Prison Bitch Ch. 02

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Riley starts noticing things about Dylan.
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Part 2 of the 14 part series

Updated 08/05/2023
Created 04/29/2023
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Dylan was keeping close to Riley, as they walked towards the cafeteria to have lunch. Riley could tell the guy was nervous and almost felt the need to grab him by the shoulders and pull him by his side. He stopped right in time. This dude wasn't some woman. The guy was supposed to fend off for himself, at least to some degree. Still, the way Dylan walked like a stray dog, unsure whether his new master was accepting him or not was getting on Riley's nerves.

He was a bit caught in his own thoughts when someone talking woke him up from his reverie.

"So, you just decided to take my bitch and make him yours, Cobra?" Riley's nickname dropped like poison from the guy's mouth.

Riley sneered as he watched the head of the Niners straight in the face. "James, right?" He crossed his arms over his chest, while his boys took a step closer behind him. Mirroring their move, the other gang did the same.

He just half turned to order shortly. "Sean, keep your eyes on Dylan. And hands."

Dylan was quickly grabbed and kept by Sean's strong hands by the waist.

"I have a feeling you dont really appreciate fine things in life, James." Riley let his lips quirk into a smirk while staring the Niner up and down.

The gang leader laughed hoarsely. "Fine things? This bitch is nothing but a cum dumpster. Nothing special."

"Then why do you care who owns his ass now?" Riley asked him, his eyes at half-mast.

The head of the Niners remained with his mouth agape. Eventually, he remembered to talk. "It doesn't matter. He's ours. Don't expect me to just sit and watch. You cut in my trade, now you take my bitch. Don't be surprised to find him with his throat cut through, bleeding in your bed."

"Who the fuck do you think you are? Mafia? You're nothing but a small timer, getting off on scaring women. Take your threat and shove it up your ass where it belongs." Riley observed with satisfaction how well his insult landed.

"James, the guards are coming," one of the Niners drew his boss' attention.

"This ain't over, Cobra." James walked away, followed by his cronies.

Riley snorted. One of the guards made a small nod and he nodded back. The cards were in place. The Niners were nothing but a bunch of mutts. It was almost too easy to be top dog in a place like that. Plus, everyone knew who he was. That was good.

"Let's have a nice calm meal, guys." As he turned, he saw Dylan shaking while still being kept by Sean. He just gestured for them to move. The blond moved automatically.

***

Later that evening, as they were getting ready for lights out, Riley could no longer bear the silence. Dylan had acted like a fucking depressed bitch all day long.

"What's with you?" he asked sharply.

"With me?" Dylan barely murmured. "Except for the fact that I'm scared shitless now, nothing's wrong with me."

Riley laughed. "Are you afraid of that idiot? He's nothing but talk."

"You don't know him." Dylan was starting to get worked up. "He could do it. He could kill me, just like that."

The blond started pacing the small cell, gesturing wildly. Riley threw his pillow on the bed and stopped to watch his cell mate.

"He put me into hospital once," Dylan continued. "He used to beat me almost every day."

"Why? You didn't put out?" Riley snorted. "Any more of that and I heard your ass was going to fall off."

"Easy for you to say. It's not your fucking life on the line," Dylan raised his voice.

Riley felt his jaw tightening. The last thing he needed was a bitch yelling at him. He had had plenty of that over the phone from Lola. He moved quickly and grabbed Dylan in his arms, shaking him. "Stop shaking like this. Who the fuck do you think I am? Do you think I'd let them?"

"You cannot stop them! They will fucking kill me!" Dylan tried to push Riley away, but he was too weak to escape that fierce grip.

At that point, Dylan just panicked. Agitated, he pushed against Riley's hard chest, yelling to be let go.

Riley had had enough bullshit for one day. He pulled Dylan closer, feeling satisfaction at how the man's taut muscles tried to fight against him. When their mouths collided, he had no idea why he was doing that exactly. Dylan's lips were soft and inviting, and he kissed them, the sensation at getting passed through that barricade making him feel desire shooting straight to his crotch. Dylan tried to fight him some more, but Riley continued his attack, until the other grew slack in his arms.

As he slowly interrupted the kiss, he noticed how Dylan was trembling slightly.

"No one is going to hurt you while you belong to me," he said patiently while caressing Dylan's back, fighting against his twitching fingers that were demanding him to go lower, grab that shapely ass and knead it in his hands.

"Why did you do this?" Dylan was gingerly touching his lips.

"To calm you down. It worked, it seems." Riley let go of the other's body, not without regret. "You were getting hysterical. Just like a fucking woman. I had to do something," he explained.

