DISCLAIMER
This story features heavy gay sex scenes in a fantasy world where prisoners are treated as slaves. Only proceeded if that's what you like and are allowed to read.
THE DOUBLE SURPRISE ENSLAVEMENT
Simon sat in the cafeteria, chewing on his lunch.
As the son of the governor, Simon knew that the inspection, which no other student knew of, was happening this very moment.
He had gotten Jimmy to place a bag of weed in Nathan's locker an hour ago, just as they had done for Cole a while back. The next surprise inspection was scheduled for this very moment, as his father, the governor, had informed him.
That nerd Nathan and his brilliance and industriousness were just putting Simon under too much pressure to do better in class.
Right now, Nathan was sitting by himself, eating with a book open next to him.
Three officers in blue uniforms entered the cafeteria, all eyes turning to them. So they didn't even wait until class started, thought Simon. The arrest was going to be a bigger spectacle then Cole's.
All hundred students stopped what they were doing and turned to the officers as they marched across the room.
"Nathan Smith?" said officer 1.
The small, pale boy brushed his smooth hair from his eyes. "Yes, Sir. How can I hel-"
The boy was struck by an electroshock stick, sending him to the ground. He pissed himself, trembling.
Simon jumped up and began filming with his phone before any of the other students got the same idea. He got as close to the arrest as possible without interfering. Other students started following his example.
"Nathan, you are hereby arrested."
The boy, laying on the ground, stared in shock at the man in uniform. "No, please, I didn't do anyth-"
Officer 2 placed a boot on Nathan's chest. "You were in class when that other boy was arrested a month ago, right? I remember you were the only one who didn't get up to make fun of him."
"Y-yes, but please, whatever it is, I didn't do any-"
Officer 2 removed his boot, pulled Nathan up off the floor and tore his shirt apart.
Meanwhile officer 1 said "This is the usual full arrest, but the governor wants to set an example, since this is the second arrest in this school in just a month. You will be treated less kindly than the last one."
Within seconds Nathan was submitted to the same procedure that Simon had seen on Cole not long ago.
The skinny boy was undressed and collared with a rope that served as a leash. His hands were tied to his ankles and his legs were spear by a shoulder wide bar.
Simon got a great shot of Nathan yelling in tears as he had to sit down on the butt plug, impaling his virgin hole. The plug was clearly adult sized, not accounting for teen offenders, of which Nathan was a particularly small example.
The little boy didn't stop whining about his innocence, but no one was about to help him.
Then he stopped crying all of the sudden – he almost smiled.
"Wait" he said, "it's my first offence. Cole had a dad already in prison, so he was judged right away, but I don't. I get a fair trial. I will turn out innocent, you will all see."
Simon cringed. He hadn't thought of that. If Nathan walked free, it was possible his involvement would be found out. This was bad. That nerd boy was way too happy for someone bound, naked and humiliated, crouching in his own piss.
Officer 1 shoved a gag into Nathan's mouth. The one that went too far down the throat so that it kept tickling the gag reflex.
Officer 2 said "No way, Nathan. The school wants to send a message to all drug users here. Your sentence has already been approved. You will not see a judge."
Simon grinned as the arrested boy yelled muffled screams of despair and coughed as he choked on the gag. Spit dripped from his mouth and mixed with the tears and snot as he gagged more and more violently, trying to talk despite the thing in his mouth.
Simon leaned in and asked an officer. "Excuse me, good man. What exactly is the sentence?"
"Let me see. The usual really. It says here: all personal possessions given away or destroyed. Everything created by him destroyed. All embarrassing personal information released. Just the usual as expected."
Officer 2 put a thick belt around Nathan's waist. "This is a new experimental device. If you are in a certain position, nothing happens. Otherwise you will receive shocks. Now, bend like that."
He shoved Nathan into a position with his ass out, his head raised and his back arched as far as humanly possible. The boy stared at the officer with watery eyes.
The detainee was led outside, waddling and wincing. Every time he dared to keep his beck arched and ass pushed out to the maximum, the belt shocked him.
Officer 3 who had said nothing up to this point, turned to Simon.
"You're the governor's son, aren't you?"
What could be the meaning of this? Simon was getting nervous. It was unusual to have three officers come to one arrest.
"Yes, I am. What is it you need?"
"Your father has told us he is concerned about you. Come with me."
