Chapter 1 - in which Tommy is convicted of sexual deviancy and begins induction into the correctional facility.

It all started to go wrong for Tommy when he was raped by a police officer.

18 year-old Tommy was the earnest and hardworking son of a less-than-virtuous single parent. He had been found to be in possession of a small amount of marijuana, left by his father. The police officer who raided Tommy's home was an intimidating man, a good foot taller than the young, slender Tom. Tommy's father was out of the house at the time, most likely looking for work, so the officer offered to give Tommy a break: allow the officer to take Tommy's anal virginity, and he would agree to forget the drug incident. The officer warned Tommy that he would face jail time and a criminal record if he didn't agree. Tom really had no choice.

Poor Tommy, as a straight teenager, was terrified at the thought of allowing another man to fuck his tight, virgin sphincter. Agreeing to be fucked was considered sexual deviancy and punishable by law. It was also, as he soon discovered, wickedly painful.

The burly police officer had a thick fuckstick that was eight and a half inches from tip to base, far larger than Tommy's thin six inches. Oh, how Tommy begged to let the officer just let him suck off the menacing tool instead. But the officer would have none of it. A young, hot, virgin piece of ass was hard to find, and this corrupt cop was hard and horny for it.

And so, bent over his own bed in his dad's grimy apartment, Tommy lost his virginity to a man twice his age, and with no lube other than the man's liberally applied spit. The pain was unbearable for poor Tommy and he cried and yelped with every sudden, cruel thrust. The officer fucked the boy deep, hard and fast for 30 minutes straight, before finally firing a thick load across the weeping boy's backside.

Poor Tommy was abandoned alone on his bed. He felt mentally broken and was in physical agony.

Unfortunately, it was only the beginning.

The officer in question had secretly planted cameras to monitor Tommy's room prior to the drug bust. He was a true pervert and had enjoyed watching innocent Tommy undress himself and jerk his pretty, slender cock each night. He had also caught the entire rape on film.

True to his word, the officer abandoned all charges of drug possession. However, he was able to present the department with an edited version of the footage, which appeared to show incontrovertible evidence that Tommy had consented to anal sex from another man.

Tommy's trial was swift and brutal. Tommy's testimony was quickly disregarded in light of the video evidence against him. His father was of little help either, having shown up to testify inebriated, and so was shortly found in contempt of court. (He would get his comeuppance for his poor parenting and addictions later in life, not that it would be of any consolation to Tommy.)

As the judge put it, "The evidence against the defendant is unambiguous. Clearly he is a sexual deviant and a compulsive liar, and as such a threat to civil society. I therefore sentence him to indefinite treatment in an appropriate correctional facility."

Correctional facilities were a modern phenomenon. The country's conservative sexual deviancy laws had meant that prisons had become highly overcrowded. Instead of taking up valuable prison space, homosexuals were sent to "facilities" that existed ostensibly to correct their sexual deviancy, although the success rate was poor. The public did not care; voters made it clear that sexual deviants were to be thrown to the wolves if that's what it took to keep them off the streets.

Rather than enact a death penalty or spend millions staffing the facilities, the government came up with a simpler solution. Men who had engaged in aggressive acts of deviancy, like rape, were considered to be less mentally unwell than those who would choose to willingly submit themselves to perverse sexual acts. So, violent sex criminals were given a choice: either go to trial to face prison time and a position on the sex offenders' registry, or agree to do their time in luxury by staffing the correctional facilities. The hope was that the correctional facilities would become an organised hive of depravity; and that the sexual deviants who could be salvaged would have their deviancy brutally fucked out of them.

This was the kind of mentality that Tommy was now subject to. The system had declared him to be sexually perverse, and there was no support structure to help him. His life from now on would be a sequence of pain and humiliation for the pleasure of others.

Tommy was kept in solitary confinement at a regular jail for a few days following the trial. During that period he had been assigned to the largest correctional facility in the country.

