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...

Training of a Bondage Slave: Eliza Jane Day Two

Sexy and flexible Eliza Jane is back for day two of her training. Xander trains Eliza to take his dick while she is restrained in the hardest bondage positions: two suspensions, a wide open doggie a...

Training an Obedient, Squirting Whore

Zoey Parker wants to be an Obedient Whore for Tommy Pistol. Zoey submits her submissive, shaved pussy to her slave trainer and begs to learn at the tip of his hard dick. ...

All Natural Beauty Learns to Beg For Cock

Zoey Laine learns the hard principles of Gratitude, Eye Contact and Availability at the end of a stick on Training of O. Zoey loves nipple clamps, canes, gags, bondage and getting fucked hard with t...

Slave Training Rikki Rumor

Cute blonde loves to be taught discipline and servitude while getting fucked hard by brutal slave trainers. ...

Veruca James’ Anal Submission

All natural submissive slut Veruca James loves being put into tight predicament bondage that balances pain in her luscious natural tits and pleasure in her tight little pussy, while Xander Corvus te...