Latest 'Caning' updates from Free Kink Men

Cazden Hunter in 'Wants Cock In His Hungry Pig Hole RAW'

Cazden Hunter - Wants Cock In His Hungry Pig Hole RAW

Naked and chained up with a fetish mask covering his mouth Cazden Hunter can't escape his bondage as Arturo and Dominic explore his hot body and let him know he is all theirs today. They bite his nipples, squeeze his uncircumcised cock and cane his chest and muscular abs. Arturo licks Cazden's ripe uncut dick clean as Dominic humiliates him and whips him with the flogger. These leather clad Daddy's jerk Cazden's cock to the edge over and over again and punish him for almost cumming. His nuts are swollen and cherry purple from holding it all in. Next Cazden is on his knees with wrists cuffed together as he slides his tight hole down onto a massive dildo. It barely fits in his ass but his hungry pig hole won't have it any other way. He rides that fat cock all the way up and down stretching his hole so good while he sucks Arturos hard dick.Just when you think he can't take anything more in his butt Dominic presents an even bigger, thicker knob for his ravenous ass. Finally Cazden gets his hole stuffed with real cock and gets it from both ends. Arturo face fucks his pig and Dominic pounds his ass. They switch places so everyone can get in on all the hungry swine hole action. Cazden sucks Dominics dick while Arturo fucks Cazden's ass until they both shoot hot loads all over their little piggy.

Ashley Ryder in 'Piss Boyz: Thom Barnes and Ashley Ryder'

Ashley Ryder - Piss Boyz: Thom Barnes and Ashley Ryder

Tom Barnes has Ashley Ryder in his on his back, strapped to a mattress. He sucks Ashley's nipples and grabs at his cock. He hits Ashley's muscular chest and abs with a wooden cane. Tom pulls Ashley's cock out and starts sucking. He whips out his own cock and fucks Ashley's mouth. Ashley gets jerked off and denied an orgasm. Tom flips him over onto his stomach and spreads Ashley's legs and then his ass cheeks. He dives in face-first and licks Ashley's hole. Tom sticks Ashley's cock and balls in a pump and pumps it up. After a few hard spanks, Tom puts a huge dildo onto a strap-on and plunges it into Ashley's hole. After that, Tom fucks him with his real cock and cum on his asshole. Tom stands over Ashley and pisses in his mouth. He shoves his cock down his throat and orders him to drink the rest.

Rocky Maximo in 'My Little Bitch: Rocky Maximo and Matthew Grande'

Rocky Maximo - My Little Bitch: Rocky Maximo and Matthew Grande

Rocky Maximo makes Matthew Grande his Little Bitch in their first Kink shoot. Blindfolded and bound to the St Andrews cross Matthew Grande squirms and groans as the sadistic Rocky Maximo manhandles his plaything. Rocky crops and canes all the sensitive parts of Matthew's body turning his skin red and splotchy and then counteracts the shocking pain with tickle torment causing Grande to burst out laughing as he jerks around trying to escape his bondage. All that laughing soon turns into whimpering moans as Rocky grinds a huge sinister looking dildo up Matthews tight hole. He is gagged and hogtied to a fuckbench with his legs spread wide open just taking it deep and hard as Mr. Maximo gets his little bitch ready for real cock. Finally flipped over on the bench with his ass up high Rocky fucks Matthews tight hole until he shoots his hot load all over Matthews face.

Cesar Xes in 'Isaac X and Cesar Xes: Interrogation XXX RAW'