Simon swallowed hard. Had his father learned about his weed smoking? Was he about to be enslaved?
The boy followed the officer with his head hanging low.
THE REUNION
Nathan went through the same process that Cole had gone through.
His name was now L106. He was hairless everywhere. The effects of the injections were setting in.
L106 was covered in streams of sweat, salivating heavily, had a painfully hard and leaking erection and was desperate for an orgasm that would never come.
The boy was pushed into a chamber and not, as he had expected, brought to the loading area.
As he lifted his head, he was struck by surprise. "Simon?"
At the other end of the room, Simon sat in a chair. He was clad in the same full body leather overall that all the officers here wore, but his head and face were uncovered. He didn't wear boots, letting his bare feet collect the filth of the facility's urine and cum-stained floor.
"Hello, Nathan. Wait, I mean L106." Simon chuckled. "My dad thought I was wasting my time in school when I should be out in the real world, training for my future career."
Simon got up and quickly stepped across the room. He collared the shocked L106 and bound the collar to the floor, forcing L106 to stand bent over. The overseer Simon gently stroked the prisoner's back and patted his bare, smooth ass almost lovingly.
"Can you guess why we're here? I'm the new guy, so I need to train. I'm going to test all the special procedures on you, before I'm getting to enjoy a job at the facility."
L106's mouth was pried open by a huge gun-like thing.
"I'm not only going to try all the regular stuff, but also special procedures."
The prisoner's teeth were melted away by a heavy laser. But Simon wasn't satisfied and injected a syringe into the boys tongue.
"Usually we let prisoners use their tongues, so they can give better blow jobs, but in special cases where we want them to be silent forever we disable their tongue. You'll just have to use the deepest parts of your throat to satisfy any guards who need to get off."
L106 wanted to break free and run – more than anything else. How could Simon be so cruel? But at least, it wasn't Simon's fault. Surely, if the boy knew that Nathan was innocent he would be less brutal.
Simon leaned in, his hand sliding into L106's butt crack. As an unlubricated finger poked the prisoner's asshole, Simon whispered in his ear.
"You know why I don't want you to ever speak again? So I can tell you this."
He leaned even closer and at the same time inserted a second finger. L106 was trembling from the stretching pain, but desperately wanted to know what Simon had to say.
"I didn't really like you much, so I had Jimmy put the weed in you locker."
With wide eyes, L106 screamed his lungs out, but Simon only laughed. The enslaved school boy struggled and clenched his sphincter, but this only amused the new guard in training and made him insert his finger further.
The prison boy tried to speak but his tongue was useless. Simon shoved a plug into the stretched ass. L106 screamed with the physical and emotional pain.
"And now another injection. You know, I always thought it was unfair that a used asshole stays a little bit stretched. Makes it less painful the next time, and where's the fun in that?"
He shot a syringe in the bend over L106.
"Luckily, this little thing will keep your anus tight. Even more so, it tightens the sphincter beyond its normal tightness, so that even a small dick will feel like a giant one."
Out of the blue Simon whipped his test subject with a thin paddle on ass and back, striking glowing red lines into the slim, helpless boy.
There was no way for L106 to calm down. His skin was getting sliced by the whipping, he was horny as hell and sweating all over. He would never speak again but knew a terrible secret that would save him. And the one guy who was responsible for it all, could do whatever he wanted to him.
Simon freed L106 from his collar allowing him to stand up straight.
"On your knees prisoner."
The sadistic boy pushed his test subjects head onto his feet and had him lick with his now otherwise useless tongue. L106 had to work his way up the leather uniform, kissing and licking every spot.
When he arrived at the top, almost standing straight up, Simon spit in his mouth and pushed him back down. The feet and uniform worship began again until Simon's filth stained feet had reached the acceptable level of cleanness.
L106 was ordered to stand still.
He was beginning to feel the effect of the sphincter-tightening. His hole was clenching all on its own. With the plug still in him it was getting more and more stinging.
Simon shot another injection into the sweating boy. Specifically his balls below the pulsing, leaking erection.
"This one is usually reserved for very difficult cases. It constricts the blood flow from your dick, so your erection isn't just permanently hard with some throbbing pain, but truly mind-bogglingly excruciating. You'll barely be able to touch it."
With that, Simon slapped the reddening, pulsating penis.
