Imprisonment Ch. 02

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Friday morning came too early for Justin MacDowell, who looked the picture of misery as he sat working at his desk in his small office at the prison. He’d barely been able to sleep since Wednesday, when the warden had discovered he’d been skimming money from the sales of prisoners’ belongings to auction houses. The only way he’d been able to keep his job, and avoid spending time in a cell himself, was to agree to the warden’s twisted punishment arrangement. So today, after work, he’d be escorted to a room with four prisoners whose families he’d shorted, and they would be allowed to do as they liked with him. The fact that the warden and two guards would make sure he was not killed or maimed was scarce consolation.

Justin looked up, face pale, when the warden came to his office at the end of the day. Andrew Fairfax was relatively young for his position at 33, having taken over the job just two years previously. He was tall, a good six inches taller than Justin, with dark, almost black hair and piercing blue eyes. He was slim but muscular, surprisingly fit for someone who worked in an office all day. He looked down at the young man almost cowering behind his desk and grinned. “It’s time, MacDowell. Come along.” Justin stood, already trembling slightly, and went to his superior’s side. The older man placed a hand on his shoulder, and led him down the hallway.

Justin remained silent and pale as they walked along, eventually entering a large room near the infirmary. The prisoners were already there, standing against a wall. The room was almost bare, but there were four wooden chairs, a table, and a cot. Justin shivered when he saw what was on the table – just as the warden had threatened, there was a large, heavy wooden paddle, a thick leather strap, several lengths of rope, and a jar of petroleum jelly. There was also a riding crop and something made of metal that Justin had never seen before.

The warden led Justin to the center of the room, standing beside him facing the prisoners. “Justin MacDowell, meet Jim Hayes, David Winn, Andrew Scott and Michael Smith. I’ve already informed them about what you did and given them their instructions.” He gave Justin’s shoulder a little squeeze. “He’s a pretty little thing, isn’t he, lads? Soft skin, long hair, so slender – he’s almost like a woman.” The men all stared at Justin, leering and smirking, as the young man blushed hotly, wringing his hands.

Fairfax then led him over to the table, smiling. “So like I told you, I’m providing the men with some nice things to use on your thieving little arse. I imagine you know what most of them are. But this one’s a little unusual.” He picked up the metal object, which was shaped much like a pear, but with the shape divided into four leaves. Fairfax turned a little screw at the bottom, and the leaves began to expand. “I picked this up at an auction some years ago. It was used for torture in medieval times – it’s called the pear of anguish. Do you know how it works?”

Justin shook his head, his expression showing both fear and distaste, but also a hint of fascination.

Fairfax turned the screw in the opposite direction and the leaves closed together, making the entire structure smaller. “Well, first, this is shoved up your backside.”

Justin gasped, dismay clear on his face.

“Now, I don’t want it hurting you TOO much, so I’ve asked that if the men use it on you, they at least grease it up with the petroleum first. And I told them not to open it all the way. See, that’s casino oyna how it’s used…once it’s inside you, the screw can be turned, and the leaves here will expand. If it’s turned all the way, it could tear the skin, but no one will be doing that. I just thought it could be a way to loosen you up a bit before they start in on you.” The man gave his secretary a predatory grin. Justin had grown even paler, his entire form trembling slightly.

Fairfax gave the young man’s bottom a pat, then went to sit down in one of the chairs, starting to wind a stopwatch. “Okay, men, have at him. Just remember what I said – I want him to be able to come in to work Monday, and no messing up his face.” He leaned back in his chair, smiling.

Justin stood, terrified, as the tallest of the men strode up to him. “Let’s get those fancy clothes off you,” he said, as he began undoing the buttons of Justin’s waistcoat. He quickly removed it and tossed it aside, starting on his shirt while speaking to the other prisoner nearest him. “What should we do to him first, Mike?”

