Here’s the entirety of Twink on Top: Penal Party, the hottest story yet in the Twink on Top series! It’s a Brutewood Medium Security Penitentiary story, and it’s in the 50 Twinks Top 50 Tops megabundle for a great value.
It was the most enjoyable party Ted Halloway had ever been to. He knew perfectly well that it was only this fun because he had been in prison for a year and a half before it happened. It was the first enjoyable event in his entire time behind bars. So it felt like an evening in heaven.
It helped that there were no women. That meant the biggest alphas and thugs danced with gay girlish twinks like Ted as though he was a girl — Ted didn’t like cross-dressing, so he wasn’t as popular as certain other inmates, but still, he got closer to some sexy men than he had in quite awhile. He even got to kiss an incredibly hot redneck named Bubba, whom Ted had been drooling over for months.
The guards watched like it pained them to see inmates having a good time. Supposedly — Ted wasn’t privy to this because he was a pitiful twinky queer — all of the gangs were told that they’d be punished if anyone got in a fight during the party. That was why it went off without a hitch.
There was no alcohol, but the guards did allow a little weed in for the night. That was probably a wise decision, Ted thought; alcohol would make men fight, but the weed just made them giggle. Without any women among the inmate population, the feminine gays like Ted were treated much like women. He was feted as a queen by the entire prison.
But all good things come to an end, and this penal party was no exception. Ted was disappointed to hear the music come to stop. The guards bellowed at the inmates to head back to their cells Everyone slowly lined up, dragging their feet, grumbling and claiming they weren’t going to stop partying even as they did stop. But a part of Ted was at least happy that the party had gone off without a hitch — there was no fight, no smuggled-in booze, no one got hurt. That meant there was a chance the guards would allow another party in the near-future.
“Halloway, hey, Halloway… Ted!” boomed a male voice. It was one of the guards, Officer Armstrong, who grinned and grabbed Ted off the line. “Come on,” he said.
“What? What’s wrong? What happened?”
“Nothing’s wrong,” Armstrong said. “You’re gonna have a second little party.”
“Do I have a choice?” Ted wasn’t sure what this was and he was nervous. He didn’t trust Officer Armstrong, whose voice was always menacing. It sounded like a threat even when all he said was it’s going to rain today.
“Well… yeah, I guess,” Armstrong said. “But come see what it is first. You won’t say no. If you refused this, I would be… more shocked than I have ever been in my life.”
It was hard to argue with that, and Ted was intrigued, so he followed Armstrong into an old disused showering area — he didn’t trust Armstrong in general, but he did trust him not to be a murderous psychopath or anything like that; he might strike back extra-judicially against an inmate who had wronged him, not someone easygoing and rule-abiding like Ted. Inside the dingy old shower were a handful more guards, all brimming with nervous smiles, and seated on the ground in the center of the shower, was Chowder.
Chowder was the leader of a gang called the Nineliner Mob. He was white, heavily tattooed, nearly inch of his body covered in Gothic letter, naked ladies, wild animals and an outline of Massachusetts over his left pec. He had a handsome jawline with deep dimples. His broad chest was hairy, and he had developed a six-pack since coming to Brutewood. He was also the tallest inmate in the facility; at nearly seven feet tall, he struggled to fit through doorways and down corridors.
He winced but smiled at Ted. His friendly grin wasn’t unusual — he was outgoing and charming, but he didn’t let that get in the way of business. He was one of the few big alpha males in Brutewood whom Ted had never sucked off. That was because he had a bitch named Sammi, whom Ted hated. Chowder fucked Sammi publicly, hard and often; Ted was jealous because he loved to get fucked hard by alpha thugs like Chowder. Ted normally preferred black thugs, but Chowder was insanely hot and his Boston accent aroused Ted every time he spoke.
“So, uh… Ted,” Chowder said. “I was, uh… I put togethah that pahty. I was… y’know… Uh, I had to arrange it all.” He laughed nervously into his hand.
“Chowder… come on, we ain’t got all day,” Officer Armstrong said. “Don’t drag this out.”