"Then it increases your pre-cum production, so you will drop cum like you're dropping tears right now. It's our personal lube factory, so we guards save on spit."
L106 was kicked in the legs from behind, sending him to the ground. Simon freed his dick from the leather pants. It was sweaty from being tugged away in the leather and hadn't been washed since the last gym class at school.
Simon rammed it down Nathan's throat with one quick push and held it in place by clutching L106's neck. The face fucked boy chocked and coughed violently, filling the room with the sound of his suffering. If anything had been in his stomach, he had vomited right there. His face turned red as his airflow was cut off. Simon released him just as his vision began to fade.
"We're going to have to work on that one. But now it's time to try out the piercing gun. I was thinking nipples, tongue, ears, nose and belly button. What do you think?"
L106's torment lasted until it was time for all prepared prisoner's to leave.
THE TRANSPORT
Simon led L106 on a chain into the cargo area.
"Here, my friend is where we will part ways, but not for long. There was one other prisoner who demands my attention. Have fun on your journey. See you soon."
L106 was kicked into line and chained up to another prisoner – a big, tall man with a beefy ass full of red whip marks. More man were chained up behind him, putting L106 somewhere in the middle of his particular line. The group was dragged into the nearest truck and drove off.
It was summer now and the heat inside the vehicle rose quickly. The man behind L106 was rubbing off on the boy's little ass, but didn't otherwise hurt him.
It wasn't long before the first big guy shoved his dick into a smaller one in front of him. As if on cue, the guy behind L106 began poking the little teen hole that Nathan couldn't help presenting. He had to keep his legs far apart to stand stable inside the truck as it took turns every now and then.
While Simon had removed the plug at some point, the feeling of tightness hadn't gone away. It was as if the boy was clenching as hard as humanly possible even when he relaxed as much as he could.
The man behind him found it almost impossible to get his dick in – almost. But eventually Nathan got fucked. Immediately he knew that he would have to muffle his screams or draw attention.
The line of prisoners shifted as more and more sex occurred, leaving a bit of space for Nathan to lean forward. The chain around his neck dragged his head to the huge ass in front of him.
As the dick from the man behind him found its way in and dry fucked his inhumanly tight hole, L106 knew that he could not contain the screams of pain.
He pressed his face into the butt cheeks before him but slipped off on the sweat and grease. His only option was to press his lips on the asshole directly.
Looking around he saw that he wasn't the only one doing so. It had to be a deliberate design. He briefly wondered how many other slave boys had done this.
However it wasn't as easy for him. The man in front of his face was really tall. L106 had to stand bent forward on his toes to reach the ass.
But the dick in his ass was too much and he couldn't help screaming. He was the loudest person in the truck by far. He had to do something else.
Since the man was so tall, Nathan leaned even more forward, not on his toes anymore. The huge, thick dick of the man in front was semi hard, hanging between the beefy ass cheeks with a pair of huge balls.
It was his only chance.
L106 hurt his neck reaching as far forward as he could and took the dick head in his mouth, sucking to keep it in. he drank all precum flowing into his mouth and ignored the sweat dripping on him from the man's crotch and ass crack.
He was relieved at how well it worked. The pain in his ass was more than he had ever bared or thought possible, but at least he was quiet. The dick in his mouth muffled his sobbing nicely.
This play continued for almost an hour.
All prisoners were desperate for a drink. The sweat and piss on the floor was so dense, that it formed a puddle throughout the truck.
As the truck stopped the men sighed collectively, but the door opened to reveal, not the facility, but an empty field.
L106 let go of the dick in his mouth, his lips and tongue sore beyond description. The dick in his guts popped out and he could feel his ass tighten back up almost instantly.
An overseer knocked on the truck wall. "Alright you lot, we're letting you have a drink. Out with all of you."
The prisoners were led to a nearby pond and took turns kneeling down to dunk their heads under water. It was wonderful. L106 filled his stomach with the refreshing liquid. He felt a thousand times better.
As he looked up, he saw that the truck had driven off without any of them returned.
Two overseers had stayed behind as well.
"The facility is half an hour away, by foot. If you can all make it in twenty, you will be spared an additional whipping. Now run. Chop chop."
The chains made it almost impossible to move fast, but the slaves tried their best, hopping and bumping into each other along the way.
L106's was so short that the chains dragged him up with every few steps, choking him over and over.
