James was in quite the predicament -- he was kneeling at the feet of his burly, masculine cellmate, his lips swollen and slick from sucking Kyle's cock, tears streaming down his face, his cute blue eyes wide with horror. Kyle's monster dick bobbed and jerked in front of his face, wet with spit and pre-cum. James couldn't imagine that cock fitting in his ass -- it was the thickest dick he had ever seen, even in porn. But if he didn't bend over and offer his ass up willingly, Kyle would just make him. He was his cellmate's new bitch -- if he didn't play nice, Kyle would just hurt him, would fuck him all the more brutally for resisting and take his frustration out on James' vulnerable, sensitive balls.
When Kyle let out a low, warning growl, James immediately sprang into action -- he didn't want to get his balls beaten. Surely that would be worse than taking that monster dick up his ass?
"Please," he sobbed, even as he stood up to do as he was told. "Please, I can't, I've never taken a dick. You're too big, you'll rip me apart, please." His lip was still bleeding from where Kyle had hit him. Everything more than a few feet in front of him was blurry without his glasses. He was a tiny little weed compared to the huge, muscular man in front of him.
"If I have to tell you again, boy, you know what'll happen," Kyle said, narrowing his eyes at the pathetic boy in front of him. He reached down, stroking his thick, meaty cock a few times. The head was sloppy with pre-cum and spit, his cock throbbing in time to his pulse. All he wanted was to bury his dick in Kyle's tight ass and blow his load.
James hesitated for a second longer before wilting like a flower out of the sun. He peeled his underwear down with trembling hands, his cock still sticking up proudly. It was nothing compared to Kyle's -- a mere five inches, and not all that thick. Kyle's cock was easily twice the size of his, possibly even thicker. Stepping out of his underwear and standing there, a skinny teenage boy, barely nineteen, he knew that his life was over. There was nothing he could do to stand up to this man. If Kyle told him to bend over, James would have to bend over, or risk something worse.
Crying like a baby, far too aware of the laughter and jeering from those that could see him in the cells opposite, he leaned over the bottom bunk, trapping his cock between his stomach and the grimy mattress.
"That's it, there's a good bitch," Kyle husked out, eyeing James' pale, round ass and his straining thighs. "Stick your ass out like you're all in heat for my dick." He stepped closer, smearing the head of his dick over James' buttocks. "You got a real pretty ass, bitch. I'm gonna enjoy stretching it out until it swallows my dick like it's made for it."
Shaking, James helplessly did as he was told. Fisting his fingers into the filthy sheets, he stuck his ass out as far as he could. He trembled when he felt Kyle's hot, thick dick smearing over his skin. James closed his eyes and took in a deep breath, just waiting for it. He knew it would hurt -- it would probably hurt worse than anything that he had ever felt, but maybe if he just got it over with, Kyle would leave him alone.
"Oh yeah, you're gonna be a real good, obedient bitch, I can tell. Maybe I should fuck faggots more often," Kyle said, sliding his huge, warm palms up James' inner thighs. In one powerful motion, he wrenched the boy's legs apart, forcing them wide so that James was completely exposed to him. Kyle looked down at his pretty pink pucker and grinned -- he really was going to enjoy turning that tight little asshole into a cunt. Leaning down, he spat slickly on the hole, laughing as he felt James jump. "Relax, cunt," Kyle said. "You'll like this. Most faggots do."
Kyle wasted little time with teasing James -- he just pressed one thick finger against the boy's tight, twitching hole before forcing it inside, twisting it back and forth, screwing it into James' ass. As much as Kyle wanted to fuck the boy, he knew that fucking a virgin open on his huge cock without stretching him out a little on his fingers first would hurt him, too. He didn't care much if he hurt James, but Kyle wasn't much of a masochist -- when he slid into James' virgin asshole, he wanted it to be tight and slick, not chafing him with the vice-like friction.
James gasped as he felt Kyle's finger penetrate him -- even the man's fingers were thick. James had played around a few times by sticking a finger up his ass, but Kyle's fingers were twice the size of James', and his hole burned and ached as it stretched. Sobbing into the sheets, James trembled in place as his cellmate violated him, stretching his hole open until it ached and burned.
The boy's hole was deliciously tight. Kyle's dick twitched just at the thought of getting inside that tight, hot hole. He didn't really give a shit about James' comfort, or how much he hurt the boy. As far as Kyle was concerned, James was just a hole to fuck. If anything, he kind of liked it when he hurt his bitches -- it made them clench around his cock so nicely. Twisting his finger inside the boy, he quickly added a second, ignoring James' muffled gasps and whimpers as the stretch hurt him. Kyle fucked him brutally on his fingers for a couple of minutes, opening him up, scissoring his fingers mercilessly as James twitched and cried out in pain under him.
Pulling his fingers out with an obscene, slick sound, Kyle parted James' buttocks and looked at the other's pink hole. It was already starting to look like a cunt -- where it had been tiny and tight before he had shoved his fingers into the boy, it was now slick and open. He watched as James clenched, returning his hole back to that tight, pink little pucker. By the time Kyle was done with him, that pretty pink hole would be gaping open and leaking come like a well-bred pussy.
"I'm gonna fuck you now, James," Kyle husked out, spitting onto his opened hole to make the first slide nice and slick. "I'm gonna shove my big dick all the way into your virgin hole. I'm gonna rape your guts." Kyle grinned, stroking his throbbing cock. "Don't worry, you'll learn to love the feel of my huge dick opening you up. By the end of the month, you'll be begging for my dick. You'll be able to take my fist up your pretty pink asshole. Of course, it won't be so pretty and tiny then, but I'm sure you'll learn how much pleasure your ass can bring. Especially to other people." Kyle laughed and slapped James' ass.
"Now, I want you to reach behind you and open up your cheeks for me. I want you to give me your asshole like a good bitch. I want you to thrust your cunt back at me and open yourself up like the faggot you are. Because really, deep down, you want my dick. You crave it. You want it so bad you can fuckin' taste it," Kyle said, gripping his own dick at the base, aiming it at James' virgin hole.