The Inmate

Rob Winthrop bought a house abutting a prison so he could service inmates through the fence, but he never thought they’d have meat like this! His name is Tanker, and he’s got the goods if Rob is willing to cough up some dough…

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Rob Winthrop knew it would work eventually, it was just a matter of time. He had bought the house on Theodore Street both because it was a good investment — it was undervalued due to its neighbor — and because it abutted a prison, and there was nothing Rob loved more than hardcore prison thugs, mafioso and toughs of all kinds.
Of course, prisoners weren’t simply allowed to roam around all the time, or really any of the time. So Rob went for frequent walks along the couple of acres where his property shared a boundary with the prison, but there was never anyone outside whose attention he could get.
It was a wooded area, and on the prison side of the fence, there was a dirt road about thirty yards past the property line. Rob could barely see it from his property. That was the only thing he could see, since the trees were too dense to actually see the prison yard or any buildings.
But he could hear people talking between three and four o’clock in the afternoon — there was a distant, dull roar every day in that time. That, he deduced, was their rec time. The prison yard must have been beyond the trees somewhere.
Every day he hung out there in the afternoon, waiting for an opportunity. Finally on a Monday afternoon he saw a young black man in orange prison pants, shirtless, creeping down the dirt road. He was on the lookout for people following him, but he didn’t pay any attention to the far side of the fence, so he didn’t notice Rob standing there.
“Hey,” Rob said when he got real close.
“Aaah!” He yelped and put up his fists like he was about to box. Of course there was a fence in the way, and he screwed up his eyes.
“What’s your name?”
“What? Who the fuck are you?”
“Sorry, sorry,” Rob said. He was too nervous to think clearly. This guy was a handsome dark-skinned thug with cornrows and bluish tattoos covering most of his body below the neck. Most prominently, there was a dagger inserted in his chest above the heart, with blood seeping out and covering most of his torso. Another wound, a bloody gash, was tattooed over his sternum. Rob took a deep breath, entranced by the man’s muscles, which gleamed with sweat. “I’m sorry. I’m Rob. I live here.”
“In the woods?” He wrinkled his nose.
“There’s a house over there,” Rob said. “Are you… escaping?”
“What? No, man, what the fuck are you talking about?”
“You were creeping along like you were hiding.”
“I ain’t want no one to follow me,” he said. “I’m allowed to be here.”
“What is this road?”
“Nothin’. It’s s’posed to be a nature trail or some shit. No one ever uses it,” he said.
“Why are you here?”
“None of yo’ business, dude,” the prisoner said with a sneer like dude was a slur.
“What’s your name?”
“Also ain’t none of yo’ business.”
“I don’t want to get you in trouble,” Rob said. “Do you want me to jack you off through the fence?”
There was a long, awkward silence. The man peered deep into Rob’s eyes to see if he was kidding. His chest muscles flexed and he stepped close to the fence.
“What?”
“I really wanna get you off,” Rob said. “If you tell the others, I’ll jerk anyone off. And I swallow..”
“Anyone?”
“No diseases, no fatties, no old people,” Rob said.
“You nasty.”
“Yeah,” Rob said. “What’s your name?”
“Tanker.” He curled his lip like he was disgusted.
“Tanker? That your last name? Or your nickname?”
“Fuck you. Lick my dick,” he said. He spat on Rob’s face through the fence. Then he raised his eyebrows like he wanted to see if Rob would walk away or not. But Rob loved being spat on and treated poorly by prison thugs like him.
Rob dropped to his knees. He reached his fingers through the fence, getting just enough leverage to pull on Tanker’s loose orange pants. That lowered them. His dick flopped right out the fly of his coarse, gauzy prison-issue boxer shorts.
“You got a lighter, man?” he asked.
Rob nodded. He handed it over while licking on the shaft of Tanker’s dick. It tasted unwashed, but not exactly dirty — it tasted like cramped sweaty men, like Tanker had been spending time with other men in such a tiny area that his body, and his cock, brushed up against his homeboys and cellmates. That was precisely what Rob had hoped it would taste like. He gurgled merrily, and Tanker twitched like he hadn’t expected it to feel this good.
He lit a hand-rolled cigarette with the lighter, which he then pocketed. The woodsy smell of cheap marijuana filled the air — that must be why Tanker was sneaking into the woods by himself. He didn’t want to get caught with weed and he didn’t want to have to share it with anyone.
His dick perked up and jerked. Rob switched to swallowing the whole thing, or as much as he could since it kept getting thicker while it hardened in Rob’s mouth. Soon it was so thick Rob struggled to get more than the first inch or two into his mouth.
He paused and took a deep breath. He needed to focus on relaxing his throat, and he told himself over and over to relax. He was so excited that his plan was finally working.
“Damn, dude, I ain’t had a mouth like this in a minute,” he said, taking a deep drag on his joint. “You like homeboy meat, huh?”
Rob blushed. Thwacking that massive brown cock over his face, he smiled up at Tanker. “I like prisoner meat,” he said. “I don’t care too much about its color.”
Tanker nodded. He bucked his hips, slamming his dick forward. His entire body pressed on the fence, which swayed with his weight. His flesh pressed against the chainlink fence.
“Deep-throat that shit, man, swallow it,” Tanker said. He sounded frustrated, his fingers stretching through the fence the best he could, like he wanted more than anything to grab Rob’s head and pound him.
But Rob wanted to tease him a little. He slathered spit with his tongue all over the sensitive tip of Tanker’s dick, until the saliva dripped down onto the ground in long, thin tendrils. Rob knew how good this felt, and how powerful Tanker’s instinct would be to ram his dick into Rob’s mouth.
He didn’t though; he couldn’t. He could do nothing more than grab the chainlinks, gyrate his waist like he was humping the fence and moan loudly. He bit hit lip and bucked his hips. He fingered Rob’s hair through the fence, trying to grip it but all he succeeded in doing was pulling a few hairs out of Rob’s head.
“Damn, quit teasin’ it, man, come on, swallow it. Swallow it, man. Swallow it,” Tanker said. Rob lazily stroked it, giggling at Tanker’s exaggerated reaction.
