“Wheels of Sisyphus” – by Hayden, Book 2b, Chapter 20a

Chapter 20a – The prize of success…

Revolutions: 1 564 428


The crowd, gathered in a circle, hollers and cheers as they watch the scene unfold before them. At the centre of the wide ring, two large men, glistening with sweat and oil, are intertwined with one another, knotted and strung together, slippery muscles, arms and legs, squirming, grinding against one another like in the throes of rough sex.

Yet this is no pleasurable activity, for these hunks are Convicts 32 and 33, engaged yet again in a struggle for male supremacy in the battle arena of the Pit. Oiled up and shackled at their ankles to the ground with the same short chain, the convicts are forced to wrestle each other in an attempt to immobilize the other. Then, they must stroke the other’s cock till it cums. Simple rules, difficult strategy. And it is all to play for. My and Jimenez’s convict have each won a game and this is the riveting tie-breaker.

33 is now a staple of our New Year’s parties, this now being its third time in a row at the Pit. Since its first failure, I was determined that it be given another chance to prove itself. After all, 33 is to be my model convict. And it’s also my reputation on the line, dammit! Saying all along that convicts made the best wardens was a brave statement to make and since we lost, it was absolutely necessary that 33 not fuck up again.

So it was that I started 33’s training regime 8 months in advance. 33 was provided yet more of the experimental supplements as well as an extra portion of convict gruel during the evening feeding. As such, 33 bulked up and grew stronger. Unfortunately, Jimenez, having not got my memo on this, cried foul and refused a rematch claiming it wasn’t fair that I got a head start, since wardens usually begin training of convicts for the Pit at the same time. Thus, after discussing with the doctor, and in the interest of creating a true rematch of the ages, the match was postponed. However, we were allowed to begin the use of the performance-enhancing drug one year in advance.

Instead, on the second occasion, 33 was challenged by convict 92, a broad-shouldered, smooth-skinned black convict serving 2 million for illegal gambling. In charge of 92 is Warden Fessel, one of the newest wardens serving at SisPen, but one with much experience in the prison system.

However, that meant the old, broken system. The one of decaying standards and corrupt correctional officers, and inmates being nothing but a drain on the State’s resources, serving nothing but time. In this new system of hard labour, discipline and punishment, wardens too had to be at peak physical and mental fitness, constantly alert at their job to oversee and train their convicts, in order to squeeze the most out of them.

Needless to say, we wiped the floor with 92. 92 failed in all three games, which were a repeat of last year’s. But then again, what could it do against the powerhouse that is Convict 33? In the first game, 33 pulled its 100 revolutions faster than any convict had ever done before, to the astonishment of the crowd. And in the second, 33 employed the little amount of wits it possessed to fool 92 as it exhausted itself in the tug-of-war pulling the Wheel, as 33 maintained its ground as best it could while conserving strength. 92 was equally a monster of a convict to look at, but it was 33 that truly possessed the strength in those muscles. As 92 tooks a short pause to recover its strength, 33 quickly pressed its advantage, completing its revolution before 92 even knew what was up.

Finally, since 33 had already won 2 of the 3 games, it was determined that the reward would be greater for it if it triumphed in the third. The same went to convict 92, except that its punishment would be even greater if it failed in this last task. As the convicts were shackled to the floor to begin giving head, this time 33 made no mistake. Without flinching, it swallowed my manhood whole, as 92 looked on in shock and horror. With great skill, 33 worked my shaft with its mouth until I blew my load. Business-like, I stepped aside, as it continued to service the other wardens without flinching. In the end, 33 was able to serve 5 of us, while 92, after costly hesitation, managed only 3.

Shouts of praise and loud applause were showered on the victor and it was given what was promised, though all the while cursing under its breath that we were “perverted fuckers”. To 33 was given as usual beer for the evening, a day’s rest tomorrow, and a dirty rag to hide its manhood for as long as the rag lasted (by the rough nature of convict labor the rag lasted a mere two weeks). And as a further reward, 33 received a plate of steak and fries, hand fed by me to it as it hung on its X-cross in the Pit. 92 on the other hand was branded with its convict number on its ass and, as an additional punishment, tattooed with the word “INFRACTIONS” over its shoulders, the same word that is tatted on my back. No doubt this was intended by Warden Fessel to humiliate me and 33 if we had lost, as if him and Convict 92 even stood a chance. How naive.


