Here’s the entirety of Str8 Till Dark: Prisonmates, which is now permanently free in the Kindle Store and on Smashwords! It’s part of the amazing Str8 Till Dark series of gay erotica about men whose straightness bends when the lights go out!
As Brian curled up on the floor to get some sleep, he tried to decide whether this had gone better or worse than he had expected. It was hard to tell. He had predicted a catastrophically bad entrance to prison life — that was just the way his mind worked, constantly coming up with disastrous possibilities. But it wasn’t really as bad as it could be. The worst part was simply that Brian had no protection. Nothing good had happened to him, which was bad, but nothing too bad had happened to him either, and that was good.
Brian had covered up his anxiety when he strode into Brutewood prison. He was a handsome young white man with long hair he kept pulled back into a ponytail. Given everything that he knew about prison life, he fully expected to have gay sex.
He was fine with that, more or less. Brian was straight, but he loved being anally penetrated by dildos or fingers. He had never actually taken a cock in his ass, and he was willing to try it — giving it up in exchange for protection behind bars was not his ideal scenario for experimenting with getting fucked, but he wasn’t too upset about it either.
Officer Armstrong shoved him into the prison cell and shut the door. It was much larger than Brian had thought it would be, but there were already twelve people there. There were also only twelve bunks, while Brian was the thirteenth person.
“Turn around and stick your hands out,” Officer Armstrong said. He sounded bored.
Brian was not bored. His heart felt like it might pound through his chest. He stuck his cuffed hands through the opening in the doorway. Officer Armstrong unlocked the cuffs.
“There’s not enough bunks,” Brian said. He shook his head to unlodge his hair where it stuck to the back of his neck.
“Then kill yourself,” Officer Armstrong said as he walked away. He laughed, the deep, baritone sound resonating in the steel-lined prison corridor.
Brian turned around. Twelve dour black man stared back at him. No one said anything. Brian had always been an outgoing and friendly young man, so his mind raced as he tried to think of something to say.
“So, uh… guys… I guess we’re prisonmates, huh?”
Someone chuckled dryly, but no one responded. Six of the men were playing poker, and they resumed the game without looking at Brian. Three others were taking turns working out, doing improvised pull-ups on a bar they had set up in the middle of the cell. The bar was also for hanging laundry, but they had taken all the clothes off before exercising. Their corded muscles gleamed, and Brian felt small and vulnerable.
He supposed he was meant to sleep on the floor. There was plenty of room in one corner, and he had been given a sheet, a blanket and a pillow, which smelled like piss though it looked clean. Brian wanted to cry.
He took a deep breath. He had been told what to do, and he had rehearsed it. He thought for sure he could pull it off.
He went to the biggest thug in the room. He was a tall, middle-aged black man with a burly body brimming with muscle and bravado. He was not exactly dressed like a thug — not like the others, he had a trimmed mustache, well-fitting pants, just a few tattoos, but he still talked like a pimp as he encouraged the others in their workout.
“C’mon, nigga, yeah! Push it!” He barked, slapping a younger black man on his ass as he lifted himself up and down doing pull-ups.
“Hey, uh, excuse me, uh,” Brian said, trying to get the man’s attention. He blushed. “My name is, uh, Brian-“
“Nice to meetcha, Brian,” said the large man. Despite his relatively polite words, he spoke with a crude sneer on his face and a harsh look in his eyes. “Whatchoo want, whiteboi?”
“Uh… I’m just, I was told… uh… I know this can be a dangerous place-“
“Hurry the fuck up and say it.”
“I want your protection!”
“Please protect me,” Brian said. He blushed again. “I… I’ll let you fuck me. I promise. I’ll… You can fuck me. I’m not gay, but, uh-“
The man cocked his head to the side. “My name is Samson, Brian. I ‘ppreciate yo’ offer. But I gotta decline.”
“Yeah, whiteboi, we ain’t like that no mo’.”
“We don’t rape whitebois.”
“That’s against the rules nowadays.”
“No one here gonna fuck wit’ you, whiteboi.”
“Ha! Queerbait!” That was Officer Armstrong, who was walking past the doorway. Brian blushed. He hadn’t meant to offer in front of a guard.
And so that was that. They dismissed Brian, who blushed and stumbled back to the corner of the cell he had decided to use as his bed. They ignored him after that. He wasn’t sure how to take that. Had they only said no because Officer Armstrong was there? He didn’t know. They hadn’t promised he’d be safe outside of the cell, and he didn’t trust them in the slightest.