“How long has it been since you blew a nut?”
He paused for a long time, seemingly trying to decide whether or not to lie. “I ramrodded this punk a couple weeks ago,” Tanker said.
“Who’d you ramrod a couple weeks ago?”
Tanker shrugged. “This prisoner. He Mexican.”
Rob nodded.
“He only charge twenty bucks for anal,” Tanker said. “I ain’t have the money for that though. I had to pay other ways.”
“What other ways?”
He thought for a long time. He chewed on his inner cheek. Then he shrugged. “I stabbed a homeboy. Ain’t kill him. He was a bad homeboy anyway.”
Rob relaxed his throat and deep-throated him, all in one smooth motion without warning. Tanker moaned so violently it sounded like it hurt. His humped his hips forward, pressing his crotch so hard into the chainlink fence that it bowed outward.
Precum flowed down his throat, its sweet and salty flavor assaulted Rob’s senses. It tasted frustrated and horny, exactly like a man who hadn’t had sex in months. Rob rammed his own head so far down that his nose nestled itself in Tanker’s untrimmed pubic hair.
“Ah, god-damn, boy,” Tanker swore. His entire body pressed against the chainlink fence.
He took a deep breath and snorted. He pulled away from Rob then, sneering at him. “Fifty bucks, sissy,” he said.
“What?”
“You wanna keep gettin’ me off?”
“Yeah.”
“Then pay me. Fifty bucks.”
“If I don’t pay you, you’ll just walk away?” Rob had every intention of paying him — he was going to hand over money even if Tanker hadn’t asked — but he wanted to see if Tanker would seriously claim he would walk away. Rob didn’t believe it. Tanker was too obviously horny to blueball himself.
He shrugged. “I can jack off,” he said. “I know you want it, and I know you got money. You got a taste of it. You know how big it is. Pay me.”
Rob slyly turned around. He shook his ass in Tanker’s direction. He pulled out his wallet and counted out fifty dollars — he didn’t want Tanker to see how much cash he actually had, or Tanker would just demand more.
He handed the money through the fence. “Hey, if you bring me other guys like you, I’ll pay you. If you get them to accept twenty bucks, I’ll give you the other thirty.”
“Hell yeah,” Tanker said.
“Gotta keep it low-key, or the guards will find out,” Rob said. “Make sure you-“
“Don’t tell me how to handle the prison, bitch,” Tanker said with a growl through gritted teeth.
“Oh. Okay, sorry. Just don’t get caught,” Rob said. He stuck his face into the chainlink fence, so his mouth squeezed through one of the openings. It was just big enough for his lips to fit through to the other side. He stuck his tongue out and wiggled it.
“Beg me fo’ it.” Tanker spat in the palm of his hand, and wiped it over his gleaming cockshaft as he stroked it.
“What?”
“I say beg me fo’ it. I like hearin’ pussies beg,” Tanker said.
“Please let me touch your dick some more. It tastes so good, and it’s so big and you’re so tough, I just need it. I need your dick in my throat, Tanker, sir, and I want to all of your cum. I want you to drown me in cum,” Rob said.
Tanker gurgled. He spat on Rob’s face through the fence. He stuck his dick through the fence and swayed his hips, trying to slap Rob over the face with his manhood. Rob had to move his head to be in the right position though. He moaned as its meaty thickness thwacked onto his cheeks. Tanker chuckled dryly.
Opening his mouth, Rob chased Tanker’s dick. He didn’t use his hands, he just tried to swallow it while Tanker rotated his hips to tease him over and over again.
“Chase it, sissy, huh? You gonna catch it or what?” He laughed some more.
Then Rob did catch it. Tanker stopped moving for a moment, and Rob deep-throated his dick as far down as ever. Tanker moaned and stretched. He raised his arms and gripped the chainlinks, his unwashed muscles beaded with sweat as he slammed his entire body into the fence.
The precum flowed freely. It was clear he would have cum already if there wasn’t a fence in the way, meaning he couldn’t plow the way he liked, he just kept spasming inside Rob’s mouth.
“Damn, man, I wish I could hold onto you,” Tanker said. “You’d regret this, fo’ sho’, bitch. I don’t hit boys nice in the butt. I’d be grabbin’ yo’ scalp and rammin’ you till you throw up, man.”
“I wouldn’t regret that. I’d love it,” Rob said.
“What?”
“That’s why I like prison thugs,” Rob said. He blushed and looked down. He kissed the tip of Tanker’s dick, the piss-slit winking at him as he flickered his tongue into it. “I love servicing cruel machos like you.”
“Can’t grab yo’ head,” Tanker said. He took a deep drag off his joint, which he had to hold carefully with two fingers now.
Rob had an idea. He took off his belt and passed it through the fence to Tanker. He took it having no idea what to do with it at first, then he got the idea.
Rob pressed his face against the fence again, and this time Tanker fed the belt through as well. He had to whip it around Rob’s head — Rob helped guide it — and wrapped it over Rob’s scalp. That meant Rob couldn’t back his head away. He wasn’t unable to move away, since he could still lower his head, but his head was immobilized enough for Tanker’s massive dick to throat him down.
“Take a deep breath, bitch,” Tanker said. He took one last puff on his joint, which he then swallowed without extinguishing it. Rob inhaled deeply of the scent of Tanker’s unwashed crotch.
Rob was still exhaling when Tanker jammed his dick down Rob’s throat. That now-familiar flavor of masculinity, dirty clothes and stainless steel hit Rob’s tongue, and he groaned as it shoved into his throat.
That triggered his gag reflex, but Rob was good at suppressing that, and in any case, Tanker seemed to like it. He grunted and pulled on the belt a little tighter. He held his dick deep in Rob’s throat, relentless even as Rob began to squirm and choke. Massive quantities of saliva dripped in clumps onto the ground at Rob’s feet.
One of Tanker’s hands remained on the belt to keep it taut, while the other squeezed a pair of fingers over Rob’s nostrils. It was a tight fit, since there was little space in front of Rob’s face, but he managed to do it, and that forced Rob’s throat open a little wider.