The real challenge came in a year. Immediately after this party, both 32 and 33 were put under special training regimes, designed by their individual wardens, and tougher than anything we had attempted here before. Yet these were the champions we selected. The ones we judged able, based on extensive experience, to endure the most brutal and intense discipline we could inflict, to forge them into model convicts, ones which other wardens could look up to as guides on how convicts were to be handled here at Sisyphus Penitentiary.

For 33, besides maintaining the allocation of a larger portion of food and a healthy helping of supplements, I made a slight (but entirely legal) modification to 33’s work regime, forcing 33 to perform 1600 revolutions a day, regardless of State-time, ignoring the state mandated requirements dividing S-Time and P-Time for a year. At first, 33 was forced to spend more time on the Wheel each day to fulfill my quota. But over time, its body accommodated this further requirement, the training having great effect on it. As the New Year came along, it regularly reached and exceeded this daily quota of revolutions. In this case, the convict was still required to pull 16 hours a day, regardless of the number of revolutions, as per its sentence.

For 32, Jimenez demanded first and foremost complete obedience and submission. 32 was gagged throughout State Time, and denied the ability to speak for a year. The only responses it was allowed to give were done by hand. Its arms locked to the Penitent’s Collar while working, 32 was allowed to say either “Yessir”, given with both palms opening and closing twice, or “Nosir”, given by clenching its fists. And this was only if it were asked a question, to which it had to respond immediately or be punished. Jimenez focused on keeping 32 alert and active at all times, and would frequently issue commands or ask questions at random times during the day, requiring 32 to respond promptly. This allowed Jimenez to dominate the mind of 32, making it entirely reliant on the warden himself, forcing it to hinge on everything Jimenez would say or do.

Thus, was the rematch prepared. And the stakes were raised even higher.


As the convicts hung on the X-frames at the start of this evening I revealed to them what was to play for. To the victor, would go a pair of workboots, which the convict could keep throughout its sentence, a potentially game-changing piece of clothing, since when worn, the shoes would allow the convict better traction on the cold concrete floor of the prison cell, and would certainly allow it to complete its revolutions easier and faster, significantly shortening the time required to complete its sentence.

But for the loser, I revealed in my hand, a set of metal rings the size of walnuts. “These are nipple rings,” I said, as the convicts looked in horror. “Thick and heavy. Convict grade. They will be pierced into the tits of the losing convict, to be worn permanently by it for the remainder of its sentence.”

Thus, we began the first game – the game of endurance. “Preparing one of yous to receive your piercings,” Jimenez had said. Each convict hung from its X-frame situated next to one another. Two vertical beams on dollies were then wheeled in and placed in front of each convict. Each beam had a pulley and a metal chain on it. On one end, each convict held the chain in its mouth. The chain went through the pulley hanging vertical on the side of the beam, and the other end connected to two nipples clamps latched now onto the nips of the convict. The convicts bit hard on the chains in their mouths as the clamps first bit into their man tits, but soon the pain would get a hella lot worse. Short, heavy chains were hung one after the other on this main chain, first on 32 then on 33, weighing it down and increasing the strain on both their mouths and tits. The first one who screamed would cause the chain to fall down and they would lose.

Both convicts exhibited tremendous amounts of endurance. Both convicts gave everything, their bodies outstretched, abs sucked in, pecs pushed up and forward as far as possible in a vain attempt to ease the weight on their nips, their breath shallow, their faces cringed up in determination. After exhausting all the heavy chains, hanging weights were next brought in and hooked unto the chains. The convicts seethed through their teeth, but remained apart from that silent, each lost in its own individual torment. The wardens looked on in wonder at the raw determination of these convicts not to give up. But eventually a winner had to be declared, when all the chains and weights had been used up. Slowly we began the use of the Punishment Units, shocking first 32 then 33, beginning at Level 1 and for 5 seconds. At last, at the last second on Level 4, 33 let out an earth-shattering shout of pain and frustration, releasing the chain from its mouth. The chain went through the pulley and the mass of metal chains and weights that had stretched its nips so far from its body came crashing down with a clang. With its victory secured, 32 let go a second later, moaning and squirming in its bondage. The crowd cheered as we moved onto the second game.