One morning, Tommy was taken from his cell and ordered to strip bare. After being walked through the prison he was transported into the back of a small van along with three other prisoners. All of them were buck naked, strapped into their seats and bearing a shiny red ball gag between their teeth. Soon, Tommy was also strapped in and gagged and was driven off to his new home.

The first order of business for a new inmate at the facility was a health checkup. Little Tommy was escorted, still gagged and nude, by two brutish guards into the facility's medical wing.

Most of the staff at the correctional facility were violent sex criminals who took pleasure in the pain and suffering of others. The two thugs dragging Tommy along were relied on as enforcers, and were both built like bouncers. The pair both sported a skinhead look, with shaved bald heads and tattooed muscle bulging out of their leather uniforms. One of them had cut off the sleeves of his leather jacket, to reveal broad, hairy arms. They were the kind of men you do not want to meet in a dark alley.

But not every staff member was a musclebound goon. There were plenty of specialist roles that needed filling, including physicians. Doctor Wormwood was a middle-aged doctor convicted of abducting and raping a client. Now he had a position in the correctional facility, and it happened that today he was in charge of inspecting young Tommy.

And so Tom found himself strapped face-up onto a table, gag still in place (making his jaw ache), legs spread, while an older man inspected every inch of him. As he went, the doctor kept taking notes. For instance, the doctor spent a long time investigating young Tommy's arse pucker for tightness. The doctor made a note on Tommy's record - "virgin tight". He also felt up Tommy's arms and chest. Tommy's muscles were not as developed as those of a seasoned athlete, but he had a lithe swimmer's build. The doctor noted Tommy's blond hair and green eyes, and how sweet the scared boy's lips looked stretched around the gag. Yes, Tommy was a pretty one. That would be unfortunate for him. Sometimes the ugly-but-clever ones could strike a deal with the staff and live something resembling a normal life. Sadly, that would be unlikely to happen to Tommy.

The doctor made a few more mundane assessments, like height (5 foot 6 inches) and weight (135 lbs). Then he announced his assessment.

"Based on what I can see here - your shrunken cock size, poorly developed muscles, small testes, absence of body hair, and homosexual tendencies - you appear to be suffering from a lack of testosterone. Sadly, we can't do much to stimulate your natural testosterone. However, in his report, the officer who brought you in described a daily masturbation habit." The doctor tutted disapprovingly while subconsciously rubbing his boner through his trouser pocket. "You're jeopardising whatever testosterone potential you have. So I'm putting a stop to that today."

The doctor opened a drawer and searched through it briefly before pulling out a small plastic device. "This cock cage ought to do the trick. The inner lining is covered in stiff plastic spikes. It won't be a problem unless you get erect." The doctor smiled to himself. A few months without relief and Tommy's dick would be in constant discomfort. And he was already planning a few ways to accelerate the process.

"In the mean time, I'm recommending you for some extreme anal stretching therapy. Your ass much tighter than most of the faggots that come through here so it's important for you to get up to speed with the others in the program." Actually, the doctor was just looking out for one of his friends, who had been asking for a tight ass to fuck and then brutally ruin.

"Now, before we can begin your correctional procedure, there is the matter of your induction. All inmates here have to go through an induction procedure before they can begin their therapy. You're no doubt aware that we have one of the biggest correctional institutions in the country. So you could say we have the pick of the litter when it comes to staff. Anyway, the point is that we like to make an impression on newcomers." The doctor smiled an evil smile as the pair of thugs walked up to the table. "In the next room there are a handful of men who want to give you a welcome you won't soon forget. That's a polite way of saying that they're eager to rape your sweet little ass. Not one of them has a dick shorter than 12 inches. It'll be good preparation for tomorrow's anal stretching."

The doctor couldn't help but laugh at the look of horror spreading over Tommy's face. "Take him away, boys," he ordered before returning to his paperwork. The two gorillas started wheeling the desperate teenager out of the office, still strapped down and exposed. Down a short corridor was a room already full of cigar smoke and three mean, rough, biker-looking types. Tommy's guards wheeled the boy in and closed the door behind him. Then they shucked down their jeans to reveal, to little Tommy's horror, a pair of oversized mega-dongs.