They didn't make it in time.
REUNION
Since L106 had already gone through the procedures that the facility offered, he got to wait them out, kneeling on the sidelines.
Before the sorting happened he was called into the office of the chief overseer. Simon was waiting for him.
"Bend over, L106."
Simon fucked the artificially tightened ass of his prisoner, enjoying the screams and tears he caused. Nathan had thought he could get used to it, but Simon fucked not like the man in the truck. He fucked mean, poking every corner of the little teen's insides, varying the speed and angle. Hammering away one moment, slowly sliding all the way in and put another moment.
"You know," he said between thrusts, "there was one loose end I had my dad fix for me. So in a minute when the sorting is over you're getting to see your companion. He's also tongue tied like you, just to make sure."
The door opened and an overseer pushed a boy inside. He was a processed prisoner, about L106's age.
Despite the pain and horror he had endured, the former boy Nathan was still shocked at what he saw.
Simon's best friend Jimmy was a prisoner. Why would he do this? L106 knew that Jimmy was part of Simon's schemes, but this was not the punishment he wanted. Simon was the one who should be punished.
"Hello Jimmy. Or should I say L155? Bet you didn't expect this, did you? Of course not."
Simon pulled out of L106 and dragged Jimmy in front of the still bent over boy.
The two sweating, erect, leaking, toothless, hairless, piss and cum dripping boys stared at each other, unable to communicate the horror they felt.
"Make out a little, I want to see you get along."
Simon pushed their heads together until they began Frenching. In the meantime he started fucking Jimmy. The virgin boy cried into Nathan's mouth.
"Never really thought about fucking you, Jimbo. But now that I can, why not? Nice ass, actually. Your hole isn't ultra-tightened yet, we'll have to fix that soon."
Simon's thrusts intensified until Jimmy broke the "kiss" and cried with loud sobs. The new overseer grabbed Jimmy's face, inserting his fingers into his mouth and spreading it to force the prisoner's head up and make his back arch nicely.
"You L106, lick my feet till I'm done with this one. Fuck, this is nice. I never thought my best friend could have such a nice ass, I need to share it with all my colleagues."
L106 crawled between Jimmy's legs - precum dripping onto his back – to get to Simon's feet. He worked his tongue into the space between the toes, his tip touching the ground underneath.
L106 was terrified and felt sorry for Jimmy, but he was also glad that he was not the one getting fucked this time. The abused boy above him didn't stop screaming and whining, completely unaccustomed to the pain of a dry dick entering his teen hole.
"Since you're both going to be category A prisoners, you could expect a relatively nice life, with office work and free time. But I asked if I could keep you, and guess what: they said yes."
Jimmy groaned even louder between his tormented grunts.
"I was going to make it a surprise but I...uh, ah!"
Simon came into the humiliated former best friend's ass. He shivered with pleasure as the prisoners tears dropped on L106's ass, who was still licking the bare feet before him.
The overseer pulled out, thick cum streaks running slowly out of the sore ass. L106's head was struck by a foot, and he was pulled up by the neck.
"Lick it all up."
L106 sucked in all the overflowing cum and buried his face in the sweaty, reddened ass cheeks of the boy who had helped getting him arrested. He worked his tongue into the hole to get all cum he could find, afraid of Simon's wrath if he missed a drop.
Afterwards both naked boys were allowed to drink water from a bucket, which they did greedily even though it was clearly mixed with piss.
The prisoners knelt in front of Simon who was relaxing on a chair, his legs spread.
"One foot each, lick it clean. The floor in here is quite filthy. But what else is to be expected since you slaves can't control your bladder or cum flow."
He took a sip from a can while the two humiliated boys went to work.
"I don't like calling you numbers. How about you L106 are from now on Asslicker and you Jimbo are Faggot. Yeah, I like the sound of that."
The overseer grabbed a paddle and began softly slapping the backs and asses of the boys cleaning his feet.
"As you know, when you're arrested the worst secrets we can find about you are made public. But I thought both of you were much too tame. Asslicker, you had a few interesting sites in your browser history, but I took the liberty to add some more controversial pornography and online orders for sex toys."
The slapping turned harder and less focused.
"For you Faggot, I wrote a diary on your computer. I know you're perfectly straight, but the other students don't. So I wrote page after page of how much you're in love with our fat, hairy, ugly gym teacher."
