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Imprisonment Ch. 03

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Justin looked up with a sigh as the warden opened his door at the end of the workday Friday. He’d been dreading this day all week, and he was just now starting to be able to sit down comfortably after the abuse his backside had taken the previous Friday. He’d considered perhaps trying to stretch and loosen his opening so the next round of penetrations wouldn’t hurt so much, but he was so sore that he couldn’t bring himself to touch the area for long. Besides that, it made him feel dirty. So he’d just used ointment to help the little tears in the skin heal, and for now he wasn’t feeling much pain. He knew that would soon change as he looked up at his boss with a defeated expression.

“Come along, Justin.” When he stood, his superior put an arm around his shoulders and escorted him down the hall. In recent days it seemed he’d been calling his secretary by his first name more and more often, whereas in the past he’d normally been “MacDowell.” Justin wondered about the change, but didn’t ask Fairfax about it. He remained silent as he once again was led to the nearly empty room with four prisoners and the same number of guards waiting.

He looked over to the table which held the implements and petroleum jelly Fairfax provided and noticed a few differences. The paddle had been removed from the inventory, and now just the thick leather strap and riding crop remained. There were still the lengths of rope as well, but Justin was relieved to see that the metal pear of anguish had been removed. Then he saw a new metal object and stole glances at it nervously as Fairfax introduced him to the prisoners. He couldn’t help looking apprehensively at the largest of the prisoners as well, a man who must have been over six feet and four inches tall. Justin was only 5’6″, and very slight. He shivered at the thought of how easily that towering man could hurt him. Of course, Fairfax had asked these men, like the others, not to hurt him so badly that he couldn’t come in to work on Monday. But there were plenty of excruciating things that could be done that wouldn’t leave lasting damage.

After introducing him, Fairfax led him to the table just as he had last time, apparently wishing to explain something to him again. “Well, I took away the paddle and the pear since those were used on you already. I think you should experience a little…diversity.” He smirked as Justin blushed. Then he picked up the metal object. It had handles like a pair of pliers, but the end consisted of three curved metal prongs. “This is a medical device…a speculum. It actually works in a pretty similar way to the pear, but it wasn’t meant for torture so the edges shouldn’t be so sharp. It’ll just open you up.” Justin said nothing, just stood there with a red face. Fairfax gave his backside a pat and retreated to his chair. “Have at him, lads.”

The tall man headed for him first, and Justin grew pale as his waistcoat, tie and shirt were roughly removed. The man then opened his belt and yanked it out of the loops on his trousers, then doubled it up and smacked his rear with it. “Get out of your shoes and trousers, kid. Underpants too.” Shaking, Justin lowered his trousers and underpants and stepped out of his shoes, leaving him in calf-high black socks attached to sock garters just below his knees. The man laughed and pointed. “Check out the fancy socks. We’ll leave those on just for fun.” The other prisoners chuckled as Justin blushed crimson. The tall man then strode casino oyna over to the table and chose the heavy leather strap, walking back and sitting in one of the two chairs available, dragging it next to another chair first.

“Hey, Jack, bring the kid here and hold his arms for me.” Another prisoner, around Justin’s age with blonde hair, shoved Justin towards the chairs, where the tall one reached out and dragged him over his knee. Jack sat down in the other chair and roughly yanked Justin up by his arms so he was lying across the laps of the two men, just as he had last week with different prisoners. Jack reached down and untied the ribbon holding back Justin’s hair. Justin heard the man laugh as his hair fell around his face. “Look even more like a woman with your hair down. Could put you in a dress and no one would be able to tell.”

The tall man set down the strap and squeezed Justin’s backside with one large, rough hand. “He’s got a girl’s arse too. All smooth and soft.” The hand moved down between the young man’s legs and Justin yelped in pain and shock as a few of his pubic hairs were yanked out. “You oughta just shave these. Ain’t got much.” The other prisoners laughed, watching. One of them spoke. “Whip his arse good, Tim.” The tall man chuckled. “Oh, I will.” He took a handful of Justin’s hair in his hand and gave it a yank. “You sorry for trying to cheat our families, boy?”