“They said we could have the pahty if I did somethin’ aftah it, to prove I’s really serious about makin’ sure the party was good. I had to show I was gonna make sure it went off without no fightin’ or nothin’,” Chowder said, sucking his teeth every other word. His thick Boston accent made it sound like his mouth was full of cotton balls. He rolled his eyes and sighed. “Ted… will you… please fuck me.” The guards all whooped and hollered. Ted blushed even harder than Chowder, who bit his lip. He took Ted’s hand in his like he was gonna propose. “Will you let me suck yo’ dick and take it in the ass and lick yo’ ass but only fo’ five seconds? And no kissing, and no tellin’ nobody aftahwahds.” That sounded like something that had been carefully negotiated with Armstrong.
“Oh wow,” Ted was so excited his knees were weak. He looked to Officer Armstrong, who had a gleeful smile on his face — Chowder was often in trouble for fighting with the guards, so they were understandably glad to watch him get fucked.
Everyone looked at Ted, who didn’t know what he was expected to do. He looked down at his feet, too scared to say anything.
“You gotta say yes,” Armstrong said with a chuckle. “If you wanna do it.”
They all laughed at Ted’s excitement and Chowder sighed again, like he had hoped Ted might say no. He took off the plain blue baseball cap he wore — the only non-religious hat anyone at Brutewood Prison was allowed to wear — and ran his fingers through his clipper-short hair. He sucked his teeth and spat on the ground. He looked at Ted sternly. “No tellin’ nobody. ‘Specially not Sammi. I can’t let her find out I cheated on her.”
“Sure! Okay. I promise, nobody will find out,” Ted said. “I hate Sammi. I never talk to him. I-“
“Call Sammi a her.” Chowder said. He narrowed his eyes to slits, making it clear that was a threat.
Ted gulped. He knew Chowder, like most Brutewood alphas, referred to their bitches as a woman; Ted had simply forgotten because he was so excited. “Okay. Yeah, I won’t tell her. Or anyone else. I swear.”
Chowder stood there, his confidence gone as he very slowly dropped his orange prison jumpsuit. The guards laughed and clapped, hooting like he was a stripper. They demanded he dance as he undressed. “That weren’t paht of the deal,” Chowder said grimly. The guards seemed to accept that, but they had fun cheering him on, pretending he was stripping like a dancer even if he wasn’t.
The sight of his bare chest made Ted’s heart skip a beat. Chowder had been a violent thug, but one of those rather fat swaggalicious men whom Ted thought were hot even if they had a belly. In his time in prison, however, all of that fat had melted away, leaving behind a mass of muscle that bulged from his skin as though begging him to get fat again. Ted had seen him naked in the shower, of course, so this was hardly the first time, but this was closer and more exciting. Ted literally felt drool escaping from his lips as he caught whiff of Chowder’s post-party musk.
“If I evah catch you lookin’ at me in the showah like you lookin’ at me now, I will rip yo’ goddamn ahm off and smack yo’ face off with it,” Chowder said.
“Uh, Chowder-“ Officer Armstrong cleared his throat. “That’s not okay. You can’t control how people look at you.”
“What I can’t control is my reaction when some queehboy look at me like he wanna eat me up,” Chowder said through gritted teeth. “You may not fuck me in yo’ imagination, okay, not aftah today.”
“Fine. I’m sorry, queehboy. Or Ted or whatevah. I ain’t tryin’-a police yo’ mind.” He rolled his eyes at Armstrong’s stern face.
Ted still didn’t quite trust him, but he had already discovered that making it obvious whom he thought was hot was a bad way to stay safe in here. Chowder wasn’t the first prison alpha to forbid anyone from having gay fantasies about him.
“It’s okay. I won’t, Chowder, I promise. My dream man is Dwayne ‘The Rock’ Johnson, and I’m sorry, you’re not hotter than him,” Ted said. That was accurate, at least. Ted blushed as the guards and Chowder all laughed together.
Chowder dropped his dingy prison-issued boxer, which had faded bloodstains ominously covering the crotch area. Ted wondered where that blood had come from. Was it Chowder’s? Probably not, he thought.
“Well, you the queeh, right? How do we proceed?” Chowder scowled.