The other man started unbuckling and removing Justin’s belt with a grin. “I say we paddle his arse good and hard first, that way it’ll hurt more when we fuck him.” With a shove, he brought Justin’s trousers and underwear to his knees. The man ripping off his shirt laughed. “Sounds good to me.” The other man gave Justin’s bared backside a stinging smack, ordering him. “Step out of your shoes, kid.” Shaking, the young man obeyed, a red handprint forming on the smooth pale skin of his rear. Soon he found himself dragged toward a chair and roughly pulled across the tall man’s knees. “Fetch me the paddle, Mike.” The other two men just watched for the time being, smiling and laughing.

“Here you go, Jim,” said Mike as he presented the paddle. It was large, about a foot and a half long and nearly an inch thick, with holes drilled in it to reduce resistance.

“Thanks. Why don’t you sit here next to me and hold his arms down in case he tries to reach.”

Mike dragged a chair over and sat down, roughly yanking Justin’s upper half up into his lap and gripping his wrists with his rough hands. Justin couldn’t hold back a little whimper of dismay as he was handled, the other man now running his large hands over his backside. “He really is a pretty little bitch, isn’t he? Wish he was in my cell.” Mike laughed. “Me too.” He reached down to brush Justin’s hair away from his face, patting his cheek. “We’re going to have a lot of fun with you.”

Justin squirmed, blushing bright red, as the tall man, Jim, set down the paddle and started first to spank him hard with his open hand. The man’s large, calloused hand was nearly formidable as a paddle itself, and he spared no strength in laying blow upon blow on the much smaller lad’s backside. “You sure do turn red quickly, kid…what’s your name again?”

“J-justin…” he spoke falteringly, trying hard not to burst into terrified and humiliated tears. He felt like a little boy again, squirming and blushing across his father’s knee. Only it was worse – so, so much worse. The man spanking him laughed. “You’re a cute one, Justin.” After a couple minutes of heavy, sustained smacking, he picked up the paddle and drew it back to his side, bringing it down with a heavy whack on Justin’s small, reddened backside. The young man let out an agonized yelp, still trying his best to hold back tears but quickly losing his composure. After two more vigorous blows he choked back a sob, his narrow canlı casino hips bucking with the impact. The man holding his arms chuckled. “Look at you, you’ll be crying like a wee baby. Teach you to take money away from poor people’s families, won’t it?”

Justin soon gave up trying to hold back and sobbed out loud, tears streaming down his red face as blow upon blow descended on his throbbing bare bottom. He couldn’t remember ever feeling this helpless. He squirmed and flinched, but couldn’t go anywhere. His cries grew more and more anguished, escalating from pained whimpers to harsh, gasping sobs. Finally, the smacks ceased and he heard the thud of the paddle being laid down on the floor. A large hand roughly rubbed his sore, now bruised backside. He heard Jim speak. “Well, we’ve had some fun with him now – Andy, Dave, you want to take a turn?”

Before he could collect himself, Justin found himself briefly dragged upright, then roughly dumped across the laps of two new tormentors. His wrists were held again, and he heard a new voice ask, “Hey, Jim, bring me the petroleum and that metal thing.” Still crying pitifully, Justin felt a shiver course through his body. The man holding his wrists spoke next. “Hey, boy, you should thank us for getting you ready before taking turns with you.” Justin only whimpered, and then the man roughly yanked a handful of his hair. “Say ‘Thank you, sir.” The anguished young man responded tremulously.

“Th-thank you, sir.” The man named Dave had a hand on his sore behind, squeezing the battered flesh. He lifted his hand for a moment, and Justin yelped in surprise as a slick finger was thrust quickly into his entrance. The man crooked his finger, then worked another in alongside it, laughing. “Oh, you’ve got a nice tight little arse, haven’t you? And hardly any hair between your legs. If I couldn’t see your balls I’d think you were a girl.” He yanked his fingers out, and Justin sighed, momentarily relieved. But then he felt something cold and hard pressed up against his hole, and choked back another sob. Soon it was insinuating its way inside him, stretching and filling him. It didn’t hurt very much – yet. It was just cold and foreign, pressing deeper and deeper inside his most private place.