Finally Tanker allowed Rob to take a break. He let go of one end of the belt, and Rob’s body instinctively pulled away. He let out a hoarse, choking gasp for air.
“You okay?” Tanker asked as though he was unused to it, like he rarely inquired after anyone’s wellbeing.
“Hell yeah!” Rob exclaimed as enthusiastically as he could with a throat crying out for more oxygen.
Tanker looked dourly down at him. “You got a nice throat, bitch. If you was my bitch, I’d tattoo some pussylips on yo’ face.”
“I’d like that very much, Tanker.”
“You got a marker?”
“Uh… Yes!” Rob had forgotten he had his work bag with him because there was lube and some other stuff in it, including a sharpie. He handed it through the fence.
Tanker chuckled again, suppressing a smile, like he hadn’t really thought Rob would say yes. He did as Rob hoped though, and he drew some labia on Rob’s lower and upper lips. Since he had to do it through the fence, the drawing wasn’t very good — just a blurry smear of black ink really — but Rob couldn’t see it anyway, so he wasn’t disappointed. Tanker pocketed the marker.
Then he put the belt back in place again. His cock was still rock-hard and throbbing, looking even darker now that it was moist with saliva and bile and even some of Rob’s oxygen-starved tears.
“Let’s see how you manage, bitch. You can take dick, I give you dat, but can you take it right? Gonna make you throw up, bitch, I swear to god,” Tanker said once Rob was back, belted to the fence with his mouth open. Tanker hocked a big loogie into Rob’s open mouth.
This time, he didn’t just deposit his cock directly into Rob’s throat. He held onto his head through the belt and explored Rob’s gullet, humping his dick in from every direction and even moving it in a wide, slow circle. He seemed to be trying to make Rob gag — and succeeding, laughing each time — so he fucked his throat every way he could, as if it was a disreputable fleshlight.
“Love hearin’ dat sound,” Tanker said. “The sound of a bitch chokin’ on yo’ dick, ‘specially a pussy like you. Hell yeah. Choke up some more, bitch.”
Rob gurgled. He tried to say yes, sir but since his mouth was full, he succeed only in tickling Tanker and triggering a heave in his stomach. More saliva flowed over Tanker’s dick, soaking his pants.
“I think I’ve made a mess,” Rob said as he gasped for air. “Sorry.” Tanker’s orange prison pants were soaked with Rob’s spit-up.
Tanker shrugged. “I’ll tell e’ryone I got off with a bitch. They won’t care. I ain’t gonna say who you is.” He paused. “If you here all the time, man, they gonna see you. I can’t control who get a nut off, y’know, I can’t get paid if they know when you gonna be here. Why don’t you just schedule it wit’ me? Then I can send you homeboys when you ready, and you pay me.”
“Okay,” Rob said.
“You best pay me, motherfucker. I got connections on the outside. They can put a hurtin’ on you if you try and stiff me,” Tanker said. He spat again, aiming for Rob’s face. But his spitwad hit the fence, and only a few drops splattered onto Rob.
“Okay. I’ll pay,” Rob said. “No problem. I’ll be here at three o’clock every day.” He lazily stroked Tanker’s pulsating cock, which dripped with saliva. Rob spat more up and onto the shaft. “You can meet me and bring whoever you want. I’ll hide behind this tree, so if someone else comes through they won’t see me.”
Rob knew he could get more prison cock if he just hung out here. He could tell anyone who came by that he was jacking off anyone, and he’d probably have dozens of men coming through. But he didn’t do that for a couple reasons. First of all, most prisoners were really not very handsome — the average age of an inmate in America was sixty-two, and a lot of them were fat as well — but Rob felt confident that Tanker would only bring his gang buddies over. They’d be younger on average, and no doubt having a better physique than most. Besides that, with dozens of inmates crowding the fence, it was likely that fights would break out, and guards would soon learn what was happening. If the prison administration made this a solid fence, or electrified it, or just added a second fence a foot away from the first one, it’d be impossible for Rob to get anyone off.
And the most important reason to let Tanker bring him men was that Rob liked the idea of Tanker bringing men here and keeping them quiet. The only downside was that Tanker was a black prison thug whose buddies were no doubt also black prison thugs, whereas Rob enjoyed a little diversity — he would have to offer Tanker extra cash to bring rednecks, mafioso, bikers and more.
“I’ve got an idea, Tanker,” Rob said as he licked the shaft and suckled moistly on the tip. Tanker’s whole body writhed and he nearly orgasmed right then, jabbing his salty cocktip into Rob’s mouth. The belt had fallen to the ground, and Tanker was too distracted by pre-orgasmic pleasure to notice. He gripped the fence with his hands and even bit the chainlinks, dick throbbing on Rob’s lips. Rob giggled. “I think you’ll enjoy it.”
Rob turned around and undid his pants — since he had already taken his belt off, all he had to do was stand and his pants fell down.
“Aw, damn, dude, you want me in yo’ ass?”
Rob nodded.
Tanker chewed on his lower lip. “I promised my mama I wouldn’t do that. She don’t like ugly.”
“Oh well, you don’t have to do it,” Rob said. “I don’t wanna make you break a promise to your mom and-“
“I ain’t say no,” Tanker said. He sighed. “Gimme more money.”
Rob shrugged. “I’m not paying you more every time,” he said. He handed over the hundred-dollar bill from his wallet. Tanker’s eyes opened wide like he had never seen a hundred-dollar bill before.
“Damn, you really want my dick in yo’ ass, huh? Well for a hundred and fifty bucks, I’ll stick it in anything,” Tanker said. “Come on, back dat ass up.”
Rob got down on his hands and knees. He backed up until his ass was pressed against the fence.
“Nah,” Tanker said. “You gotta get up higher. I got some self-respect. Ain’t gonna ram a male down in the dirt, like a fuckin’ swine.”
Rob blushed but agreed. He raised his ass higher. Since Tanker was so tall, it wasn’t easy, and in the end, Rob had to stand and bend over to grab his ankles.