"Why this? Why kiss me?" Dylan pressed further.

"It's how I calm down my women when they go cuckoo like this," Riley said and shrugged.

"I'm not a woman." Dylan crossed his arms over his chest like he was trying to defend himself against something invisible.

"You kinda are," Riley said, a bit amused. "Hey, don't be so ungrateful. I could have just slapped you to your senses."

"Do you beat your woman?"

Riley now felt his hands itching for something else. "No, but I feel like in your case, I might make an exception."

"It's not like I'm your woman. I am so much less than that." Dylan leaned onto the wall, looking down.

"And what exactly makes you say that?"

"Except for being a cum bucket for your guys, what am I exactly?"

Riley sighed. "Look, Dylan, sweetie, I saw a bit from your body of work, so to speak. You used to stuff your holes with cocks for a living. Alright, so right now, you're not paid for it, but at least you get protection. I'm not going to beat you, and you'll be treated right. I won't let the guys disrespect you, even if they fuck you. My momma raised me like this. Can we have this shit clear?"

Dylan nodded but he continued to keep his eyes down. Riley groaned. "What now?"

"I'm not that bad, you know. I know I cannot say anything, seeing what I did for money, but... I am still a human being, you know?"

Riley nodded. "And you'll be treated like one. There'll be no beatings, and if you ever feel like taking a break from fucking, just tell me and I'll let the guys know that they should butt off for a while. Think of it as the price you pay for not getting yourself beaten or worse. Since you already like this stuff, it shouldn't be so hard."

"Do you think just because I'm gay, I should just like any cock?" Dylan was staring at him with his sweet cat-like eyes.

"Isn't it how it works?" Riley shrugged. "And you used to be a gay porn star, so that should count for something. You didn't mind stuffing your holes with any cock that had to fuck you, right? I don't suppose you got to choose all the dudes you were shooting with."

"Yeah, I guess so," Dylan said softly and started making his bed.

Riley grabbed his hand and made him sit next to him. He caressed the smooth cheeks slowly, staring Dylan in the eyes. "You have nothing to fear, alright?" Dylan nodded and tried to look down, but Riley kept him in place. "Do you understand? Don't go be wishy-washy about it. I want to hear you."

"Yes," Dylan admitted. Dismissed, he hopped on the upper bed just when the lights went out. "You know what, Riley?"

"What?" Riley asked.

"You're a pretty swell kisser."

Riley laughed. "Been told that before. Good night, sweetie. Sleep tight."

"Good night, Riley."

Soon, they were both asleep. Riley dreamed of fucking Lola for the entire night.

***

In the morning, his erection was so bad he was sure he could crush coconuts with it. Groaning, he dragged himself to the toilet, letting the huge stream ease his pain.

He barely noticed Dylan starting to brush his teeth next to him. The blond was stealing glances at his cock. Riley frowned. "Don't you get enough cock in your life?" he asked morosely.

Dylan quickly averted his eyes. Without a word, Riley started brushing his teeth, too.

"I'm not the one who started it," Dylan said under his breath.

"What did you say?" Riley frowned.

"Last night, you kissed me," Dylan continued, although he started to back down and pretend to be occupied with tidying up his things.

"Just to make you shut up," Riley said, while leaning against the sink and watching his cell mate going about his business.

"Yeah, right," Dylan snorted.

He was suddenly grabbed by his shirt and made to face a very angry Riley.

"Do you want me to kick your ass? Do you?"

Dylan didn't look impressed by that display of power.

"If you hate on gays, just act like one already," Dylan said through his teeth. "Let me know who I'm dealing with."

"Oh, really?" Riley stared him down. "The night wasn't a good adviser in your case, it seems. Don't try to play me, sweetie. I'm not that kind of man."

"I just want to know what to do around you," Dylan said exasperatedly.

Riley relaxed. "You don't have to do anything. And I have nothing against guys like you. I just don't get you. What's wrong with pussy?"

"I don't know. It's part of who I am. And... I just wanted to tell you. The fact that I like guys doesn't mean that I enjoy getting fucked just by anyone."

Riley let go of him and scratched his head. "But you got fucked by dozens of guys before."

"Yes, but I didn't have to deal with those I didn't really like."

"You're trying to tell me you were a picky whore?" Riley quirked an eyebrow.

"I'm trying to tell you that I have the right to like whoever I want. Getting fucked like this," Dylan gestured around, "is not some kind of fantasy come true, as you may think."