Both boys were trembling as they cried, thinking about how their former peers were thinking about them now and how their own families must see them in retrospect. They would forever be Simon's property.
THE TRAINING
Nathan and Jim (or rather, Asslicker and Faggot) went through a training program at the facility designed for prisoners used for sex. It was a new program that the governor had recently introduced.
A boy was strapped to the floor in crouching position, his knees bent. A dildo was shoved up his ass and activated, as it was on top of a drill that hammered the dildo in and out of the prisoner's hole.
A second such device was lowered from the ceiling and shoved into the prisoner's mouth, his head secured with metal bars. Slaves here learned quickly to get rid of their gag reflex, as their guts were attacked from both sides by merciless machines.
Metal bars held them in place, teaching them to arch their backs and keeping their legs spread.
This procedure was repeated for an hour at a time on five occasions daily. The rest of the day was spent working out to add mass in a lean bulk, leading to prisoners looking like fitness models, except for their toothless mouths and bold heads.
These types of prisoner were usually housed with category A but Simon arranged for Asslicker and Faggot to be caged with the category C inmates.
In the evenings when the other sex trained prisoners had spare time, the two boys served Simon. Either they licked his feet or shared the duties of rimming his ass and sucking his dick. On most days the overseer also liked to watch the boys make out and caress each other. If there was no transgression for which they could be punished, they were punished anyway.
Even though Asslicker and Faggot couldn't speak, they felt that they became a sort of friend to each other. Two boys united in their fear of Simon.
Both were often shared with the other overseers, but few fucked as mean as only Simon could.
The day neared when the training would be over and the boys would be transferred to another job.
AT HOME
The two boys were in Simon's dark trunk, driving to a location they didn't know. They were tied in a 69 position, but with their heads between the other boy's thighs, ass on mouth.
Asslicker started rimming. He had done this so many times in the last week, that it had become a comforting reflex. See a hole – lick the hole.
Even though Faggot was straight, he reciprocated. They were friends after all, in a way. And there was nothing else to do for the heavily sweating boys, in the trunk that smelled more and more from the piss that dripped out of them.
As they arrived, Simon opened the trunk and untied them, only to put collars on their necks. Just tight enough to keep them chocked a little bit.
The overseer was wearing casual clothing: a tank top and sweatpants. His hair was nicely arranged with a fair amount of product.
"Look you two, I'm having guests over and I want you to be on your best behavior. You're going to serve beer and snacks and entertain my guests with anything they ask of you. Now, let's go."
Apparently, they were at Simon's house.
The guests he had mentioned was the entire who-is-who of the school's student body. Both boys and girls. The chuckled madly as the prisoners entered. Asslicker recognized most of them, some he had called friends, but all had been popular for what he remembered. Many pictures were taken.
Asslicker was introduced to the hollering crowd and sent to the pole to dance, that was prepared in the expensively furnished party room. He had never learned how to dance, but after enough kicks and slaps, he learned how to move his hips to the audience's satisfaction.
Faggot kissed the feet, shoes, socks and crotches of his former classmates, teammates, stoner buddies and best friends, while they casually talked about what was going on at school.
The sweating, precum dripping, dancing Asslicker was used by Simon to demonstrate a proper punishment, leaving dozens of red lines on his ass cheeks before he was sent back to the pole.
At some point the governor himself joined the party, fucking Jimmy's throat. He had often seen the boy when Simon had brought him over and remembered quite well that Faggot was actually straight.
Meanwhile Simon retreated to his bedroom with two of the best looking girls, just to return after an hour and pick up two more.
This left the prisoners at the mercy of the mostly male school kids who took the opportunity to try if they remembered the punishment procedure correctly. They inflicted their punishment on Asslicker without allowing him to stop dancing erotically.
Just when Asslicker thought he was about to collapse, more exhausted then he had ever been during sex training, the sun rose over the horizon.
Simon's guests said their goodbyes and the prisoners were led into the lobby after cleaning the party room. Simon was still naked, covered in lipstick kiss marks.
"Alright you two, I'm gonna catch up on sleep. Here's a list of choirs around the house and garden. If I wake up and anything's not done, you will hate what's coming your way. Bye."
The list was five pages. Asslicker and Faggot looked at each other in terror. It was going to be a hard life, serving Simon.
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