Desmond is a petite, effeminate prisoner in a big tough prison, so he never thought he’d find himself in a Twink on Top situation. But that all changes when a tough guy Boston thug named Chowder really wants a party, even if that means this muscular alpha will have to bend over and take whatever Desmond wants to give!
Can Desmond handle this particular slice of Twink on Top?!
Or read it right here
It was the most enjoyable party Desmond Talley 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 girlish sissies like Desmond as though he was a girl. He even got to kiss this redneck named Bubba, whom Desmond had been drooling over for months. On the outside, Desmond was invisible at a party — to women, he was a short, negligible pansy, and to men, he was not a woman.
But in prison, he was a king. Or maybe queen.
The guards watched like it pained them to see inmates having a good time. All 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, Desmond thought. Alcohol would make men fight, but the weed just made them giggle and become overly entranced by nature documentaries.
But all good things come to an end, and this penal party was no exception. Desmond was disappointed to hear the music stop, and the remaining joint roaches were combined into one, then quickly smoked. The guards bellowed at the inmates to head back to their cells. Everyone lined up, dragging their feet, grumbling and claiming they weren’t gonna stop partying even as they did stop. But Desmond 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.
“Talley, hey, Talley… Desmond!” boomed a male voice. It was one of the guards — the one the inmates call Officer Crabgut — who grinned and grabbed Desmond off the line. Desmond was surprised that he said his first name. The guards never call inmates by their first name. “Come on,” Crabgut said.
“What? What’s wrong? What happened?”
“Nothing’s wrong,” Crabgut said. His belly chortled, his off-gray beard hairs gleaming with sweat or maybe liquor, Desmond was pretty sure the guards were drinking in the monitor-room. Crabgut looked like a drunk. “You’re gonna have a second little party.”
“Do I have a choice?” Desmond wasn’t sure what this was and he was nervous. He didn’t trust Officer Crabgut, whose voice was always menacing. It sounded like a threat even when all he said was it’s going to rain today. Crabgut was notoriously corrupt. That’s not always a bad thing — he was the one who brought weed in — but it did make him untrustworthy. Not that Desmond ever really trusted prison guards.
“Well… yeah, I guess, you can choose,” Crabgut 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 Desmond was intrigued, so he followed Crabgut into an old disused showering area. Inside the dingy 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 a leader in a gang called the Jagged Right. He was 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 prison. 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 Desmond. His dimplesome 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 prison whom Desmond had never jerked off. That was because he had a bitch named Sammi, whom Desmond hated. Chowder plowed Sammi publicly, hard and often. Desmond was jealous because he loved to get plowed hard by alpha thugs like Chowder.
“So, uh… Desmond,” Chowder said. When he spoke, his Boston accent either aroused Desmond or made him laugh, it was hard to tell. “I was, uh… I put togethah that pahty. I was… y’know… Uh, I had to arrange it all, dawg.” He paused like he was expecting a big reaction. “I got the weed, I got the gangs to come together, even the Mexicans-“
“Chowder… come on, we ain’t got all day,” Officer Crabgut said. “Don’t drag this out.” An underhushing from the other guards suggested they thought similarly.
“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 on his teeth every other word. His thick Boston stawk made it sound like his mouth was full of cranberries. He rolled his eyes and sighed. “Desmond… will you… please stick me up the ass.” The guards all whooped and hollered. Desmond blushed even harder than Chowder, who bit his lip. He took Desmond’s hand in his like he was gonna propose. “Will you let me jerk 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 Crabgut.
“Oh wow,” Desmond was so excited his knees were weak. He looked to Officer Crabgut, 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 it up the ass. All the guards were beaming.
Everyone looked at Desmond, 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,” Crabgut said with a chuckle. “If you wanna do it.”
“Yes!”
They all laughed at Desmond’s excitement and Chowder sighed again, like he mighta hoped Desmond would say no. He took off the plain blue baseball cap he wore — the only non-religious hat anyone at this prison was allowed to wear — and ran his fingers through his clipper-short hair. He sucked on his teeth and spat on the ground. He looked at Desmond 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,” Desmond 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.
Desmond gulped. He knew Chowder, like most prison alphas, referred to their bitches as a woman. Desmond 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 draining as he very slowly dropped his orange prison jumpsuit. The guards laughed and clapped, hooting like he was a stripper. They demanded he dance and shake his ass as he undressed. “That weren’t paht of the deal,” Chowder said, lips clenched grim as a reaper. The guards seemed to accept that, but they got more and more into cheering him on, pretending he was stripping like a dancer even if he wasn’t.
“Whoo-hoo, Chowder!”
“Let’s see ya pussy!
