Prison Story

by mysteria27

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma, Gay, Anal Sex, Oral Sex, Safe Sex, .

Desc: Erotica Sex Story: Michael Brand is a drug dealer that gets convicted of a felony and goes to jail.

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 went to them.

Michael was a drug dealer. He’d been selling drugs since he was eighteen. He made friends with somebody who was in the mob. They gave him clients and he did quite well for himself. He gave his cut to the mob and the rest was his. He had several runners that ran the drugs for him.

Life was great for many years. He had a few stints with the law and had to spend a few months in the can. He never had to do any serious time. Not until one of his new runners was part of a drug sting. He was the rat that gave him up. Police were sniffing around his business and he was caught. Caught with enough meth and other drugs that would land him in jail for the next ten years. Michael had fucked up and it was nobody’s fault but his own.

The judge gave him no leniency, because he’d been in the can before for drugs. He made an example of him. Ten years with chance of good behavior. If all went well, Michael would be out in five years. The worst part was not being able to say goodbye to friends. Not being able to have sex with any women before being thrown back inside.

Whatever you hear about prison sex is all true. You can be a bad motherfucker and still get your ass drilled. When Michael did his first stint in jail, his prison cell mate Jacob was a horny son of a bitch. The deal was if Michael had sex with him, Jacob would offer him protection. Protection was gold in jail. Michael was happy that Jacob offered him protection. With the protection, he’d have to give Jacob blow jobs. Michael knew this was the only way. He swallowed his pride and gave Jacob what he wanted.

There were all different groups in jail and if you didn’t have somebody watching you, you’re everybody’s bitch. Michael did what he had to do to survive. It was important that he stay in one piece. The first-time sucking cock was more like an adventure. He wasn’t sure he liked it. By the second night, he enjoyed giving Jacob head. Jacob liked how horny Michael made him. Jacob liked looking down at him. Michael was pretty. He was a great cock-sucker and didn’t want anybody to know how good he was. He’d keep it to himself and offer Michael protection. Michael knew he had to be the best, so he gave it his all and, in the end, he too liked it.

Every night and every morning he got on his knees and stroked Jacob’s cock up and down and all around. When his cock was hard as a baton, he’d opened his mouth and accepted the big cock down his throat. Jacob would run his fingers through Michael’s hair and pump his cock deep down his throat.

Michael made all the wet sucking noises and after about twenty minutes, Jacob would release his sticky white cum down Michael’s throat. Michael would swallow it down. Jacob would call Michael his bitch but only really did that when other inmates were around. He had to make it seem liked he owned Michael. Jacob was caring with Michael. I think he really fell in love with him.

That all changed after about six months when Jacob stabbed another inmate and was sent to another jail. Michael then got another cellmate. His name was Big Bob. Big Bob was ripped and had a temper on him. Michael would show him what he could do with his mouth. Bob liked the blowjobs, but he wanted to have sex with Michael. He was a little rough with him. I think he got off on that kind of a thing. Michael knew that Bob wanted his ass. He accepted that he’d get fucked. He just didn’t know when or where it would happen.

Michael had laundry duty and Bob and his crew entered the room. He told Michael he wanted his ass. Michael was okay with it. Bob’s crew looked out for the guards. Michael took his jumpsuit off and assumed the position. Bob slid on a condom and squeezed some lube onto Michael’s asshole. He slowly entered Michael’s asshole. He was extremely tight, and it took many tries before slamming his dick up inside Michael’s asshole.

Michael grunted and just enjoyed it. He stroked his own cock while Bob fucked his asshole. The crew just watched the door. They never joined the two men. Bob was an okay guy. He too offered Michael protection. Nobody bothered Michael for the rest of his time in the can. He had sex with Bob and everything was okay.

Prison is a nasty place to be. Men have sex with other men. Guards have sex with the prisoners. The only way to survive is to meet somebody who will offer protection. Life in jail is no happy fairytale. Nobody wants to talk about their stints in prison. Everybody turns gay in prison. If they say otherwise, they’re lying.

Now Michael was going back. Back to the joint where he did time the last time. He was now prisoner 6578123. He hoped to be able to meet somebody who could offer him protection in exchange for sex. Michael wanted to just mind his business and do the time. He hopes to get in good with the guards and hopefully get out sooner for good behavior.


On the way going to the jail, the prisoners were all locked up together like a chain. Michael wasn’t scared because he knew how it would be. He just sat quietly thinking how he fucked up his life. He wished he had done good in school. His parents would have paid for college. He got used to making money. Drug dealers make lots of money. Even when he was a kid he sold pot to his friends.

If he was a better kid and went to college, he might not be going to jail right now. He wouldn’t be worrying about things that would never occupy your mind. Michael was hoping he wouldn’t be fucked with tonight.

Finally, they arrived at the jail. The guards unhooked the main lock and the prisoners all walked out still chained in a line. They walked into the jail where they were processed. They all got their mug shots and were fingerprinted. They were given badges to wear with their pictures and prison id.

They were brought to another room where they had to take off their clothes.

“Take your clothes off and bend over!”

The men and Michael did as they were asked. The guard went down the row making sure the prisoners didn’t have any drugs. After that was done, each inmate was given a jumpsuit, shoes, underwear, sheets, blanket and a pillow. They brought each of them to their cells.

Michael wondered who he’d bunk with. When walking down the hall, the men were whistling and calling the new inmates derogatory names. The guard opened the cell and Michael walked in. There was a guy about his age. He checked Michael out. Michael walked into the cell and the guard closed the gate.

The man was already on the bottom bunk. The two men just checked the other out. The cell wasn’t very big. There was just the two bunk beds and a urinal. This would be his home for the next ten years. So many things ran through Michael’s mind. He knew he’d be having sex with Gerard. He was fine with it, if he’d offer protection.

“My name is Gerard. Aren’t you a pretty thing. The men will love you. Fucking hell! I must have won the lottery. Who are you sweetie?”

“The name’s Michael. Nice to meet you.”

Michael extended his hand to Gerard. Gerard pulled him close and felt his buttocks.

“You’re mine! You will do as I say when I say. Got it!”

“Yes sir! I’m happy to be your bitch. If you offer protection. I’ll do whatever you want as long as you keep me safe.”

“Yes. I’ll protect you and you can keep me happy. I haven’t fucked a pretty thing like you in ages. I like that you’re so willing. That’s hot. You ever been in jail before?”

“Yup. Been here a few times. I’ll be happy to have sex with you. Just keep me safe!”

Gerard wanted Michael and he planned on having him now. Gerard took his clothes off and pointed down at his cock.

“Suck my dick! Show your master what a good boy you are!”

Michael did as he was told. He got down on his knees and opened his mouth. Gerard pushed his cock into his throat. His cock tasted like warm sweat. Michael took as much of Gerard’s cock into his mouth. He made sucking noises which pleased Gerard. Gerard held the wall while playing in Michael’s curls. Michael loved sucking cock. He’d show Gerard what a good cock-sucker he was. He’d take his time with Gerard. He’d drive him crazy with lust.

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Story tagged with:
Ma/Ma / Gay / Anal Sex / Oral Sex / Safe Sex /