“Uh… I guess… You should suck my dick,” Ted said. His voice had never sounded so weak and so flamboyantly gay, at least in his mind.
“Hope this party was worth it,” Officer Armstrong said. He crossed his arms over his chest. “Get on your knees, Chowder. I mean… Chowdah.”
Chowder glared at him but sunk to his knees. He was nearly seven feet tall, so even on his knees, his face was even with Ted’s shoulders and neck. He was nowhere’s near close enough to suck Ted’s cock.
As Ted dropped his own pants, Chowder slunk lower and lower. In the end he laid on his back, propping himself up with his arms. Ted felt weak and cold, but he was glad no one was looking at his own body, which was skinny, pale and trembling with anxiety. He strained to spread his legs wide enough to straddle Chowder’s chest. He wanted to touch him, but Ted was still nervous about this — if there was one ironclad rule of prison life that nobody ever broke, it was that slim gay weaklings like Ted did not top massive alpha thugs like Chowder.
Yeah, suck it, Chowdah!
Fuck his face, Ted!
“Just foh’ the recahd, I’m doin’ this cuz I want to,” Chowder said. He spat on Ted’s dick. “I could say no. These mothahfuckahs ain’t got proof I agreed to nothin’. And I done it before. Not in prison of couhse, but back in the day, me and my boys shared some blowies on the downlow. Ain’t no shame in that-“
Less gabbin’, more suckin’!
Chowder glared at the guards, but he sighed, and seemed to decide that just going for it was the best way to get started. The longer he drew it out, the more they were going to tease him. He opened his mouth, took a deep breath and closed his lips around the tip of Ted’s dick.
He gagged even before his tongue touched it. He closed his eyes and his entire muscular chest roiled with disgust, but he didn’t slow down even a bit. He let the rest of Ted’s dick slide deeper even as his eyes frantically darted around as though looking for a way to escape.
Almost immediately Ted felt a surge of pride and confidence; he felt better than he ever had since coming to Brutewood, and even before that. He pushed his dick in even deeper, ignoring the angry look in Chowder’s eyes.
“Come on, make more spit,” Ted said, making the guards laugh. “You’ve gotten blowjobs before. You know how to do it.”
Chowder did as he was told, even as his nostrils flared and his eyes filled with hostility. He choked up a mountain of saliva — since he was such a huge man, he produced a truly copious torrent of spit — that dripped down his chin and into his bare crotch.
A shudder of desire ran through Ted’s body as he gripped Chowder’s broad shoulders. His inhibitions melted away. Chowder was crisscrossed with scars and tattoos, including a handful of bullet wounds on his back. Ted reached down to caress his body, savoring the feel of his rippling muscles.
That made precum leak from the tip of his dick, which reawakened a torrent of sputtered gagging from Chowder. The guards laughed and clapped, again hooting and hollering like they were watching a strip show.
Suck that dick/Suck it like I ain’t rich/Suck it like a bitch/Suck it till you sick/Like you ain’t nevuh turn a trick/Yeah, suck that dick
One of the guards was rapping; Ted wasn’t hip enough to know for sure whether he was freestyling or repeating a popular song. It sounded rehearsed though.
Chowder pretended it didn’t bother him, but Ted could feel him bristling at the teasing. It was funny how Ted could sense Chowder’s reactions through his muscles’ twitching and the way his throat clenched around Ted’s spasming cock, like Ted could read Chowder’s mind through his body. Chowder arched his back as he nestled his nose deep in Ted’s crotch, easily deep-throating every inch of Ted’s cock. His new position meant his ass rose in the air.
Ted lusted after it. He couldn’t believe he was going to get to fuck Chowder in that ass, and he wondered if Chowder had ever done it before. He tried to reach but Chowder was too tall for Ted to reach his ass with his dick in Chowder’s mouth.
“Okay, you said you will lick my ass, right?” Ted asked, remembering that suddenly.
Chowder pulled off his dick. Thin tendrils of spit connected his greenish face to Ted’s cockshaft. Chowder grumbled. “Fo’ five seconds, that’s all I agreed to.”
Officer Armstrong laughed. “That’s just a minimum, Chowder. You can lick his ass as long as you want. We got all night.”
“No!” Chowder said.