The sight of his bare chest and his rippling muscles made Desmond’s heart skip a beat. Back on the outside, Chowder was a violent thug, or so said the grapevine from Boston, but one of those rather fat swaggalicious men whom Desmond thought were hot even if they had a belly. Chowder always carried himself like a macho, no matter his physique. In his time in prison, however, all of that fat done melted away, leaving behind a mass of muscle and a well-worked barrel chest that bulged from his skin as though begging him to get fat again. Desmond had seen him naked in the shower, of course, so this was hardly the first time, but this was closer and more exciting. His fat cock swayed between his massive thighs. Drool escaped from Desmond’s lips as he caught whiff of Chowder’s post-party musk.
“If I evah catch you lookin’ at me in the showah like you looukin’ at me now, I will rip yo’ goddamn ahm off and smack yo’ face off with it,” Chowder said.
“Uh, Chowder-” Officer Crabgut 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 sissy look at me like he wanna eat me up,” Chowder said through gritted teeth. “You may not plow me in yo’ imagination, okay, not aftah today.”
“Chowder!”
“Fine. I’m sorry, sissy. Or Desmond or whatevuuh. I ain’t tryin’-a police yo’ mind.” He rolled his eyes at Crabgut’s stern face.
“It’s okay. I won’t, Chowder, I promise,” Desmond said.
Chowder dropped his dingy prison-issued boxer, faded bloodstains ominously covering the crotch area. Desmond wondered where that blood had come from. Was it Chowder’s? Probably not, he thought, or he’d a-got his cock cut off.
“Well, you the sissy, right? How do we proceed?” Chowder scowled.
“Uh… I guess… You should swallow my dick,” Desmond said. His voice had never sounded so weak, at least in his mind.
“Hope this party was worth it,” Officer Crabgut said. He crossed his arms over his chest. “Get on your knees, Chowder. I mean… Chowdah.” He chuckled and glanced at the other guards as though expecting them to think his joke was hilarious.
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 Desmond’s shoulders and neck. He was nowhere’s near close enough to get Desmond’s cock in his mouth.
As Desmond dropped his own pants, Chowder slunk lower and lower. In the end he laid on his back, propping himself up with his arms, a position that made his pecs bulge. Desmond felt weak and cold, but he was glad no one was looking at his own body, which was skinny and trembling with anxiety. He strained to spread his legs wide enough to straddle Chowder’s chest. He wanted to touch him, but Desmond was still nervous about this — if there was one ironclad rule of prison life that nobody ever broke, it was that slim weaklings like Desmond did not top massive alpha thugs like Chowder.
“Yeah, swallow it, Chowdah!”
“Throat him down, Talley!”
“Just foh’ the recahd, I’m doin’ this cuz I want to,” Chowder said. He spat on Desmond’s dick without touching it. “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 dome on the downlow. Ain’t no shame in that-“
“Less gabbin’, more swallin’ nuts!”
“Mollywop him, Talley!”
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 held Desmond’s shaft with his fingertips, like a disgusting snake. Then at last he opened his mouth, took a deep breath and closed his lips around the tip of Desmond’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 Desmond’s dick slide deeper even as his eyes frantically darted around as though looking for a way to escape. Desmond’s pubes enveloped his nose.
Almost immediately Desmond felt a surge of pride and confidence. He felt better than he had since coming to prison, and even before that. He pushed his dick in even deeper down Chowder’s tight throat, ignoring the angry look in Chowder’s baby blues. A tight, squeezing warmth spread through his senses.
“Come on, make more spit,” Desmond said, making the guards laugh. “You’ve gotten dome before. You know how to do it. Make it wet.” He wanted to call Chowder his bitch, but he thought that might be a step too far for the mountainous Bostonian.
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. His chest muscles became soaked and goopy.
A shudder of desire ran through Desmond’s body as he gripped Chowder’s broad shoulders. His inhibitions melted away. Chowder was crisscrossed with scars and tattoos, including a scattering of bullet wounds on his back. Desmond reached down to caress his body, savoring the feel of his rippling muscles and their firmness beneath his touch.
That made precum leak from the tip of his dick, which reawakened a torrent of sputtered gagging from Chowder. It sent a frisson up Desmond’s spine. 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; Desmond wasn’t hip enough to know for sure whether he was freestyling or repeating a popular song. It sounded rehearsed though. Maybe a Macky P song.
Chowder pretended it didn’t bother him, but Desmond could feel him bristling at the teasing. It was funny how Desmond could sense Chowder’s reactions through his muscles’ twitching and the way his throat clenched around Desmond’s spasming cock, like Desmond could read Chowder’s mind through his body. Chowder arched his back as he nestled his nose deep in Desmond’s crotch, easily deep-throating every inch of Desmond’s cock. His new position meant his ass rose in the air.