But there was nothing to do. He couldn’t force them to promise he’d be safe everywhere in prison. He’d just have to come up with a different plan. Maybe, he thought, movies overdramatized prison life. Maybe it won’t be that bad.
The lights turned out. The evening had gone by faster than he thought. His prisonmates stayed up talking for a long time, but Brian didn’t complain. He zoned out and pretended he was asleep.
And so that was why he laid fitlessly on the floor, wondering how this was going to turn out. Maybe, he thought, he shouldn’t have asked to get fucked. That might have been bad advice.
Once the prison was quiet, however, a few whispered voices filled the air. Brian couldn’t tell if they spoke thinking he was asleep and couldn’t hear, or if they wanted him to hear it.
“You gonna fuck that whiteboi?!”
“Hell nah. I ain’t down wit’ dat.”
“I betcha big-nigga do it.”
“Fuck you, asshole. I ain’t down wit’ dat gaybones shit. You know who gonna do it? That whiteboi got it right when he offer Samson-“
“Hey!” Samson’s deep voice boomed. “Shut yo’ stupid nigga faces.” Samson was the biggest and oldest and, it seemed, he was in charge. No one talked for a few minutes. Then someone chuckled, which caused someone else to laugh. Soon the cell was full of deep-voiced thugs laughing, at what Brian couldn’t tell.
“Samson gonna get gay as shit, we all know it.”
“Shut the fuck up!” Samson got up and stalked around the cell like he wanted to figure out who had spoken. “None of you say jack-shit, motherfuckers. I ain’t no kinda queer.”
Brian was still nervous. The more they insisted that they weren’t going to fuck him, the more sure he was that they were. He really wouldn’t mind trying it. He just wanted the option to change his mind partway through, and of course he wanted to be assured he’d be protected while he was locked up.
Samson went back to his bunk, while the rest of the cellmates gradually fell asleep. Brian was wide awake. He soon gave up hope that he’d be able to sleep at all tonight. It was going to be a fitless night without rest.
Soon the cell was silent aside from the noisy breathing and occasional stirring of his prisonmates. Officer Armstrong walked by every half-hour or so but he didn’t look in the cells. Far away, Brian heard an inmate snore, but it wasn’t loud enough to keep him awake.
He yelped when someone touched him. A heavy hand pressed down on his mouth. Callused, rough skin rubbed against his face.
“Sssh…” Samson’s gravelly voice filled Brian’s ear. Brian squirmed, but Samson held him down. “Don’t worry. Ain’t gonna hurtcha. Relax. Chill out, whiteboi. Sssh…” Brian tried to stop moving, but he was instinctively frightened with that hand muffling his mouth. The knowledge that he couldn’t cry out if he wanted to made this terrifying.
Finally Samson calmed Brian down by removing his hand and planting his lips on Brian’s. Brian had never kissed a man before, and he had never thought a straight thug like Samson would kiss him, especially out of nowhere like this. It was so unnerving that Brian did stop fighting back, exactly as Samson intended.
“Good. Relax, whiteboi,” Samson said. He kissed Brian again on the neck. “I ain’t gonna hurtcha.”
“Sssh… whisper,” Samson said.
“Sssh. You wanna sleep wit’ me?”
“We can share a bunk if you want. You can suck my dick like you want, and I’ll fuck you. I ain’t gonna promise you protection though.”
“Cuz you don’t need it. I always take care of my family, and if you in this cell wit’ me, you my family. You my prisonmate, whiteboi,” Samson said. “If you wanna get fucked cuz you love gettin’ fucked, just come sleep in my bed. You gotta get up and out on the floor real early, so no one sees you. I got a rep to protect. The guards don’t allow us to make love.”
“Oh, well…” Brian felt like kind of a prick. He was glad to have protection, and he didn’t care about doing anything for or with Samson if he didn’t need to. Was it wrong to accept Samson’s protection without giving him anything in return.
But on the other hand, Brian did say that he had wanted to try this. He wanted to see what it was like to get fucked, and he could think of no one better to introduce him to the world of sodomy than the sexy massive prison-thug Samson.
“Okay-“ Brian said. Before he could say anything else, Samson had scooped him up in his arms and brought Brian to his bunk.