Cesar Xes - Isaac X and Cesar Xes: Interrogation XXX RAW

Tied down to a chair with a sack over his head Cesar Xes can't move and he can't see. Isaac X has complete and total control over Cesar as he looms over his sexy sensory deprived detainee with the cane threatening to beat him up real good if he doesn't tell him what he wants to know. He clamps his nipples and strikes his muscular chest with the cane. This is a kinky interrogation and Isaac will do whatever it takes to get what he wants. He unleashes Cesars long cock from his tight jeans and spit polishes his dick while pulling the chain on the nipple clamps. Isaac has Cesar by the balls as he wraps his nut sac in a chained leather pouch and reminds him of all the nasty dirty things he's going to do until he talks.Now standing gagged and restrained Isaac delivers another load of corporal punishment with flogging, slapping and then inspects the slutty hole Cesar has to offer. It turns Mr X on to inflict all this pain as he watches Cesar twist and groan and try to get away. His dick is stiff and needs to be sucked so he removes Cesars mouth gag and replaces it with his thick cock. Cesar knows how to suck cock and boy is it hot! Isaac is so turned on he voraciously eats Cesar's ass out and then fucks his juicy hole out until he cums all over his face. Cesar licks it all up and then Isaac lets him jerk off and shoot a fat load.

Kristofer Weston in 'The Suffering of Scott Ryder: Part Two'

Kristofer Weston - The Suffering of Scott Ryder: Part Two

Leather Daddy Kristofer Weston gets his boy Scott Ryder suited up in leather for a day of fun. He fits the hood around Scott's face before locking it shut. Next is the leather straight jacket that fits snug above Scott's caged cock. Helpless in bondage, Scott is at whim of his Daddy.Kristofer spanks his boy's ass red before pushing a fat plug in his hole. Ass full, Scott sinks to his knees to service his Daddy's hard cock. After sucking to Kristofer's satisfaction, he's strapped down with his legs and arms up in the air.Scott moans as Kristofer reminds him he's just a hole and stretches his ass open on different dildoes. After the fattest one is securely tied in his hole, his Daddy brings out the cane. Soon Scott's thighs are decorated with red stripes and his Daddy fills his ass with a hot load before plugging it up for the foreseeable futureWatch: 'The Suffering of Scott Ryder: Part One'

Micah Martinez in 'Savage Cock: Dale Savage Torments and Fucks Micah Martinez - RAW'

Micah Martinez - Savage Cock: Dale Savage Torments and Fucks Micah Martinez - RAW

Micah Martinez is completely naked in a cage with a raging hard on. Dale Savage has some kinky ideas about what he wants from his plaything so he starts with the zapper on Micah's most sensitive parts. Dale overwhelms Micah with quick, hot bursts of electricity on his muscular chest, his balls, tongue and ass. Then out of the cage with wrists tied behind his back Dale attaches several tight clover clamps to Micah's balls and then canes his thighs and ass causing him to yowl in pain with every strike of the rod. Mr. Savage then crams his cock in Micah's mouth and deep throat fucks him until he is gagging and drooling all over his dick. With his wet slippery cock Dale savagely fucks Micah's tight hole. He pounds that ass deep and hard and then blows his load on Micah's face. Micah did such a good job pleasing Mr Savage now its his turn to get off. Dale sits back while Micah cleans his dirty leather boots and stroking his big, hard dick shoots his hot cum far and wide.

Chris Damned in 'Raw Indulgence: Chris Damned and Johnny B.'

Chris Damned - Raw Indulgence: Chris Damned and Johnny B.

Tattooed hottie, Chris Damned has the handsome and lean Johnny B. lying on his back, bound with rope to an all black table. Both wearing only black jocks. Chris shoves an apple in his mouth to shut him up. Chris smacks Johnny's balls and puts clothes-pins on his arms, nipples, and his sack. Chris smacks him with a cane and climbs on top of the table for a sixty-nine suck off. Johnny's throat gets stuffed with Chris' girthy cock while Chris helps himself to a mouthful of Johnny's delicious dick. After that, Johnny gets soaked in piss and then fucked raw from behind. Chris flips him over and fucks the cum right out of Johnny.

Ricky Larkin in 'Foot Fanatic'

Ricky Larkin - Foot Fanatic

Ricky Larkin loves feet and today he has Brian Bonds bound, naked and at his mercy. Ricky licks, sucks, canes, slaps and tickles Brian's feet. Brian loves the attention and struggles in bondage as Ricky tickles him relentlessly. Then Brian gets his fill of feet. Ricky takes off his boots and has Brian worship his socked feet before stripping them off and revealing his naked feet. Brian kisses and licks Ricky's beautiful feet as well as he can in bondage. Then Ricky jerks Brian off and rubs Brian's cum all over his feet. Brian eagerly licks Ricky's feet clean.


