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.”
Leonard writhed under him, with Phil covering his mouth to reduce the noise level, until Phil had established a steady rhythm and then, resigned and pleasure beginning to fight with the pain, Leonard settled down, reached under his belly, and began to stroke himself to completion.
Finished and going up on his knees, Leonard sprawled under him and moaning, Phil pulled a piece of chalk out of a crevice at the end of the bunk and leaned over Leonard’s gasping body as Leonard followed his movement with his eyes, not knowing how soon Phil would want to be inside him again. Phil reached over to the wall the bunk was pushed into and added two stroke marks to three rows of marks, marked off in fives, that stretched the length of the bunk.
When first seeing those, Leonard had thought that Phil was counting the days he’d been in the prison cell. That wasn’t at all what Phil was counting.
“You OK, Lenny? You OK with it?”
“Yeah, I’m OK,” Leonard answered through a whimper.
Phil palmed the young man’s butt cheeks and spread them again. He leaned down and blew on the hole, which elicited a moan from Leonard and caused the hole to open like the lens of a camera for him, ready for his cock again. He’d get around to that in a bit. If you’re breaking fresh meat in in this prison, you needed to get it done fast. Yeah, he thought, a shot like that would made a good ending for a video.
* * * *
“I may have found a job for you, Juan.”
“I hope so. I’m desperate, Mr. Lindstrom,” the young Hispanic man answered.
“As I understand it, you have to find something within the next two weeks or go back to Woodward to serve out your sentence.”
“Yes, sir, that’s right. I’ll take anything at this point.”
“That’s good to hear. There are two functions to the job. It’s in a auto repair garage and you’ve been trained for that, haven’t you?”
“Yes, sir. At Woodward. I started about the time you left the prison. You were head of the auto repair studies, weren’t you?”
“Yes at the end.”
“And what’s the other part of the job?”
“What were you in for?” Phil asked, leaning across the desk that was in his combination office and bedroom in the work program half-way house. He’d been in a position of authority and trust when he’d left the prison for this program himself, so he had been given a job to place other guys in the program in jobs. Auto mechanics had been the skill he himself had mastered while in prison, so he got young men like Juan here, who also studied auto mechanics, to try to place.
“Ah, solicitation--prostitution,” Juan answered.
“You were a rent boy, right?”
The young Hispanic hesitated, but he finally answered in the affirmative. “But I don’t understand what . . .”
Phil was giving him a hard look.
“Oh, the guy with the job wants to fuck me.” Juan’s voice made clear that he was miserable that his crime had been raised.
“He wants to fuck whoever he gives the job to, Juan. And not just once. He wants a bedmate as well as a mechanic. I’ve shown him your photo and your rap sheet, along with those of some other guys here needing jobs. He’s interested in you. You’ve been selected over others. We can’t find employers without revealing what the potential employee’s crime was. This employer asked for a young prostitute when I talked to him--one that would take his cock along with the job.”
“But this is supposed to be a rehab program; I didn’t think it was supposed to send me back to what got me in prison to begin with.” It came out of Juan in a whine.
“Life is tough, Juan. We have to build on the skills we have. Maybe when you have proved yourself as a mechanic, you can trade for a job without other strings attached. But you’re within two weeks of going back in the slammer for another year. Which will it be? This or the prison? I have other guys I can offer this job to if you don’t take it.”
“This, I guess,” Juan said, in a whisper. “Where and when do I have to go?”
“It’s not sure yet. The employer wants to see what he’ll be getting--not the auto mechanics part; the other part.”
“He wants to fuck me before he decides?”
“He wants some form of evidence. A video of you will do, he says.”
“He wants me to do a solo? On a video. How do I get a video done.”
“We can do it right here, Juan. There’s a bed over there, and, if you’ll look over there and there, you’ll see video cameras set up. We’ll take the film right here. But not just a solo, Juan. A solo will be nice, but he wants a film of another guy fucking you.” Phil was unbuttoning his shirt.
“You? Here?” Juan asked, almost hyperventilating because Phil had stood up from the desk, unzipped his fly, and fished out a monster cock.
“No time like here and the present,” Phil said cheerily. “Strip and go over to the bed, please. I’ve got to get the cameras turned on.”
Juan was small of stature and Phil was large boned, especially the bone between his thighs. Juan had been a prostitute, though, and was nailed regularly in prison, so he took it like a champ and gave the camera a good show.
After a solo act completed with an ejaculation, Phil planted himself on his back on the bed, and Juan climbed onto his midsection, pointed toward Phil’s feet, and rode Phil’s cock until Phil decided that the film needed some spice. First, he pushed Juan’s torso down between his legs, laced his legs under Juan’s arms to hold them out and immobile and locked his ankles behind Juan’s neck. At Phil’s command Juan hooked his ankles onto Phil’s shoulders on either side, Phil held Juan’s legs close into his side, and then he subjected Juan to a rocking fuck, raising his torso a bit and rocking back and forth, controlling the stroking of his cock in Juan’s ass.