The second game challenged the convicts’ strength. For this, I wanted to try something new – a concept for a new form of convict hard labor I had been tinkering with during my free time. Whether it goes beyond planning remains to be seen. We installed two rowing machines, custom made by one of the warden’s here, with exceptionally heavy handles to resemble wooden oars of ancient galleys. The convicts were shackled in a rowing position and made to row 300 strokes with both arms as fast as possible, with the fastest declared the winner. 32 and 33 proved themselves up to the task, performing as excellent galley slaves, rowing in smooth regular cycles, with arms and shoulders bulged up and red from this forced exercise. They endured stoically the shocks we gave them when they slowed down, focused entirely on their task.

This time, there was no camaraderie. Whether it was because of the prizes and punishment at stake, or whether Jimenez’s training finally got to 32, 32 and 33 gave no quarter to the other. There was no exchange of friendly remarks throughout the evening, no spurring on of the other. Each convict wanted to win. And here it was 33 that pulled ahead, achieving the required 300 just a minute before 32. 32 groaned as it failed and Jimenez delivered a Level 7 shock to its balls to show his displeasure.


For the final game, the convicts must fight to force submission from the other. In order to draw this wrestling match out long, and to make it funny, Jimenez and I have our convicts oiled. We apply this oil by hand. I spread the liquid over 33’s pecs as I rub the substance all over its hard body and its chiseled face, feeling the crevices between the prominents muscles that make up the frame of the convict’s body. The convict grimaces as I end with a short stroking of its cock and balls to lubricate it.

The convicts are unchained from the frames and brought to the middle of the Pit. There they are chained on their ankles via a short chain to one another, that goes through a ring bolted on the floor. The wardens make a wide circle around the convicts, giving them space to maneuver.

And so the fight begins. The convicts begin to circle around for the first five minutes, as each attempts to spot and exploit any momentary weakness in the other.

Cat-calls and shouts of laughter fill the room, but the convicts are focused solely on each other. The short chain on their ankles encourage close contact and quicker action, but the convicts allow themselves time, studying their opponent with intensity, ready to pounce at any perceived chance. How boring.

“Get on with it!” I demand, shocking 33 with a Level 4 via the Punishment Unit. At once, spotting this weakness, 32 lunges at 33, surprising the convict as they both tumble to the ground. The crowd roars in jubilation.

The fortunes of the fight sway constantly. First, 32, the younger and more agile, has the upper hand, with its hope in securing a quick victory by the surprise move it just made. Yet, this quick victory literally slips out of its fingers. It did not take into account the oil covering their bodies, and thus 32’s attempt at a stranglehold fails, as 33 simply slips out of the knot made by the convict’s arms. 33 attempts too, to grab 32 by its waist and lift it, but gains no traction on the narrow waist of the convict, allowing it to quickly slip past the hold, and jump 33 from behind, causing both convicts to fall on the ground again.

There is a constant tossing and turning, aided by the shean of oil and sweat spread on their overtaxed bodies. Yet despite all the strength they possess, each convict finds it hard to get a grip on their opponent, as they grate and grind against one another, groaning and grunting from their exertions and frustration. Their performance is truly mesmerizing.

Finally, 32, by some stroke a fortune is able to turn this stalemate around by flipping their tightly entwined bodies over, so that it is above and 33 on the ground. Now it has the upper hand! The crowd cheers. But a look of shock comes over 32’s face as it realizes that the main objective all along is to get its opponent to cum. Puzzled, this gives 33, the stronger of the two, just the motivation and time, to push sideways against 32, forcing the young blond convict to fall over, and its grip on my clever convict is loose.

