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Punish the recruit! - part 01 West Barnstable
Release Year: 2019
Video language: English
Watch their wild unrestrained urges take control and make them do things shocking, kinky, and ultimately sexy.
Format: Windows Media
Duration: 14:55
Video: 1280x720, Windows Media Video V8
Audio: 125kbps
File size: 551.7 MB
DOWNLOAD FROM FILESMONSTER: Punish the recruit! - part 01
Odds And Ends Markle
Although his rig consists of various pieces of kinky gear, the most unique.
Format: mp4
Duration: 12:37
Video: 1280x720, AVC (H.264), 3899kbps
Audio: 153kbps
File size: 374.7 MB
DOWNLOAD FROM FILESMONSTER: Odds And Ends
Bullied No More Miston
Him to convulse in all directions without hurting himself.
Format: mp4
Duration: 25:51
Video: 1280x720, AVC (H.264), 3899kbps
Audio: 153kbps
File size: 768.1 MB
DOWNLOAD FROM FILESMONSTER: Bullied No More
Ransom - part 01 Sarona
Release Year: 2019
Video language: English
Having been subjected to some of the most extreme anal action ever captured on camera, you'd be forgiven
Format: Windows Media
Duration: 11:08
Video: 1280x720, Windows Media Video 9, 4932kbps
Audio: 187kbps
File size: 414.8 MB
DOWNLOAD FROM FILESMONSTER: Ransom - part 01
Turning The Tables Petoskey
It is our pleasure to be working with him and we look forward to presenting his videos on this website.
Format: mp4
Duration: 7:44
Video: 1280x720, AVC (H.264), 3900kbps
Audio: 153kbps
File size: 229.8 MB
DOWNLOAD FROM FILESMONSTER: Turning The Tables
Dominic Pacifico and Josh Mikael Kozhikode
Stuffing raw poultry with chef Dominic Pacifico is putting some dirty thoughts into his assistant Josh Mikael 's mind! After filling up a gaping bird for a cooking demonstration, Josh exposes his furry ass to the chef in hopes that he is in the mood to stuff something else. After complimenting Josh's big hungry hole, Dominic uses his fingers and hard cock to fill him up. Dominic barebacks Josh's soon-to-be gaping ass as Josh begs the chef to give him more. When rawing him simply isn't enough, Dominic finally satisfies his horny assistant by stuffing his entire hand into his eager hole. Wearing only a cock ring and leather boots, Josh climbs onto the counter to ride Dominic's clenched fist. Dominic holds his arm steady as a grateful, gaping Josh bobs up and down on his thick forearm. For only a moment, the chef removes his hand from Josh's ass to admire the man's wrecked hole. Dominic shoves his fist back inside of Josh to continue the anal destruction before the hairy assistant shoots a load of sticky cum out of his cock. The pleased chef exclaims that he finally has enough gravy for his stuffing.
Format: mp4
Duration: 23:40
Video: 3840x2160, AVC (H.264), 14652kbps
Audio: 125kbps
File size: 2.5 GB
DOWNLOAD FROM FILESMONSTER: Dominic Pacifico and Josh Mikael
Prison means lust - part 03 Fernwood
Release Year: 2019
Video language: English
Submissive men are captured and taken down, their assholes being entered with huge insertion toys. These are some of the most intense and personal examples of male domination.
Format: Windows Media
Duration: 14:51
Video: 1280x720, Windows Media Video V8
Audio: 125kbps
File size: 550.1 MB
DOWNLOAD FROM FILESMONSTER: Prison means lust - part 03
The Casting Part 1of 2 Little Chalfont
He flails helplessly and no matter how hard he pulls on the springs they always win by returning.
Format: mp4
Duration: 17:05
Video: 1280x720, AVC (H.264), 3898kbps
Audio: 153kbps
File size: 507.5 MB
DOWNLOAD FROM FILESMONSTER: The Casting Part 1of 2
Proper Drill - part 03 Booker
Release Year: 2019
Video language: English
Not even the most rock hard muscled studs can escape punishment & submission on .Watch the hottest studs get tied down, fucked & submitted.
