Video Description: Beautiful, submissive sweetheart Jessica Kay is back for another sick and twisted epic. And of course, she's brought her plump, hot ass back with her. This time, Dr. Mercies is in good spirits, because life's been treating him well. But he wonders what it would be like to be an anal BDSM pervert in other times and places. So he takes Jessica on a crazy painal domination journey across 40,000 years. This session is surreal but also real. It includes painful anal fucking in a straightjacket, cave woman beating, witch dunking, and severe ass punishment in the scold's bridle.

Video Description: Sarah has been on other Kink sties before, but never has she been tied, tormented and not given any cock to distract her from the pain. Today she has to face her suffering head on, at at the hands of The Pope none the less. He doesn't go full throttle on this slut because she's new to him, and he doesn't want to break her...yet. We begin with her tied in a standing position that will eventually morph into a more complicated predicament tie. She is spanked and flogged before her pussy is made to cum uncontrollably. Next, Sarah is face down on a fuck box and she learns what foot torment feels like. She is made to beg for the bastinado and her screams prove her suffering to be real. Her mouth and pussy are fucked to close out this position. In the final scene we have her on her back with one leg up. The flogging continues and she screams louder than before, but this doesn't stop The Pope. He makes her cum more until she is begging for that to stop as well.

Video Description: Charlotte Sartre is a very disobedient inmate at the all women's prison. She's been keistering anal toys and copulating with the other female prisoners. The Butthole Prison has brought attention to the Warden on this issue. Anal Warden, Dee Williams is a no nonsense busty MILF who has been known for doing extraordinarily cruel and unusual things to her female inmates. Charlotte denies she's done anything wrong and seems to think she can prove her innocence by NOT being able to fit any toys into her a€?tight assa€?. If the anal toys don't fit, you must acquit. Unfortunately for anal hungry Charlotte, try as hard as she can to keep her asshole tight, it just wants to stay open and suck up everything in its path. You could drive a truck through Charlotte's loose butthole. Dee starts with a nice firm over the knee spanking. Charlotte's tushy turns bright red and she writhes with pain and pleasure. The spanking isn't enough punishment, so Dee starts fingering and plugging Charlotte's asshole with toys. Charlotte's ass starts gaping wide open and Dee knows right away that she has caught her Anal Toy Smuggler and needs to administer a full anal examination. Dee then has to check the entire asshole so she performs a body cavity search putting her entire fist into Charlotte's ass. Determined to understand how Charlottes has been getting all these toys past the prison inspections, Dee has Charlotte demonstrate how she was able to stretch her ass out for keistering. Charlotte puts a giant red butt plug in Dee's asshole so that Dee can see how easy it is to hide things in buttholes. After learning how Charlotte is doing her bad deeds, Dee must perform one last punishment, She straps on a huge anal dildo and strap on fucks her poor, powerless inmate, leaving her asshole gaping wide open.

Video Description: Olive is super excited to shoot for Whipped Ass, and she wants it all: spanking, flogging, fucking, anal, pussy licking...everything! She's a natural submissive, ready to please, and with Cherry Torn calling the shots, she gets it all and more! Cherry spanks her and inspects her, teaching her how to show gratitude, and the importance of asking for permission before cumming. Every time Olive cums she has to ask, and she has to endure pain at the same time. Olive is spanked relentlessly, then paddled on her feet and desperately hungry pussy, testing her endurance. She's then rewarded by getting her wet cunt finger-fucked. Cherry hands her a vibrator and Olive cums repeatedly. Olive is then put in a partial suspension with a ball gag and her ass out, and Cherry flogs her sweet ass, tenderizing her for what's to come. She climbs in front of Olive and makes her eat her wet, slutty pussy, and her tight asshole, making her cum again and again. Olive is finally spread open while Cherry fucks her pussy with a strap on. She pounds Olive and crops her, all while using her hole in every way. She turns her over and fucks her ass, making her cum multiple times. Finally, Cherry slides her fist into Olive's worn cunt and fists her, which Olive simply can't get enough of, and she cums hard, just before Cherry decides enough is enough, and says no more!

Video Description: Alexa has been waiting to shoot for Hogtied, and the wait is finally over. We get her tied to a wooden chair with her nice ass out to do with as we please. We shove a massive dildo down her throat and then mount it in front of her on the large wooden column to keep it buried in her slutty throat. The Pope attacks her backside with a viscous flogging and then destroys her feet with bastinado. Next we find Alexa in a hogtie with her hands pulled into a brutal strappado that keeps her pressed against the top of the cage. She is cropped and the shocked with a zapper to make this bitch scream even more. Her pussy is stuffed with another dildo and fucked until she begs for it to stop. In the final scene she is face up on a box with her legs spread wide and her hands pulled securely over her head. Her body is covered in clothespins and then The Pope flogs the pins to an unbearable pain level. We finish her off with a few more orgasms and send this slut on her way.