Prison Bitch - Cover

Prison Bitch

Copyright© 2023 by Daemon D. Hart

Chapter 1

Erotica Sex Story: Chapter 1 - A bigshot lands in prison. A prison bitch catches his eye.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma   Consensual   NonConsensual   Gay   Fiction   Gang Bang   Anal Sex   Analingus   Oral Sex  

Riley O’Connor yawned and stretched, while waiting on the long bench. It had been just bad luck to be caught for such a mundane petty crime. Had he been sober, he would not have stolen that car, and right now he could have been someplace else, probably chilling with a cocktail on the table and a blonde with big tits in his lap, instead of waiting to be admitted into a correctional facility. There had been much worse things he had done throughout his 32 years of existence, and, although he had thought about retiring, right now, he was thankful he still had a reputation to precede him.

“O’Connor, get up, you’re in Unit B,” the guard spoke monotonously while shoving a blanket and a pillow into his arms and gesturing for him to follow.

“Do I get the royal treatment or what?” He asked.

“Your gang waits for you,” the guard added morosely. “Since they asked for you nicely,” the man said ironically, “why say no?”

Riley shrugged. He didn’t exactly have friends on the inside, since he had always been clever enough to dodge the police, but it was good to know he had been already recognized for his worth. He kept his shoulders relaxed, walking behind the guard, like he owned the place. But his eyes were wide open. There was no such thing as free lunch, and being identified right away for who he was could be both a reason to rejoice and one to be worried.

Tall and strong, he was easily towering over the guard. The other didn’t look intimidated at all. Riley smiled inwardly. The guard might think he was tough and almighty with that gun in his holster, but he probably had no idea who Riley was. He wasn’t called Cobra for nothing. Although he loved money and making as much of it as possible, he had as much trust in his muscles as he had in his brain.

He was pointed towards one of the larger cells. He dropped his blanket on the bottom bed and looked around. The guard was as good as gone in an instant.

There was a small mirror above the sink, and he checked his face in it. His jet black hair needed a haircut badly, and there was also plenty of stubble he had to get rid of and fast. On the other hand, they made him look more like he belonged to the place. He rubbed his chin, pondering if he should grow a beard. He gave himself a small wink. The chicks always digged him. He was handsome and loaded, and, as Lola often used to say, he had the bluest eyes a sinner had ever been allowed to have.

He didn’t have to turn to know he wasn’t alone.

“Riley O’Connor,” he heard one guy talking and only then he turned.

“In flesh and blood,” he answered while taking a good look at his visitors.

There were only three, but they looked like they were some kind of a welcoming committee.

“We’re Sean, Andrew and Tamy,” the man spoke, making a small gesture to introduce the other two who just nodded.

Riley maintained a straight face, while he evaluated the trio. They could have been anything from car thieves, which he also was, by the way, to cold blooded murderers. Riley had a reputation, but murder had never been on the menu.

“We heard they got you for stealing a car.”

“Yeah, a bit of an overlook from my part,” Riley grimaced.

“Rumor has it you’re eating from gold spoons. Why did you steal a car?” The man questioned.

Riley looked him up and down and leaned onto the skin. With a smile, he answered.

“I was drunk and angry at my woman. You know how guys are when they don’t get any.”

The trio laughed, and Riley instantly thought of a pack of hyenas. On the upside, they seemed to be kind of dumb, and, in Riley’s book, that meant they could be manipulated.

“Man, I bet you now wish you tapped that,” the one called Tamy spoke.

“Ah, well, that ship sailed now,” Riley opened his arms to express his helplessness. “Now what’s up with you guys?”

“We need a boss. You fit the bill,” Sean spoke directly. “Soon, we’ll be sent to our cells, so I’ll make this short. Will you do it?”

“Who are you, exactly?” Riley cocked his head to the side.

“We’re the Greenies. We’re the toughest on the block. But we need a face, someone to represent us. You’re one of us.”

The man looked behind to check for guards.

“What do you say?” He pressed.

“Give me until tomorrow,” Riley didn’t back down.

That gave him enough time to find out what these Greenies boys were all about and if it was in his best interest to become their leader.

Guards yelling were a good sign it was time for them to hit the hay. When one of them came to close the door on his cell, Riley went straight ahead.

“Two nice bills for you for some info.”