Format: Windows Media
Duration: 19:57
Video: 1280x720, Windows Media Video 9, 4882kbps
Audio: 187kbps
File size: 744.1 MB
DOWNLOAD FROM FILESMONSTER: Proper Drill - part 03
Heavy Rubber Demo Part 1of 4 Asahikawa
With role playing scenarios and all the bondage gear you could handle.
Format: mp4
Duration: 12:49
Video: 1280x720, AVC (H.264), 3899kbps
Audio: 153kbps
File size: 380.6 MB
DOWNLOAD FROM FILESMONSTER: Heavy Rubber Demo Part 1of 4
Brandon Bent Over Klickitat
Brandon, 20 years old, came to us needing to pay the rent on his much-too-expensive condo. Tom gave him his first spanking on the the day before this video was shot, but told him he was going to need to do more than one video to earn the amount of money he needed. Brandon begged off, stating that he couldn't take any more, so Tom agreed to let him come back in a couple of days to shoot this video.
Tom knew Brandon would come back because Tom wouldn't pay him anything until all of the videos were shot. What Tom didn't know, and what Brandon learned earlier this morning, was that if he didn't pay today, he'd owe a substantial late fee. So Brandon's ass was still a bit red when he showed up for this video.
Tom starts in on Brandon with a ping pong paddle, his hand, a leather slapper, a deceptively painful small oak paddle and a five-gallon paint stirring stick that has Brandon's ass quivering involuntarily. As the video continues, you'll see sweat running down Brandon's arms as he struggles with the pain. You'll see his ass and thighs shaking and quivering as the punishment continues.
Format: mp4
Duration: 16:54
Video: 1280x720, AVC (H.264), 4748kbps
Audio: 178kbps
File size: 610.8 MB
DOWNLOAD FROM FILESMONSTER: Brandon Bent Over
Ransom - part 04 Grubbs
Release Year: 2019
Video language: English
After finishing his chores of cleaning up around the workshop he whips out his massive hard cock and decides to have a little me time.
Format: Windows Media
Duration: 12:07
Video: 1280x720, Windows Media Video 9, 4932kbps
Audio: 187kbps
File size: 452.0 MB
DOWNLOAD FROM FILESMONSTER: Ransom - part 04
Ethan's First Spanking Toluca Lake
First Contact Video! This is one of Tom's favorite spanking videos. Before this video, Ethan had never been touched by a man. His reactions to Tom spanking him are very noticeable and numerous. He looks great bent over a man's knee with his round butt exposed, and you'll see the action from several angles.
Ethan came to us after his friend did a j/o video for our other site, RedHotStraightBoys. Ethan's friend has refused to do a spanking video for a long time. The friend finally agreed to a spanking video, but, before it was even scheduled, he told Tom his friend (Ethan) would like to do a video. He sent Tom some photos of Ethan, and Tom immediately scheduled this shoot.
Like virtually all of our other models, Ethan asked no questions about the spanking in advance, except for how much he'd be paid. And, also like the others, it's clear Ethan presumed his spanking would be mechanical and involve little physical contact. Ethan is very surprised when Tom orders him over his knee, and he's more surprised by the amount of hand-to-butt contact (though it's hard to imagine a spanking without it), and more surprised still when Tom adjusts his package for the camera.
Like the other boys, Ethan tries to smile and appear at ease with what's going on. But the severity of the spanking wears on him and has him reacting audibly to the spanking. Ethan is fighting back tears through much of this video. At one point he even wipes away a tear. Apparently Ethan had expected the spanking to hurt a bit physically, but not as much as it did. And what Ethan really hadn't counted on were things like submitting to being over a man's knee and being told to strip down. He just hadn't counted on the stark reality of the spanking Tom deals him.