“Spread yo’ cheeks, bitch. I can’t get a grip,” Tanker said. He jabbed his dick towards Rob’s hole, but he couldn’t get any leverage to spread his cheeks.
This was a very difficult position for Rob. He had to use both hands to separate his asscheeks, which meant he couldn’t support himself on his hands. He was bent over, head nearly on the ground with his hands in the air behind his back.
A twinge of pain hit him, followed by a long, slow melting pleasure that wrapped over his bones in waves, emanating from his ass. It took a long time for the pleasure to build, but Tanker’s rock-hard cock explored Rob’s ass and found his prostate soon enough.
Despite his claim that he had promised not to plow a man in the ass, Tanker did not plow like someone who wasn’t used to it — that made Rob wonder if that had been a lie, if maybe Tanker only said it to get more money out of Rob.
“Keep yo’ cheeks spread, bitch,” Tanker muttered whenever Rob’s hands slipped. It didn’t slow him down any, now that his cock was in Rob’s ass. His fingers slipped through the fence and fingered his cheeks desperately, trying to get a grip on his flesh.
Soon his entire cock pulsated in Rob’s ass. Precum flowed within him, and Rob could feel the man’s dick throbbing, the orgasm bubbling under — Rob sensed it growing with each thrust of Tanker’s dick.
If Rob had any hands free, he would have been jacking himself off and would have undoubtedly cum already (at least once). But he couldn’t stop spreading his cheeks, even for a moment, or Tanker would bark at him to get back in position.
“You tryin’-a get away from me, bitch? Stay there. Stay in position, ya fuckin’ sissy,” Tanker roared through the fence.
But Rob didn’t stay in position. For the first time since this had begun, he didn’t do what Tanker said. Despite the pain it caused in his ass, Rob lifted his head and upper body.
The motion sent waves of agony through Rob’s spine as his ass moved around Tanker’s dick. Meanwhile Tanker moaned and grunted like he was surprised. He had to focus to keep his cock deep in Rob’s ass while it moved, but he managed to do so.
Rob lifted himself up until his entire upper body leaned against the fence. Tanker was still deep in his ass, and his upper body leaned against the other side of the fence. So they were close enough now that Rob could feel Tanker’s solid muscles writhing, and he could feel the sparse body hairs scratching at Rob’s smooth back skin. Just the wiry edges of the chainlinks separated their bodies.
“Oh, you down fo’ that standin’ shit, huh?” Tanker muttered. He slammed his hips, whistling in appreciation at the new position. “That’ll do nicely, baby.”
His fingers pinched Rob’s back and his asscheeks, as he tried to grab ahold of him through the fence. All he could manage was a few pinches.
But his face was right behind Rob’s head, and his hot breath condensed on Rob’s neck and cheek. Rob even rolled his head to the side, so his face was against the fence. Much to his surprise, Tanker kissed his cheek through the fence, moaning as he did. He nibbled seductively on Rob’s earlobe.
Though his words were still menacing, Tanker’s voice broke and showed some affection as he neared his orgasm — Rob could feel it coming deep in his own ass. Tanker’s cock, which seemed to be getting bigger with every passing thrust, rammed easily in and out now, like Rob’s ass had been built just to accommodate Tanker’s manhood.
“I love the way yo’ asshole feel around my dick, boy,” Tanker said softly. “It feels real good. You got a nice ass. I like destroyin’ it, boy. I love it. I think I might love you, bitch. You love me?”
“Yes, baby!”
“Good. I don’t love you, you too nasty. You too dirty,” Tanker said. “You don’t love me neither. You love my cock, right?”
“Yes! Oh god, yes, I love your cock!”
“‘Course you do. E’ryone loves Tanker’s cock ‘ventually,” he said. He gasped. “Gonna fill you up in a minute. Beg me fo’ it.”
“I want your cum inside me! I wanna feel yo’ baby batter flowing into me, please!”
“Jack yo’self off, baby,” Tanker said. He nibbled on Rob’s earlobe again, then kissed him on the cheek. Rob nearly collapsed in shock as Tanker even kissed him on the lips the best he could — since Rob’s face was sideways on the fence, it was an awkward kiss, but it felt perfect to Rob. “You love me, baby.”
The switch from calling Rob a bitch to calling him a baby was unexpected, and it made Rob croon with desire. No one like Tanker had ever called him baby before.
The sensations in his ass were incredible, mind-blowing. It felt like he was being ripped apart yet at the same time it felt so good Rob had trouble remaining upright. His knees were weak. His own dick throbbed in his fingers.
“C’mon, I wanna blow,” Tanker said. “I’m gonna fill you up so good, but I ain’t doin’ it yet, baby.” He kissed Rob on the lips again. “I wanna feel you cum, okay? I always make my prison punk jack off when I ram him, that way he clench down when he cum. C’mon, finish yo’self off.”
Rob’s mind whirred — that confirmed that Tanker was lying about promising not to be a ramrod (or at least it confirmed that he had never upheld that promise). That made Rob feel a little better, since he didn’t like the idea of making someone break a promise to his mother and pastor.
His whole body undulated as an orgasm hit him. It was the most powerful climax of his life, since it began in his prostate and kept building as Rob stroked himself off. By the time his first few drops of cum landed on the ground at his feet, the pleasure was already so intense it wracked his body like a seizure.
And then Tanker reached orgasm as well. He grunted and moaned, cursing indecipherably as he slammed his dick into Rob’s ass one last time. He held it there, unmoving, for what felt like forever, while Rob clenched and writhed.
A spurt of white-hot cum sprayed within his ass, followed by more. Then it flowed out like piss, a long, constant stream of creamy cum that felt so good Rob moaned as loud as he could.
“Take it, baby, gonna fill you up, hell yeah… Gonna drown yo’ ass in nut, baby, gonna fill you up so much it come out yo’ ears…”
Tanker’s whole body flexed, then relaxed and he groaned. He slapped Rob’s ass, sending a wave of bliss through both men’s bodies. Tanker’s balls drained wad after wad of his seed, so much so that it dripped out of his ass and flooded his innards. Rob felt it seeping throughout his body, soaking into him until it was everywhere, like he was becoming one with Tanker.