One of the men, the only black man, untied and lifted off the ball gag from Tommy's quivering mouth, offering some much needed relief for his jaw. The relief would be shortlived, however. As soon as Tommy opened his mouth to plead with the men around him, it was filled with the big, black head of the older man's prick.

"Shh, boy… now listen. You're not gonna be a world class cocksucker on your first day, so I'll keep it simple. Just relax your throat, and try not to gag, and this will all go smoothly. Let us do all the work," the man said, sighing as he started to fuck poor unwilling Tommy in the face.

Meanwhile, the first lubed prick was lining up with little Tommy's ass crack. If he had thought that his first rape with an 8.5-inch police officer's dick had been hell, what he was about to experience was going to be a whole other level of pain and suffering. The hairy stud grunted as he began the long, slow task of filling up Tommy's tight ass with 12 inches of hard, horny, brutal muscle bear cock.

All in all, over the next few hours, Tommy would take over 60 inches of cock up his sweet ass. His throat would get it easy, for now. But poor Tommy would be in no condition to walk for the rest of the induction process. Instead, he would have to be wheeled around, naked, by the same burly captors who had fucked him in the first place. His arse would rage and burn until the next morning, but by then he'd be due for a serious session of stretching.

Although it hurt worse than anything Tommy had felt before, the anal muscles are surprisingly resilient. Over time, it would naturally heal and return to its original tightness. But the staff in the facility had no intention of allowing nature to take its course. Instead, they made it a point of pride to stretch out every inmate's asshole until it was permanently gaping. It was felt that this reinforced their status as worthless fuckholes. Poor Tommy would discover all this himself, in time.

---

Next time: Tommy gets some ink and metal in the Body Modification Department, and discovers his very special sleeping arrangements as arranged by Doctor Wormwood.

Chapter 2 - in which Tommy is branded and begins a programme of nighttime treatment.

Tommy's "welcome" party had arranged in order of size such that each man's dick was longer than the last; each could say that they had fucked the sobbing boy deeper than before. For Tommy, it was sheer, brutal agony. He could feel every throbbing inch of manly cock raping his tight hole with acute sensitivity. The pain was worse than he could have imagined, with each veiny prick stretching his hole painfully wide before depositing its sticky load.

Which was to say nothing of the face fucking he was forced to endure. As the men around him grew increasingly impatient, the fucking became faster and deeper. Tommy's jaw ached from the pressure and his throat throbbed with every punishing thrust. The smells and taste of pricksweat filled his mouth and nostrils and the boy nearly threw up on several occasions.

Eventually it was all just too much for Tommy and he felt reality fading as he blacked out. The men around him continued to fuck his unconscious body for some time before finally losing interest and moving him on. Tommy was left to be wheeled into the final room of his induction.

-

Tommy came to some time later with a vicious slap to the face. He found himself in bondage again, this time in a tall black leather chair. Ropes restrained his joints while leaving most of his body exposed. Tommy looked up to see another menacing man gazing down at him.

This was Boxer, one of the tattoo and piercing experts at the correctional facility. The higher-ups had decided long ago that each new inmate was to be branded in unique and humiliating ways. Boxer was not appreciative of his job, being an artist at heart, but many years ago he'd drank too much and fucked some crybaby college kid, so he'd been forced to accept a role in a correctional facility. While Tommy had been sleeping, the man had been drawing up some ideas for his captive canvas, and had set up the camera equipment. He thought it was best not to mention to the boy that he was filming the entire procedure.

Tommy was shivering in his chair. His ass was still incredibly sore and leaking man juices. He felt sick and dirty. He wondered if he would ever be able to feel clean again. Little did he know he was about to receive some very permanent body decorations which would make that difficult.

Boxer would have been obviously a tattoo artist, or at the very least a skinhead, in the general population, but to be fair to Tommy he was not wildly different from many of the staff members the boy had encountered so far. A leather vest and chaps covered the man's intricately inked body. The vest was open in the middle and Tommy could see all over the man's bulging chest and abs. Boxer was clearly a fan of violent, gothic, and sexual imagery as it adorned every inch of his back and torso, as well as the sleeves across most of his arms.

