Tag Archives: gay inmate

Cellblock 5: An 18-Year Old Meets The Prison Sharks

Here’s the beginning of a great new tale, Cellblock 5: An 18-Year Old Meets The Prison Sharks, from Brutewood Medium Security Penitentiary!

Greg leaned back against the sharp, wire fence enclosing the yard and pulled a cigarette from the left pocket of his bright orange jumpsuit. His spirit took a downward spiral when he fiddled around for a light and realized he had none. He knew where he could get some matches; cell block #5. A tall, sandy-haired man with a dimpled chin and blue eyes took blowjobs for payment. Greg just wasn’t sure he was ready to get on his knees . . . yet. The thought of a mouth full of cock turned him on, but he had never truly been with a man and he was nervous about the other prisoners making fun of him. After all, this was his first week in the pen and at the age of 18, he felt like a wounded dolphin surrounded by hordes of hungry sharks. Many of these men were seasoned, and knew the ins and outs of the system. Not Greg. His relatively shy and aloof nature was not helping him out, either.

He hadn’t even noticed that time in the yard was up until a husky prison guard with a chin full of short stubble pushed him along the edges of the fence, corralling the prisoners back into their pens. The door to his cell creaked open, and Greg caught a glimpse of his cellmate, Mason, lounging on the bottom bunk waiting for him. He couldn’t help but notice the bulge in Mason’s jumpsuit. Mason was lying flat on his back, but his obvious erection lifted the lower half of his orange jumpsuit, elevating it in this air. Mason sat up when he saw Greg, quickly covering his crotch with a hand and slightly tugging at it. He walked over to the open toilet in the cell and whipped out his large, veiny manhood and began pissing into the can somewhat awkwardly. Greg grinned. “I hate trying to pee with a boner,” he joked. Mason smiled. “I was going to try to rub one out before everyone got back to their cells, but I see they cut yard time early today.”

Greg felt his own flaccid penis stiffen a bit at the thought of Mason alone in his cell masturbating to no end. He often noticed bulges in Mason’s jumpsuit, and knew his cell partner was horny quite often. Greg often tried to ignore them, but when he caught a glimpse of Mason from the side, his swollen soldier was obviously at attention, sometimes half-cocked, other times in full salute.

The Prison Guard and the Submissive Prisoner

Here’s a sample from The Prison Guard and the Submissive Prisoner, a new story by Curtis Kingsmith!


Jerry’s heart felt like it was about to pound out of his chest. He couldn’t breathe. He couldn’t think. He couldn’t do anything but stand there and blush as he dropped his shorts. As an openly gay man, he didn’t mind the idea of being naked in front of Officer Armstrong — he had always had an exhibitionist streak, after all — but the actuality of it was more nerve-wracking.

He didn’t know what he was supposed to do. He stood there in front of Armstrong, with his cock dangling between his legs. He had covered his crotch with both hands, but Armstrong barked at him to stand at attention. Now Armstrong was just sitting at a desk, filling out paperwork, ignoring Jerry completely.

“How tall are you?” Officer Armstrong asked.

“Uh, five feet, seven inches.”

“How much do you weigh?”

“One hundred and thirty-five pounds,” Jerry said. He blushed. He was skinny. Before the trial, he had been working out regularly and gained weight, making it all the way up to one hundred and fifty pounds before the stress of his arrest had let to him eating less and less. Now he was a skinny fuck again.

Officer Armstrong snorted. “You best be thankful I won’t put you in with those animals. They’d eat you alive.”

“Uh, what?”

Armstrong looked up and furrowed his brow. “You’re a weakling, a pussy, and you’ve got a tiny dick,” he said, sneering as Jerry blushed. “If I put you in the jail with a cellmate, you’d be someone’s bitch in no time. Unless you wanna be a faggot…”

That was that, Jerry thought. He had wavered on whether or not to be openly gay while he was in prison. He had been leaning towards being out up until now, but it sounded like Officer Armstrong was not very tolerant. It was better, Jerry thought, to fly under the radar. If it was expected that he’d be straight, he’d be straight. He had been in the closet for years, he could go back in for six more months.

“No!” Jerry exclaimed. He blushed, not sure if that was too overeager or not.

Armstrong sighed and stood up. “Turn around and bend over,” he said. When Jerry didn’t do it right away, Armstrong repeated himself. “If I have to bend you over, I will. You won’t enjoy that, motherfucker!”

Tears welled in Jerry’s eyes as he bent over. His asscheeks spread and cold air hit his butthole. He heard Officer Armstrong putting on plastic gloves. He was going especially slow, drawing this out to torture Jerry. He opened up a container of lube and smeared some on his finger.

“Tell me when this hurts,” Officer Armstrong said. He rammed the tip of his finger in.

Should I say that it hurts now? Jerry wondered. He didn’t want to sound like a pussy, but a straight man would be in pain right away, wouldn’t he?

He straightened his back and said, “It hurts, man.”

His finger wiggled in Jerry’s ass, and Jerry squealed in pain to cover up the excited pleasure he felt deep in his prostate. He blushed, but luckily his head was down near Armstrong’s polished black leather boots, so Armstrong couldn’t see his crimson cheeks.

“Man? You don’t call me man, maggot. As long as you’re in here, I am your god. I’ll let you call me sir instead of master, but if you call me man again, we’s gonna have problems, boi,” Armstrong said, his finger curled up inside Jerry’s ass.

It brought tears to Jerry’s eyes even as it made his cock stand up straight. He tried to think of something else, anything else, but his mind was entranced by the agony and bliss emanating from his asshole.

More of Armstrong’s finger slid inside his ass. It was his middle finger, the longest, and it was thick too, like a slab of sausage sliding inside him. Jerry moaned.

“You like that?”

“No-oh…” Jerry said, his voice breaking partway through. Did that sound like orgasm or agony? He couldn’t tell.

“Kiss my boots,” Armstrong said.

Jerry did so. The black leather was cold and astringent, and it distracted him from the pain in his ass. Jerry tasted the bitterness of shoe polish and the funk of Armstrong’s sweaty feet behind that.

Armstrong began ramming his finger in and out of Jerry’s ass, chuckling at how easily he managed to do it. He wiggled his finger too, as though trying to explore every inch of Jerry’s large intestine. He cackled when at last Jerry threw his head back and screamed, a note of pleasure distinct and obvious in the tenor of his voice.

It must be obvious he was gay now, Jerry thought. His cock was rock-hard and leaking precum. His spine undulated as his ass worked its way up and down Armstrong’s finger, instinctively fucking himself.

“You a faggot, ain’tcha?” Armstrong asked. He grabbed Jerry by the back of the neck, keeping his finger in Jerry’s ass, and lifted Jerry’s head up.

Breathing hard, unable to focus on lying due to the finger in his ass and the strain in his cock — he knew he could claim his erection was simply due to anxiety; that wasn’t impossible. But he didn’t think he could pull that off. Armstrong was looking at him like a disgusting species of bug.


Armstrong sneered. “You think I’m hot?”


Armstrong shook his head. “You’s disgusting, faggot,” he said. “But you’s a bit useful to me too. Don’t you tell no one I did this.” He took a deep breath, sighed and wrapped his left hand around Jerry’s cock.