At last it was all over. Rob had no idea how long the climax had lasted, but it felt like forever. His knees were weak. When he finally pulled off Tanker’s dick, a tremendous sense of relief overwhelmed him, and he could do nothing more than stagger away and collapse onto the ground.
Tanker took a deep breath and wiped his cock off with one hand. He wiped his hand off on a nearby tree. He grimaced at Rob when he saw how his hand was now covered in sticky santorum.
“That was good, baby,” Tanker said. He sighed. “You got a nice ass.”
“Thanks. I love your cock. When you’re released, you can come see me,” Rob said. “I’ll let you stay with me. As long as you fill me up every day, you don’t have to pay any rent.”
He nodded. He frowned. “I ain’t gonna be released till I’m nearly fifty.”
Rob shrugged. “As long as you still got that dick, come see me,” he said with a giggle. “Don’t forget. You get thirty bucks for bringing me men.”
“Don’t pay ‘em nothin’,” Tanker said. He pulled his pants up and walked a few feet away. “Just gimme fifty bucks each. I’ll tell ‘em you do it for free. They’ll do it for free. Hell, I might be able to make ‘em pay a few bucks.”
“You’re gonna get paid from both ends?”
Tanker smiled broadly, and wiped the sweat off his dark brown brow. He licked his lips and squeezed his dick in those orange prison pants. “I’m a pimp, baby. That’s why I’m in here in the first place. Courts don’t like pimps.”
“That’s a long sentence for pimp.”
“Three strikes, baby, and I tried to shoot a cop.” He paused. “I did shoot a cop. He lived though.”
“Oh, cool. You’re gonna be my pimp.”
“That’s right, baby,” Tanker said. “I loves ya, and I’ll make sure you get treated just like you deserve. You do whatevuh I say, baby, or I’ll make you go find some other pimp to bitch-slap you.”
“Okay.”
“Good. Come back tomorrow at three,” Tanker said. “And bring some cigarettes. Menthol. 100s.” He walked away without waiting for a response. The bare muscles of his sweaty back flexed as he strode through the woods back towards the prison.
“Okay. Love you too, Tanker!” Rob stood there and watched him disappear into the woods, and he was so aroused by the experience that he stood there and jacked off again by himself. He daydreamed about Tanker coming to visit him outside of prison, a little older, a little grayer, but still full of all his prison thug appeal.
Rob couldn’t wait for tomorrow.

The Prisoner Bottoms

Rob has paid for “seven minutes in heaven” with the inmate of his choosing, but that inmate turns out to be the alpha male thug Nutter, who’s got a secret desire of his own. Nutter can’t wait to get Rob alone so he can learn what happens when he puts a twink on top!

Can Rob handle this prison-life rough trade turned upside down?!

Read it now as an ebook!

Read the whole thing here!

Rob strode into prison with as confidence as he could muster — he didn’t want to look like he was a sniveling weakling precisely because he was about to act like one — but his ego quickly deflated. He was searched, poked and prodded by Officer Budinsky. It was demeaning, and it made Rob feel like a prisoner. It both helped and exacerbated the problem that Officer Budinsky was a handsome man himself, with a sturdy physique and a big square jaw.
But Rob wasn’t here for Officer Budinsky. Rob had paid to meet an inmate.
He walked through the state prison increasingly nervous at the hooting, shouting, whooping and thudding he heard in the cells lining every corridor. He was glad when they at last came to Cell Block Omega, which Budinsky had said was not in use due to a sewage line break.
Spread among the cells of Omega Block were eight prisoners who met Rob’s criteria and were willing to let Rob’s tiny twink body service them. Rob had been daydreaming about setting this sort of encounter up for years, and he never thought he’d go through with it until a few months ago, when he realized he needed to just bite the bullet and try. The worst that could happen was being refused by the prison guard he approached.
“Wuddup, Booty!” came a voice from one of the cells.
“Fuckin’ A, man, c’mon, hurry it up!”
“Tell him I’ll do it! Tell him I got the biggest dick, Booty!” They called Budinsky ‘Officer Booty’, maybe because he had a big ass crammed into his too-tight uniform pants. He had powerful trunk-like thighs and thick arms.
“I’ll make his bigguh, I got tasty cum, tell him I’ll be gentle, Booty! Tell him my cum works a treat!”
“Nah, nah, my jizz is the most effective, swear to God, nigga!”
Rob did not tell Budinsky that he thought ingesting the semen of strong, testosterone-laden men would make him bigger, stronger, tougher or possessing of a larger penis. Rob did not believe that, and Budinsky never even asked if that was why he was setting this up. It seemed he assumed though, as several of the hooting inmates made reference to it.
Seven minutes ought to be enough, Rob thought. That was all Rob paid for. Budinsky assured him that these men would be horny and ready to take charge, so the brief duration wouldn’t be a detriment to the experience. Rob wanted to be held down and rammed hard, slapped, treated like a submissive prison bitch, and he was told most prison “bitch-outs” took only a few minutes. The sight of empty cells and the hollering of men in a far off block made him hard even before he had seen a single inmate. This whole prison smelled of men. You could tell no women ever came here, not past the visitation area. Rob had had to adjust his erect cock in his pants several times on the walk through the prison.
The one in the first cell was tall and lean, with dreadlocks and hawkish features. He spoke with a faint island accent, but Rob suspected that was an affectation, he was probably from like Delaware or somewhere humiliating like that. No wonder he was pretending to be from anywhere else. He had an East Coast stawk that was his deeper than his Caribbean lilt. He flopped his dick between his fingers and showed off his perfect six-pack. “Yo, mon, you like me-uh treat you poorly? I will ram you senseless, whiteman. You will cry when I am uh-done wit’chou. I will plow the sissy-boy outta you, and then I gonna plow it right back in.”