Format: mp4
Duration: 16:16
Video: 1280x720, AVC (H.264), 4744kbps
Audio: 178kbps
File size: 587.2 MB
DOWNLOAD FROM FILESMONSTER: Ethan's First Spanking
Caught In The Act vol. 17 Fishers Hill
As a reminder, please wear your masks during this pandemic. Over the New Year Holiday I had dinner with a small group of 4 people. One week later we all tested positive, with one person fighting for his life in the hospital right now as I'm typing this. Please be careful out there.
Format: mp4
Duration: 28:19
Video: 1280x720, AVC (H.264), 4834kbps
Audio: 309kbps
File size: 1.0 GB
DOWNLOAD FROM FILESMONSTER: Caught In The Act vol. 17
Load Taking Cum Whores Chennai
Release Year: 2009
Cast: Lorenzo, Axl Mews, Damien Silver, Orion Galvani, Adam Fine, Jore Wu, Lany Ritz
Genres: BDSM, Fetish, Anal, Oral, Mask, Rimming, Big Cock, Dildo, Toys, Vacuum Pumping, Deep Throating, Interracial, Tattoos
Video language: English
These guys love to take cum whether it is in the mouth or in their ass! There is some threesome action along with one on one. These guys wear mask and cockrings to bring a spark to their sexual appeal. These boys have one thing in common! The love of dick and cum! So cum and watch these guys pound away.
Format: Windows Media
Duration: 1:21:07
Video: 640x480, Windows Media Video V7, 2255kbps
Audio: 125kbps
File size: 1.4 GB
DOWNLOAD FROM FILESMONSTER: Load Taking Cum Whores
Hector's First Spanking Keswick
First Contact Video! This is a long, hard spanking/paddling. Hector is a 20-year-old straight boy who needs money to pay for college. He wanted to do a video, so he sent Tom pics and they set up a shooting date. However, when Hector showed up, it was clear that the pictures he had sent were not current. Tom decided to spank him, anyway. He goes at Hector with his hand, a small oak paddle, leather slapper and a bamboo spatula. The video ends with a severe round with the bamboo spatula that has Hector groaning, kicking and cursing.
It seems like Hector struggles with what his reaction to the spanking should be. Tom doesn't coach the boys, so what you see is either how Hector wants to appear, or how he thinks Tom wants him to react. He is in pain, but it seems like he is trying to pretend he isn't. By the end of the video, as the pain takes over, you see Hector's true reaction. After the shoot was over, Hector told Tom that he was ready to walk out just a few minutes into the video because it hurt so much. But he needed the money for tuition and books, so he stuck it out.
Format: mp4
Duration: 18:14
Video: 1280x720, AVC (H.264), 4793kbps
Audio: 181kbps
File size: 665.0 MB
DOWNLOAD FROM FILESMONSTER: Hector's First Spanking
Academy Chair Marbach Am Neckar
Cold water survival suit and climb into the cell where his wrists were shackled.
Format: mp4
Duration: 11:00
Video: 1280x720, AVC (H.264), 3900kbps
Audio: 153kbps
File size: 327.1 MB
DOWNLOAD FROM FILESMONSTER: Academy Chair
Chuck Gets Plastered East Springfield
This is a video from the archives which we recently re-edited. Our friend Chuck gets his head cocooned in plaster so a cement positive of his head can be made. The positive would be used as a template for creating a custom form-fitting metal helmet.
Format: mp4
Duration: 11:56
Video: 720x480, AVC (H.264), 2918kbps
Audio: 184kbps
File size: 271.7 MB
DOWNLOAD FROM FILESMONSTER: Chuck Gets Plastered
Recruit's Troubles - part 04 Haines Falls
Release Year: 2019
Video language: English
We attach electrodes to their balls and shock them . We beat their feet. We stretch them on the rack, their perfect abs sucked in hard. We crucify them, every muscle in their bodies bulging.