Once the man was satisfied that Tommy was awake he moved back to a table where he was working on something. While working he spoke to the boy in deep growls.

"I wouldn't do that again if I were you. Fall unconscious, I mean. The doctor said to make sure you were lucid for the whole experience. And you don't want to show these men any signs of weakness. Take it from somebody who's seen a lot of kids like yoi." Boxer had finished prepping the needle he was about to use. As he turned walked towards Tommy, the boy broke into a cold sweat.

Tommy was deathly afraid of needles. The last time he had taken a medical jab at school he had fainted in front of the entire class. That had been years ago, but the experience still haunted him. He absolutely could not imagine getting a piercing, let alone a tattoo. But now he suddenly realised that he was sitting, naked and strapped down, about to be pierced and marked, forever. He began to shake more violently as tears rolled down his face. The camera caught the pained expression on the boy's face as he felt his body become paralysed with fear.

The poor boy had to close his eyes while Boxer quickly pierced the trembling nipples and slotted in some small studs. Tommy might have to upgrade after a few months to a ring, but this would do for now. The pain was sudden and fierce, but it was over mercifully quickly. Tommy was still shaking but nervously opened his eyes. He was able to watch as Boxer readied the tattoo equipment.

There's something incredibly invasive about body branding. Boxer was more interested in tattoos with artistic depth, but even he had to admit to a perverse thrill in permanently marring a vulnerable body.

First on the agenda was the word "FAGGOT" emblazoned across the boy's stomach. No, it wasn't very subtle, but Boxer was under orders to make the most humiliating tattoos he could think of. This tattoo would make it impossible for Tommy to ever take his shirt off in public in the unlikely event he escaped the facility or received a pardon. The boy would be arrested quickly for public obscenity. He also tattooed "CUMDUMP" and "COCK SLUT" across the inside of the boy's lower arms, down to his wrists.  A black and white outline of a leather-bound muscleman was tattooed across he boy's slim chest along with instructions to "DISCIPLINE ME". Finally, Tommy's lower back had a small "STRETCH ME" message inked above the arse crack, a message that would no doubt amuse the anal trainer Tommy would be meeting later.

For his part, Tommy spent the entire procedure trying to remain calm and still and not to hyperventilate. The tears started to flow when he saw the first message emblazoned across his abdomen, but continued to flow for the rest of the procedure. By the end, Tommy was a snivelling wreck. The teenage boy's suffering was giving Boxer a raging stiffy, but he was a professional, and kept to his work. When the tattoo on his back was finished, Tommy had hoped that this marathon inking session was over.

But that was not the case. Tommy watched in horror as Boxer approached the boy's head. As the tattooing device touched Tommy's forehead, it became too much for him. Little Tommy fainted on the spot, for the second time that day. Boxer decided to spare him any further suffering and tattooed the word "FUCKHOLE" onto Tommy's forehead in permanent black ink while he was unconscious.

It turned out to be a little too much for Boxer as well. As soon as he finished his job, he reached into his pants and pulled out his own pierced prick. Furiously, he jerked off his aching hardon, another monstrously huge organ, partly for the benefit of the camera but mostly to satiate his raging randiness. The sight of the poor boy, strapped down, unconscious, his body thoroughly defiled, was intensely erotic to the perverted artist. He fired his load all over the boy's peaceful, but now forever obscene, face and forehead. With a sigh of pleasure, Boxer starting collecting the dripping spunk off the sleeping boy's face and feeding it down his throat with his fingers. When the man was satisfied, he switched off the recording equipment, and washed Tommy down.

Were Tommy to ever get out of the facility, he would be considered obscene unless he wore the most conservative clothing possible. Long sleeved shirt, long jeans, and a hat that covered his forehead. The only skin he could afford to show was his face, hands, and feet. But he could worry about that problem when (if) he came to it.