It was not a large mattress. Samson was a huge man, well over six-feet tall and built like a brick fuckhouse, as Brian’s grandmother would have said. Samson barely fit in the bunk by himself. When Brian crawled in with him, he was forced to cuddle with Samson’s iron-like muscles.
Samson smacked his lips. He kissed Brian on the ear, and he slowly pushed Brian’s hand to Samson’s crotch. Brian gulped and stuck his fingers through the fly of Samson’s prison-issued shorts.
“There you go, whiteboi, you doin’ nice, keep at it,” Samson said with a low, rumbling groan. He whispered but his voice was so deep it rumbled and echoed in Brian’s ear. “You gay?”
“No,” Brian said. “I, uh… I-“ He gulped. “I like to, uh… I use dildos. Like, on myself.”
“Oh? You like anal?”
“Yeah-“ Brian grunted as Samson rammed one of his fingers in Brian’s asshole. It was his pinkie finger, but he was a big man so it was hefty, and it was callused and rough. Brian squirmed and yelped again.
“You like dat, whiteboi?”
“Uh, no-oooooo!” Brian’s voice broke because his pain turned into pleasure all of a sudden as Samson’s finger hit his prostate. Brian tightened his ass around his finger. “I mean…”
“Ah, yeah, I see dat, you like it. Good boy,” Samson said. “I teach all these niggas in here how to love it when I fuck ‘em. That’s a lesson e’ryone learn sooner or later. I’m glad you learnin’ it sooner. It’s a good lesson, ain’t it?”
“Uh… yeah,” Brian said, his mind too focused on his asshole to think about what Samson was saying. He didn’t even stroke Samson’s dick as he endured the finger-fucking; he just laid there, pinned between Samson and the wall, with his hand gripping Samson’s half-hard dick but not stroking it.
“You wanna suck on it? I’d mighty ‘ppreciate it,” Samson said. He guided Brian’s head. He didn’t force it, but he did give Brian a push.
Brian did want to try it. Samson was ungodly sexy, and the more Brian endured his finger in his ass, the more Brian wanted to experience it all. He didn’t even mind if his other prisonmates found out.
So he allowed Samson to push his head into Samson’s crotch. Brian opened up and swallowed the tip of Samson’s cock.
The taste was powerful and sudden, an explosion of salty meat in his mouth. Brian gagged but that just opened his mouth a little wider, and Samson pushed his dick in farther. Samson groaned and started to move his pinkie finger in and out.
Samson began to writhe as though the blowjob felt so good he couldn’t control himself. His dick stiffened all the way up in Brian’s mouth. He loved the musky, unwashed flavor, and he loved the way he could feel Samson’s heartbeat in the throbbing of his dick. Samson’s muscles tensed when Brian’s hand caressed his chest.
“Told you, nigga,” someone said, and someone else giggled knowingly.
“Samson, we knew you was gonna do it.”
“Samson fuckin’ dat whiteboi! Least surprisin’ thing evuh.”
“Hey! Shut up!” Samson barked. “You gonna get Off’cer Armstrong lookin’ in here.”
They all settled down a little, but it didn’t last long. Now that he knew everyone else was awake, Brian was very self-conscious. His mouth made loud, moist suckling sounds as Samson worked his dick deeper and deeper, and every few seconds Brian choked despite his best efforts. Samson’s finger in his ass made noise too. Brian couldn’t tell how loud it was to everyone else, but to him, it was deafening.
“You doin’ okay, whiteboi, not bad ’t all,” Samson said. He caressed Brian’s head and kissed the air. Then Brian gagged very loudly and Samson clucked his tongue caringly. He grabbed Brian by the ponytail and dragged his head off Samson’s cock. It was such a crude, barbaric action that Brian was surprised when Samson kissed him on the lips. His tongue plunged into Brian’s mouth, but just for a moment.
He returned Brian to sucking his cock. Samson sighed. “You like dat? I don’t kiss boys a lot, okay? I don’t like it much, but I wanna show my ‘ppreciation for you suckin’ my dick nice.”
There were more moist sounds filling the air. At first Brian thought maybe his other prisonmates were having sex. That would be nice, he thought, because it would make him feel less self-conscious.
But then he realized that wasn’t true — they weren’t fucking each other, they were masturbating. They watched Samson’s finger disappear in Brian’s ass in the dim light as though it was an exciting movie, and all eleven of them stroked themselves off. They were each standing or at least sitting up on their cot and watching, cock in hand.
