Prison Bitch Ch. 01

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A prison bitch catches the eye of a new prison bigshot.
4.4k words
4.55
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27

Part 1 of the 14 part series

Updated 08/05/2023
Created 04/29/2023
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Author's note: This is going to be a story in 14 chapters. It's going to start rough, but it's going to evolve into a romantic relationship, and it's going to have a happy end.

Prison Bitch

1.

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.

"No, not that kind. He did porn movies for homos."

Sean was satisfied seeing Riley finally surprised.

"They say he gives head like an angel."

"Really poorly chosen comparison there," Riley chuckled. "So he's a real fag. A certified one. And?"

Sean hesitated. "When he came here, he was like a prize or something. Gangs fought over his ass. The Niners fucked him in front of everyone to show they're top dogs," he spoke.

"That's some nasty shit," Riley frowned. "I guess he's not that big a prize now, is he?"

"Actually, he kind of still is," Sean spoke so low that Riley could barely catch it.

"How so? If the Niners are doing to him what you say..."

"They do, but all the others still want him."

"Why? With an entire Fag Army around, I'm sure there's no shortage of available holes."

The younger male scratched his head again. "You should just see him."

"Why?" Riley felt his interest piqued for some reason.

"He's a looker. You know, like a movie star and shit. And he used to do some wicked porn, before coming here. He earned some prizes and stuff like that."

"Prizes? For gay porn?" The boss was intrigued now.

"He was like a big shot."

"Why? He has like a 20 inch cock or something?"

Sean snickered. "No, he only played bottom. You know, the guy who takes it up the ass."

"Alright," Riley spoke. "Let me see this one. If he's as you say and everyone wants him, then we'll take him."

"Take him?" Sean asked confused.

"Yeah. Sean, do you know how poor shmucks only look up at guys who have the best women hung on their arms? If this fag you are talking about is the equivalent of that, we need to have him."

Sean stopped, his mouth hanging open.

"But, boss, you don't fuck guys."

Riley shrugged. "It doesn't matter. We'll take the Niners' bitch, we'll make him ours, and the Niners can chew on their fingers, while we'll parading this fag porn star all over the place."

"Boss, you're a genius," Sean exclaimed, still keeping the same idiotic look on his face. "Wait until the guys hear about this. They all want to fuck him."

Riley grabbed his arm. "About that. We want to be better than the Niners, right?"

Sean nodded.

"Then listen here. We're not punks, like the rest. We're gentlemen. This means no beating, pushing around, stuff like that, even if the guy's a bitch."

"What about fucking?" Sean showed his disappointment.

"That I'll let you. But you'll do it as I tell you and only in my presence."

"That's kind of weird," Sean crossed his eyes, while trying to think.

"Hey, you came with this bitch idea. We drop it and I'll think of something else."

"No," Sean hurried. "It's ok. If we get to fuck him, I don't care."

"Now tell me the guy's name."

"It's Dylan."

"Dylan and...?"

"I don't know. That is his name as a porn actor. He was with some porn house, Blue Velvet or something like that."

Riley didn't need any other details. As soon as Sean was away from his sight, he went straight to the computer room.

The guard nodded at him and he chatted the guy up a bit. Choosing a station far from the door, he began his research.

Apparently, stories of the guy being arrested were all over the web. The mug shot was usually not flattering at all, but Riley's eyebrows rose when he looked at the guy. For once, Sean hadn't said bullocks. The blond staring at him dejectedly from the mug shot had the plumpest lips he had ever seen. His face looked like he belonged to royalty, not a correctional facility or the porn industry. His hair looked soft and a little too long for his own good. His eyes were green, like a cat's, but they held no malice or mischief in them. The high cheekbones made him look a bit haughty, but they were masculine, which caused a bit of confusion in Riley's brain. If the guy had been perfectly effeminate, Riley would have had no problem understanding why all the guys in the joint housing him for the time being were so crazy about this one. He still looked like a male, although a really handsome one. He could easily imagine what kind of reaction he had caused, now putting the dots together with what Sean had said.

His curiosity now running rampart, he searched further. Images of Dylan flashed on the screen. Riley coughed, a bit taken by surprise. In his mind, gay guys were chubby men in their 40s listening to Liza Minnelli and pretending to know shit about fashion and curtains.

Dylan looked better than in the mug shot. He was a bit skinny, but his body was not lanky or awkward. He had a small waist and a really nice ass. Riley's eyes lingered on the curve of that ass more than he cared to admit. Bracing himself, he clicked on the videos tab.

The blond was on his knees, while guys came to spray him all over his beautiful face with their loads. Riley gulped. So gay guys seemed to be into bukkake, too. As Dylan stood up, and started playing with the sperm on his face, with an almost ecstatic look in his green eyes, Riley pressed escape with the speed of light. He was about to close the browser, but he remembered something. He typed his search quickly.

"Best Bottom of the Year, Best Oral Performer... I'll be damned," he sat back in his chair and pressed his hands together behind his back.

Alright, the guy was a prize. He was a gorgeous looking porn star who now lived like in one of his movies. Only that this time it was real, and Riley could bet Dylan wasn't happy at all with being fucked by a bunch of low lifers, and that because he wasn't paid for it.

He stood there, staring at the guy's mouth, and an idea came to him. As a boss, he could set some rules. With Lola being a perfect bitch over the phone again, he had to keep some options open.

~~~

Riley entered his cell casually. The blond sitting on the bottom bed stared at him frightfully.

It looked like Dylan had lost some more weight since put in jail. He still had beautiful lips, though, perfectly arched and ready to be used.

"Do you know who I am?" Riley spoke first.

"You're Riley O'Connor. James will learn soon I've been moved. He'll come take me back."

The brunet could smell fear from feet away. Dylan was oozing of it. He chuckled.

"He won't. Damn, it was just like taking candy from a baby," Riley spoke with satisfaction.

When he took a step forward, Dylan bolted from the bed and glued himself to the wall behind him.

"Are you going to kill me?"

"In my own cell? Do I look challenged to you or what?" Riley asked, visibly amused.

"What do you want?" The blond pressed.

"What does everyone want?" Riley cocked his head to one side, as he sat on the bed and looked intently at Dylan.

"To fuck me," the blond said simply.

"Wrong answer, sweetie. Everyone wants power, even the people kept here, inside."

"What does that have to do with me?" Dylan pressed himself even more against the wall, like that could protect him.

"It's painfully obvious only your looks got you through life. Not very far, it seems," Riley said ironically.

"You're locked up, too," Dylan blurted out, and Riley's face turned to stone.

The brunet rose from the bed and whistled shortly. Soon, the room was filled with Riley's men.

Riley took his place on the bed again.

"Alright, guys, a promise is a promise," he pointed at Dylan who looked white as paper.

"You're the man, boss," Sean spoke and the others murmured in agreement.

12