Prison Boy Training By Jon Hold Copyright© 2016 by the author Jonhold@earthlink.net
Chapter 1
He was almost 18, convicted and sentenced as an adult for a crime committed by a friend... ex-friend. And now he was belly down on a prison gym bench with a bloody nose and his cell-mate-to-be riding his butt. Not interested in the boys protestations or rights, the huge, burly man had bitch-slapped the protesting boy until the boy was bent over, taking the mans brutally large cock in his blood slickened boy pussy. The man was riding the boy hard and fast, knowing that by putting on this public display of ownership he was helping the boy avoid being raped by a long string of horny inmates. In-his-ass-mates that is! Angry, in pain, the boy had no choice but to submit to the mans demands.
It all started at a drunken High School bash. Randy, popular, seventeen, good-looking, good-family, good-money (and lots of it). A friend, playfully got him really, really drunk. Puking, pissing in your pants, passing out drunk. The last thing he remembered was Todd saying he was going to take him home. He was woken up in the front seat of a stolen car by a cop. A not very friendly nor amused cop. He was locked up in Juvenile Hall, with a judge that was not willing to allow bail, waiting for his court date. He appeared in court with his families lawyer, his families really good lawyer. The Judge was having none of it! He said that he was sick and tired of rich teenage brats doing as they pleased and he was going to send a message to the community about the end of young criminals getting little or no punishment. He didn't want to "hear excuses", he tried Randy as an adult and convicted him of aggravated auto theft, and then sentenced him to the maximum allowable sentence, three years in the State Prison.
He never even went back to Juvenile Hall, but was taken from the courthouse directly to durance vile. The guards let him know on no uncertain terms that he was not going to enjoy his time in their lockup. Three guards took him into a small tiled room with a big central drain, stripped him naked, cut ALL the hair off his body and did a DEEP body search for "contraband". In the process they handled him, happily, with unnecessary roughness that left his tits red and deeply bruised. His butt cheeks were red from being spanked while they used a garden hose to flush any hidden drugs or weapons out of his guts. Three times. Stuffing a big butt plug in his ass, a bigger one each time to hold the water inside him until he was cramping hard enough to expel the ever larger enema's in hard streams. Each time they held him down in his own shitty water with their boots while they beat his ass with their belts for, "messing up their floor" and for "making the worst damn stink that they'd ever smelled." Then they dressed him in old, worn out prison clothes with multiple tears and holes that showed pretty much everything the "young punk" had. Especially since he only had the raggedy bottoms and a t-shirt two sizes too small with no underwear at all. Then they turned the new meat out into the general population.
A population of hard worked inmates who's sole entertainment was fucking the weak. When he was released into the "community room" and the guards had left, he became aware that he was the center of attention. The very lustful attention of over a hundred sex-starved stallions and the boys who were forced to bottom for them, though, truth said, some of the bottoms didn't take much forcing.
After ten minutes of staring a huge, burly, muscle freak got up from his chair and walked over to the boy. "Come with me!" He demanded.
Randy had barely moved his lips to say, "Fuck You!" when the big man moved so fast that Randy never saw the fist coming that split his lip, bloodied his nose and took the fight right out of him. The slender boy had never been struck before in his entire life—by anyone. He was totally stunned.
The man took him by the neck with an iron hard grip and marched him over to a bench bolted to the floor. The spectators on the bench got up and quickly moved back into the crowd to get the hell out of the big mans way. Digger ripped the rotten rags off of the boy and pushed him face down on the bench, telling him that unless he really wanted another punch in the face he'd damn well better not move until told to do so.
Poking a finger into the trembling youth's spank reddened behind, Digger said, "I see the guards have started warming you up." With that he stepped over the bench and sat down on the boys muscled back and started smacking his already red butt cheeks with both hands, one cheek after the other until the boy was begging him to stop. He got up off his victim saying, "OK, I'll stop. Of course, asking me to stop spanking you is the same as asking me to fuck you! That what you're doing?"
Randy twisted his head around and there was the man, standing between his legs with a huge erection sticking down the leg of his pants. He gasped and told the man there was no way he was going to let anyone fuck him.