Then he heard sinister laughter – from the man holding the pear as well as the ones watching – and felt the presence inside him grow larger, pressure building inside him. He heard himself cry “No!” and then his hair was yanked again, harder. “No one told you to talk, whore!” He began to cry again, softly at first, as the pear continued to expand in his body. It was definitely hurting now, sharp edges pressing against delicate tissue. Finally it stopped expanding, but the man then started to rock it to and fro inside him. Justin sobbed, utterly humiliated. Eventually the metal stopped pressing so hard against his inner walls, and then was withdrawn from him with a sickening slick sound. The man who’d been tormenting him gave his bruised backside a heavy slap and chuckled. “Now it’s time to feel something a little warmer in your arse, pretty boy.”

Again he was lifted to his feet, and dragged over to the cot nearby. He gasped, the breath knocked out of him, as he was shoved onto his stomach. Someone grabbed his legs, and he found himself draped over some pillows, hips raised. Then he felt hands around his ankles. Rope was tied around them, and his ankles were lashed to the lower corners of the bed, leaving his legs obscenely spread. The process was repeated kaçak casino with his wrists. As he tried to hold back more tears, he felt slick petroleum jelly being rubbed around his sore opening, and with no warning someone drove into him, entering him all at once, slamming his hips against his traumatized bottom. Justin screamed and dissolved into sobs. The metal legs of the cot creaked as the prisoner pounded him relentlessly, rough hands gripping his hips and occasionally smacking his bruised, aching buttocks. All coherent thought left his mind – all he could process was the pain of the rough penetration, the throbbing of his beaten backside, the chafing of his wrists and ankles against rough rope, the sound of the cot banging against the concrete floor. Broken, gasping sobs escaped his mouth and tears streaked his face once more.

By the time all four men had their way with him, Justin was a limp, weeping wreck, barely conscious. Faintly he heard Fairfax announce that the hour was up, and he heard the footsteps and laughter of the prisoners making their retreat. He heard solitary footsteps then, and Fairfax began to untie his ankles.

“There, there, all over for the week. You paid your dues. Good boy.” Justin felt mild surprise through his pain at hearing honest compassion in the older man’s voice. He felt even more surprise when, after untying his wrists, his superior lifted his naked body into his arms and cradled him, carrying him towards the door. Through the haze of tears, he noticed a guard gathering up his discarded clothing, as another one held the door for Fairfax to pass through.

Fairfax led him into the infirmary, where a room had been set aside for them. He was laid down gently on a cot, face down, and Fairfax stroked his hair. “I’m just going to clean you up. Then I’ll take you to your flat in my carriage. Think you’ll be okay spending the night alone now?”

Justin responded weakly, testing out his voice. “I…I think so.” He buried his face in a pillow then, humiliated at the thought of his supervisor tending to him as he lay bruised and exhausted with the semen of four men dripping from his abused arse. He lay still and silent as Fairfax gently wiped his sore body with damp, warmed cloths and only whimpered quietly as he gently dabbed ointment around the stinging skin of his opening. He spoke shakily. “A-am I bleeding?”

“A little. But it should stop in an hour or two. Think you can sit up?”

Justin sat, a few tears running down his face as the weight was placed on his tortured backside. Fairfax stood in front of him, smiling slightly with an unexpectedly affectionate expression, and wiped the tears from his secretary’s freckled cheeks. Then, to Justin’s complete surprise, he leaned in and kissed his forehead. “Poor thing. You did well. Just remember, it’s this or being in there with those men every day…just imagine what they’d do with you.” He began helping Justin into his clothes, getting him back on his feet and putting his coat on for him, even brushing his hair gently and tying it back away from his face once more. Then he picked the young man up in his arms again, eliciting a little cry of surprise from him. “Shh, it’s okay. I know it hurts you to walk, so I’ll just carry you out.”

Justin lay silent in the older man’s arms as he was carried to the waiting carriage, and lay curled up on the bench seat with his head in Fairfax’s lap as they drove to his flat. Fairfax stroked his hair soothingly, and by the time they reached home he was nearly asleep. Fairfax even carried him up the stairs of his flat block, asking for his key when they reached the door, and gently deposited him in his own bed.

“Sleep well, Justin. See you on Monday.”

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