This was not the time for Juan to raise any objections. He reverted his thoughts and actions back to his earlier life. He had been a prostitute; he was a prostitute. Nobody was fooled that the system would give him a real opportunity to change. He gave Phil and the cameras whatever they wanted.
After several minutes of this, Phil changed the position, while keeping his cock in Juan’s channel. He pulled Juan’s torso up to where it lay on Phil’s chest. He put Juan into a full Nelson hold, with Juan’s fists pressed into the coverlet on the bed, and then he laced his legs through Juan’s and lifted and spread them. One of the cameras got a straight shot of the thick root of Phil’s cock, as he stroked deep inside Juan’s hole and Juan writhed and groaned at the deep fuck.
When Phil was ready to come, he pushed Juan down to the floor at the end of the bed, sat on the end, grabbed Juan’s head, and held it in place as he jacked off on Juan’s face. He made Juan clean off the cock with his mouth--and turn his head toward the camera, with Phil cupping his chin, and smile for the world out there.
“There, I think that will get you the job,” Phil said, as he looked down at Juan, who had collapsed in a heap onto the floor at the end of the bed.
Later, Phil retrieved the film from the cameras and spent some time at his computer desk splicing up two copies of a single film. “Good enough for the Internet,” he muttered, which was good because, although one copy was going to the auto garage owner, another one was going on a subscription site Phil had opened up on the Internet as soon as he’d gotten out of prison.
Just as he thought would be the case, the garage owner loved the video--and, ultimately, loved having Juan in his bed. He passed on his appreciation to some of his friends, and when Phil left the half-way house to reopen his jewelry business, he received an award for the number of men in the program he’d managed to place. No one, though, remarked how many of the men he placed had been in prison for prostitution.
* * * *
Phil looked the young man standing before him across the jewelry story counter over from head to toe. He looked down on his luck, but he also looked presentable. He sported a ring in his eyebrow and a few tattoos were in view, but there were clients who would like that--especially if there were more piercings and tattoos. A slim build, but the mounding in his T-shirt indicated sufficient muscling. He did look desperate.
“I’m not a pawn shop, son,” Phil said. He made sure he said that these days and watched the follow up. He didn’t want to get trapped in a sting again.
“No, I want to sell it outright.”
“I couldn’t give you anything near its worth if the deal is just for the necklace.”
“I don’t understand.”
“How desperate are you? I could ask you if you stole this piece and even if you said no, I could give you maybe $60 for it. If you throw in something else of value to me that costs nothing for you and that you have more of, I could just not ask you where you got this and I could give you $900 for it.”
“$900? What else could I throw in?”
“Well, you could come back to the back and I’d provide a meal--and let you take a shower, and I’d even wash your clothes for you. You could have a lie down and then I would pay you $900 and take this necklace from you.”
The young man gave Phil a sharp look. “You want me to lie down for you. You want to fuck me, don’t you?”
“What did you do for your supper last night?” Phil asked. “Was it worth as much as I would pay you? You take your position right across the street from here, son. I see you getting in men’s cars. What would you be doing for me that you don’t do for strangers in cars whenever you can?”
“$900, eh?” the young man said, seriously contemplating the deal now. “For a fuck.”
“For whatever I want in a three-hour span, starting with the meal. And an hour of it on camera.”
As soon as Phil had been released from the work program, he’d come back and reopened the jewelry store. It wasn’t the store, though, that was making the big profit. There was a small apartment in the back of the store, and Phil had set it up as a film studio with equipment to enable him to create films and to put them up on his subscription Web site. He made three times the money from that operation now than he made from the store front.
“I don’t know,” the young man said.
“You’ll be done before your customer rush tonight out on the street, and how much do you think you’ll make from that?--and you’d still have this necklace to unload. It feels hot to me. I wonder how hot it is and how much you’d like to be arrested for prostitution and have this found in your possession. Tell you what, I’ll up it to $1,000, but you’ll have to sign a release for the film, and, as I said, when the clock starts ticking on the deal, it will be three hours I have to do as I want with you.”
* * * *
The young man, who said his name was Jack, to which Phil said, “OK, if you say so,” sat, naked, at the table, a three-quarters-finished peanut butter-and-jelly sandwich on a plate in front of him. His chair was pulled back from the table and he was slouching down in the chair, his arms thrown back over the chair back, and his head, likewise, arched back. Phil was sitting in a chair close to and at the side of him, watching the expression on the young man’s face as he slowly beat off Jack’s cock with his left hand. His right hand was buried between Jack’s thighs, with two fingers in Jack’s ass.
Phil was quite pleased with the young man. He wasn’t muscle bound by any means, but he had a good body, he was attractive, the red hair on his head and bush were an interesting red, and he did have more tattoos and piercings: little bar bells in his nipples and a colorful tattoo covering a shoulder and his right pec.
