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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...
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