The guard looked straight at him. It looked like this one knew who Riley was. He just nodded.

~~~ Becoming leader to the pack called the Greenies didn’t look like such a bad deal after all. They were a rowdy bunch, and they didn’t have a boss. Rep was everything, and Riley knew it. According to the guard, they had tried a few stunts to prove themselves and it hadn’t work so well. With gangs all over the place, their situation was far from ideal. It looked like quite a project for Riley, who was notorious for turning shit into gold. And the shits he had just met had potential, potential he could work with. Sean was going to be happy in the morning upon hearing Riley’s answer.


“So, who are the movers and shakers around?” Riley demanded.

Sean was his self-appointed lieutenant and Riley didn’t mind putting the little prick to work. In his mid-20s, Sean had the energy and the desire to rule, but, unfortunately for him, he didn’t have the brains for it. However, Riley had to praise him for being able to understand that at least. The rest of the pack were punks, all of the same age or younger than Sean. It was now up to Riley to get them on their way to stardom.

“The Niners are moving all the fun stuff. The KPD bully outsiders for protection money and the Fag Army is just selling ass.”

Riley grimaced. “Really? The Fag Army?”

Sean shrugged. “They have a solid business.”

Riley took a small look at his lieutenant. Sean was not the brightest tool in the shed but he was not a bad looking kid. His military chopped hair was probably an attempt to make him look tougher, but he was still wet behind the ears, Riley could tell. He had good muscles and Riley counted on that.

“I don’t get fags,” he shook his head. “I mean, my hairdresser is one, and I’m sure my favorite chef, too, but, really, bending over for a guy...” He tsked in displeasure.

Sean looked the other way.

“What?” Riley asked intrigued.

“It’s prison, man. As you can see, there are no girls around.”

“And what’s wrong with your own hand and some porn mags?” Riley pointed out.

“Hey, it’s not like I’m the one taking it up the ass,” Sean said in his defense. “But some of the fags here give really good head. They are worth every penny.”

Riley thought about asking Lola to give him a blowjob in the visitation room. That, if she cared about moving her ass to visit him. By now, she should have found out about him and his new situation. He didn’t care about calling her. He had been too busy talking to his lawyer. Normally, he would have gotten off the hook, but the judge hadn’t been one to impress with money. Plus, Riley had the distinct sensation the guy just didn’t like him. He shook his head. Getting his business in order had been a priority. Lola could wait, or at least, he hoped so.

Now, to the business at hand, so to speak, he stared intrigued at his lieutenant.

“So, you’re all fucking guys around?”

Sean averted his eyes. “Sometimes. Come on man, give me a break. I’m here for two years, and it’s been only half a year. I thought just like you. But ... Well, sometimes even a guy’s mouth or ass is better than your hand.”

Riley didn’t press the matter. “It’s not my business, so you can do whatever you want. But don’t lose face by doing this fag stuff, alright?”

“Quit breaking my balls man,” Sean spoke embarrassed. “And this stuff is normal here. I wouldn’t be caught dead doing that on the outside, but here it just is.”

“Alright, I’m not going to argue with you,” Riley decided to stop torturing his subordinate, especially since the poor guy was now red up to the tips of his ears. “We have more important business to talk about. We’ll cut into the Niners’ playground. They are making the most money, that’s why they’re our target. We’ll start easy at first. Liquor, cigarettes, none of the heavy stuff. That will give me plenty of time to get cozy with the guards. Which is the most likely to be on our side and which are those who Niners have in their pockets?”

Sean started talking animatedly. Riley listened carefully. He didn’t intervened until the guy was done with all he knew.

“Good work, Sean,” he patted the guy on the back, and the younger man smiled, inflating his chest. “Now I’ll put some things in motion. You and the others are in charge of finding clients. Choose your delivery boys wisely, ok?”

Sean agreed happily. Riley was satisfied. If running a business was not so different on the inside, then he would not find the time to get bored.

~~~ Riley looked at the beaten guy, and frowned. There were a few stitches and that was going to heal. But it was a slap on his face and that could not be tolerated. Something had to be done.

“What do you say, boss?” Sean was agitated and was moving around too much. “Should we go to war with the Niners? That will teach them to mess with us.”

“War is not always profitable, unless it’s a war of attrition,” Riley spoke, crossing his arms over his chest. “Get well, boy,” he touched briefly the man lying on the white bed.

He took Sean by one shoulder and dragged him away. “We must think of something clever to do. Something that will sting,” Riley thought out loud.

“Beat up one of his, too!” Sean reacted, but Riley squeezed his shoulder to stop him from becoming too agitated.

“No. They expect that. They will walk in groups and you may get more than you bargained for. Plus, our good business depends on guards seeing us on our best behavior. Now, Sean, think. What’s most important for the Niners?”

“Money.”

“We’ll get there, but in time. We’ll have the most money in this joint. What else?”

“Respect,” Sean added.

“So doing something that will make them look bad will not sit well with them. However, beating one or more of them will only give them the opportunity to strike back and we need more guards on our side for that to work well. It must be something that not even they can openly do something about, because it will make them look even worse.”

Sean scratched his head.

“What does their boss like to do best? Eating, drinking, playing cards, drugs?”

Sean looked like he had been struck by genius. “I know!”

“Well?” Riley pressed, a bit annoyed with how slow Sean could be at times.

“He likes fucking his bitch.”

Riley sighed exasperatedly. “What’s with you, guys? Haven’t you gotten enough pussy in your lives? There’s only sex for you.”

“Easy for you to talk. I heard you always fuck supermodels and shit.”

Riley tsked. “I’m not into the anorexic type.”

“What’s that, anorexic?”

“Women fainting because they’re eating just salad all day long.”

“Are there bitches who do that?”

Sean seemed genuinely impressed with Riley’s knowledge of models’ eating habits.

“Yes, and they’re not my type. I like my woman to have tits and ass.”

Sean sighed deeply. “Yeah, me too. Now, boss, listen to me. If we fuck his bitch, that’ll send a message.”

Riley seemed to ponder. In the meantime, Sean was getting more and more excited. “Yeah, we’ll make his bitch our cum dumspter and send him back.”

“Really? That’s your brilliant idea?” Riley said ironically.

“What’s wrong with it?” Sean seemed surprised with Riley’s lack of trust in his plan.

“All you have on your mind is fucking. What’s the deal with that bitch, anyway? Is the guy’s lover or something?”

“Nah, they just push him around, make fun of him all day long. Too bad, though,” Sean added.

“What’s too bad?” Riley asked, already bored with Sean’s obsession over sex with men behind bars.

“This guy, the bitch, I mean. He’s a pro. He used to be in movies and shit.”

“What kind of movies?”

“You know, porn.”

“Poor shmuck. He went straight from fucking pussies to being one,” Riley shook his head.

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