The young man gave a few jerks, told Phil he is was going to come, and then did so, his spunk arcing up and landing on the remnants of his peanut butter sandwich.
“Take a shower and clean yourself out,” Phil said. He watched the young man pad toward the bathroom, admiring the curve of his buttocks. It would look good on film.
“Hey, whatyer’ doin’,” Jack said when, naked, Phil slipped into the shower with him.
“I paid for three hours of whatever I want,” the older man said. “Now, down on your knees and suck me off.”
“Wowser,” the young man exclaimed from below Phil’s chest. “You didn’t tell me what you’re packing. You think you’re going to nail me with this?”
“I know I am. You signed a waiver already, and I don’t think you’re leaving anytime soon. I took your clothes. Now, shut the fuck up and suck.”
Several minutes later, Jack exclaimed. “Hey what now? What are you . . . oh, shit. Oh FUCK!”
That’s what Phil did, he bent the young man over at his waist, demanding that he grab his ankles with his fists, and then fucked him from behind under the cascading water from the shower. Jack was an experienced prostitute. After the first bit of complaining Phil was too big for him, Phil no longer was too big for him and just stood stationary, while Jack moved his ass, fucking himself on the monster cock.
Phil got more artistic on the bed, under the lights and the quiet whirring of the cameras. Phil fucked Jack from behind, both of them on their knees on the bed, with Jack’s legs streaming behind Phil’s; Phil embracing Jack’s torso from behind, one hand cupping Jack’s chin and arching the young man’s head back into the hollow of Phil’s shoulder, where their lips occasionally could meet, and Phil’s other hand cupping, fondling, and squeezing Jack’s balls, while Jack slowly jacked himself off. When the fucking became frenzied, Phil pushed Jack down, shoulders and cheek to the bed coverlet, grabbed his hips, and pistoned his channel hard to a shared ejaculation.
A second go had them both on their butts, their torsos propped up on the elbows, the two facing each other, while their pelvises met in the middle, their legs streaming around the other man’s hips, Jack’s butt cheeks resting on Phil’s upper thighs as, his cock buried in Jack’s ass, Phil thrust his cock forward rhythmically and Jack thrust his passage forward in synch to take the cock as deep as he could. Phil decided that this was one experienced street prostitute and that he’d have to sign him on for follow-up vids.
Later, Phil sat on the side of the bed, with Jack reclined in front of him, his hands on the floor and his legs streaming back around Phil’s hips, while Phil clutched the young man’s hips and pulled his ass channel on and off his cock.
Near the end of the three hours, Jack, exhausted, lay on his belly on the bed, his right leg stretched out straight behind him and his left leg bent and thrust out to the left. Phil had just come off his back, having covered him close and fucked him deep. Jack was panting softly and moaning almost inaudibly. Phil grabbed one of the video cameras and commanded, “Grab your cheeks with your hands and spread them. There, that’s nice.”
He filmed a close-up of Jack’s hole, reamed extra large for Phil’s specifications. That shot was becoming a signature closer for Phil’s Internet films.
Before he left, Jack signed for two more filming sessions, and after Jack left, Phil took the necklace to the hidden safe in the back of a bookshelf. As he figured it, the necklace was worth $5,000. Jack obviously had stolen it, as he didn’t have a clue what it was worth. Phil would have to be careful unloading it, though, and he probably wouldn’t get more than $3,000 for it on an out-of-state sale.
He moved on to splice together the various camera angles of his session with Jack so that he could get it up on the Internet by 11:00 p.m., the start of his clients’ favorite browsing time.
* * * *
“You’ve done very well in reaclimating, Phil,” his probation officer was saying.
Phil didn’t fully hear him. His eyes had gone to a swishy young man flouncing around the open-cubicle room the probation officers worked in. He seemed to be some sort of mail clerk. Phil had seen him in a gay bar on 4th Street, though--more than once. And he’d left with different guys--all obvious tops--each time. Phil wanted him for the movies. He’d make for variety, especially if he squealed when he was penetrated.
“Excuse me? What were you saying?” Phil asked.
“Your rehabilitation has gone well. A classic case of success. You came through your imprisonment well, have kept your nose clean, and are back running your jewelry store. It’s a breath of fresh air against so many other cases where a man has come out of prison a more hardened criminal than he went in.”
“Yes, I’m grateful for the system having brought me back on the path and rehabilitated me so well,” Phil said, his eyes still following the flighty young man around the vast room of shelf-high cubicle walls. His mind was planning how he would blackmail and fuck the mail clerk to the best advantage on a film for his Internet subscription site. Maybe in a side split, holding one of his legs straight up and showing his thick cock working in and out of his small hole, Phil thought. The clients would eat that up. But should he do it before or after he went up to northern New York to unload the necklace he had bought from Jack along with other pieces he had acquired on the sly?