Rob preferred men with a little meat on their bones — as much as he wished he could get on his knees and jerk the dreadlocked man off through the cell bars, Rob thought there was someone better in one of the other cells. It’s a good thing he never became a prison guard, cuz he would spend all his time on his knees in front of these men.
Then he passed a burly black man with a wild beard and a sour look on his face. He nodded at Rob, ran his tongue under his upper lip and said, “Damn, whiteboi, you look good enough to eat.”
But Rob moved on. He wasn’t quite right. The next one was Latino and bald-headed. “You wanna be my puta?” he asked as Rob walked past.
The fourth person was heavily tattooed. He didn’t say anything, he just nodded at Rob and bucked forward as though he was going to attack Rob through the cell bars. Rob instinctively shrank back and blushed when the tattooed thug cackled at him.
As soon as Rob came to the fifth cell, he knew he had found his man.
“So, you the man who wanna be my bitch, huh?”
His smooth baritone made Rob blush. He quickly hurried to the end of the corridor to see the others — that just seemed polite, after all, they had come all the way here — but he knew what he wanted. That man in the fifth cell was tall and broad-shouldered, with a powerhouse physique, dripping with muscle and meat. His skin was camel brown and moisturized like a warrior, smooth and glistening, you could tell the sweat would gleam on him. Looked like he scrubbed up though, he was clean and smelled like industrial soap. He didn’t have a six-pack, just a tiny belly, barely enough to grab on to, but that was the perfect size for Rob. There was a crucifix tattooed over his sternum and a gun on each bicep.
“Yo,” he said with a big wide, shit-eating grin when Rob chose him. “I’m Nutter.” He undressed Rob with his eyes, and his dick visibly shifted in his orange prison pants.
“Charles Everly,” Officer Budinsky said. “Mister Everly here is an armed robber and an arms-trafficker-“
“I sold one gun, Budinsky, don’t be dramatic,” he said. He snorted and avoided looking at Rob. “So you the one who wanna be a prison bitch, huh? Ain’t nevuh heard of no one who want that. But you kinda look like a bitch, so it ain’t hard to believe. It’s been awhile for me. I enjoy holdin’ a nigga down and makin’ him cry uncle — not that I stop then, it’s just nice to hear him cry — but I might like-“
“Don’t hurt him, Mister Everly,” Budinsky said. “I’ll be right out here.”
“You think my cum is gonna make yo’ dick bigger, huh?” Nutter asked.
Rob shrugged. “Not really. Some people do. I’ve never been convinced,” he said. “I’m just doing it because I want to.”
Nutter nodded like that was a very good reason. He glanced at Budinsky, who unlocked the cell. “Can we put the curtain up?” Nutter asked with a sultry rumble to his voice.
Officer Budinsky looked to Rob, who blushed again and nodded. “Please! Let’s do that. I wanna have the real prison bitch experience.” Rob’s heart felt like it might jump out of his chest. This was really happening! He couldn’t believe he’d put it off for so long, then it turned out to be easy, and now Rob was gonna get wrecked by Nutter’s huge slab of alpha male prison-starved meat.
“Oh, yeah, that’s what we gonna have, the real prison bitch experience,” Nutter said. He laughed, and the men in the other cells joined in. “I am gonna treat you bad, whiteboi, bad in all the right ways. Hope you wasn’t intendin’ to walk outta here.”
“Destroy ‘im, Nutter!”
“He picked Nutter?”
“Damn-“
“He don’t want a Mexican. Don’t nobody want a Mexican. Even Mexicans is itchin’ to get away-“
“Nutter! Nutter! Wreck his asshole!”
Rob had never felt so weak and submissive. His dick was rock-hard, and it started leaking precum the moment he heard the lock slide into place. The door was shut, and the prison cell was stuffy. Nutter’s smell and body heat filled the air.
“Gonna destroy you, pansy,” Nutter said with a sneer. He quickly hung up a sheet that blocked the cell from view. Rob shivered as he anticipated what was going to come next. Nutter towered over him by more than a foot, and he must have outweighed Rob by a hundred and fifty pounds or more.
“Make him squeal like a piggie, Nutter!”
“I will!” he called out. Once the sheet was hung up, however, his smile changed. He sunk down so he looked Rob right in the eyes. It almost felt like he was going to kiss Rob. He whispered, “Yo, I got a proposition for ya. I been in this place fo’ a long time, and I done had a million prison bitches. I plowed ‘em up, and I wrecked ‘em, and I moved on to the next. I wanna do somethin’ different.”
“Oh… like what?”
“I want you to ram me,” he said. He looked down and bit his lower lip. Then, for the benefit of everyone listening on the other side of the curtain, he called out, “You know what prison lube is? It’s how we get a bitch to deep-throat. Lemme spit in yo’ throat, lube it up real good.” He spat on the ground, and everyone cheered him on. Then he whispered again, “I wanna taste yo’ dick and feel you inside of me.”
“Are you serious?”
“This is a serious place, and I am a serious nigga,” he said, his face flat. “Come on, honky. I know you came here to bottom, and I’ll plow the shit outta you — literally — if that’s whatchoo want. But I wanna get it up the ass. I can’t let anyone in here know a white man got me up behind. That’ll ruin my rep. So this my only option. I ain’t think I ever gonna have the chance to bottom for a pretty boy like you. Whatchoo think?”
“Are you serious? Hell yeah,” Rob said, focusing hard to keep himself from being too loud. This was all happening so fast, it was hard to recalibrate his expectations. It wasn’t what he had come in here for, but he couldn’t imagine anything more enjoyable than plowing Nutter’s massive body.
“Alright,” he grinned. “Let’s hurry up, or we gonna run outta time. Seven minutes ain’t much.” He hesitated, then stooped over and kissed Rob on the lips. He was halting and slow. His tongue pushed into Rob’s mouth.
Though his passion was lacking at first, a few seconds in, Nutter let out a moan that resonated in Rob’s mouth. His tongue suddenly moved, clobbering Rob’s own tongue, and his thick fingers grasped Rob’s shirt. He ripped it, buttons flying to the bunk and dingy toilet in the corner of his cell.
“I ain’t hear him squeal yet, his mouth full?”