-

When Tommy woke up, he found himself in a small, dark room. He realised he was in a loose, spread-eagled bondage position on a mattress. Tommy had a splitting headache from stress and the throbbing pain of the tattoo on his forehead. His nipples, arms, legs, stomach, and asshole ached as well. Tommy's whole body was feeling a sense of low, persistent pain, but at least he was comfortable and not as tightly bound as he had been before. He felt completely exhausted.

Above his head a TV switched on. It was playing silent gay porn in which the young bottom was being brutally fucked by a series of larger men, and loving it.

Two men opened the door to the room and stepped in. They didn't say a word, but they brought a large set of headphones and placed it onto Tommy's protesting head, strapping it on so that Tommy could not shake it off. They plugged in the headphones into a nearby console and dialled up the volume to maximum. Tommy could suddenly hear every thrust, grunt, and scream of the porno, amplified into his ears. It wasn't loud enough to be painful, but loud enough to prevent the boy from ever falling asleep.

Tommy started to plead with the staff to let him go and switch it off, when he felt a small prick in his arm. One of the staff was injecting something into him. Tommy started protesting louder as the staff finished and left the room.

This was Tommy's nighttime "treatment".

Dr. Wormwood enjoyed subjecting the inmates to occasional sleep deprivation. The adult human body is fairly resilient to a lack of sleep. Tommy might feel terrible, he might even hallucinate and think he was dying, but a little bit of rest and he would more or less recover to normal. The doctor did sometimes fantasise about the possibility of subjecting a single inmate to sleep deprivation and torture, 24/7, for weeks on end, until their heart gave out. Just to get a clearer idea of the limits of human tolerance. And a little bit for kicks.

Wormwood was not a psychologically healthy individual. Working at a correctional facility was not helping.

The rationale behind Tommy's "treatment" went as follows: Wormwood wanted to "cure" the boy of homosexuality by pairing the gay porn with the pain and discomfort of the cruelly spiked chastity device. In order to make sure that Tommy was awake and aroused, he had injected the boy with a mixture of testosterone, stimulants, and a large dose of sildenafil (viagra). The theory was that the association between arousal and pain would override the association of gay sex with arousal.

Of course, since Tommy was actually straight, the treatment was creating a previously absent association with gay sex and arousal, despite the pain of the device. Over time, being trapped in an all-male environment of sexual tortures would transform the previously straight Tommy into the depraved homosexual that he was originally accused of being. He would either learn to find a perverse thrill in the tortures he endured, or continue to suffer indefinitely.

For now, poor Tommy could only try and get some rest while enduring the agony in his crotch and desperately try to quell his unwanted erection.

Chapter 3: In which Tommy meets with his sadistic anal trainer and has a very painful first session.

When the men came to collect Tommy, he offered no resistance. As soon as the headphones were off he fell asleep immediately. He had no awareness of the men groping his tender nipples or his itchy red crotch.

The men were on a schedule, however, so didn't waste much time before lifting up the limp boy in a fireman's carry and escorting him to the morning's assigned activity. Once they reached the small, brightly lit chamber, they secured him face-down on a sawhorse, with his thighs tied up so as to ensure they boy's butt was pushed provocatively in the air. Once satisfied the restraints were tight enough (they were actually cutting into the boy's slender frame), they abandoned him.

A short while later, Diederik (or Derrick as he preferred to be called) arrived and gave a cursory inspection of the still-unconscious teenager.

Derrick was an ex-military man of Scandinavian descent, although he had been born and raised in the same country as Tommy himself and typically spoke in the local accent. Derrick had become obsessed with bodybuilding since he was a teenager - his idol had been Schwarzenegger himself. As the man grew up and saw his body explode in size, he began to get a sexual thrill out of intimidating others. He joined the navy and was modestly successful, but found the experience too sexually frustrating; the man's arrogance and cruelty were repressed by the rules and regulations.

