A Taste of Prison

By Tommyhawk1@AOL.COM
Artwork (c) 2002 by Voyeur

Illustration of Guerrito

"Yeah, you wanted to see me?" Matt said to Mr. Caine. He was dressed in the uniform Mr. Caine's office had supplied him, even though it reminded him uncomfortably of the prison uniform he had so recently discarded. But when you take a job as a security guard for a private mansion, you don't get to choose what you wear. The problem was that he didn't yet have a shield or anything to help break up the blue-denim look. Light blue shirt over dark blue pants over black shoes. It reminded him of his home for the past five years, and even now he was on probation, he couldn't fuck up this job no matter what. So he bit back the complaints and stood there, feeling like less of a man, because a taste of prison still lingered, wearing these clothes.

There was a lot of "man" to Matt Bates. Six foot three and two seventy-five, and there wasn't any fat to any part of it. He'd spent his five years in prison making lavish use of the exercise equipment, pumping iron for two hours a day, until he was a mountain of muscle encased in a body covered with tattoos and rank chest hair. His head was shaved and a blue tattoo of a dragon wrapped around his bare scalp with the head reaching down to peer toward his nose. With his bushy eyebrows just below the dragon's snout, it gave him a perpetual-looking scowl. His cheeks were cherubically round, which didn't diminish his raw, fierce expression in the least, even in a pose of submission.

Mr. Caine looked up from him from behind the severely functional desk; this room was his home office. He was dressed in a full business suit even though it was nearly ten o'clock at night. "Yes, Bates, thank you for coming in. I want to talk to you about a little independent project I need your help with. It's the reason I hired you, frankly."

"Yes, sir?" Matt perked his ears at this. What the fuck did Mr. Rich Bastard Caine want of him? Independent project. "I'm not doing anything that would violate my probation, sir." He warned.

"No, no, of course not." Mr. Caine went on. "Have you been reading the newspapers lately?"

Matt shook his head. "No, sir, except the classifieds when I got out." He'd been too busy with his own parole and the processing of getting out of prison. Too much going on to sit and read about other people's problems.

"I hired you because you have recently experienced prison."

"Yes, sir." Matt carefully kept his voice level. He didn't like being reminded of prison, it had been five years of hell, only made tolerable because he was one tough bastard, and even then, he'd had to watch his ass every second of that five years.

"I'm about to go into prison."


"I've been convicted of securities fraud." Mr. Caine informed him. "Your formal job will be to guard my property until I get out of prison. I was told by the prosecuting attorney that he was going to push to dump me into McCormick Prison. The general population."

"Oh." Now Matt understood. He'd gotten this job, a puzzling one to get when you're a con on parole, and are hired to be a security guard, not that he had griped about it. "So what do you want from me? Information about which guards to avoid and which prisoners to watch out for?"

"Yes, in part." Mr. Caine paused. "I've been informed by others about that, though your viewpoint will be appreciated. I've been told more than I ever wanted to know, so I'm fully aware of what goes on in prison. I'm aware of what's going to happen to me if they put me into the general population. As the district attorney has threatened of me, if I don't inform him about my associates, which I can't do. A securities broker who breaks client confidence never gets to work as a broker again."

"I can understand that." Matt agreed.

"So I'm bound for prison. And look at me, you know what'll happen to me in the general population." Mr. Caine was younger than Matt by maybe a half dozen years, one of those young, overeager, fresh-from-college, wanna-be-rich types. They get busy, make money hand over fist and buy big houses and expensive things, get into debt, get into shady deals to make the money to cover the debts, and then they're talking to guys like Matt because now they're going into prison where they'll get gang-banged daily for the duration of their stay.

"Yeah, I know what'll happen to you." A pretty boy like Ronald Lawrence Caine really shouldn't be dumped into general population, with his salon-dressed hair of deep, russet-brown, smooth, nearly-feminine face of soft lines and deep pastel-blue eyes, a body less masculine than beautiful, the form captured time and again by the old Greek sculpturers to express their deities. Yeah, the goons in McCormick were going to be all over this guy like flies on shit.

"So I need your help."

"How?" Matt wanted to know. "Man, there's nothing I can do to stop those guys. They'll claim you and sell your ass for cigarettes until even you won't want yourself any more."

"I know. But you see," Mr. Caine gulped and looked younger than he was, "I have to know what it's like."

"What it's like?"

