Chloe Cherry Gagged and Bound
Chloe Cherry sits, gagged and bound to a wooden chair in a red pleated skirt that's been pulled up to show that her hairy pussy has had an hitachi vibrator secured directly beneath it. Chloe's wrists...
Newbie Skylar Snow Endures and Indulges
Introducing Skylar Snow, a brand new strawberry-blonde busty babe here for the first time on The Training of O and here at Kink.com. Skylar Snow is not here to pretend for the camera, she's here to e...
Abella Danger Fucks Man in the Ass in her First Divine Bitches Shoot!!
Abella Danger is no stranger to Kink.com. She has been restrained and fucked in every conceivable fashion. But the one thing that she has never done is peg a pathetic man in the ass and abuse his exp...
Training a Pain Slut: Busty Melissa Moore’s First Submission
Welcome the stunning Melissa Moore for her first submission to The Training of O. This natural busty brunette is extraordinarily obedient and has a cock hungry dripping pussy and mouth. This slave de...
Liberation in Bondage: Dresden Returns!
Blonde pain slut Dresden is nervous as she enters the dungeon of the renowned Mona Wales. Luckily, Mona knows how to make shy slaves open up. First, Dresden strips for her Mistress. Once naked, it's ...
Shy College Slut, Roxanne Rae, Gets Ass Fucked in Tight Rope Bondage!!
It is always the quiet ones that you have to watch out for. Sexy girl next door Roxanne Rae returns to The Training of O to continue her training at the hands of the sadistic Ramon Nomar. Don't let h...
The Final Armory BDSM Orgy with a huge group orgasm!
In this last installment of the final Armory Orgy party, Nora finally earns her right to serve by Cherry's side. In Aiden's words, "If you have to lick every foot in this place, that's what is going ...
Ariel X is Tormented in Brutal Bondage and Double Penetrated
Ariel and The Pope have a long time relationship of working together and every time they do it is pure magic. The way Ariel submits to him is amazing, and the way he controls her is a sight to see. A...
Blonde Submissive Bombshell Kleio Valentien Gets Punished and Pleasured in Strict Bondage!!
Alt goddess Kleio Valentine and her big tits return the brutal metal and leather bondage that is Device Bondage. To say that Kleio has a perfect body is an understatement. Toned, tanned, and taut, he...
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 pi...
Abuse in the Workplace
Christian Taylor can't seem to get a moment's peace at work with his boss, Jaxton Wheeler constantly tormenting him. Once the timing's right, and Christian has the whole place to himself, he decides ...
Hot boy next door beaten into the ground!
Kaden Alexander is a gorgeous boy next door with a body made for torment! He is warmed up on the wall with fast slaps, paddling and punches that get his big hard cock bouncing around as he bucks and ...
The Pup Master – Introducing: Master Pacifico
Master Pacifico, clad in full leather, walks into the dungeon to find a sleeping slave lying naked in his cage. Alex Hawk is awoken and dragged out of his cage by his collar and ordered to worship Ma...
Connor Patricks – Ass Torment
Conor Patricks is no stranger to pushing his limits here with KinkMen, so naturally, his next obstacle is the 30 Minutes of Torment challenge. He begins in the chair as heavy fists pound against his ...
New house slave offers himself to the sexual desires of Master Colter
Dangling from the ceiling, with his head locked in a stock, Chance Summerlin awaits for house dom Jessie Colter. Master Colter inspects his boy and demands to hear how he intends to please his new ma...
Slender stud humiliated and abused at the hands of his muscled tenant
Alex Hawk has been very patient with his tenant Jaxton Wheeler and the rental agreement for his gym, but now months have passed and Jaxton still hasn't paid and Alex is fed up. When Alex gives Jaxton...
Muscled hunk begs for his master’s abuse
Leather slave, Dolf Dietrich awaits on bended knee for his master Christian Wilde, begging to feel his touch. Mr Wilde obliges with heavy punches to Dolf's muscled torso before working up his fat coc...
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 leathe...