Digger just shook his head as a comment on the kids inability to learn quickly. Resigned to his fate Digger sat back down on the boys back, with his whole weight this time, focusing the boys attention on trying to breath. Sighing, he went back to his rhythmic spanking of the youths bright red ass. Eventually the kid finally broke, long after any of the bets placed on his resistance were surpassed, much to Diggers delight. His bet had been that the boy would last longer than ANY of the bets placed against him. It took the kid another ten minutes of punishment to discover the proper submission protocol, "Sir. Will you please fuck this worthless nothing in the ass, Sir." Only then did the big man take off his pants and rape the now submissive, even if not exactly willing, boy.
When he was done, and had rested up a bit, the big man put his pants back on, took the still crying boy by the neck and frog-marched him back to his cell. He told the sissy faggot waiting there to get the hell out.
"Where am I supposed to go?"
"I don't give a shit. Just not here and never come back in less I tell you different."
The little queen gave Randy a hate-filled look but didn't move until Digger slapped the crap out of him. He ran out of the cell holding his cheek and glaring at Randy as if it were all his doing. Randy didn't have a clue what the hell was going on, with himself or anyone else! Digger clued him in. He pushed the boy against the wall and belted him a good one in the gut. "You paying attention now?"
Gasping for breath, Randy wheezed out, "Yes. Sir. I'm listening."
Chapter 2
Randy's introduction to prison life was harsh. Learning to live in prison even harsher.
He quickly learned that his new master, Digger, was really high in the "Do Not Fuck With" prison hierarchy. He also quickly learned to not get very far away from his new `Master'. Being Digger's boy made him highly desirable commodity. Stealing him and using him would gain the perpetrator a real move up in status. Digger would be no longer on top or as highly respected if someone could steal is boy from him. Randy's one experience with that taught him the value of being Digger's boy, and the value of protecting his "owner".
Digger was busy talking with several other high-ranked prisoners and didn't notice when Randy decided he wanted a drink of water. The bubbler was just around the corner of "C" Block so he ducked around the corner, right into the arms of three young champions just itching to make their place in the sun. They were pretty much on their way to doing that when Digger came around the corner.
Steel was released from maximum-security isolation four days after digger had claimed his new boy. His new boy was not looking very happy, had Two Black Eyes, a very red butt, and acted like a mouse trapped by a large and mean cat. Digger put the new boy's nose in the corner and asked him to please move without permission so they could beat him again. Only this time he wouldn't be working by Himself. Because Steel just loved working a boy over... real good.
Digger and Steel sat on the lower bunks and put their heads close together so they could talk without being overheard.
"What's with the new kid, Digger?"
"Ahhhh, you know, the usual bullshit. From what I hear the kid got a pretty bad deal in court. Then the front end crew worked him over real good. Then they turned him out into the general population—wearing nothing but a couple of old rags. Looked like the boys were gonna rape him until the cold, dead body fell apart. So I... "
"...picked up another stray. Ain't you never gonna learn, Digger?"
"I'm tellin' ya Steel, this is a good one. I think he might end up being the best we've ever trained. I'm tellin ya, Steel, this boy's got real potential. We get him trained right, one of them old San Francisco queers `ill pay a fortune for him. We're gonna need some cash when we get out of here. Right?"
Text for Dining Room d'Fight:
A big, ugly bruiser with swollen knuckles on both hands and a nose that looked like it had been remodeled by a street roller, started taunting Steel and calling him a "chicken-shit little prick". Steel started to get up. In a command voice no one in the prison system had ever heard before, Randy got up and said, "Steel! Sit Down!" Startled, Steel sat down. Randy turned to the ugly bruiser and in a nancy, effeminate, prison bottom boy voice (that NO ONE, in or out of prison had ever heard him use before), he said, "Oooh. The big bad man gonna pick on the big man because he's afraid of the real chicken-shit little prick?"
Enraged Mr. low IQ turned and closed with the lightweight little faggot. When he got close Randy took a quick step forward, his open right hand slapped his attacker in the chest, twirled... and was standing quietly behind the big man. A sort of startled look on his face, our bad guy looked down at his chest, wheezed, turned sort of purple colored, and fell like a big tree that had just been cut down, smashing his face into the concrete floor when he finally landed. Randy sashayed back over to his chair just as the guards showed up. They examined the prostrate man and one guard said, "He's dead!"