Odin Strokes in 'Hard and Raw: Brian Bonds and Odin Strokes'

Odin Strokes - Hard and Raw: Brian Bonds and Odin Strokes

Odin Strokes is gagged, tied up and strapped down on a wooden cross. Master Brain Bonds loves to have his way with a sexy struggling man and Odin is the perfect little piece of meat for him to devour. In a dimly lit dungeon Mr. Bonds unleashes new sensations on his toy Odin with the cane on his tender thighs and sensitive feet. Then he licks his toes softly and sucks Odin's uncut cock. Master Brian strings Odin up on the cross and slaps his ass again and again turning it all red hot. Then he crops Odin's sexy back and kisses his ass to get him ready to fuck. With legs spread wide on a swing Master Brian wants his ass fucked hard and raw by Odin Strokes and that's exactly what this horny slut gets.

Adam Knox in 'HARDCORE:Adam Knox and Spencer Reed'

Adam Knox - HARDCORE:Adam Knox and Spencer Reed

Muscle God Spencer Reed, booted and harnessed, drags a bound, half-naked Adam Knox into a warehouse and ties him bent over an oil drum. Spencer pulls out his thick meat and marks his prey, blasting a geyser of hot piss all over Adam, before shoving his cock into the bottom?s mouth. Adam chokes on the girth, trying to please his top, his spit dripping off the man?s meat. Spencer turns to his captive?s upturned ass, slapping and fingering it until the bottom?s smooth cheeks turn red. Spencer taps a bamboo cane against Adam?s ass, thighs, and balls until his skin grows flushed, Adam crying out as the cane leaves its marks, and pulling hard against the ropes, seeking escape. The muscle top relishes the young man?s helpless body, getting Adam to count out the punishing strokes from a new bentwood cane. Adam bears up under the assault, impressing his top, who gets a thick finger, and then his impatient cock into Adam?s abused hole, grunting as he gives Adam his hard-earned reward, taking pleasure in his captive?s tight, jockstrapped ass. Then Spencer pulls Adam off the drum and guides him back onto his meat, Adam?s cock bouncing, his sack pulled tight by a steel ballstretcher. His hands still bound, Adam works the ropes until he can jerk himself with one hand, before Spencer pushes him down on the ground and covers Adam?s hard, smooth body with thick wads of cum. Gentler now, Spencer holds Adam against his massive harnessed chest and allows Adam release, Adam still gazing up at Spencer for approval as he shoots his load all over his own chest.

Pierce Paris in 'For Better or For Worse: Stepbrothers Fight and Fuck Before Wedding'

Pierce Paris - For Better or For Worse: Stepbrothers Fight and Fuck Before Wedding

Pierce Paris is not about to let his stepbrother Vander Pulaski tie the knot with his beau. Pierce remembers all the nights they spent together and he's not going to let Vander forget the bond they share. Dressed in leather pants, leather gloves, leather boots, and a leather harness, Pierce ties his brother up in his wedding tux and blindfolds him. Vander can't believe Pierce is doing this today of all days. He struggles in bondage and ties to convince Pierce to let him go so he can get married. Pierce is upset that his stepbrother would even dream of pledging himself to a monogamous relationship with someone who is not Pierce. All those shared blow jobs meant something to him, and he's not about to let his stepbrother ruin their family. He rips off Vander's clothes and flogs his brother's chest, ass, and cock. Vander yells for Pierce to stop, but he can't stop the smell and sting of his brother's leather on his skin from turning him on. Next Pierce ties Vander to mattress springs. He hangs weights from Vander's balls and climbs up on the mattress to fuck Vander's mouth. Vander doesn't want to at first, but he has no choice but to take every inch of his stepbrother's monster cock in his mouth. Then Pierce puts nipple clamps on Vander's sensitive nipples. He hooks up the clamps to a tens unit and sends electric waves pulsing around Vander's nipples. Vander squirms, and cries out as Pierce kneels down to swallow his cock. Pierce loves the taste of his brother's cock. Vander continues to protest so Pierce decides he needs more punishment. He puts Vander in another suspension with an o-ring gag and canes his ass, thighs, and sensitive feet. Vander screams as Pierce decorates his thighs with lovely red stripes. His toes curl as Pierce canes his feet. Then, Pierce sinks his cock into Vander's ass. Vander moans as Pierce fucks him relentlessly. Finally, he jerks his brother off with leather gloves and then comes all over his brother's face.