Format: Windows Media
Duration: 9:36
Video: 1280x720, Windows Media Video 9 Advanced Profile, 4687kbps
Audio: 62kbps
File size: 321.4 MB
DOWNLOAD FROM FILESMONSTER: Recruit's Troubles - part 04
Paddling James Grand Coteau
James, age 20, is back. This time it's for a harsh paddling.
This video begins with interview footage from James' first visit. A couple of questions are repeated from his full interview video, but almost all the questions are new and regard his history of physical discipline (which we have not included in any other video). James has been disciplined extensively, so it took a bit longer than usual to discuss his history.
After those questions, Tom orders James to bend over a couch for a stern paddling. This is the leveling of paddling that a son of Tom's could expect as punishment if he had done something fairly serious like a senior prank that went awry and resulted in a bit of damage to the school (which is something that did happen in Tom's family).
The very first stroke of the paddle stuns James and leaves marks on his ass. Apparently he hadn't taken Tom seriously when Tom told him it would be a very hard paddling. He starts to ask Tom a question after the third stroke, but Tom lays down the law by telling James to be quiet and keep his eyes on the camera. Just 5 strokes in, James' already-red ass is quivering uncontrollably and he is reacting audibly.
Though he is no stranger to physical discipline, James really struggles in this video. At the end of this paddling, his ass is deep red with bruises forming. At the very end of the video, James looks over his shoulder and gives Tom a look that you won't want to miss. It says everything about what James was expecting as opposed to what he got.
Format: mp4
Duration: 17:38
Video: 1280x720, AVC (H.264), 4816kbps
Audio: 180kbps
File size: 646.4 MB
DOWNLOAD FROM FILESMONSTER: Paddling James
Kneel Glandorf
The facility was a dream come true for many of us to are attracted to jail cells.
Format: mp4
Duration: 23:55
Video: 1280x720, AVC (H.264), 3899kbps
Audio: 153kbps
File size: 710.5 MB
DOWNLOAD FROM FILESMONSTER: Kneel
Ashtray Kiefer
Ok, enough said about this combination of gear and restraints, check out the video.
Format: mp4
Duration: 13:22
Video: 1280x720, AVC (H.264), 3899kbps
Audio: 153kbps
File size: 397.4 MB
DOWNLOAD FROM FILESMONSTER: Ashtray
Self Bondage Electromagnets Part 4 Estacion Central
The self-bondage chair in this video was built by our friend Louis who has also experimented with electromagnets. You can see videos of his electromagnet gear in two updates on this website titled 'Chair Test' and 'DYI Self Bondage'. (use the search window at the top-left of this page) Louis has a background in electronics and mechanics so it wasn't to difficult for him to create his gear. In any case, after his hurtle with building this chair he kinda lost interest in it, probably because it took too much effort to put himself into it. As a result, he loaned it to Bind and I. We cleaned it up, made some modifications, and as you will see in this video, Louis's chair is a really hot piece of gear. We salute Louis for his inventiveness with the chair, along with his generosity loaning it to us and letting us modify it a bit. The main modification we did was to replace Louis's lawn sprinkler timer with a pair of mechanical timers. These two mechanical timers are much easier to set and offer redundancy in case one timer fails.
Format: mp4
Duration: 16:03
Video: 1280x720, AVC (H.264), 4870kbps
Audio: 309kbps
File size: 609.2 MB
DOWNLOAD FROM FILESMONSTER: Self Bondage Electromagnets Part 4
The Metal Man - Part 1of 3 Harmony
This gas-mask museum explained to me how this man became motivated to start.
