 8 years for som...

Wild Boys Ch. 01

by ClarenceKonrad on Aug 21, 2018
Gay Male

"What's your name?" "Jimmy. Coleman." "Starting now, you're number 070512. It's your new name, so don't forget it." The bus started its way from the back of the court where a judge had sentenced me to one year in a reeducation center. The guy said I was lucky, and that because of his good mood today, I wasn't going to a real jail. A guy like you wouldn't...

Prison Bitch

by mainsjoseph7 on Sep 5, 2017
Gay Male

How did I end up here? A few hours ago I was in the local gay bar socializing and getting drinks from just about every guy there. Having never been to a gay bar before, I was surprised by all the attention I was getting. My name is Joe, I'm 26 but I look ten years younger than I am. Which trust me can be annoying sometimes. The last thing I remember clearly...

LaCour Academy Ch. 05

by Voldemory on Aug 18, 2017
Gay Male

After Draven went to sleep everyone was shaken. Josh was pale as a ghost and the rest of them were quiet as if in thought. I couldn't help it anger took over me and I lunged at Josh. My face was beet red and I was on fire. "What the fuck did you do to him? I'm gonna kick your mother-"I stopped I know Josh better than anyone else he is like my other half I k...

Ex-Con Next Door

by CrimsonClown on Sep 1, 2017
Gay Male

Mark and Dan had spent most of their years in the suburbs living a quiet life where they never quite experienced any trouble. Mark was a working man at a law firm who spent most days at work and met Dan nights for romance, while Dan the loyal fiancé who spent most of his days in the local gym working as a personal trainer. Dan was a larger more muscular man...