"Yeah. Knowing is less scary than not knowing. If I'm going to get butt-fucked in prison, I need to find out what it's like to get butt-fucked."

Matt's face crinkled, in confusion rather than rage. "You want me to..." Then it dawned on him. "You want me to fuck you? Here and now?"

"No, no, not here. Come with me. Downstairs, in the basement."

"I don't know about this."

"A thousand dollars." Mr. Caine babbled. "I'll pay you a thousand bucks, cash, right after, if you'll do this for me. I have to know. Please, man! Don't let me find out when I get there! I couldn't handle it, man, I'd go nuts!"

Aw, Jesus, what did I do to deserve this? Matt asked the heavens in silence. I get out of prison, supposed to keep my nose clean and my behavior in the law, and I got some guy wanting me to rape his ass in the basement?

But what choice did he have? It was this job or no job. "All right, but only once, you get me? One time and that's it!"

"Don't worry about that. Tomorrow, they'll take me into custody and haul me off to McCormick Prison." Mr. Caine assured him.

So Matt followed him out of that office and through the beautifully appointed house. He'd always dreamed of living this way, some day, it was why he'd gone into crime. Not that burglary had worked out for him, naturally.

The basement wasn't dark and dingy, but it had a concrete block in one corner and bars across the opening. A fucking fake prison! How long had this guy been setting this crap up, anyway?

He peered inside when he got there. Yep, it had a small prison-style bed and a chair. No prison toilet, anyway. Maybe this guy had paid someone to quick-install the prison bars over the door to a small room that had already been there. Buy an old bed and chair and stick in there and presto, a fake prison cell.

"Give me five minutes and then come on in." Mr. Caine told him. "From there, just treat me like this was a real prison and I was the guy you were out to fuck. Get as rough as you need to, I need the real experience here. A taste of prison life. It'll make the real thing a lot easier to take."

"No, it won't." Matt predicted.

But Mr. Caine went on into the cell, and started tearing off his clothes.

Matt waited until the man was down to just a pair of boxers, the clothes he kicked underneath the bed. Lay down on the bed. "All right, I'm ready." He breathed a heavy breath as he said that.

"Okay, but remember. You asked for it." Matt said.

"I know. Just do it like it was real."

So Matt walked in and stood over the man. Shit, he was a fucking pretty piece of man-ass! Matt had taken other men in prison, most of them willing but some not so much. This guy was prime meat, all right.

He reached down and began to undo his belt. He moved in complete silence.

Mr. Caine couldn't bear the silence. "What are you going to do?" he asked.

"Shut up!" Matt growled.

"I only asked what...."

"Shut up, punk!" Matt grunted.

Mr. Caine started to get up. "Look, I'm not looking for any trouble, but..."

When he got to his feet, Matt, who had just finished unbuttoning his fly, hauled off and slugged Mr. Caine right in his stomach.

"Oof!" Mr. Caine doubled over and Matt grabbed his shoulder and spun him around and shoved him back onto the bed. As the man was bouncing and trying to get his wind back, Matt pulled his pants and briefs down and grabbed Mr. Caine's boxers by the waistband.

"Oh, oh, God!" Mr. Caine moaned.

"Ah, shut up, you're going to get it and you'll love it!" Matt snarled.

"Please don't hurt me, please! I can pay you money, man, I have money...."

"Shut up or I'll let you choke on this a while first!"

"Oh, God! Please, let me put something on it, at least!"

"Fuck that!" Matt told him as he yanked those boxers down those pretty legs and revealed the small, pert, pair-of-bubbles-shaped ass. "Man, that's a pretty butt you got on you. I'm going to love it, don't you worry, I'm going to love you right."

"Oh, man!" Mr. Caine moaned.

"This is what happens to you in prison." Matt reminded him. "Best you get is a bit of spit like this!" He hawked noisily into his palm and rubbed it on his dong. He had a major mean organ on him, ten solid inches of hard man-rod, and the spit he laid on only gave it a light shine. "Then they just pull your butt apart like this." His big paws of hands on those bubbles pulled them apart like a ripe melon, and the split between, an area of slightly darker color than the pink-white bubble cheeks, and then his cock was plowing into that cleavage, like a chisel splits a chunk of firewood in two. He missed the sphincter on the first stab, but then he jabbed again, a little lower down and this time his glans pierced the tender tucker of flesh and he knew he had the right spot.