“Yes! Yes, I’m very sorry!”

“Well, you’re about to be sorrier.”

A mere second later a large, heavy, calloused hand crashed down on Justin’s defenceless, upturned backside. He flinched at the first blow, his narrow hips jerking as a red mark formed on his pale, smooth skin. There were only the faintest remnants of last week’s bruises still showing. The man named Tim continued to smack him mercilessly in a rhythm, first on Justin’s left cheek, then his right, then in the center of his aching bottom. He only paused once Justin had begun to cry, barely making a sound but with tears streaming down his red face.

“Apologise again, you snivelling brat.” He gave Justin’s flaming red bottom a rough squeeze.

“I-I-I’m very sorry! I won’t do it again!”

“Not good enough.” Justin tensed as he saw the man reach for the strap, and howled in pain when it was brought down heavily with a loud crack across both cheeks of his tortured bottom. He was sobbing loudly after just a few blows, and soon lost track of how many times the strap had descended. The man was ruthless, continuously laying the heaviest and most frequent stripes against the sensitive undercurves of the young man’s backside. But he didn’t neglect the rest of his bottom or upper thighs either, working the skin to a brilliant red from the top of his bottom halfway down to his knees. By the time he finished, bruises were forming and areas of the skin were puffy, starting to blister. As for Justin, he was a sobbing, gasping mess, the hair around his face damp with tears, a small puddle of them even forming on the floor.

The strap was laid down, and Justin heard the tall man speak. “Hey, Johnny. Bring that metal thing and the petroleum over and you can play with him.” Justin lay helpless and crying with one man holding down his legs and another restraining his arms as a third came over and roughly shoved two slick fingers into his entrance. His body flinched and squirmed in discomfort from the careless penetration, but he grew still when he felt something canlı casino cold pressed up against his aching hole. He whimpered in anxiety, but at first the smooth slide of the prongs inside him felt almost pleasant, the cool metal soothing the stretched, sore skin of his opening. Moments later, however, the relief he felt disappeared as the prongs were spread wide, pulling his hole even further open than the fingers had. The prisoners laughed at his boyish whimpers and the one holding the speculum gradually opened it up as far as it would go, spreading poor Justin’s entrance a couple of inches as he whined and squirmed. “Alright, that should be enough. Should we tie him up now?”

The tall prisoner, Tim, responded. “I dunno, there’s enough of us to hold him down. How about we just bring him over to the bed and lay him on his back and put his legs in the air? Someone can hold his hands and someone else can pull his legs back.”

Jack, the one next to him, laughed. “That does sound like more fun.” Justin felt the metal slip back out of him just before he was roughly yanked to his feet and dragged over to the cot where he was unceremoniously dumped on his back. Jack got behind him while Johnny sat at the side of the cot and grabbed his wrists, keeping his hands behind his back as the fourth prisoner, a middle aged man, walked in front of him and put his hands under his knees, pushing his legs back. As his legs went into the air, Jack grabbed his ankles and pulled them back further until Justin’s bottom was slightly lifted from off the mattress.

Justin shut his eyes as the prisoner in front of him lowered his trousers, not wanting to watch the man’s face as he defiled him. He felt more petroleum being smeared around his entrance, and then the man’s cock pressing into him. The insertion didn’t hurt much in comparison to having his hole stretched by the speculum, but once the man started thrusting the pain caused by the slamming of his pelvis into Justin’s bruised and welted backside was agonising. It wasn’t long until he was sobbing again, and that was only the first of three hard fuckings he’d receive that evening.

When Fairfax announced the time was up, he heard Jack groan. “Aw, I didn’t get to have a turn with him.” His limbs were carelessly released and his legs fell back to the mattress. Exhausted and sobbing, he curled up on his side on the cot as the men retreated, the room growing quiet. He heard Fairfax’s footsteps approach, and he was gathered into the older man’s arms. This time he didn’t immediately begin to carry him out, but sat on the cot and held Justin gently in his lap. He stroked the lad’s hair softly and murmured “There, there,” and Justin started crying even harder. Something about the gentleness, the kind words, after such harsh treatment just overwhelmed him. Fairfax kept stroking his hair. “Poor baby.”