Randy shook his head and got up. Asking one of the guards to move, he took off the mans right boot, made a large deal about keeping the mans filthy sock as far away from himself as possible before dropping it on the floor. Two, two-fingered slaps to the man's arched instep and the man started, with an explosive shudder, to breathe again.
The cops hauled the "fighter" away and Randy spent the night in solitary and got the best sleep he'd had since his two men started pestering him all the time.
Steel and Digger and Steel and Steel and... tried to find out what exactly had happened and all Randy would say was, "...looked like a heart attack to me." The third night after the "incident", Steel started spanking the hell out of Randy's bottom, demanding a better answer. Digger told Steel to lay off and drop it.
Steel stopped spanking, but kept his boy across his knee. "Why'd you do it? Take a risk of spending the rest of your life in State Prison?"
"The asshole was fucking with one of my men."
After he thought about that for a while, Steel looked over at Digger, "Remind me to never bitch-slap you when he's around."
Digger thought for a few seconds, "Yeah. Sounds fair to me. You cover my ass, I'll cover yours. You think he can take both of us?"
Steel grinned, "What say we not try to find out."
They shook hands. Nothing really changed in the cell after that. Randy got seriously fucked that evening just like always.
Out of the cell all three were given more respect, and a wider berth. The asshole ended up in the State Maximum Security Prison under the three strikes law for aggravated assault charges. Randy got his brains fucked out by his roomies the day the asshole was shipped off to his new home. Randy did his best to aid and abet his men in their self designated task.
Chapter 3
Digger managed to talk the Warden into having the three cellmates released on the same day. They walked out of the gate together, Steel holding Randy's hand. Digger and Steel headed for the bus stop where they would be able to start spending the munificent twenty dollars the State had so grandiosely showered upon them. They had split Randy's money between them, anything their boy wanted, he could come to them for, that's the way it had always been and that's the way it was always going to be. There was a taxi waiting at the bus stop. Randy dragged Steel over to it and opened the back door, "Come on, Digger, get in first" he called out. Digger and Steel looked at him, Steel gripping the boys hand hard enough to express his unhappiness to a boy who was spending money they didn't have. "How do you think we're going to pay for a cab?" Hissed Steel.
The cab's already paid for, I charged it to my Dad's company." Randy said, proudly having provided transportation, taking care of his Masters without them having to ask. A little rattled because they didn't seem to like the idea.
"Oh! So now we owe your Dad for his `favor'", Digger growled, obviously unhappy.
"No! I inherited 40% of the company when I turned 18. So I was spending MY money. But, I can pay for it with a credit card if you want me to, or cash..." he said, handing his wallet to Digger, who opened the wallet. He saw a bunch of plastic and quickly counted over a thousand dollars in cash. One five hundred dollar bill, five hundreds, and a bunch of fifties, twenties, tens, fives and even a few singles. He gave Randy a look that bespoke a long session discussing this `surprise'. A session that Randy was not likely to enjoy overmuch.
Randy got into the middle of the seat so that he would be between his Men.
Digger handed the wallet to Steel, who looked into it and said, "Holy Shit! What the Fuck!!!" After looking more closely at the contents of the wallet he asked, "Why are these credit cards all in metal colors?"
Randy looked at Digger for permission to answer the question. Digger just nodded. "Because they are all no-limit cards." Randy explained.
"Huh?"
"There's no limit on any of those cards, Master. I can walk into a bank, ask for a million dollars and the cashier will ask me to please wait in one of the private rooms while they get the money from the vault."
"Damn!" Steel said. "That's freakin' awesome!"
Digger just gave Randy another dirty look. Mentally counting up the ass whipping and/or discipline sessions his bottom boy was going to need to get him back into line.
Chapter 4
An hour later the taxi pulled up in the circular driveway in front of a white. 3 ½ story "Home" set on 5 ¾ landscaped acres in a (very) private neighborhood. They got out of the Taxi, Randy got a hundred dollar bill from Digger, who had put Randy's wallet into his back pocket, and tipped the driver, who promptly said, "Thank you very much, Sir!" and took off before anyone could change their mind.