Quickly, 33 grips 32 in a joint lock, so that its arms are legs are splayed away and unable to bend. 33 has its body twisted tight against 32, but in its quickness has its body the other way around: 33 on top and its body the other way around so that its mouth was on 32’s crotch. Then to everyone’s amazement and bewilderment, 33 shows its ace in the hole. With a deep breath it swallows 32’s cock, stroking it with its mouth! 32 is taken aback that this is actually working and desperately tries to return the favour, but 33 keeps its own groin far away from 32’s mouth. But the 15 minutes long grind against another oiled up naked body is just too much stimulation for the young horny buck, and it groans in defeat, as cum quickly erupts from its manhood, spilling onto the prison floor.

Victory at last!

Red in the face in rage and humiliation, 32 curses and screams as it is brought to and harnessed into a dentist’s chair, as Jimenez berates his convict for failure.

“You fucking stupid convict. You get what you deserve,” says Jimenez, as he himself slowly applies the needle, piercing the convict’s tits, which are extra-sensitive from ejaculation, eliciting a scream of agony not heard since the convict received its first shock from the Punishment Unit on the very first day of its sentence. The large and heavy nipple rings were then attached, a permanent sign of its defeat, always to be worn by it for the remainder of its sentence.

But to the victor go the spoils. 33, despite looking exhausted and beat up, smiles at its victory over such a tough opponent.

“No empathy for 32?” I ask.

“We’re convicts. Each day is hell. What’s a little bit more pain? We’ve already hit rock-bottom performing for you lot. And it can’t get any worse than it is already,” it replies. Or so it thought, the fool.

I shackle 33 back on the X-frame and bring the workboots. I help 33 put them on. They fit perfectly.

“Just so you know,” I say. “I only brought the pair that fit your shoe size down here, rather than 32’s, because I was confident we would win. You’ve done well, 33.”

“Thanks for the compliment, Torque,” it says. “To be honest, I couldn’t have done it without you and your training.”

In this surprising show of friendliness, I bring the rest of 33’s rewards. I tie the rag around the convict’s waist to shield its manhood, however temporary, from the eyes of the ravenous wardens and all-seeing cameras in its prison cell. I also get a burger and fries from the party table and hand-feed the immobilized convict. The convict consumes the food greedily, along with 3 bottles of beer.

As the party drags on, other wardens come to compliment the muscled victor of this year’s games, mentioning that this was without a doubt the best year yet. Meanwhile,32 in humiliation, is strung back to front on its X-frame, unable to see the night’s proceedings as further punishment, groaning occasionally as it begins to learn to accommodate the new torment of the rings, now attached to its freshly-pierced and over-sensitive nipples, weighing them down.

It truly was an amazing night! And at last, I am able to one-up Warden Jimenez, proving once and for all, that convicts made the best wardens.

“Well done, Torque,” Jimenez answers graciously. “You win.”

“We all win,” I answer diplomatically, loudly so everyone can here. “We’ve had the best party yet.” Cheers all around.

Eventually, I decide to hit the bed and ask two of the youngest wardens still wanting to stay on to bring 33 back to its cell when the party is over.

“Good night, 33. Have a good rest tomorrow and, of course, happy new year!” I say.

“Leaving already, Torque?” the cheeky convict asks mockingly. “You’re quite the wimp. The party’s just getting started! I was just about to tell the wardens about the first time I bamboozled the Senator’s daughter before I got caught.”

“No, I’m too old for this staying up late shit. Plus, I already know your story. It’s all in the files. There’s quite alot of bullshit in there.”

“Alright. Your lost, mate,” it says, as I turn around and leave.

And so, I exit the Pit and make for my room upstairs, a smile on my face, as I ponder the things in store for the convict this year. ‘Mate’ it just called me. That smug bastard. We’ll see if it’ll be calling me ‘Mate’ when it finds out what has been planned. For this is the year that Convict 33 of Sisyphus Penitentiary will be broken!




1 thought on ““Wheels of Sisyphus” – by Hayden, Book 2b, Chapter 20a

  1. What an incredible epic! Detailed to the max, uberhot, and horny. The situations, so well-described- are just perfect. I also like the way you play with a range of emotions- I actually find myself caring about these guys!

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