Justin sputtered. “D-don’t make fun of me!”

Fairfax kissed his forehead. “I’m not making fun of you, Justin.”

Justin blinked and looked a bit confused, but said nothing.

“Let’s get you cleaned up.” Fairfax stood, carrying Justin again to the empty room in the infirmary. He was laid carefully on a cot as the guard following them set down his now neatly folded clothes and his shoes on a nearby chair. Justin sprawled out on his stomach, stretching his sore limbs. Once again Fairfax efficiently cleaned the prisoners’ semen from Justin’s abused body. The last time he’d only applied kaçak casino ointment to the young man’s entrance, but due to the blistering caused by the strap he decided it’d be best to anoint his entire reddened backside. Justin lay, quiet at first, as his superior’s hands smoothed the slippery substance over his stinging skin. After a few moments, however, he became aware of a surprising and unwelcome sensation – the gentle gliding of Fairfax’s hands over his heated flesh was starting to make him aroused. He wondered in dismay how he could even feel pleasure after enduring such an ordeal, and his face began to redden once more. When Fairfax’s fingers descended between his legs and brushed his scrotum, he gasped.

“What’s wrong, Justin?”

“N-nothing, sir.”

Fairfax soon finished, and helped Justin to his feet. Justin tried to immediately cover himself, but Fairfax restrained his hands gently. He looked down at Justin’s erection, then back up to his flushed face, and smiled. “There’s no need to look so embarrassed. It’s perfectly natural.” He began to guide Justin over to a chair, sitting down and pulling the young man into his lap, Justin’s back against his chest. The young secretary let out a small cry of surprise.

“Shh, it’s okay. We can’t leave with you in that state, can we?” Justin blushed furiously as Fairfax’s arms encircled him, and cried out again as fingers were delicately wrapped around his erect member. Fairfax steadied him with a hand on his chest, and kissed the back of his neck as he started to stroke him intently, hand still slick with ointment. “Don’t be embarrassed. You’ve had a hard night, let me make you feel a bit better, okay?” Justin remained silent at first, and Fairfax kept on insistently pumping his arousal in and out of his slick fist until the younger man began to pant and moan helplessly. Fairfax held him close, stroking faster and faster until Justin released, spattering his own chest and his superior’s hand with warm fluid. Fairfax chuckled softly and withdrew a handkerchief from his pocket, gently wiping Justin clean.

Justin’s body slumped in exhaustion, and his voice was tremulous when he spoke. “Wh-why did you do that, sir?” Fairfax gently turned him around until they were facing each other, Justin’s slender legs draped on either side of his boss’ lap. Fairfax rested a hand on his secretary’s throbbing scarlet backside. “Like I said, I wanted to make you feel better. Besides, you’re very cute.” He smirked and leaned forward, kissing Justin’s lips softly. Justin gasped and blushed, but said nothing. It was just too much for his tired mind to process at the time.

“Come along, let’s get you dressed. I’ll take you home in the carriage again.”

Once Justin was dressed Fairfax carried him to the carriage just as he had the previous week, helping him to lie down on the bench seat, stroking his hair as they travelled. “Do you remember how many families you took money from?”

“No, not exactly…”

“It was twenty-one. We’ve got eight out of the way now, so that leaves thirteen. I’ll bring the last five in all together. So just three more weeks and it’ll all be over.”

Justin sniffed. “Still seems like forever now.”

“Don’t worry. I’ll take good care of you.” Justin lay still, wondering what that could mean as Fairfax continued stroking his hair gently. But he didn’t ask.

When they arrived at Justin’s flatblock, he blushed as one of his neighbours, a rather nosy old lady, watched Fairfax carry him up the stairs. Fairfax helped him out of his coat when they reached his flat, then guided him over to his bed.

“Rest well, Justin. I’ll see you on Monday.”

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