"You always tip like that?" Steel asked incredulously.
"Yes. You guys want to see the house?"
They went into the house and were greeted by a butler, who took their jackets and baseball caps. "Welcome Home Mr. Randy... Gentlemen."
Randy lead them to an elevator that took them up to the attic, which had been converted into a playroom with a half-court basketball floor, arcade games, pinball machines, and a complete soda bar.
Then down one floor to servants quarters, mechanical rooms and, separated by a wall, guest quarters.
Down another floor to the "family rooms" where the bedrooms looked big enough to hold a convention in, with bathrooms sort of hard to believe actually existed.
Before they went down to the ground floor, Randy lead them out onto a covered verandah that overlooked an olympic sized swimming pool (Randy loved to swim and had regularly won medals and trophies since he was ten years old), the stables, a huge barn, truck garden, formal garden, with maze, and, in the distance, many trees of all sorts. Digger turned and looked directly at Randy, who's fucking house is this, Boy?
"Mine, Sir. I inherited it from my grandparents."
"NO SHIT?" popped out of Steel, who looked a little overwhelmed.
Randy grinned, the devils light in his eyes, "Would I shit you, Man of Steel?"
Digger popped him one in the back of his head and asked, seriously, "Are you shitting us, Boy?"
Looking contrite, Randy replied in a very soft voice, "No, Sir. I would never lie to either of you. Not ever!"
Steel, ever practical, asked, "If you've got all this money, why didn't your lawyers get you an appeal or something?"
"They did! But I told them not to do anything about it. By then I wanted to stay with you and Daddy Digger."
For the historical record, neither Digger nor Steel had anything to say. They just stared at this strange boy like he'd suddenly turned into a poisonous insect or reptile or time bomb or something...
"Sirs. May I please just talk to you one-to-one, no top/bottom, master/slave, man/boy or anything else like that. Please, Daddy Steel. Please Daddy Digger. Please?"
Digger and Steel looked at each other through eyes that had known each other for decades.
Digger turned and said, "Speak, Boy... uh, Randy."
"Thank you, Sirs. Look guys, I inherited a lot of money and property. I know how to make even more, and I have. Lots more" He walked over to a wall plate and touched it.
"Sir?"
"James, would you please come to me."
"On my way, Sir."
Digger looked at the doorway, "How can he find you in this place?"
"He's a butler. He always knows where HIS master is!"
The men had only seconds to think that over before the butler himself walked out onto the patio.
"Gentlemen," Randy made the introductions, "this is James Kallworthy. He worked for my grandparents since his father was the butler here and he was a little boy. Now he takes care of me and what has become my home. He is to be treated with respect at all times. He is the only one besides you two who has ever dared spank me."
"James, this is Samuel Evelyn Harley Sweet, known as Digger, he's Australian just in case you didn't hear his accent." Steel had the balls to laugh, Digger just said, "what the fuck?" wondering how his boy had discovered his full name, something even the authorities didn't know. "...And this upstanding member of the criminal element is Fred Sanford Caulkins, usually called Steel, probably because that's what his cock's made of. They took care of me in prison, cared for me, trained me and protected me from the guards and the other inmates. I need you to listen and be witness for me. Are you biddable?"
"Oh, I wouldn't think of restraining your revelations. I'm just ever so curious young master of mine!"
Randy winced, knowing that James had every intention of NEVER letting him forget that he'd told Digger and Steel that he was James' Master. "James, these men are my Masters, and will be as long as they choose to be. I'm asking them to join our family in this house, to be one of us. Some people would consider some of their training to be quite severe, even torture. I think of it as them trying, for my own good, to get my attention. James, my dearest and best friend, I truly love Digger and Steel. I love their bodies. I love their souls. I love every way they have sex with me, the way they talk to me, how patient they are training me, over and over until I finally learn the lesson so they can move on to the next lesson. I hope they never lose interest in training me, disciplining me and having me as their boy. I need your approval and support before I can totally give myself to them, James. I will do as you say."