Format: mp4
Duration: 21:57
Video: 1280x720, AVC (H.264), 4848kbps
Audio: 309kbps
File size: 829.9 MB
DOWNLOAD FROM FILESMONSTER: The Metal Man - Part 1of 3
Jason on the Bench North Eastham
It has been over a year since Jason's first spanking. He's now 20 years old and finally has returned for the second spanking that he had committed to do shortly after his first spanking. Before that happened, Jason moved over 400 miles away. In the the past year he contacted Tom three times asking to borrow money so that he could come back to town and do his second spanking video. Tom loaned him money on each occasion, not because he really expected Jason to show up, but because he knows Jason has family here and would eventually come to town. At the time of the third loan, Tom told Jason not to contact him again until Jason was already in town, whenever that might be. Now Jason has finally made it to town and it's time to pay the piper. He not only owes the money he borrowed, but also wants to make some extra money. Tom told him to come over and they'd work something out.
Jason is just a very irresponsible boy for whom discipline is a foreign concept. His parents, too busy with their own lives, never even tried to impose any serious consequences on Jason as he started to make lasting bad decisions in his life. He has a victim mentality when it comes to the consequences life itself is now imposing on him. But when he's with Tom, all of that nonsense goes out the window. Here he's held accountable.
This video has Jason strapped to Tom's spanking bench in a highly vulnerable and humiliating position. Tom uses his hand, a leather strap/paddle, a ping-pong paddle and a birch on Jason. Once his ass is red and hurting, Tom breaks out his Wartenberg wheel and rolls its sharp needles across Jason's raw ass. He then uses his electric paddle followed by a heavy-handed session with the belt. Next comes a bamboo slapper and a leather whip, which has Jason complaining loudly and struggling against the straps holding him in place. Jason whines, kicks and begs through most of the video, unable to cope with his well-deserved punishment. At several points in the video, he even starts biting or sucking on his thumb, hand and even the spanking bench. Jason was cocky and defiant through much of his first video, but this time Tom quickly puts him in his place.
Format: mp4
Duration: 16:33
Video: 1280x720, AVC (H.264), 4796kbps
Audio: 181kbps
File size: 604.3 MB
DOWNLOAD FROM FILESMONSTER: Jason on the Bench
Kevin Bent Over Belvidere Center
Kevin is a straight, corn-fed farm boy from the Midwest. He's also a military boy, one of a few good men. When Tom met Kevin, he was looking for odd jobs to pay off some bills. Tom offered him the chance to do spanking videos, and Kevin said he'd do them even though "it's pretty gay."
In this video, Tom straps Kevin to a work bench and goes at him with a variety of implements: a leather slapper, paint stick, flog, riding crop and his hand. He also takes the flog to Kevin's back.
As a Marine, Kevin and does not want to show any reactions, but he doesn't realize that his silence is only making Tom go at him harder. The paint stick and riding crop are particularly painful and Kevin can't help but gasp and curse under Tom's relentless strokes. By the end of the video, Kevin's ass and back are red and marked with welts and Kevin is clearly reconsidering the choices he's made.
Format: mp4
Duration: 15:55
Video: 1280x720, AVC (H.264), 4793kbps
Audio: 180kbps
File size: 580.8 MB
DOWNLOAD FROM FILESMONSTER: Kevin Bent Over
Kyle Suspended Pinto
This is the third part of Kyle's spanking. Having already put Kyle over his knee and on the bench, Tom now suspends Kyle right-side up and then upside down. Tom uses his hand, a long, painful shoehorn and a ping pong paddle on Kyle's already-raw ass. Normally a shoot wouldn't include this much spanking, but Kyle had insisted on a higher-than-usual fee. He was unpleasantly surprised and embarrassed at having to go over Tom's knee and at being strapped to the spanking bench. He liked the idea of being suspended even less. Like so many others, Kyle should've asked for the particulars before agreeing to the shoot. When you're midway through an all-or-nothing shoot, it is too late to negotiate. Besides, Kyle made it clear in his interview that he loves to tie up women and get rough with them. It's only fitting that he should experience it from the other side.