Devin Trez in 'OBEDIENCE TRAINING Devin Trez Disciplines New Dog with Intense Bondage'

Devin Trez - OBEDIENCE TRAINING Devin Trez Disciplines New Dog with Intense Bondage

Kink Men newcomer Devin Trez is ready to train a new puppy in his dungeon. Clad in all leather, this black muscular handsome dom commands your attention. With each step of his leather boots on the cold wooden floor, his new toy Tony Orlando trembles while fully restrained to the wheel. Tony begs to suck his master's cock, but he doesn't know what he is getting himself into today. Devin Trez reveals he is hear to train a new dog since his last one ran away. Tony begs to not be made a dog, he just wants to suck cock, so the cane comes out first. Devin knows obedience starts with the sensitive areas and takes the cane right to Tony's hard cock. He beats Tony's body red with cane welts. Tony resists but is made to wear a leather puppy mask. This dog will break today. Devin spins the wheel that Tony is strapped to and lands him upside down ready to suck on his masters bone. Devin takes out his huge hard cock and shoves it down Tony's puppy masked throat. This gets Tony gagging and barking like a dog for more. Tony of course isnt complete with out an anal plug dog tail. With this rammed down his ass, Devin jerks off his toy for an inverted cum shot. Tony cums all over his masked face. This was only part one of Tony's obedience training. Next up Tony is bound in rope to a cross and the flogger comes out. Devin inflicts a brutal corporal punishment on Tony's backside. On all fours, Tony is cropped before strapped to a intense fucking machine. Unable to move, Tony's nipples are clamped and Devin pours hot red was all over Tony's chest. This gets Tony screaming and howling. Finally the master is ready to deliver a brutal fucking. Tony is bent over and Devin rams his hard cock into Tony's ass. This pounding delivers a huge cumshot from Devin all over Tony's whimpering face.

Nate Grimes in 'Hung stud Nate Grimes - The Pit - The Chair - The Gimp Room'

Nate Grimes - Hung stud Nate Grimes - The Pit - The Chair - The Gimp Room

Nate Grimes is a real player in his personal life, and has been a fan of the KinkMen sites for some time now, but he's never experienced anything like the 30 Minute Challenge. He starts off in the pit, his hard cock dangling between his legs as Sebastian starts warming him up. Nate begs for more once the punches come out so we give him the flogger to really get him screaming. Strapped to the chair, his sight is removed and clover clamps decorate his torso as Nate breathes through the pain. His senses are driven wild once the sharp pinwheel glides across his body, tormenting his clamped skin until he begs for mercy. For his last challenge, Nate is made to ride our gimp's hard cock, all while enduring a caning on his thighs and ass. As if his nipples weren't sore enough, we finish him off with a zipper of clothespins across the chest before having him shoot his load all over the dungeon floor.

Brian Bonds in 'takes the 30MT Challenge!'

Brian Bonds - takes the 30MT Challenge!