Ted turned around and bent over as though he was going to get fucked, as that was the only position that raised his ass high enough for Chowder to lick it. Chowder looked away, breathed deeply through his mouth and closed his eyes.
He dove between those cheeks and slammed his tongue in. He was so forceful — and his tongue was so big — that it almost hurt. Chowder rimmed him more aggressively than anyone had ever rimmed him before, and Ted got the impression that Chowder had never done it before, not even on a girl. Chowder definitely enjoyed receiving rimjobs from his bitch and he always demanded more tongue-in-ass action, but since Chowder was so much bigger than Sammi, he needed as much tongue-penetration as possible, as deep and as hard as possible. Now Chowder’s cock-sized tongue shoved into Ted’s ass and explored there, hesitatingly as Ted’s ass-juices smeared over Chowder’s square-jawed face.
But Ted then felt a ripple of pleasure emanating up his back as Chowder’s tongue explored his prostate. Chowder moaned into his ass and gagged without slowing down. Ted’s eyes rolled back in his head as pleasure walloped his petite frame. Chowder’s tongue suckled every drop of grime out of his ass, even as Chowder himself sputtered and choked on it.
Three! Two! …
The guards conspicuously stopped counting, but Chowder pulled away from Ted’s ass anyway. He spat on the linoleum shower floor. He wiped his face off with one hand, and his chin waggled but he kept it together. He sniffed, pointedly ignoring the guards as they cheered. He glanced over and saw one of the guards had bared his hairy ass — extremely hairy, nearly gorilla-like — and winked his asshole in Chowder’s direction.
If you enjoyed that, give Officer Torelli a try! He got all the ass-hair you could eat, boi! He be a ass-buffet for ya!
Chowder grimaced and looked away. He sighed as he stroked Ted’s dick with one meaty callused hand. It was the worst handjob of Ted’s life, but it was also somehow the greatest, its lack of rhythm and rough texture sending shockwaves of bliss through Ted’s body while slowing down his arousal enough that he was no longer nearly ready to blow his load.
Time for the ass, Chowder!
Give up the booty!
Chowder snarled at the guards. He turned around and bent over. His initial position was laughably impossible — he simply put his hands on the floor, sticking his ass in the air so high Ted’s short little body couldn’t even reach it. Ted had to stand on his toes to touch Chowder’s asscheeks and tap them, signaling him to lower himself.
Best get down lower, or we gonna need a winch and a pulley to do this right.
Chowder dropped to all fours. He had a nice plump ass, just enough padding for Ted’s taste — a remnant of when Chowder was fat-bodied in his pre-prison life. There was a tattoo on his left asscheek, an arrow pointing to his asshole and the words Cop Kissing Zone.
Ted separated those thick blubbering cheeks; at first it was difficult because Chowder instinctively flexed his cheeks, keeping them tight, but he forced himself to relax. His crack was lined with sweat-matted hair. Each of Chowder’s asscheeks was bigger than Ted’s head, making Ted feel truly tiny by comparison. He took a deep breath and pushed his dick in.
Chowder bit his lip so hard it drew blood. He breathed through his nose and snorted like a rampaging bull. His face turned bright red from both pain and humiliation. The muscles of his back tensed, lines flexing and curving, distorting the tattoos as he stretched.
Lookit him take it! Like a bitch!
Damn I wish we could fuckin’ tape this. Put it on the Internet, make a goddamn fortune.
“You bettah not!” Chowder said, but for once his voice was not bristling with confidence and machismo. It sounded like a whine, not a threat. He hung his head.
Ted hadn’t topped anyone since before he came to prison, so this was a refreshing experience for him. He pushed his dick in deeper and deeper, using copious lube (which was provided by Officer Armstrong — that seemed sweet, Ted thought, he didn’t need to do that; prisoners usually used hog fat from the prison kitchen, so Armstrong was being nice by providing actual lube). Chowder’s ass was clearly virgin, so tight that Ted struggled to shove every inch in his hole.
Chowder was on all fours, so the more powerfully Ted slammed into his ass, the more Chowder was forced to lower himself. He winced and dropped his hips, making it easier for Ted to fuck him harder. To his credit, Chowder managed to take every inch even though it was obviously difficult for him.