Brian had never been more aroused. He had also never been more embarrassed, but right now the arousal was more prominent in his mind. His own cock was rock-hard, and he tried to jack himself off the best he could crammed into the tiny bunk with Samson.
“Alright, whiteboi, we gonna see how much fun you really is,” Samson said. “Is it okay if I fuck you?”
“Yes, oh god, please, do it,” Brian said. He blushed, not that anyone could see in the darkened cell. His mouth was empty then, and Samson moved with catlike grace despite his huge size and bulky body.
Samson kneeled against the wall, crouched awkwardly so he fit beneath the bunk above his head. His cock stuck straight out. He wrapped his arms around Brian and had him kneel right in front of Samson’s crotch.
His dick rammed right in. Brian’s ass was already open and loose from the fingering, but Samson soon added some lube anyway — it was hog fat, or lard, that he had stolen from the prison kitchen — and his massive dick slid right in.
“Yeah, whiteboi, take it, take e’ry inch of that nigga meat,” he said with a laugh. The others all joined in chuckling, but then shushed each other.
“Yo, guards gonna hear, man, shush.”
Brian squirmed as he endured the ass-fucking. It started off painful, then felt so good he had to suppress a moan again, and then it hurt again before it became a low, slow, melting pleasure that made him wiggle like a worm.
His body was limp and submissive. Brian felt like he was falling because he kneeled on the bunk in front of Samson, who was also kneeling, but the bunk wasn’t really wide enough for both of them to sit up in front of each other like that. So Brian was suspended over the air, held aloft only by Samson’s arms keeping him in a bear hold. If Samson let go, Brian would plummet face-first onto the floor.
The pressure and pleasure in his ass was so intense Brian couldn’t even moan. He kept his mouth open but the only sound that came out was a strangled moan.
One of Samson’s hands remained in place, wrapped around Brian’s chest and holding him in place, while his other hand roamed south. Brian had a feeling he wasn’t supposed to say anything about it as Samson’s hand wrapped around his dick. Brian spasmed and gasped. The other prisonmates laughed quietly at Brian’s frenzied reaction, but they didn’t know Samson gave Brian a reacharound as he fucked.
“Hey,” Samson whispered into Brian’s ear, his chest muscles writhing and flexing against Brian’s back. “You wanna be the coolest whiteboi evuh?”
“Whatchoo think, whiteboi?”
Brian’s mind struggled to focus on Samson’s words. He gasped and squirmed in Samson’s muscles. What had seemed awkward and strange at first was now deeply arousing. Brian loved the feel of potent, hairy, masculine power flexing against his flesh, and Samson’s throbbing fuckstick demolishing Brian’s ass. It was better than his girlfriend’s purple strap-on, which had been Brian’s go-to orgasm device for a long time.
His prostate tingled with such intensity that Brian could barely speak. He managed to say, “yeah”, not caring what the plan was — he would do anything his ebony sex-god of a cellmate wanted.
“Open yo’ mouth, whiteboi,” Samson said. He pried Brian’s mouth apart. “Yo’ prisonmates gonna nut in yo’ throat. This is like all of us sayin’ hello, okay? We gonna be good friends aftuh this. You gonna taste our nuts, nice and creamy goin’ down yo’ throat, okay?”
“Oh god yes,” Brian said. He opened his mouth.
Instantly two cocks pushed in at once. There were some deep grunting noises, and someone pushed someone else.
“Get outta my way.”
“I’m first, nigga, move!” In the end, both men shot their loads just seconds after Brian got the first taste of cockmeat. They had both been on the verge of orgasm already. Creamy, salty cum invaded Brian’s mouth. The flavor was not exactly tasty, but it was savory and Brian wanted more.
A loud clanging sound erupted, and everyone jumped “Hey!” Officer Armstrong stood outside the cell. He had slammed his nightstick on the door. “I’m gonna turn on the light in about five seconds, shitweasels. Ya hear me? If I see somethin’ in there that I gotta intervene about, you had best believe I am gonna shove this entire prison up your stupid shitweasel assholes!”
A moment of silence filled the air, and then Officer Armstrong began counting. “Five!” He banged on the door once more. Everyone in the cell burst into a frenzy of activity. Brian was annoyed to slide off Samson’s cock and crawl, still shuddering from the aftershocks of his interrupted orgasm. “Four! Three! Two! One!”