Brian starts against the wall, his cock already bulging out of his underwear before Sebastian tears them away. He starts Brian with some light CBT before pounding away on the stud's chest with leather gloves. It's not until the flogger comes out that Brian starts screaming from the pain, before moving onto the pit.Brian is sprawled out and exposed for Sebastian to work him over with a caning. With a few good stripes down Brian's legs, Sebastian decides to add a series of clothespins to his chest to match. Brian can hardly handle the pain as the cat-o-nine tails whips against his flesh, so Sebastian rips the clothespins off and beats down the tender flesh before finishing him with one more whipping.Blindfolded and bound to the ass-less chair, Brian drools all over himself as a spider gag pries his mouth open. He feels the sting of the electric zapper prodding him all over his body and on his exposed ass. Sebastian then jams his hand up Brian's ass and fucks him without mercy. With a hand in his ass, Brian screams at the top of his lungs while being finished off with the zapper for one more round of abuse. After all three challenges, Brian has his cock milked until his cum is sprayed all over the floor.

Ruckus in 'Convict Series - In Prison, You'd be my Bitch!'

Ruckus - Convict Series - In Prison, You'd be my Bitch!

Cody Winters is so curious about prison, so he's about to get a first hand experience...

Hugh Hunter in 'Cock hungry leather studs play in a dark basement'

Hugh Hunter - Cock hungry leather studs play in a dark basement

The bare sliver of light in the basement contours Hugh Hunter's ripped body in leather as he waits for his playmate, Jessie Colter. After what seems like an eternity in Hugh's horny mind, Jessie arrives with a hard dick and flogger, ready to give Hugh a night he'll never forget. Hugh worships Jessie's pits and cock before receiving the heavy lick of the flogger. Jessie ties Hugh against the cold brick wall and places clover clamps on Hugh's eager nipples. Erect from the pain, Hugh presents his cock to Jessie's mouth before a mean caning. Hugh returns the favor and hungrily sucks off Jessie before having a load forcefully milked from his balls. Still in a cumdrunk daze, Hugh finds himself in a fuck sling as Jessie admires his hard body. Hugh begs for a rough fucking from Jessie and gets exactly what he asks for before Jessie blows a heavy load straight into his mouth. The playmates share a taste of Jessie's cum before Jessie slinks back into the shadows.


Connor Maguire in 'tests his slave's hunger for pain'

Connor Maguire - tests his slave's hunger for pain

The sweet, earthy smoke of a fine cigar exits Connor Maguire's ripped body and fills the narrow corridor leading down to the basement. There, Slave #002 awaits his master, slung in ropes from a rusted chainlink fence. Connor blows smoke in the slave's face before groping the slave's eager cock. #002 receives an ample caning from Connor, thanking his master through the sharp blows from the cane. The painslut slave's dick bulges as his body is covered in clover clamps and more swift caning. Connor takes the slave from the fence and secures him on the rack. With his back contorted into a severe arch, the slave worships cock and has his balls crushed. The slave begs for mercy as Connor flogs his open chest, but Connor refuses. Instead of mercy, there is only pain and pleasure, and the slave is made to chant that mantra as the flogging intensifies. Connor suspends #002 from the ceiling and pounds his massive cock deep into the slave. He jerks a load from his slave before having him eat it off his leather glove. The slave is brought to his knees and hungrily takes his master's cum. Satisfied, Connor walks off, commanding #002 to wait at attention for the next dom.

Adam Herst in 'Tormented Without Mercy - Connor Patricks suffers tight metal bondage'

Adam Herst - Tormented Without Mercy - Connor Patricks suffers tight metal bondage

Connor Patricks has been locked away for days in Adam Herst's workshop, stripped of his clothes and dignity. Adam rouses Connor from sleep in a cramped cage, and face fucks the boy through the bars. Harder thrusts answer Connor's pleas for release. Adam binds Connor upright, blindfolding the boy with arms outstretched to hold heavy weights. Connor's tormentor warns him against dropping the load as he licks Connor's torso and legs with a riding crop. Adam raises the stakes with a clothespin zipper on both sides of Connor's body, tying the line to the weights. He puts Connor's nerves to the limit with the threat of a cattle prod and finally sticks his plaything. Gravity wins. The falling weights tear the clothespins from Connor's body. Legs dangling overhead, Adam next traps Connor under piping, contorting the boy into an inverted spread eagle. Adam delivers a caning and foot torment before a rough fucking. He continues the fucking into the night, splitting Connor's legs wide apart with belts on a platorform. Connor has the cum worked from his balls as Adam rams his giant cock deep into the boy's hole. By now, Connor's spirit has totally broken, and he accepts Adam's cum with a willing mouthful.