"Wait just a second." Riley raised his hand to make Dylan stop a little. "Why does it matter what I think? You'll have to put up with this shit, because this is how things are."

"What if they weren't?"

"Well, there's no point in fantasizing about what ifs, either. You're a prison bitch and you should just be thankful for getting a better owner this time around."

"And if I'm not thankful? What will happen to me?"

"Are you really trying to get on my nerves? Jeesh, it's like I'm living with a woman." Riley rolled his eyes. "Keep your sexy ass in line and you'll be fine, ok? How many times do I need to tell you?"

"Why do you keep on saying these things?"

"What things?"

"If you're not into guys, why do you think I have a sexy ass?"

Riley's jaw went slack. "It's just a figure of speech, for fuck's sake."

"And the kissing? And the fact that no one is allowed to fuck my mouth?" Dylan continued.

Riley pushed by him to get out. "I don't see why I have to put up with this shit right now."

Dylan remained unmoved for a few seconds, then hurried after Riley.

***

For the remainder of the day, he remained glued to Riley, but the man didn't care about even looking at him. By the time they had to go to bed again, Dylan felt like pretty much a nervous wreck. "Riley," he called meekly. A noncommittal grunt was the only answer. "I'm like... Sorry, ok?"

"Ok." Riley sighed.

"I was out of line. You're a good owner. I should appreciate that."

"Yeah, you should." Riley still sounded pissed. "Why don't you?"

Dylan looked away.

"Come on, since you've started talking, just do that. Talk."

"The problem is, you're good to me."

"How's that a problem?"

"No one has ever been good to me without a reason. I just want to know yours."

"Alright. But I've told you already. And since you have to put up with my gang and their horny cocks, this means you are paying more than enough for this so called kindness."

"The same I had to pay before, actually less... For more. You're different." He still didn't dare to look at his owner.

"Well, just consider it your luck then. Although I really cannot see it that way."

"Let me repay you somehow," Dylan offered, licking his lips nervously. "It would help me sleep better at night."

"You don't have anything to offer, sweetie. Stop troubling your pretty head."

Dylan's eyelashes fluttered for a split of a second. "I could give you a blowjob."

"No."

"A handjob?"

"No."

"A goodnight kiss?"

"You're pushing it, sweetie."

"Ok, I'll shut up now."

"Good. Just don't bother about it anymore. As long as you'll look nice and pretty next to me, making the other idiots in this joint drool after you, that's enough for me."

"I just don't get you."

Riley patted his head briefly. "You're a good looking guy. And it looks like everyone wants to fuck you here. Like any expensive car or whatever that comes in short supply, you're a sign of status. Do you understand?"

Dylan nodded.

"Glad I've cleared the air with you. Now, upsy-daisy and get some sleep," Riley ordered.

The words were accompanied by a gentle slap on Dylan's ass, making his eyes grow wide. "Really? Riley, for a guy who's not gay-"

"Shut up and get to sleep. You're so much like my woman that I cannot help it."

Riley was not entirely honest. Lola had never managed to rub him the wrong way so easily. Dylan was really a champion in his own way.

***

"I'm off over the next two days," he informed Dylan.

"Where are you going?" His cellmate was obviously uneasy.

"I managed to get myself a conjugal, so I'm going to fuck my woman's brains out into the next week," Riley said with satisfaction.

"Oh," Dylan said shortly.

"Don't worry. Sean is in charge, so nothing bad will happen to you."

"Ok."

"Well, have fun. And by the way, Sean has clearance to fuck you, along with other two who he will choose." Dylan's face fell. Riley frowned. "What's the matter? It's not like they're 20, right?"

"It's not that. You're leaving."

His eyes were darting sideways again. Riley sighed. "You're a bad liar, Dylan. How did you manage to handle so many cocks to become the fucking bottom of the year, if you hate it this much?"

"Because I was high most of the time," Dylan breathed out.

"So?" Riley shrugged. "Pop a pill, get a shot, whatever works for you, if that's the problem."

"I'm clean now." Dylan's lips trembled.

Riley shook his head. "You really have great timing for getting off drugs."

"Yeah, I guess so. Whatever, I have no idea why we're talking about that."

"Because I asked, and get it through your pretty head that you should never lie to me. Sean knows he must treat you right. So try to enjoy it. They're not bad guys, after all."

Dylan continued to nod, his eyes still glued to the floor. Riley grabbed his chin and made him look up. Damn, he had beautiful eyes, Riley thought. For a second, his eyes traveled to the pouty lips. He was going to get enough pussy soon and put that mouth out of his head.