That hairy Italian guard had his dick out now, wagging it in front of Chowder’s face. Ted couldn’t hear his words because he was overwhelmed by pleasure and the boisterous laughter of the other guards drowned out the hairy guard, but it was clear he politely offered Chowder to suck his dick. Chowder just blushed and kept his eyes pointed away, even as the guard followed his face with his massive, uncut Italian cock.
Eventually Ted was just on top of Chowder, his feet no longer on the floor at all. Chowder’s broad muscles rippled beneath Ted’s face, and he licked the salty sweat that beaded on his skin. Chowder writhed beneath him.
Ted didn’t know how normal this was — he had only ever topped with thin gay twinks like him. He felt like a weird circus novelty, like a midget fucking a strongman to a shocked crowd. Chowder panted like a dog beneath him.
“God-damn, man,” Chowder said, his fingers and toes curling as though trying to dig into the linoleum floor of the prison shower.
Yeah! Get ‘im good, Teddy!
Lookit his little body on top of Chowder. Looks like a kid whose big bro is lettin’ him beat him up.
Ted blushed at the guards’ closeness. They were peering into Chowder’s ass as though they had never seen anal sex before and weren’t sure what was actually happening. Ted was a private person by nature — the public nudity, showering and toilet use of prison life had been difficult for him to adjust to — so having an audience like this was nerve-wracking for him.
His orgasm came on too soon. Ted was disappointed, but not surprised. As he felt it arising deep within him, Ted wasn’t even sure how long it had been — it felt like just a few minutes, but at the same time, it felt like hours. Surely Chowder would have complained if it had taken that long though, he thought.
The most powerful orgasm of his life ran through him. Ted’s entire body shook and trembled, and he moaned so loud he blushed as the guards erupted in a mixture of embarrassed grunts and excited shouts.
Cum sprayed within Chowder’ ass, a thick and copious loud that filled up every inch of his insides. Chowder moaned too, matching Ted’s voice, and he buried his face in his forearm. Then he grabbed the blue baseball cap he had thrown on the ground, and he buried his face in that instead.
One of the guards pulled the cap away and looked Chowder in the eye. Chowder’s red face was tense and a few tears of pain and embarrassment drifted down his cheek.
“Who’s the pussy-faced bitch now?” the guard asked. “Hope the party was worth it.” Chowder snarled and grabbed his hat back as his ass clenched again around Ted’s dick.
Exhausted, Ted fell back. His ass plopped out of Chowder’s ass, and Chowder breathed a sigh of relief. He stood and blushed as the guards laughed at the river of cum dripping down his trunk-like, tattooed thighs.
“Hey!” Chowder barked. “We said no bringin’ it up again after it’s done.”
“Ain’t done yet,” Officer Armstrong said. “It ain’t done until you both get your clothes on. Whatchoo think, Chowder? Was the party worth it?”
Chowder hurriedly threw his underwear on, wincing when he accidentally touched his ass and reawakened a torrent of sensitive pain. He put his jumpsuit on and then hurriedly slipped into his shoes when the guards made it clear they counted that as well. “Yeah,” Chowder said. “The party was totally worth it.”
Ted slow-walked it, both because he didn’t mind the guards teasing Chowder and because he was too overwhelmed to really focus on anything but the aftershocks of orgasmic pleasure wracking his body. But when Chowder was done and he saw Ted wasn’t, he shot him a few dirty looks until Ted jumped in action.
Soon they were both dressed. Ted still felt weak-limbed from the power of his climax, and he could still taste Chowder’s back-sweat in his mouth.
True to their word, the guards stopped teasing as soon as both inmates were dressed again. There was still some scattered laughter, especially when Chowder winced and skipped a step while he walked towards the door behind Officer Armstrong.
“Hey, if you want — and you don’t think Sammi will mind — you can fuck me later. As hard as you want,” Ted said. “If that, y’know, makes you feel better.”
“I know I can.” Chowder’s voice dripped with menace. “I will.”
Ted smiled. That promised to be almost as good as what had just happened. He couldn’t wait. The next couple days promised to be exciting.