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Completely blind and restrained in a straight jacket the prisoner is uncomfortably chained to the ceiling, helpless against Sir’s will. The prisoner’s cock at is at full attention as Sir begins to painfully tease him. With a short break from the torment the prisoner struggles against the restraints, reminding himself that he is screwed. Sir returns, armed with a flat fiberglass batten that stings the prisoner’s thighs and balls. Looking to potentially leave welts Sir then upgrades to a thin bamboo reed.

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The boy is helplessly strapped down to the gurney and Sir is going to make the most of it. The leather strap slaps down on his reddening ass but the boy’s moans are barely audible through the bondage tape mask. Then Sir makes him protest by striking his ass with the welting ball which builds up a fury of deep red hot pain. When the boy can’t take any more Sir returns to the strap and finishes with a face fucking.

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The boy, chained to the punching bag, takes hit after hit but Sir will not be contented with the usual spots. Once the boy’s chest is warmed up Sir takes to his groin with straight punches and knees. Even Sir’s embrace serves only as distraction as he comes in for another low blow.

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Helpless against Sir’s teasing of his cock the prisoner moans and jerks in vain as Sir violates his ass with his fingers. Sir releases his hands and the prisoner begins edging himself while still inverted. With Sir’s finger back in his ass the prisoner blows his load onto his own face.

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Sir visits the boy in his cell, giving us a rare close up of Sir pissing. The boy greets him with the customary blowjob. When Sir is getting ready to cum he permits the boy to lick his balls until Sir blows his load in a long enthusiastic shower.

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Sir lays Mr. Kristofer into the sling and removes the cold shackles from the prisoner’s ankles. Sir then widens the prisoner’s hole with his baton. Once the prisoner is well loosened Sir pulls out his cock and has the prisoner strengthen his erection for what comes next.

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Puppy puts the prisoner into a complicated horizontal rope suspension. He is careful to keep prime targets open for future use, his intentions are brutal and the prisoner eagerly awaits his punishment. Puppy is quick to get the balls rolling… pun intended.

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In a full straight jacket and chain suspension the prisoner is subjected to rough impact play as his legs flail in the air causing the chains to bite him mercilessly. The prisoner remains rock hard through the torment. Sir comes back, lube in hand, and begins to tease the prisoner’s prostate.

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“But I’m a good puppy…” to which the boy replies, “you should see what he does with bad puppies!” which, of course, diverts Sir’s attentions onto the boy who has been aiding in the puppy’s torment. The boy laughs and whines as Sir tickles and punches him pausing only to torture the puppy’s tits. When they’ve had enough Sir lets them double team his cock.

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The boy’s eyes are transfixed on Sir as he orders him to open up and deep throat his nightstick. The boy is then bent over the prison toilet and made to take a beating to his junk and ass. Sir then face fucks the boy but instead of cumming he showers the boy in piss.

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“Warning: Do not misuse this piece of equipment” It was so clearly printed on the Roman chair, one has to wonder if this includes fisting. Tonight the bitch wants to know if he can finally take puppy’s paws which happen to be larger than your average paws. So much lube, so much whining, so much begging, and such shiny rubber pants… it was a “full” evening.

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The boy finds himself in quite the situation. The ass hook got his attention but the nose clamp tied to the ass hook really kept him on his toes… If that wasn’t enough Sir makes it a point of taunting the boy adding insult to injury.

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The prisoner patiently waits, chained to the urinal, for Sir’s return but his patience is rewarded by being stepped over as Sir goes to piss right in front of his face. Once finished Sir turns to face fuck the cock hungry prisoner. The toe of Sir’s boot then finds it’s place on a helpless cock as he works toward a howling orgasm.

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What was supposed to be a very serious forced workout scene turned into a hyper-competative farce as the mostly naked prisoners fail to one up each other through their sets, stumbling on almost every exercise. Puppy is then forced to keep them moving by stinging their asses with a fine carbon fiber rod that gets them unleashing profanities as they try to keep pace.

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Sir tests the limits of puppy’s balls with a single tail. Ferociously whipping his thighs, head, and wrapping he makes puppy whelp and squirm. It begins to be incredibly difficult for puppy to hold still as Sir ramps up the scene.