Connor Maguire in 'The Interrogation'

Connor Maguire - The Interrogation

Jessie Colter is unprepared for an enhanced interrogation at the hands of a twisted Connor Maguire.

Patrick Isley in 'Tormented with mousetraps and fucked into submission'

Patrick Isley - Tormented with mousetraps and fucked into submission

Patrick Isley has no idea why he is detained and no idea what Officer Connor Maguire has in store for the night. The officer handcuffs Patrick to the cage, stripping him down and forcing him to worship hard police dick before introducing Patrick's tender muscles to the crop. Officer Maguire continues his game, pinching down on his nipples and balls and surrounding his vulnerable toes with mousetraps. The officer subjects Patrick to an unrelenting flogging as Patrick dances, unsuccessfully, to avoid the mousetraps. Officer Maguire then binds Patrick to his motorcycle, caning his ass and thighs before pounding Patrick's hairy hole. Officer Maguire finishes off his prey by busting a load of cum right into his mouth.

Sebastian Keys in 'My Life Changing Experience on 30 Minutes of Torment - Sebastian Keys'

Sebastian Keys - My Life Changing Experience on 30 Minutes of Torment - Sebastian Keys

After several excruciating months of planning this shoot, the day had finally come when I would put myself through 30 Minutes of Torment. I knew right off the bat this was going to be one of the most challenging moments of my life as soon as Van stopped the clock and said: "We're not doing the usual 30 minutes today, we're going as long as we have to." My first challenge was to bring out the anger inside me. As Van wailed on me with the paddle and flogger, the more I screamed, the harder he would hit. My next challenge was one I never saw coming, the infamous Chinese Water Torment. Wooden spears kept me in place with electrodes down my thighs and an electric butt plug shoved up my ass, tormenting me alongside the ice cold water dripping on my forehead. After pushing through the water torment, Van brought me to the padded cell, bound in rope for my final test. To complete my transformation, I had to bring out my inner dom, despite my submissive bondage as Van slammed me hard all across the room. The torment didn't cease until I proved that I AM MR KEYS.

Connor Maguire in 'House Dom Connor Maguire - Extreme Torment and Ass Violation'

Connor Maguire - House Dom Connor Maguire - Extreme Torment and Ass Violation

House Dom Connor Maguire finally steps up to the 30 Minutes of Torment challenge. The Bamboo Garden - Connor starts things off brutally, tied to bamboo chutes. Van works the muscled studs chest with some hard punches before caning his ass. With his cock hard, and tied up Connor endures more caning and nipple torment. The Pit - Strapped up with belts and balancing on pegs, Connor takes the flogging of his life as Van wields two floggers. We've seen him dish it out but the hunk can really take a beating too. With a dildo mounted on the platform, Connor squats on to it, enduring the ass torment as well as the stress position with another round of hard flogging mixed in. The Water Station - With Connor's entire torso feeling the agonizing pinch of the numerous clothes pins we hit him hard with the water. Each clothes pin is held by twine causing it to pull on the stud's flesh whenever he tries to avoid the intense spray. After a round of breath play Connor has gotten through his 30 minutes and cums hard after the day's session.

Adam Ramzi in 'Super Hunk Adam Ramzi - Tormented and Ass Violated'

Adam Ramzi - Super Hunk Adam Ramzi - Tormented and Ass Violated

The Pit - Adam Ramzi walks into the pit and has his hands and feet chained down for Van to warm him up with punches and pulling hard on Adam's balls. He pushes through the pain as the flogger is brought out for more torment. - The Chair - Adam moves one step closer to completing 30 Minutes of Torment, his second challenge is the chair. He's tied down tight as clover clamps pinch all over his entire body. A caning on his thighs before receiving the electric zapper makes Adam fill the room with his screams. - The Gimp Station - Finally for his last challenge, Adam's bent over to swallow the gimp's hard cock as his beautiful ass is caned some more. To complete his challenge Adam must take every inch of the gimp's cock and blow his load!