Mr. Caine howled. "Oh, oh, guard! Guard! Someone help me, please!"

"Yell all you want." Matt growled at him. "Fucking guards don't care. Hell, some of them may come in and want a turn at you. So shut the fuck up before you get yourself really chain-fucked!"

"Oh, oh, God!" Mr. Caine sobbed, but he said it softer.

"You wanted to know what it's like in prison. Keeping your mouth shut about your fucking little pansy buddies outside? Man, you're so fucking stupid, you belong in the general population! All you're good for is to get this pretty ass fucked over and over. And you'll get it when you get there. Trust me on that. The pretty ones get really messed up, the first weeks. The lucky ones get bought by one of the big ones, the rest are on their own. They don't last long, either they hang themselves or they end up in the psych ward. It ain't pretty."

"Oh, God! What can I do?" Mr. Caine moaned.

"Tell the D.A. what he wants to know." Matt said and he punctuated that by shoving his cock into that lovely, lovely ass.

"Ahh-ahhhhh!" Mr. Caine's groan sounded almost like a sigh. "I can't do that, I just can't."

"Then you need to make friends with some big, tough guy in prison and hope he keeps you for his personal fuck-toy. Then you only get rammed by one dong instead of a lot of them."

"Like you?"

"Yeah, someone like me." Matt said. "You give me a good ride, and maybe I'll protect you a while. Can you do that?" He shoved his cock the rest of the way in, now he had his cock in that sweet, pretty ass all the way up to his ballsac.

"Huh-unnnhhh! Yeah! Yeah! I can do that." Mr. Caine groaned and he grunted, wriggled and Matt felt the ass accommodating his prick. Shit, now it felt good. Fucking an unwilling ass was more about domination than pleasure, you get a tight sphincter that fights you and tries to spit your dick back out. And blood, lots of blood. But this ass, Mr. Caine wasn't bleeding, or not much (there was some moisture running down his balls that may have been blood), and the tunnel his prong had invaded was wrapping itself around like a warm, warm flannel blanket. Nice! Real nice!

"Hang on for the ride." Matt told him and began to thrust his cock in and out of Mr. Caine's warm butt. Mr. Caine grunted and moaned and after the first few strokes, began to move in synch with Matt's motions.

"Yeah, yeah, that's the way. Milk my cock with that ass, milk it for me!" Matt grunted.

He slapped the buttocks, hard and Mr. Caine yelped, but that also made the ass release and make the way even more comfortable. "See, I slap your butt and that makes you turn loose. You turn loose and you're an easier fuck. Now you're my little cock-pig, so let's hear you grunt. Come on, piggie, grunt for me! Grunt, you little shit-faced pretty-boy, grunt or I'll make you squeal!"

"Unk, unk, unk, unk, unk!" Mr. Caine grunted. He did sound like a pig, doing that.

"Yeah, nice, real nice!" Matt said. "Now, roll over, I want to watch your face while I fuck you. Come on, roll on my cock like a pig on a spit!"

Mr. Caine moaned but he began to roll. As he did, Matt levered himself up and onto the bed itself, into a kneeling position, and when Mr. Caine ended up on his back, he was resting on his shoulders and the rest of his body was on Matt's thighs, and his legs were splayed out, waving in the air.

Matt caught hold of those legs and now he was able to fuck-thrust into that ass, in rapid-fire motions that made the old bed squeak and shake.

"Oh, man, oh, man!" Mr. Caine gasped. "Man, I can't take this, I can't take this!"

"Sure you can!" Matt grunted. "You got all of it now, but you have to get me off. Come on, wiggle that ass and make me come! Sooner I shoot, the sooner it's over! Now get to working my butt. And squeal, piggie, squeal!"

"Unk, unk, unk!"

"I said squeal, damn it!"


"Yeah, you're my piggie, aren't you? Aren't you?"

"I'm your piggie, I'm your piggie!"

Matt looked down at this beautiful, pretty-boy man under him, and his cock was buried in this pretty ass and he owned it, he fucking owned it! "Oh, yeah, yeah, ah, ah, AHH, AHHH, I'm coming, man, I'm coming, you're mine now, I own you, coming, coming, own you, coming, AH-AH-HA-HAH-AH-AH-AHHH, GUH-HUHHHHHH!"