"If anything happens, if they try to force you or rough you up, you come to me. You've been promoted to deluxe merchandise. Top tier whores don't get slapped around, keep that in mind." Dylan licked his lips unconsciously. "I want to hear you. Say you understand," Riley pressed further.

"Yes, Riley."

"Good boy." Riley nodded briefly and patted Dylan's cheek. It was a small gamble he was taking for no reason. He pressed his lips quickly against Dylan's who made a small sound of surprise. Riley used his thumb to caress the full lips briefly. "Don't forget your mouth is all mine, ok?"

This time Dylan looked him in the eyes as he said a small yes.

"I left something on your pillow," Riley added. "It's top quality or something. Use it on your ass and get ready. I'm sure the guys will be all over you, so it's just to make things easier for you."

Dylan looked after Riley as he walked away. As he searched on his bed, he found the lube. He grimaced, but what could he do? At least, the current owner cared about his ass a little.

***

Dylan felt dread washing over him once more as he saw Sean walking in, followed by another two guys. They were new, he idly noticed.

"What's up, Dylan?" Sean winked at him.

"Just the usual," he replied. The usual like in getting fucked in the ass, whether he wanted it or not.

"We'll come visit you a few times this weekend if that's fine by you," Sean continued, looking at him a bit strange.

"Yeah, sure." Dylan shrugged to hide his unease.

"Guys," Sean said to the other two. "I go first. We need to make it quick, so the guards don't catch us with the pants down."

The other two guys laughed, as Sean guided Dylan towards the back of the cell in the area that was most secluded from prying eyes. Dylan was now thankful for lubing his ass, because Sean entered him in one go, without any preparation. He grunted at the sudden invasion and then focused on his own breathing. From experience, he knew these young guys didn't have much staying power. He just had to endure the situation and let it go.

Sean finished fast, as expected.

"How is Riley letting us to use his woman like this?" One of the other guys asked.

"He's not Riley's woman," Sean offered an explanation. "Riley's woman is a tall blonde bitch with tits like watermelons and an ass to worship for weeks. I saw her in a magazine."

Dylan felt the second cock sliding in, this time easier. In the meantime, he was all ears.

"So what's with him then?"

"Boss is only using him for bjs," Sean said again. "And no one is allowed to use his mouth."

"Oh, fuck, with these lips." The guy fucking him touched his mouth. "I was really hoping for a blowjob."

"Ah, well, dream on."

The third intervened in conversation. "Riley's not here. We'll make sure the bitch won't talk. Why not filling his mouth with jizz?"

Dylan felt cold chills on his spine.

"No way, man. If Riley finds out, he'll hang me by the balls," Sean replied and Dylan breathed out, relieved. "Be thankful. Riley says you get an ass like this out there for one thousand."

"For one night?" The third guy seemed impressed.

"For one time. And Riley knows his stuff. He owns all kinds of clubs and shit like that."

That was such a huge fat lie that Dylan felt like laughing. He had gotten paid well as a porn actor, but nothing that outrageous.

He noted with idle satisfaction how the third guy really had a small cock. No wonder he preferred getting head instead of tail. He closed his eyes and let the guy finish. The man's hands touched his abs and went up to touch his nipples. It felt weird to be touched like that. All guys in the place wanted nothing but in and out, nothing more.

"Nice," the guy fucking him hissed. "He only lacks tits to be the perfect girl for me."

Sean and the other guy laughed. "Don't play with him too much. Riley is a mean sonofabitch. He told me we could fuck him, but don't try to pull anything else."

"You're too scared," the third guy said. "The bitch won't talk. I bet he loves the attention." The man grabbed Dylan's chin, forcing him to twist his neck.

Dylan stared briefly in the guy's eyes. He was really young. And stupid. "I wouldn't bet on that, boy," he said.

The guy's sneering face turned into a frown. "Bitch, you're crazy." He tightened his grip on Dylan's chin. "I could cut your dick and fuck you with it."

Dylan tensed. He had no time to say anything, as Sean was quick to grab the guy and pull him away. "Shut your mouth. This was a favor. Now, you go jerk off. Riley trusts me, especially with his bitch. I'm not going to mess it up because of you."

The guy walked out, mumbling something.

"Sorry, Dylan." Sean patted him on the back. "Don't tell Riley, ok?"

"Ok," he said softly.

At least now he had just two guys to deal with for the entire weekend.

***

Lola was sitting on the edge of the bed, nervously twisting the jewelry on her fingers. Riley looked at her and she looked back at him.

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