Adam Herst in 'The Creepy Handyman ties his new victim up and fucks him senseless'

Adam Herst - The Creepy Handyman ties his new victim up and fucks him senseless

Boy next door Micky Mackenzie showers off in the locker room before Adam Herst sneaks up from behind and takes the boy captive. Micky struggles to get free but the rope around his body is bound too tight for any chance of escape. Mr Herst sucks on the boy's hard cock before working him over with the riding crop. A flogging is next in store for the poor boy as his captor relentlessly beats his backside. Tied down on the bed, Micky is tormented even more with a caning as he bites down on the rope gag in his mouth. Mr Herst plunges his big hard cock deep in the boys ass until leaving the boy with a face full of cum.


Trevor Spade in 'Straight hunk Trevor Spade tormented to the extreme'

Trevor Spade - Straight hunk Trevor Spade tormented to the extreme

The Chair - Straight hunk Trevor Spade comes to 30 Minutes of Torment with his first challenge taking place in the chair. Van gets the boy's cock hard before beating him with the riding crop and pinching clover clamps all over his torso. Even Trevor's tender balls feel the pain of the clamps while Van torments him with the electric zapper. - The Pit - Standing in the pit, with his hands bound behind his back, Trevor winces in pain as Van torments the boy's nipples. Trevor balances on wooden blocks as he's relentlessly beaten with the flogger. - The Water Chamber - Standing in the water chamber, Trevor has his arms bound above his head as Van warms him up with a caning. Clothespins are then pinched onto his tender skin as water blasts each one of them off. After enduring an intense water boarding, Trevor's made to finally blow his cum.

Dakota Wolfe in 'Pain slut Dakota Wolfe takes the 30MT Challenge'

Dakota Wolfe - Pain slut Dakota Wolfe takes the 30MT Challenge

The Pit - Hot pain slut, Dakota Wolfe stands in the pit as he's bound with leather belts before Van gets his cock hard. Heavy clamps are tightly screwed onto Dakota's nipples as they're tormented with the sting of the cat-o-nine tails whipping against his tender skin. Dakota pushes through the pain of his nipples before enduring an extreme flogging. - The Chair - Our pain slut moves onto the next challenge as he's bound tightly in the chair, with medical clamps pinching all over his torso and tied off to the wall. Dakota endures some CBT as electricity torments his aching balls. Each clamp is removed from his tender skin, Dakota screaming at the top of his lungs each time the clamped skin gets whipped with the crop. - The Gimp Station - Finally, Dakota moves onto his third and final challenge. He's bent over, with his hands strung up behind him as his ass endures a heavy caning. The gimp shoves his hard cock down the boy's throat before jamming it up his ass for a rough fuck. As reward for successfully completing his three challenges, Dakota finally blows his hot load all over the floor.

Seamus O'Reilly in 'Big Cock Galore - Live Show'

Seamus O'Reilly - Big Cock Galore - Live Show

Hung stud's Doug Acre and Seamus O'Reilly stand with their jockstraps in their mouths as Van gives them each their slave number, 153 and 523. After a flogging from Mr. Wilde, hot wax is poured all over both subs while being relentlessly tormented with the zapper. 153 and 523 have their legs and arms bound in the air as their exposed ass cheeks are beaten red with the paddle. Van and Christian take turns drilling the fucksall into each of the boy's holes before Christian whips out his giant cock and pounds their holes. After a heavy caning, both subs worship Mr Wilde's beautiful feet before they climb up on the sybians to see who can blow their load first. Finally, Christian orders the boy's to their knees for them to receive his massive load all over their faces.

Dayton O'Connor in 'I PROMISE I'LL PAY!!!'

Dayton O'Connor - I PROMISE I'LL PAY!!!