Desmond lusted after it. He couldn’t believe he was going to get to plow Chowder in that ass, and he wondered if Chowder had ever done it before. He said he shared dome with his baystater buddies on the downlow, but could they have done anal too? He tried to reach but Chowder was too tall for Desmond to reach his ass with his dick in Chowder’s mouth.
“Okay, you said you’ll lick my ass, right?” Desmond asked, remembering that suddenly. His voice was huffy and gaspy because he could feel the early burgeonings of his orgasm surging through his body. He wanted to drag this out though.
Chowder pulled off his dick. Thin tendrils of spit connected his greenish face to Desmond’s cockshaft. Chowder grumbled. “Fo’ five seconds, that’s all I agreed to.”
Officer Crabgut laughed. “That’s just a minimum, Chowder. You can lick his ass as long as you want. We got all night.”
“No!” Chowder snapped down over the chortles of the other guards, who all cackled up the serious look on Chowder’s face.
Desmond turned around and bent over as though he was going to get plowed, 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 Desmond 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 Desmond’s ass and explored there, hesitatingly as Desmond’s ass-juices smeared over Chowder’s square-jawed face.
“Five! Four! “
But Desmond then felt a ripple of pleasure emanating up his back as Chowder’s tongue battered his prostate. Chowder moaned into his ass and gagged without slowing down. Desmond’s eyes rolled back in his head as pleasure walloped his petite frame. Chowder’s tongue sucked 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 Desmond’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 Desmond’s dick with one meaty callused hand. It was the worst handjob of Desmond’s life, but it was also somehow the greatest, its lack of rhythm and rough texture sending shockwaves of bliss through Desmond’s body while slowing down his arousal enough that he was no longer 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 Desmond’s short little body couldn’t even reach it. Desmond 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 Desmond’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’.
Desmond 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 Desmond’s head, making Desmond 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.
Desmond 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 Crabgut — that seemed sweet, Desmond thought, he didn’t need to do that; prisoners usually used hog fat from the prison kitchen, so Crabgut was being nice by providing actual lube). Chowder’s ass was clearly intact, so tight that Desmond struggled to shove every inch in his hole.
Chowder was on all fours, so the more powerfully Desmond slammed into his ass, the more Chowder was forced to lower himself. He winced and dropped his hips, making it easier for Desmond to plow him harder. To his credit, Chowder managed to take every inch even though it was obviously difficult for him.
That hairy Italian guard Torelli took his dick out, wagging it in front of Chowder’s face. Desmond couldn’t hear his words because he was overwhelmed by his incipient climax and the boisterous laughter of the other guards drowned out the hairy guard, but it was clear he offered Chowder a taste of his dick. Chowder frowned and kept his eyes pointed away, even as the guard followed his face with his massive, uncut Italian cock.
Eventually Desmond was ramming with all his might on top of Chowder, his feet no longer on the floor at all. Chowder’s broad muscles rippled beneath Desmond’s face, and he licked the salty sweat that beaded on his skin. Chowder writhed beneath him.
His balls slapped on Chowder’s chunky asscheeks, making them jiggle and ripple. Desmond felt like a weird circus novelty, like a midget plowing 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, Desmond!”
“Lookit his little body on top of Chowder. Looks like a kid whose big bro is lettin’ him beat him up.”
Desmond blushed at the guards’ closeness. They were peering into Chowder’s ass as though they had never seen a butt before and weren’t sure what was actually happening. Having an audience was nerve-wracking for Desmond.
His orgasm came on too soon. Desmond was disappointed, but not surprised, as Chowder’s ass was too tight and too perfect to resist it for long. As he felt it arising deep within him, Desmond 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 guards would have gotten bored.
The most powerful orgasm of his life ran through him. Desmond’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. Some peered closer, while others looked away.
Cum sprayed within Chowder’s ass, a thick and copious loud that filled up every inch of his insides. Chowder moaned too, matching Desmond’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. Jet after jet of creamy jizz flowed into him and dripped down his thighs.
“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 Desmond’s dick. Exhausted, Desmond 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 Crabgut 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 pahty was totally worth it.”
Desmond 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 Desmond wasn’t, he shot him a few dirty looks. Soon they were both dressed. Desmond 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 Crabgut.
“Hey, if you want — and you don’t think Sammi will mind — you can plow me later. As hard as you want,” Desmond said. “If that, y’know, makes you feel better.”
“I know I can.” Chowder’s voice dripped with menace. “I will.”
Desmond smiled. That promised to be almost as good as what had just happened. He couldn’t wait.