“Sounds moist in there, I can kinda hear it. He plowing that fairy in the face, I think.”
“Nutter, how that sissy-boi takin’ it, mon?”
“You can’t hear him choke, nigga? Guess his bitch mouth is just too full to choke. He ain’t breathe in a minute, son,” Nutter said. “Got too much dick in there, and he lovin’ it, like a fuckin’ Big Mac and shit!” His big eyes twinkled as he pecked Rob on the lips and then worked his way down Rob’s pale, lithe body. He shuddered like he was surprised at the taste, and he stopped to suck on Rob’s nipples. Then he licked Rob’s flat belly and stopped only when he reached Rob’s pubic hair (which he kept trimmed very short).
Nutter was so much bigger than Rob that even getting on his knees wasn’t enough, he was still too tall to swallow Rob’s dick. He had to get on all fours, with his plump ass high in the air, while Rob stood on his toes in front of Nutter’s face.
But when he did get his head in position, Nutter wasted no time in swallowing Rob’s dick to the root. He seemed surprised that Rob’s cock wasn’t as proportionately small as his body was. He motioned for Rob to make some noise. An immediate shudder of pleasure wracked Rob’s body, as Nutter’s warm mouth encircled his cock.
Rob blushed but spat and sputtered, hocking up a few loogies and even sticking a finger far enough down his throat to gag once, making a sound that could be heard outside the cell. That made the other men laugh and cheer, banging on the bars of their cell.
“That sounds right, nigga!”
“Choke him! Show him how we do it!”
In no time Rob was rock-hard, and he started getting into it. Every time the men quieted down, he made it sound like he was getting throated and loving it, and they’d laugh again. Even Officer Budinsky chuckled quietly.
“You got this, Nutter!”
Nutter had a broad back, pocked with a few scars and marks, plus some dark blue prison tats that Rob couldn’t quite make out (some kind of writing, he thought, possibly Hebrew, like an Old Testament verse). He stroked Nutter’s muscles, trying to reach his plump ass, but he was much too short. Instead he grasped at Nutter’s back and shoulders, sighing as pleasure moved through him. They both threw their heads back and moaned. Rob’s moan was drowned out by Nutter’s, and Nutter made his sound exaggerated and comical so it wasn’t obvious to their audience why he was moaning.
“He change his mind about being a prison bitch, Nutter?”
“No, he ain’t! He is lovin’ every second of it! He’s serious.” Nutter guffawed, then aimed his voice at Rob. “You should commit some crimes and shit, whiteboi. You could be the queen bitch in this place!” Nutter said. His voice was joyous and light-hearted, even as his face was serious, gasping, with Rob’s dick throbbing against his nose and cheeks.
As he resumed slurping on Rob’s dick, Nutter moved his head more and more aggressively up and down. Rob felt like he was being attacked by Nutter’s massive head, which made him throw his head back and moan — he covered his mouth with a hand to muffle the sound. Nutter took Rob’s hands in his and wrapped it over his head. The sensation was exquisite, and it felt so good Rob’s toes curled and his hands formed fists at his sides. It felt so good it hurt, and Rob had to avoid moaning lest the thugs outside this cell realized what was happening.
Rob had been on the receiving end of a jailhouse-style throating on several occasions, but he had never topped for that kind of scenario.
But he wanted to give Nutter what he desired. He held onto the ragged short afro on Nutter’s head, gripping his hair, and he slammed his dick all the way in. Nutter let out a chortling gurgling sound with a moistness that made everyone else burst into cheers. To Rob, it sounded much too deep to be his own voice — he was more high-pitched and feminine than that — but luckily it seemed the other inmates didn’t realize that. They had never heard Rob before today so they had no basis for comparison.
“Ram ‘im harder!”
Nutter pulled off and laid on his back on the bare mattress on the bunk in the cell. He snorted and sniffled, wiping fluids off his face, and he smiled silently at Rob. He let his head hang over the foot of the bed. “That’s the proper position for a prison bitch, alright, pervert? Get ready to get yo’self throated.”
“Yeah, plow ‘is gullet, nigga!”
“Ram ‘im! Ram ‘im! Ram ‘im!”
Rob squealed loudly, blushing as the other inmates cheered him on. Nutter was in exactly the position Rob liked to get throated in. Rob had never in his life been on this side of it. He approached Nutter’s broad face and pushed his dick past those thick, juicy lips. His cock slammed into Nutter’s throat, making him retch and writhe atop the filthy prison mattress.
“He regrettin’ signin’ up fo’ this yet?”
Incredible pleasure rocketed through Rob’s spine. He had never felt like this, not even on those few occasions when he got to top someone. Bliss roiled his body and made his knees weak. He shuddered and moaned quietly, every ounce of concentration he could muster going towards not being so loud that he alerted the others to the fact that he wasn’t bottoming as they thought.
Precum flowed down Nutter’s throat. From the reaction on his face, it seemed he had little experience with that. Did he like the taste or hate it? Rob couldn’t tell, and in this position, he didn’t have to care. He felt like he was overpowering Nutter, whose muscular limbs contorted as he accepted the throating. His muscles flexed and bucked as though he was fighting back, and his movement made the bunk beneath him move. The sound of steel scraping against the prison cell floor caused a torrent of cheers from the other cells.
He pulled off once again, grabbed Rob’s slick dick. He lowered his head farther, so he could suck on Rob’s balls. Then he called out, “He suckin’ the sweat off my balls now, what a nasty punk he is!” He let both of Rob’s balls fit easily in his big mouth. He suckled loudly, making a sputtering sound that provoked more cheers from the other cells.
“Nasty! Can’t believe he signed up for this!”
Then Nutter pulled away, stood up and turned around, in a hurry like he had just remembered they were on a time limit. Spit clung to his lips in tendrils, and his ruddy face was moist with tears from lack of oxygen and sweat dappling his forehead. Rob too was sweaty and exhausted, sensations still flowing through his veins, and he had to focus to avoid nutting.
“Four minutes left, guys,” Officer Budinsky said. “You better hurry up.”