After leaving the navy, Derrick went to school and started working on a degree in pharmacology. The man may have been huge, but he wasn't stupid. Pharmacology helped provide access to the steroids he could use to get even larger. In the meantime, he earned a reputation on campus as a sexual predator, having increasingly non-consensual sex with both men and women as time went on. Shortly after graduating, he kidnapped a young man and spent two weeks sexually torturing him in his soundproof basement. He probably would have killed the man, if he hadn't been sighted the night of the abduction. The young man was rescued and Derrick was sentenced to staff a correctional facility.

Unsurprisingly, Derrick did not think much of little sleeping Tommy. He had no respect for people who did not appreciate the power and beauty of the male form. Tommy had obviously not put any effort into building himself into the male ideal. But Derrick also realised that the boy was completely unable to function consciously in the state he was in, and so gave him a couple of hours to sleep. Just so that he could appreciate the coming games, of course. That would also give Derrick some time to collect his things.

---

Derrick returned some time later, fully nude, his thick prick swinging between a pair of curly-haired thighs. The man was a beast, 6'8" tall with giant solid slabs of furry pec flesh and a mammoth treasure trail down a bulging 8-pack. Unlike most of the other staff, he had not defiled his body with tattoos. The man did not believe in body shaving so his body hair was completely unkempt. He also did not use deodorant, although Tommy would not be appreciating the man's scent this session.

Derrick carried with him a box full of materials he would be needing for today's session. Derrick had become renowned as the most brutal ass-stretcher at the facility. He had asked the doctor for a near-virgin arse to really take his time over. Derrick truly excelled at his job and knew how to go the extra mile while torturing a hapless inmate.

It had been two hours and Tommy was still sleeping like a lamb. Derrick pulled out a large cigar and lit it up. After leaving the military he discovered that the taste and smell of cigar smoke was a real turn on, for some reason. He hoped that Tommy would soon feel the same way.

Gently, the giant eased a gas mark over the sleeping boy's face. Tommy was so out of it that he didn't notice as the straps were drawn tightly around his head. The thick eye plates were dark and translucent, partially obscuring the light of the room.

A long tube descended from the front of the mask. This was a specially constructed mask that Derrick had designed himself. At the end of the tube was a glass chamber. Derrick took out a second cigar and lit it up. He carefully opened the glass chamber and placed the cigar inside, closing it tightly. The chamber had a thin pipe at the top that let fresh air in, to keep the cigar burning.

A short while later, Tommy woke up screaming into the mask. The sound was muffled but it was enough to make the nearby giant's colossal cock twitch. Tommy's first thought was that he was on fire. His face was hot, his eyes were burning and he couldn't breath through the smoke. His next thought was that he had died and gone to hell. Desperately, he tried to take giant gulps of air but instead filled his lungs with the tarry smoke. The combination of adrenaline, nicotine, oxygen deprivation, and raw terror nearly forced the boy to pass out again.

Derrick spoke calmly, enjoying his own cigar. "Relax, boy. Breathe slowly. If you keep hyperventilating, you'll hurt yourself." Derrick paused to take a slow, casual drag. "There's a hole in the top of the mask. If you breathe slowly, you'll survive. Might lose a couple brain cells, but they'd be wasted on you anyway." Derrick chuckled at his joke, but Tommy didn't find it very funny. "Cigars are hard to find around here. I hope you're grateful." Tommy was going out of his mind, pleading and struggling in his bondage. "I said, I hope you're grateful."

Still no reaction from the confused, struggling teen. Derrick sighed and pulled out a long, thick wooden ruler from his supplies. Lifting, it up, he proceeded to deliver an avalanche of blows, at least 20, in quick succession on the boy's very exposed ass cheeks.

Tommy immediately stopped struggling out of sheer shock. All the wind had been smacked out of his lungs. He started feeling dizzy and felt like throwing up.

"BREATHE, you asswipe!" shouted Derrick with more ferocity than Tommy had ever heard from a man. Out of terror Tommy tried to regain control of his lungs. "For disrespectin' me, I am going to paint your arse black and blue. Expect AT LEAST ten times the blows you just felt. And you had better fuckin' learn some self control. If you pass out I have some smelling salts I can bring you back around with. Then I will replace that cigar with another, fresh one, and add an extra 200 blows to the count." Derrick leaned in close to Tommy's ear. "Do I make myself ab-so-fucking-lutely clear?" Tommy was openly sobbing and trying to catch his breath back, but he nodded and moaned in agreement.

