Leonard, eyes wide open and glazed, panting and moaning slightly, lay on his belly on the bottom bunk in the prison cell, his eyes glued to Big Phil, perched on the desk across the cell, his feet on the floor, his legs spread, naked, slow-stroking his cock back toward full erection. His eyes also on Leonard, gauging where they now stood. Leonard was still wearing his prison T-shirt; his sweat pants were in an entangled pile on the tile floor at the side of the bunk. Phil's prison T and sweats were neatly folded on the table.
Leonard, in for lewd behavior—being caught, for the third time, sucking a man's dick in a library restroom where Leonard worked shelving books—had just lost his male virginity.
"First thing you need to do on the inside," his lawyer had told him after sentencing, "Is to find a protector. You're just the sort who will have a miserable time and be all torn up inside if you don't."
"A protector? Torn up. I don't understand."
The lawyer told him and the young man's eye went big and he began to tremble.
"You're an effeminate gay man. I know it's brutal to say, but you have to understand that you are as close to a woman as men inside are going to be able to get to. They will make do—with you. That's inevitable. Giving their cocks suck isn't going to be good enough for them. It's a choice of a dozen men or one. You'll have to give it up for the protector, but then it will only be him. Do you understand? You got yourself in this mess, Leonard, you need to do what you can to survive it."
Leonard had shuddered, but he slowly nodded his head. "I understand, but how—"
"I have connections in the prison. I'll make the best arrangement for you that I can. But then it's up to you to hold onto the protector. Do you understand that? He will be the only thing standing between you and the hospital."
"Yes, I understand," Leonard said, meekly.
Phil Lindstrom had been meek too when he'd entered the prison, a jewelry store owner who was in for five years for receiving stolen goods. He had been thirty-five and was pushing forty now. He was about to be released into an interim work program, but nobody was telling Leonard that.
Phil was of Norwegian stock—tall, of sturdy construction. When he'd entered prison, he'd been overweight and timid, confused on how he could have gotten here, where he'd gone wrong, and spending much of his time reorganizing his approach to life. He hadn't had any idea he was receiving stolen jewelry. He'd taken it on consignment, trusting a friend. The friend was the target of a "make an example" sting operation, though, so they threw the book at Phil too.
When he'd entered Woodward Prison, Phil hadn't faced the decision that cute little Leonard had, because of his intimidating size, being grossly overweight, his age, and because his was a white-collar crime. He didn't run with thugs—at least not then. Once he'd showered communally a couple of times, though, it wasn't the size of his belly at the time that mattered. He had young men who had been fully indoctrinated in the sexual system in the prison coming to him to ride him.
Phil had been largely asexual before coming to prison. Never married, his nose perpetually to the grindstone to keep his jewelry store profitable, his few layings with women had been unsatisfying to him and challenging to the women. His experience with men, buried in his youth by his determination to be "normal," had, however, been more satisfying. He didn't know before coming to Woodward, where trapped men had essentially two choices for release—their own hands or their fellow prison mates' bodies—what aroused him. It didn't take him long in Woodward to discover what did, especially when young men were begging him to lie on his back and let them ride his cock.
Sexual dominance in a men's prison gave a man power. Three years after he entered the prison system, thanks to endless hours in the prison gym, he was much more of a man to be reckoned with than the one who entered prison. His natural abilities and determination at organizing, his age, the height and mere muscular physical presence of him now, and where he stood in the order in terms of equipment, taken him to the top of the pecking order in the prison population, He now even was looked to by the guards to help maintain order—which they rewarded with perks.
Perks such as Leonard. "Fresh meat" is what they called new "scared rabbit" prisoners who looked and acted like Leonard did.
"You OK, Lenny? You can take it?"
Leonard answered with a groan, but then he nodded his head and whispered, "Yes, it was fine."
"You have two choices now, Lenny. You know what it entails. You can stay here, bunking with—and under—me, or you can go into the general population and take your chances. I can arrange either. Which is it?"
"I want to stay here, with you," Leonard murmured, his lawyer's advice screaming in his head.
"You know what it means then. Wherever, whenever I want."
"Yes, I know what it means."
"Most other men out there have smaller cocks than I do. You could find a protector more easily managed—maybe. Although, I got to tell you that protectors are established by the inches they have—and not just in height and wingspan."
"I'll stick here, please," Leonard answered in a small voice.
"Tell me you want it again, then."
"I want it again," he said, with a huge sigh.
Having stroked himself to full erection, and slowly rolling a Trojan Magnum on his cock, with Leonard shuddering at the sound of it snapping in place, Phil moved to the bunk and slid in on top of Leonard, pressing Leonard's legs apart with his knees. Leonard whimpered, closed his eyes, and grabbed up gobs of prison blanket, as Phil put a beefy forearm under Leonard's belly and brought the young man up to his knees.
He turned Leonard's buttocks toward the light coming in from the side of the bunk and spread the young man's butt cheeks to view his previous handiwork. He always enjoyed seeing the gaping hole he'd reamed for a first time. Sorry I don't have a camera to record this, he thought. Turning the buttocks back into place, as Leonard groaned and whimpered in anticipation, Phil positioned his hips over the young man's buttocks and let the bulb of his cock rest at the entrance, moving it around to rim Leonard's hole, disengaging to run the underside of his hard cock up the young man's crack and rubbing across the hole, before returning to rimming him, listening to Leonard's heavy panting.
This was Phil's favorite time of the foreplay. Not the first time, but the second. Teasing the hole with his cock head, his partner knowing now, as he didn't the first time, what was to come.
"Please, please," Leonard whined, his body shuddering at the rim play.
Phil didn't know what Leonard meant by the "please," and he didn't care.
The slide inside was easier for Phil now, with the hole still gaping from having been reamed within the hour. But the soreness of having taken someone Phil's size for the first time, didn't make the second time any less painful for Leonard—at least initially, before he accepted his fate and relaxed his body.
"You OK Lenny? You taking it OK?"
"Yes, OK," Leonard answered through clinched teeth. It wasn't OK, but it would have to be OK—and maybe in time it even would be good.
With a grunt, Phil entered him deep and immediately started pumping hard, muttering, "There's no easy way for you to get accustomed to this."