He looked at his two masters,tears flowing down his face, "I DO love you. Both of you. I honor, respect, obey and love both of you and need you to be my Masters. My teachers, guides and disciplinarians. You haven't seen the basement yet, but it is big and I want to clean it out and, with your guidance and approval, build you a complete dungeon so that you can provide me with the best possible training. I'm not fighting you, either of you. James has been there for me since as far back as I can remember." Tears streaming down his face, Randy sobbed, totally terrified—and totally committed. "Before I can totally give myself to you I MUST have James' approval and permission. He loved me and guided me my whole life. I hope that you can understand. Please! Please understand."
Steel and Digger looked at each other. Steel nodded to Digger who took two steps and took the crying, sobbing, confused and terrified boy into his arms, holding him tight to his chest, then putting his chin protectively, lovingly covering the top of Randy's head, holding him tightly as if he were to never let the slight boy go. "James was your first Master, Boy. You have to accept that you have always needed a Master to match your, usually well hidden, need to serve and be submissive. To be strong and successful in life, as you have been, and will be, you need a place and a time where your Master, or Masters can take control and let you be free of the need to control yourself. James is, and will always be your first Master. Until he decides to pass you on, he remains your Master, and neither Steel nor myself would have it any other way. What we had in prison was a stopgap, a forced relationship of little permanent import or concern. We, both of us, are very proud that you wanted to be our boy. We are honored by the honor you give to us. Whatever James decides is best for you, will be! But, regardless of the outcome, Steel and I hope you will remain our friend, and love us as much as we have come love you."
Randy was openly crying into Diggers chest, trying to stifle the sounds he was making. James said, "Randy,... Digger, Steel and I need to talk. Go to your bedroom and take a shower when you wash your face. Get yourself under control. You needn't get dressed after your shower. You'll be called if any of us need you.
"Yes, Sir." the crying boy said, disengaging himself from Diggers embrace. "Thank you, Digger." Looking to the last man in the room, his beloved happy friend and master, Steel, He just smiled before leaving, tears unashamedly streaming down his cheeks.
Chapter 5
Randy was clean, naked, and curled up in the middle of his big bed, his barely audible buzzing snore indicating that he was in a good place and sound asleep when the three men walked quietly into the room. After looking at their snoozing boy, and loving the way he looked, gorgeous, well-built, muscular, sleeping like an innocent babe they each sat on the sleeping boys bed. James lightly ran a tender hand down the boys spine and then the same wandering hand caressed the tight little butt that James had lusted after since Randy had been a little boy. He had never before caressed the boys body. From the other side, Steel reached down and burrowed his hand between the tender thighs and velvet covered belly into the boys groin and started gently playing with the tiny toy he found there. Digger sat at the head of the bed, leaning against the headboard, just quietly watching as his boy woke up with a sleepy, happy smile on his face, "Hi, Steel." Glancing down he saw Steels arm disappearing down to where he was feeling so good.
"Gosh, Steel. I don't know if I like your hand on my weenie or your hand on my butt the best!"
Steel just grinned one of his evil grins, and held up his left hand where the mistaken boy could see it. Randy's eyes widened and he slowly turned his head, not knowing Who, or what, had hold of is butt.
"James!" His smile was radient as he rolled over and flowed into his beloved butlers arms. "You're touching me."
"Sorry, Master Randy."
"Thou art mine Master, as thou knowest mine Master. Thou art the architect of mine soul and the prize of my love. I have wanted thee, wanted to be thine, and forever wanted thee to want me, even as I knewest thou always didst love me. I am thine, my Father. Do with me what-so-everth thou please. My life is thine." Closing his eyes, the boy-child totally relaxed into James' arms, awaiting his beloved's choice, totally putting his life and fortune into his mans care.
Digger and Steele stood, acknowledging the true Master of their boy. The boy they had trained for him. Smiling, resigned, they touched James' shoulders, not disturbing his bond to his ward, his son, before quietly leaving the room. James woke his boy and showed him the love he had always craved, the love of a whole man for his beloved boy.