Derrick was getting off on this like you wouldn't believe. Like the rest of him, Derrick's cock was freakishly, inhumanly huge. It hadn't always been that big. During his pharmacology degree, Derrick had stumbled onto the chemical equivalent of the holy grail: bona fide penis enlargement. But of course, Derrick had been reluctant to share his secret with anyone else, because he got off being the biggest alpha male out there. During his degree years, he got addicted to having an uncomfortably huge dong. He loved to hurt people with his junk. After arriving at the facility, it got even more out of hand. Derrick's prick was simply too big to fit in an asshole that hadn't been specially stretched to accommodate it. That's why Derrick had been assigned to the role of anal trainer. He eventually did share his secret pills with most of the staff, but kept the supply tight. That might explain why so many of the staff at this facility were so frighteningly endowed.

As he returned to bashing the helpless boy's upturned ass cheeks, Derrick simply couldn't help himself any more. Grabbing a jar off the desk, he used it to capture his gigantic load. With one hand on the jar and one hand beating Tommy senseless, the man had cum hands-free. One of the side-effects of the pills was, naturally, enhanced virility. Derrick could cum hands-free 3 or 4 times a day and still get it up to fuck one of his more stretched-out whores. He liked to save his cum, though, and refrigerate it so that he had a good supply whenever he felt like feeding it to an inmate.

However, Tommy had no idea that this was going on. As far as he could tell, Derrick hadn't missed a beat. Tommy just prayed to god, while choking on cigar smoke, for some small sliver of mercy.

---

Some time later, Derrick finally took a break.

It had been a long time since an inmate had made Derrick work up a sweat. To his credit, Tommy had stayed fully conscious for the entire ordeal. That hadn't stopped Derrick from really getting into the spanking, more than he had in a long time. Derrick had gone through the full arsenal of whips, chains, paddles, and of course his giant bare hands. Tommy's cigar lay smouldering and Derrick was dripping with perspiration down his swollen muscles and obscene package.

Maybe it was the thrill of being treated to an inmate who had just arrived. Maybe Tommy's pretty little butt just sung out to be abused. Maybe Derrick simply got off knowing that Tommy was most likely straight - he had read the boy's police report and it didn't take a genius to realise he had been set up. Maybe Derrick felt that god had delivered him a boy who deserved to be punished for failing to hone the gift of his body. Whatever the reason, Derrick lived to break weak men like Tommy. He felt it was his calling.

Derrick approached the boy's head and removed the gas mask. Tommy spluttered as the last of the smoke escaped and he could finally breathe fresh air. Derrick gently used a warm washcloth to wipe off the soot and grime in Tommy's face and eyes. Tommy was finally able to see his tormentor for the first time and was in awe at the giant's size and stature.

Derrick didn't say a word, and neither did Tommy, until Derrick pulled out a large ball gag. Tommy started to plead, complaining of a jaw ache, but Derrick just shushed him and forced the gag into place before tying it around Tommy's head. Tommy started to tear up in frustration as the familiar ache returned to his jaws.

Finally Derrick spoke. "I am impressed, boy. I though you weren't going to make it, but you took it like a man. I can respect that. But if you think it gets easier from here, think again. That was just the foreplay for what I've been asked to do to you." Derrick had moved round behind Tommy and was admiring his handiwork. Tommy's cheeks had transformed into a patchwork of purple and blue bruises. He would definitely feel that every time he sat down in the coming days.

Tenderly he pressed one of his fat fingers against the boy's hole. He poked inside and ran the digit around, causing Tommy to squirm uncomfortably. It was still stretched and bruised from yesterday's induction, but seemed to be recovering nicely. He'd have to put a stop to that.