Format: mp4
Duration: 10:31
Video: 1280x720, AVC (H.264), 4765kbps
Audio: 176kbps
File size: 381.4 MB
DOWNLOAD FROM FILESMONSTER: Kyle Suspended
Jeremy's First Spanking Silverlake
First Contact Video! This video shows the first time Jeremy has ever been touched by a man in a sexual way. Jeremy is a tall, fit, straight athlete. Though it's not a word Tom uses much, "adorable" is the first word he thought of when describing Jeremy (followed closely by "hot"). He has a beautiful, smooth body and a great head of thick blonde hair. But it's his ass that Tom likes best. Smooth, firm, pale and round, it's like a work of art. And it looks so good with some red added.
One of the most interesting aspects of this video is that it shows the first time a boy has ever stopped one of our spanking videos. Jeremy basically freaked out when Tom pulled his underwear down. He hopped up off of Tom's knee, pulled up his shorts and underwear, and announced that he couldn't continue with the spanking because he was "too straight" to do it. A six minute discussion followed.
The audio of that conversation contains too much personal information that would identify Jeremy, but it went down as follows: Tom reminded Jeremy that the contract he signed requires that he complete the entire spanking or he would not be paid. Jeremy said that he hadn't thought he'd be over a man's knee or that a man's hand would be on his bare ass. When Tom pressed the issue, Jeremy had to admit that (like so many of our other models) he hadn't asked for any specifics about the spanking, and that being over someone's knee with one's pants down is a very common way to be spanked. Jeremy also had to admit that he knew that the video was for an adult website, so nudity was to be expected. Still, Jeremy didn't want to go back over Tom's knee and proposed several alternative ways for the spanking to proceed. But Tom would never agree to that. As the minutes passed, Jeremy calmed down and realized that it was already too late to back out. He had already gone over a man's knee, been spanked and had his underwear pulled down. He could not undo those things. Besides, he needed the money. So he swallowed his pride and went back over Tom's knee for the continuation of the spanking exactly as Tom had planned it.
Format: mp4
Duration: 10:53
Video: 1280x720, AVC (H.264), 4760kbps
Audio: 171kbps
File size: 393.5 MB
DOWNLOAD FROM FILESMONSTER: Jeremy's First Spanking
BT - Session 221 Nenjiang
Release Year: 2016
Genres: Gay BDSM, Oral/Anal Sex, Group, Cum Eating, Punishment, Humiliation, Pissing, Spanking, Cumshot
These sadistic Tops break cock hungry bottoms with vile and degrading sessions in humiliation, initiation and total submission.
Dishing out their sleazy depravity using restraining ropes, chains, chastity, teasing and sensory deprivation our Tops punch, whip, slap, paddle, fuck and piss over dirty sex pigs until they're begging for mercy.
Their whimpers serve only to drive our fiendishTops to even more extreme punishments until they completely break them. Only then can the real torment and humiliation begin....
Nothing is off limits as the Tops gob, snot, piss and cum to complete the degradation of these pitiful submissives.
Format: Windows Media
Duration: 9:32
Video: 960x540, Windows Media Video 9, 1950kbps
Audio: 62kbps
File size: 141.1 MB
DOWNLOAD FROM FILESMONSTER: BT - Session 221
HandPacked 1, Scene #03 Aquashicola
Cast: Marko Heckler, Paul Charge, Ruben D'Angelo, Tom Franco
Genres: Boots, Cage, Chaps, Chariots, Dildos/Toys, Fetish/Kink, Fisting/Handballing, Group/Orgy, Jockstraps, Leather, Oral, Piercin
Video language: English
The action goes deeper when the guys head to a dungeon in a NY sex club for a handballer orgy that includes domination and submition, cbt, collars, spanking, cages and more! The action gets so hot some of the guys start fisting themselves until everyone in the room gets off.
Format: mp4
Duration: 36:58
Video: 720x480, AVC (H.264), 1367kbps
Audio: 124kbps
File size: 405.9 MB
DOWNLOAD FROM FILESMONSTER: HandPacked 1, Scene #03
You are here » FILESMONSTER GAY Video collection, daily update! » GAY AND BISEX PORN » GAY BDSM [FILESMONSTER] #2