Seamus O'Reilly hasn't paid up to Leo Forte's unruly gang, so they line up their asses and make him crawl in on his hands and knees, blindfolded as they bury his face in between their cheeks. Seamus gasps for air as he's held down to eat ass, while being tormented with the electric zapper. The gang ties his ass up as they line up their hard cocks to pound Seamus' tight hole. The boy begs for mercy but all he gets is a caning on his feet as the guys continue to ram him up the ass. Seamus is then bent over for another round of fucking before the guys shove a beer bottle up his ass and laugh at him as he squirts it all over the place. To finish him off the guys shower him with cum and piss before leaving him tied up, soaking wet for the cops to find.

Jacob Durham in 'gets oiled down, beaten, and fucked like an animal'

Jacob Durham - gets oiled down, beaten, and fucked like an animal

The Pit - Muscled stud Jacob Durham begins his first challenge in the pit, his arms bound behind his back as Van gets his fat cock hard. Jacob endures torturous ball squeezing before he's warmed up with the flogger. - The Chair - Bound to the chair, tight clover clamps are attached all over Jacob's torso and balls. He pushes through the pain of the clamps on his tender skin before Van surprises him with hot wax all over his body. Covered in a mess of wax, Jacob screams at the top of his lungs as each clamp is removed. - The Gimp Station - Jacob's muscular body is oiled down before enduring a caning on his ass. The muscled stud is flipped over on his back as the gimp is let loose on Jacob's hole. After a ferocious fuck, Jacob receives a face full of the gimp's cum before he's challenged to blow his own load as his final task.

Kip Johnson in 'Ass Torture'

Kip Johnson - Ass Torture

The Wall - Hung straight stud Kip Johnson stands with his hands chained to the wall as Van gets his cock hard. Kip endures the flogger as he braces himself for each blow before his next challenge in the pit. - The Pit - Clover clamps are attached across Kip's chest and all on his balls as the riding crop beats him front to back. The bound stud screams in pain as the clamps are released and he's taken to the ass station. - The Ass Station - His hole stretched wide, Kip struggles to sit on the giant bruiser dildo from "Bad Dragon", while enduring a caning. As Kip's hole swallows the dildo, Van beats him with the flogger and orders the screaming stud to finally blow his load.

Jordan Foster in 'Hot southern boy relentlessly fucked and beaten'

Jordan Foster - Hot southern boy relentlessly fucked and beaten

The Pit - Jordan Foster stands with his hands bound behind his back as Van cuts away the boy's jock. Once his cock is rock hard, Jordan endures a beating and a heavy flogging before he's taken to the chair. The Chair - With a ball gag in his mouth, heavy weights are added to Jordan's balls as clothespins are attached all across his torso. One by one Van crops the clothespins off and torments the boy's nipples as he screams in pain. The Gimp Room - Jordan is bound with his feet in the air for a caning. His torment continues as he's suspended in the air until the Gimp is ready with his hard cock. Jordan's relentlessly fucked in mid-air as Van torments him with the zapper. Finally, a rope is tied around his neck as Jordan rides the Gimp's hard cock, enduring one last flogging as he's challenged to blow his load.

Connor Maguire in 'Connorligula - Roman Gladiator Live Show - Part Two'

Connor Maguire - Connorligula - Roman Gladiator Live Show - Part Two

When judgement time comes for slave 200, Connorligula halts Genghis Van and informs him of a new slave that must be punished for attempting to set Rome on fire. Slave 300 is bound between two columns as Genghis Van and Connorligula dual flog him. His nipples are clamped down hard as 200 and slave 100 are ordered to suck cock. All three slaves are bound to the cross as their punishment continues. 300 has weights clamped onto his nipples as Genghis Van torments him with a caning. Connorligula ties 100's legs up so his ass is open wide for his hard cock. 100 dangles in the air as he's relentlessly fucked before he and 200 are brought to their knees to worship Connorligula's feet. They blow their loads all over his toes before receiving a face full of Connorligula's cum.