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...

Karlee Grey, Begging in Bondage

The beautiful buxom brunette Karlee Grey submits entirely to the dark and handsome Ramon Nomar. These two give it their all in this hot and sweaty episode of The Training of O. The scene begins with ...

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...

Two Submissive Sluts

Tommy Pistol anxiously sits in his leather chair, picks up the phone and orders two submissive sluts. Moments later a slight jingle of chains gets louder as James Mogul, holding two leashes, slowly a...

Extreme Anal Training: Anna De Ville

Anna De Ville is a pretty petite anal whore who came to The Training of O to have her ass stretched to its limits. We start with Anna tied in rope bondage with her ass in the air and a ball gag in he...

Pleasure Training: Dolly Leigh

We start in a well lit white bedroom with Dolly Leigh sitting at the edge of the bed with her skirt up, fingering her pussy. James Mogul, dressed in all black is asking her questions about her fantas...

Breaking in the New Recruit: Moka Mora

Fresh faced and eager; the stunning new bondage whore Moka Mora was blushing with excitement when she met James and Tommy for the first time. She likes it raw and was hungry for it all. But enthusias...

Petulance Training – Juliette March

The adorably bratty Juliette March is the Queen of all Pain Sluts and is super excited to be back for her fifth brutal round on The Training of O. James Mogul knows just how rough Juliette March likes...

Fear Training: Stella Cox

James Mogul and Bill Bailey double-down on training the beautiful pain slut Stella Cox to not be afraid and to keep bouncing those big natural titties. Bill Bailey sends his fat cock balls deep into ...

Domestic Training: Arabelle Raphael

What is to be done when an ungrateful wife steals money and lacks the respect that the man of the house deserves? Mr. Pete knows exactly how to fix this problem and calls upon the services of James ...

Polite Obedient Slut Takes It

Mandy Muse experiences The Training of O for her first time but is no stranger to Kink. James Mogul stretches the limits of Mandy's ass, pussy, and mind using single-tail whips, floggers, zappers, a...

Training Violet Monroe

Beautiful and sultry Violet Monroe tests her limits as Tommy Pistols guides her through tight bondage, breath play and hardcore anal sex. ...

Speech Training an Anal Slut: Ella Nova

Ella Nova loves anal sex, but first she must learn her lessons. Tommy uses operant conditioning, electro stim and a vibrator to teach Ella to talk dirty. Ella's reward is a hard anal sex, bondage an...