Some time ago, Doctor Wormwood had made it mandatory that all anal stretching must be sufficiently lubricated so as not to cause unwanted damage. The goal was to stretch the hole, but the doctor frequently found himself treating inmates whose assholes had split, or who had torn and caught an infection, or who had developed haemorrhoids, etc. At the time, some of the staff, like Derrick, had objected. To Derrick, the idea of going soft on the inmates was an anathema. The possibility that the inmate might even get pleasure from taking objects up the ass was a serious problem.

That's why the doctor had asked Derrick to devise his own lubricant that could be shared across the facility. The idea was to come up with something so devious that the inmates would beg to be fucked bone-dry instead. Derrick had worked long and hard perfecting his mixture, creating a water-based and silicone-based version. It contained a mix of high-intensity chilli extract, antiseptics like iodine, and a cocktail of chemical irritants. The chilli extract and antiseptics gave it a fiery heat that hurt like hell and made the victim sweat. The pain would fade relatively quickly assuming the lubricant wasn't reapplied, but the irritants would create an intense itch that could linger for days. The only relief was to scratch it - but since the lube was intended to be used deep beyond the anus, the only way to scratch the itch would be a vigorous dry fucking.

Donning a pair of huge rubber gloves, Derrick applied a generous amount of the fiery lubricant to the first dildo of the session. At nine inches, it was considerably shorter than even the shortest of yesterday's anal invasions. However, it was much thicker; from the base of the head onwards, the rubber cock would stretch the boy's tight chute to a 2.5 inch diameter.

Derrick smiled evilly as he prepared to introduce Tommy to a whole new world of pain.

---

Many hours later, Derrick was struggling with all of his (considerable) strength to shove home the last couple of inches of the fourth toy of the day, an 11 inch long, 2.9 inch diameter megadong. The key had been to progress in size very slowly, a fraction if an inch each time, but making sure each toy was wider and deeper than that last.

Tommy's throat had gone hoarse from screaming into his gag. His battered sphincter was stretched to the limit and the evil lubricant had found its way into every bruise and fissure along the surface. His ass ring was a circle of fire, while his insides churned in agony. His entire colon itched and occasionally convulsed, swallowing the devilish dildo deeper and deeper into the boy's gut.

Derrick was really sweating now, his tremendous muscles glistening as he PUSHED the dildo in deeper. He was determined to get this last dildo in to maximum depth before the end of today's session.

Slowly, very slowly, the boy's insides started to cave. Tommy moaned in desperation as the monstrous prick tore deeper into his bowls. Tommy found himself praying again, for an ending to this torture. Little did he know that, once the plastic dong was removed, the agony would be replaced by a desperate itch for further abuse.

Derrick was finally satisfied when the entire rubber column was embedded into Tommy's guts. He stepped back and rubbed the sweat from his brow. Punishing the boy had been a real workout! But it had all been worth it. He admired the boy's bruised and beaten arsecheeks surrounding the stretched, swollen, red hole. Derrick couldn't fucking get enough of torturing this kid. He was jerking his giant meat pole furiously, and fired another sticky load, at least his fourth since meeting the boy this morning.

Soon he would begin to slowly remove the toy from between the boy's abused buns, taking his time and fucking the kid a little with it as he went. Then, when it was removed, he would replace it with a much shorter, 2.5 inch diameter butt plug, to wear until the next session. Whichever size they started each session with would be the size of the butt plug at the end. Derrick found this helped to promote elasticity by keeping the hole stretched but allowing some room for recovery.

Derrick was understandably pleased with himself. He had wanted to leave the boy with several reminders of his subhuman status. Tommy's whipped cheeks would be agony to sit on for at least a few days, and remain uncomfortable for over a week. His hole would remain stretched and his insides would be irritated, no doubt exquisitely uncomfortable even while standing. And Derrick was also pondering whether he could give the boy a nicotine addiction on top of all that. At the very least, he wanted the boy to share his cigar fetish by the end of his sessions.

Lighting a cigar himself as he eased out the dildo, he thought to himself about all the fun he cold have with the boy in the future...