Sexy newcomer Harley Jade is an eager little submissive that brings allot of enthusiasm for cock to the table. But is she willing to work hard to get fucked? Harley learns that whips and chains stre...
Sexy Kacie Castle loves to play the punishment game. Kacie was a Bad Girl, and Seth Gamble gives her a chance to make it up to him. Kacie is told to clamp her own nipples, and from then on she takes...
Cali Carter is a big tit, big ass beauty that knows how to bounce it. But first I want to see those tits tied and clamped. After a couple of screaming orgasms, Cali shows off and tells us she loves ...
Bill Bailey puts Kira Noir to the task of fucking herself. In the ass. With her own fist! Bailey warms the slave girl up with a hard, sloppy face fucking in tight rope bondage. Then it's face down, ...
All natural hottie Alison Rey begs for her trainer's attention, and Mr Pete responds with strict bondage, strict rules and quick discipline. Alison learns the value hard work and the rewards of plea...
Big tit juicy redhead Lauren Phillips learns a very important lesson from her slave trainer: She is His Whore, His Cunt and His Bitch. Lauren endures tight bondage, gags, whips and a giant cock in h...
Hot anal loving blonde babe Riley Reyes loves when Tommy Pistol trains her to be his slave. Tommy wastes no time in teaching the fundamentals: Posture, Eye Contact and Gratitude. With the basics in ...
Highlights from the BEST Anal MILF Training Movies!Favorite MILFS Veronica Avluv, Simone Sonay and Holly Heart in the best anal MILF Training scenes that Kink.com has on offer! ...
Irresistibly cute and submissive Eliza Jane loves it when Xander Corvus put her through her sexual paces! Eliza is fucked hard in tight and challenging bondage positions: squatting, standing and sus...
Best of Training of O!This is a Director's Choice movie: previously published, but much loved! JP and Stefanos did an amazing job with this movie, and it deserves to be re-published - enjoy!The pote...
Kimber Woods is a thick ass brunette with a gorgeous face that makes all the dicks jump. But Tommy Pistol thinks she can do better, and Kimber begs her trainer for instruction to become the Best Lit...
Director's Choice! This previously published movie is worth a second look! Eager slut trainee Alina has a lot to offer, and we take it all. Her sweet young face is fucked in an inverted suspensions ...
There are so many good moments between sexy Kacie Castle and Tommy Pistol that it is hard to describe them all. Tommy commands this girl from the beginning to the end, and Kacie just sucks up the fi...
Director's Choice! This previously published movie is worth a second look!Gorgeous all natural slave in training Zoey Monroe is turned over to slave trainer Ramon Nomar for a day of anal slave train...
When novice submissive Raquel Roper meets her trainer Seth Gamble, she knows it is not going to be an easy day. Seth is In Her Grill all day long, holding her to her lesson: Discipline and Dick. Tig...
Best of Training of O! This movie is HOT and deserves a second look!The Training of O brings the newest, hottest submissive females to dungeons of the Armory for the most grueling sex slave training...
When tough and sexy Riley Nixon submits to slave trainer Ramon Nomar, she endures his twisted games of endurance, discipline, domination and hardcore sex. ...
Carter Cruise is back for her dose of hardcore sex, bondage and discipline on Training of O. Tommy Pistol welcomes Carter back with a leather bound sloppy blow job featuring a nasty spider gag that ...