His ass was much wider than Rob’s body, not because he was fat, it was just big and broad and juicy. Each cheek was nearly twice the size of Rob’s head. He lowered his ass onto Rob’s dick, slowly. Rob still stood at the foot of the bed, so Nutter crouched on all fours on the ground and backed up until his ass lined up with Rob’s crotch. His crack was choked with sweaty hair, which Rob would have gladly licked clean like a good prison bitch. He felt like he was losing his entire body in the choked masculine jungle of Nutter’s ass.
“Gettin’ in his ass now, Budinsky, cool yo’ jets,” Nutter said. “Don’t worry, he gettin’ e’ry inch of me that he entitled to. Don’t you worry yo’ sweet redneck head about that, Budinsky.”
“You alright in there, sir?” Budinsky asked through the curtain.
“Yeah…” Rob said, too embarrassed to think of anything else to say. He wasn’t sure how to say it that wouldn’t give away what was really happening in here. “I… uh, he’s treating me right.”
“That’s right, he is! Nigga please! Showin’ you how it’s done!”
“You mean he treatin’ you wrong, but he doin’ it in the right way.”
Rob gulped as Nutter penetrated himself with Rob’s dick. Rob gingerly gripped his shoulders and held on while he began humping back, gradually losing his inhibitions. Another jolt of pleasure ran up his body from the moment his dick poked through that jungle of sweaty ass-hair and into his tight hole.
When Nutter grunted in pain, he covered it up with a louder roar, an aggressive sound that made the other inmates whoop and holler along with him. Nutter threw his head back and wordlessly moaned, smiling at Rob even as he grunted out threats and insults.
“Gonna ram you so hard you wear a diaper, honky…” Nutter said out loud, with as much confidence as he could muster.
Rob was not an actor. He tried to pant like a submissive man might — he should have been better at it, since that was the role he normally played, but everything happening here was outside his wheelhouse. He couldn’t remember what kind of sounds he might normally make in the reverse of this situation.
“Make ‘im beg for mercy, nigga!”
It was clear that Nutter wasn’t kidding about having never gotten it up the ass — not that Rob ever doubted him. His asshole was so tight that Rob had to really shove to get his dick in there. There was no time for a gentle approach either. Rob pushed it in farther and farther, and when Nutter didn’t stop him, he began to ram his shaft back and forth, uncaring of his resistance or the hairs that Rob’s dick accidentally ripped from his crack.
“Teach ‘im a lesson! Fuckin’ white man, comin’ in here, tryin’-a get it up the ass and shit…”
Each time Rob rammed his dick into him, Nutter winced and blanched. The whole experience was so incredible that each time Rob thrust past Nutter’s resistance in his ass, a surge of awkward pleasure hit him and Rob moaned in a pained, struggling way. It genuinely did sound like a prison bitch getting plowed, which just egged the other inmates on.
“Wreck him! Ruin him! Show him how we do it, nigga! No mercy!”
“No mercy!”
Rob did indeed plow with no mercy. Of course it was Nutter who responded, “He takin’ it, nigga. Ain’t like a prison bitch, he been opened up a million times before. Kinda nice plowin’ a bitch who ain’t too squirmy. Gonna fill him up wit’ some nut.”
“Two minutes left, guys. You still alright in there?”
“Yes! Yes, officer…” Rob said, his excitement making everyone, including Budinsky, laugh. “I’m, uh… I’m just finishing up.” He threw his head back and moaned as wave after wave of unimaginable bliss washed over him, so intense it was painful as he lost himself in the massive muscled ass trembling before his gentle frame.
Nutter’s ass clenched when he approached his own orgasm. He had started jacking himself off. Rob tried to give him a reacharound, but he could barely reach all the way around, so he just fumbled with Nutter’s powerhouse body while slamming his dick in and out of Nutter’s jiggling, tight ass.
“Aw, shit…” Nutter grunted. “You take dick good!”
When Rob’s orgasm finally came, it felt like it had been a lifetime, way more than seven minutes. Rob yelped and scratched at Nutter’s back — he was so big and thick-skinned he didn’t seem to notice — while intense pleasure suffused both men’s bodies, in sync with each other like no one Rob had ever been with before.
Cum flowed into Nutter’s ass, a huge load that dripped out and down those giant trunk-like thighs. It splatted on the floor, but still Rob came. Nutter roared as he shot his own load into his hand and all over his chest. He managed to make the roar sound like a manly cavemanesque grunt.
Rob’s entire body went limp. He knew they were running out of time, but he couldn’t bring himself to pull out, not yet. He kept it there, stimulating Nutter’s prostate while Nutter’s body writhed and flexed with both bliss and agony, pride and shame visible on his contorting face.
Nutter turned around, his massive chest gleaming, covered in his own cum. Rob licked every inch of it, savoring the meaty feel of the man’s muscles. Nutter made sure the cum reached up to his face, so when Rob moved upward and kissed Nutter on the lips, he tasted it. He had to climb the man’s mountainous torso to get there, gripping his throbbing muscles with Rob’s delicate fingers.
They shared cum for another minute or so, stopping only when Officer Budinsky counted down the last thirty seconds. Rob was bashful and hurriedly cleaned himself up with a napkin before putting his clothes back on. Nutter just stood there, covered in fluids, his cum mingling with his sweat so it wasn’t obvious what it was. His dick dangled between his legs.
“Damn, Nutter, put some clothes on,” Officer Budinsky said when he reached zero and pulled the curtain down.
Rob was bright red, too scared he’d blurt out what happened to say anything at all. He quickly dressed and clasped the sweaty small of Nutter’s back.
“Bye, Nutter, that was amazing. You’re the best prison alpha-“
“Shut up, bitch, I ain’t tryin’-a please you,” Nutter said. “You come back here again, and I’ll fist you, punk.”
Rob just nodded and followed Officer Budinsky out. He pretended his ass hurt as he walked past the other inmates.
“Was that everything you thought it was gonna be?” Officer Budinsky asked once they were out of Cell Block Alpha.
“No,” Rob said. “It was completely different, and so much better.”