His wads blasted into that tender butt and when it did, Mr. Caine's eyes widened out as he felt the hot, salty, surging flow and he screamed out a final yell like a pig, "EEEEEE!" and then he was coming, ejaculating all over himself while Matt loaded his butt full of hot spunk, watching Mr. Caine's face flushed and softened into pretty-boy delicacy while he squirted on himself like a helpless little puppy, and then he was done and Matt was done and Matt slid backwards on the bed as he released the tension in his body and that brought him down onto Mr. Caine's body and he was lying down onto Mr. Caine, smashing the smaller body down into the old, sagging mattress and the spunk he'd shot on himself now smeared onto Matt's shirt, soaking it and Matt's sliding chest smeared it back onto Mr. Caine as he came into full contact and was face-to-face with him, their noses touching, their mouths touching, not a kiss, just two exhausted men too tired to move and then Matt's face slid down and over Mr. Caine's shoulder and onto the pillow.

After a short pause, Mr. Caine said, "So this is what it's like in prison?"

"Yeah, more or less." Matt told him, a soft voice into the ear so close to his mouth. "Most guys won't be this easy on you, though."


"Yeah, easy. I could have made you hurt a lot worse, and there are guys in there that will make it hurt you. They get off on hurting you. They'll shove stuff up your ass, too. You think my cock was big and hurt, imagine me shoving my fist up there."

"Oh, God!"

"But if you really can't tell about your buddies in the fraud, then that's what you're going to have to deal with. If I were you, I'd talk."

"Yeah, I get what you mean. Okay, let me up and I'll give you your thousand and you can go out and get accustomed to your work station the rest of the night. Tomorrow, this place will be locked up, so you'll want to make sure your work station has all you need out there."

"Yes, sir, thank you, sir." Matt said as he pulled his spent cock out of the ravished ass. Their positions had changed, fuck or not, here, he was the employee and it was time to toe the line.

So he got to his feet, pulled his pants up and fastened it, redid his belt and walked back out and up the basement stairs. He waited for Mr. Caine to come up which he did, looking the same as he had when he walked down, and back in the home office, he opened a safe and pulled out a thousand dollars, ten hundred-dollar bills, and handed it to Matt.

With that warming his pocket, Matt went out to his little hutch that would be his work station, a small guard-house like structure about five feet on a side. It was just inside an iron gate that he had a key to and could open as needed for visitors. Even a small television set to let him watch TV while he whiled away the long, nighttime hours, assuming you wanted to watch the four network stations through the antenna on the roof. Maybe he could ask for cable TV to be put in?

His only job duty was to unlock the gate and let Mr. Caine's vehicle out the next morning about seven-thirty in the morning and then his shift was done and he turned over the job to the day guard and was free until eleven o'clock tomorrow night.

Or so he thought. He got a call at three o'clock in the afternoon, woke him out of a sound sleep. He crawled out of his crummy welfare-hotel bed (little better than the prison bed he'd left or that one that Mr. Caine had stuck in his basement) and answered his cell phone. "Yeah?"

"Mr. Bates? This is Officer Phearson from Abercrombie Men's Institute."

"Yeah?" Matt knew the place, it was a cushiony men's minimum-security facility.

"We have a new inmate here, a Ronald Caine."


"He's listed you on his visitor list and we need you to fill out some paperwork to be allowed to visit him. Can you come up to our facility in the next day or so, so we can fill things out for you?"

"Yeah, I guess so." Matt would have to get permission to leave town from his parole officer, but if it was part of his job, then he'd have to get it from the guy.

"We know the separation can be painful, but we'll try to make the next three years as easy for you and your partner as we can."


"Yes, you will find our facility to be very understanding of your needs."

"What needs? What the fuck is this?"

"I don't understand, Mr. Bates. Mr. Caine has listed you as a Class A visitor. Do you know what that means?"


"Conjugal visits, Mr. Bates. Again, our facility is very understanding, you won't be inconvenienced and we can permit twice-weekly visits. We can even arrange travel on the vans that bring inmates here on occasion if you'd like."

"Conjugal visits?" Matt chewed this over. "Conjugal visits."

"Yes, didn't your boyfriend explain this to you?"

"No, he didn't. Okay, I'll be up there tomorrow or the next day, okay?"

"Very good."

Matt hung up as soon as he could after that and leaned back. He wanted job security, well, you can't get more secure than that! And a few more tastes of prison would be well worth the chance to fuck that sweet ass some more!


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