Chapter 6
Steel and Digger had managed to get as far as the State Highway and had their thumbs out. Looking like the Thugs they were, they weren't having any noteworthy success. Cars that did slow down just sped back up as soon as they could clearly see the wanna-be hitchhikers. They were pretty much ready to give up and start hiking when about sixty feet of shiny black limousine pulled up. The coachman got out and opened the back door. Randy, their erstwhile slave, got out, carrying a heavy black leather paddle. Walking straight up to his Masters he grinned a totally power-filled and gleefully evil grin. "Dad says that I'm to beat your butts until you get in the car and come home. Who wants to be first?"
Hands clenched like claws, Digger headed for the somehow bigger than real boy. Steel took his arm and shook his head "NO!". When Digger had calmed down enough Steel guided him into the back of the Limo and then got in himself. Randy, grinning at the coachman, a playmate of his childhood, kissed him and handed the paddle to him. "Here, keep this. I don't want them using it on me! They grinned at each other and Randy got a quick swat on his butt when he turned and dove into the back seat. Buddy carefully closed the door, after tossing the paddle into the back. There was no way he was taking that thing up front where his Dad could get hold of it. Better Randy's butt than his. Besides, he still owed Randy a few paybacks. When he slid into his seat the chauffeur, his father, smiled at him, "That's OK, Son. I've got one of those of my own."
Buddy decided to be very, very good, at least until his father wasn't thinking about using that paddle on his tender young butt!
Meanwhile, in the rear compartment, Randy was happily being stripped naked by men that he loved and respected, while using the intercom to ask Buddy's dad to please take the long way home...
Prison Boy Training Notes
Randy
Cop
Judge
Guard
Inmates
Digger
Steel
Text for dining room d'fight:
A big, ugly bruiser with swollen knuckles on both hands and a nose that looked like it had been remodeled by a street roller, started taunting Steel and calling him a "chicken-shit little prick". Steel started to get up. In a command voice no one in the prison system had ever heard before, Randy got up and said, "Steel! Sit Down!" Startled, Steel sat down. Randy turned to the ugly bruiser and in a nancy, effeminate, prison bottom boy voice (that NO ONE, in or out of prison had ever heard him use before), he said, "Oooh. The big bad man gonna pick on the big man because he's afraid of the real chicken-shit little prick?"
Enraged Mr. low IQ turned and closed with the lightweight little faggot. When he got close Randy took a quick step forward, his open right hand slapped his attacker in the chest, twirled... and was standing quietly behind the big man. A sort of startled look on his face, our antihero looked down at his chest, wheezed, turned sort of purple colored, and fell like a big tree that had just been cut down, smashing his face into the concrete floor when he finally landed. Randy sashayed back over to his chair just as the guards showed up. They examined the prostrate man and one guard said, "He's dead!"
Randy shook his head and got up. Asking one of the guards to move, he took off the mans right boot, made a large deal about keeping the mans filthy sock as far away from himself as possible before dropping it on the floor. Two, two-fingered slaps the the instep and the man started breathing again.
The cops hauled the "fighter" away and Randy spent the night in solitary and got the best sleep he'd had since his two men started pestering him all the time.
Steel and Digger and Steel and Steel and... tried to find out what exactly had happened and all Randy would say was, "...looked like a heart attack to me." The third night after the "incident", Steel started spanking the hell out of Randy's bottom, demanding a better answer. Digger told Steel to lay off and drop it.
Steel stopped spanking, but kept his boy across his knee. "Why'd you do it? Take a risk of spending the rest of your life in State Prison?"
"The asshole was fucking with one of my men."
After he thought about that for a while, Steel looked over at Digger, "Remind me to never bitch-slap you when he's around."
Digger thought for a few seconds, "Yeah. Sounds fair to me. You cover my ass, I'll cover yours. You think he can take both of us?"
Steel grinned, "What say we not try to find out."
They shook hands. Nothing changed in the cell after that. Randy got seriously fucked that evening.
Out of the cell all three were given more respect, and a wider berth. The asshole ended up in the State Prison under the three strikes law for aggravated assault charges. Randy got his brains fucked out by his roomies the day the asshole was shipped off to his new home. He did his best to aid and abet his men in their self designated task.
Every child in America should be acquainted with his own country. He should read books that furnish him with ideas that will be useful to him in life and practice. As soon as he opens his lips, he should rehearse the history of his own country.
---Noah Webster