He turned the cell light on. Brian groaned as bright light assaulted his eyes. Everyone was in their bunks, sheets and blankets covering their hardons.
All in all, it must have been blatantly obvious what had been happening in here. But Officer Armstrong just flared his nostrils as he looked over the thirteen men pretending to be asleep. He spat a big loogie onto the floor of the cell, then shut the door again.
“Go to sleep, shitweasels. If you’re gonna fuck, finish in the next couple minutes so I don’t have to hear it when I come back around,” he said as he walked away.
Everyone — except the two who had already cum — was eager to finish up, having nearly been blue-balled by Officer Armstrong. Before Brian could even get up, Samson was behind him again, ramming his dick back into Brian’s ass.
Brian grunted and Samson growled seductively. He wrapped all of his arms and legs around Brian’s limbs, bringing him to the ground. Samson laid on his back, while Brian submitted, resting on Samson’s chest with his ass on Samson’s massive cock.
The pain was intense once again, but only for a moment before that mind-numbing pleasure hit him once more. As Brian tasted that ebony prison-cock and drooled over its meaty goodness, he smiled. He was going to love his time in prison, he thought.
“Yeah, whiteboi, swallow my nut,” someone said as he shot a hot load of salty cum all over Brian’s face. “Let’s bukkake him. Let’s make him real messy.”
The others all agreed, but most of them were barely listening — they were already about to bukkake him regardless. Their dicks sprayed heavy loads all over Brian’s face. He couldn’t even tell how many. He knew logically it should have been eleven, or no more than eleven, but it surely felt like more. Had someone jacked off more than once? It was impossible to tell.
But his mouth and face were covered in dripping cum, which coated his skin and seeped into his flesh. It leaked down the sides and onto Samson’s body, but Samson didn’t care — in prison, these kinds of sanitary, privacy issues stopped being so relevant. A few drops of cum even found their way into Samson’s mouth, but he barely noticed that either.
The sensation of getting fucked and the taste of a torrent of cum flooding his mouth was so overwhelming that Brian didn’t noticed his own orgasm until happened. It was the most intense experience of his life. It felt like it lasted the entire nine to twelve years he was to spend behind bars — his prostate sang and danced within him, sending waves of pleasure to every corner of his body. He squeezed around Samson’s dick.
“Swallow it while I nut inside you, whiteboi,” Samson said with a moan. He rammed his dick all the way in, making Brian scream, unable to muffle the sound at all. As he spewed hot wad after wad of cum inside Brian’s guts, Samson’s callused fingers pushed semen into Brian’s mouth. He smeared every drop of that bukkake mess down into Brian’s waiting throat.
He didn’t mind touching his niggas’ cum, and Samson groaned as the taste made Brian’s body clench around him. Samson knew how to make a prison bitch’s body react the way he wanted, so he filled Brian’s mouth up with eleven loads, plus Brian’s own cum that Samson scooped up from his chest.
“Yeah, whiteboi, nice…” Samson moaned as he shot the last few drops of his own cum into Brian’s ass. He laid there, dick throbbing while it limpened inside that tight hole. He had rarely felt such a wonderful ass.
“Comin’ back soon, boys!” Officer Armstrong called out. “Finish up!”
The other prisonmates slowly made their way back to their bunks. They stopped to wipe off their dicks first with toilet paper, since most of them had done a little jousting and gotten each other’s cum on their shafts. They quietly shuffled into their beds, giggling nervously about what had happened.
But Samson remained right where he was, resting on his back on the floor, dick limpening inside Brian while Samson flopped Brian’s soft cock between his fingers.
“You wanna come sleep in my bunk?” Samson asked. “Remember, when the sun comes up, you gotta move back to the floor so the guards don’t see.”
“Okay,” Brian said breathlessly. He breathed a sigh of relief when Samson finally took his dick out of Brian’s ass.
Brian was so exhausted he fell right to sleep. He curled up in the tiny space Samson left for him, and he buried his nose in Samson’s warm bicep. He kept one hand on Samson’s belly, just low enough where he could feel the beginning of Samson’s pubic hair. He inhaled deeply of the musky scent of Samson’s sweat-dappled body.
“I love you, Samson,” Brian whispered.
“Shush, whiteboi,” Samson said. “I know you love me. E’ryone falls in love when I fuck ‘em. Don’t worry. I ain’t nevuh gonna stop fuckin’ you, Brian. So we gonna be in love forevuh.”