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: The busty and beautiful Ivy Lebelle is caught stealing Chanel Preston's hidden stash of cash! Ambushed by Chanel and woman-handled into submission, Ivy is terrified - stammering and beading with sweat - but still unwilling to give up the name of her boss. That's not problem for Chanel, who knows how to extract information from tough whores like Ivy. Trussing the determined slut up with duct tape and ripping every shred of tight clothing off of her body, Chanel buzzes a taser in Ivy's face and grazes it over her thighs, making this terrified thief scream and beg for mercy. Spanking and flogging Ivy's juicy ass, caning her feet, squeezing her puffy nipples, and slapping her ripe tits finally gets Chanel the intel she wants! Still shaking with fear and guilt at having given up her boss, Ivy begins to moan as Chanel rubs her swollen clit, sensitive from the interrogation. Sinking slowly deeper into Chanel's mind games, Ivy's tight cunt gets wet with pleasure as orgasm after orgasm is ripped from her body, struggling against the duct tape that binds her. But Chanel isn't going to let her toy go so soon! She binds Ivy onto her back, splaying the dripping lips of her pussy wide open with clothespins and fucking her with one hard cock and then another, in missionary and doggy, continuing to tear orgasm after orgasm from this hungry slut! Chanel rides Ivy's face, smearing her makeup with cum and cunt as she gets her own pleasure before flipping Ivy over and fucking her deep in the ass. This little thief whore can't stop cumming as Chanel fucks her tight asshole in missionary and doggy, screaming from the overwhelming pleasure of constant orgasm. Finally spent, little Ivy is thrown back to her boss, who's even more devious and twisted than Chanel...

Video Description: Svelte sphinx Delirious Hunter has been beating up pathetic boys in her dungeon all week and needs a release! Ready to let go, submit her body completely, and choke down a dose of her own medicine, Miss Hunter texts the one woman she knows who can deliver the pain and pleasure she craves - the divine, the infamous: Mistress Aiden Starr. These two dominatrix pros waste no time, consuming each other quickly - each in her own way. Aiden teases, chokes, humiliates, and tempts Delirious, and Delirious, quite simply, can't stop fucking cumming. Stripped out of her latex into just her stilettos and thigh high pantyhose - and with the glorious tits of Aiden Starr bouncing above her - Delirious cums while being spanked, caned, and flogged with her very own whips. Wet, pink, bruised, and begging for more, Aiden easily shoves her entire hand deep into this whore's slutty cunt, extracting orgasm after orgasm as Delirious screams against her fist. Seemingly an endless well of pleasure, Delirious begs again and again of her mistress, dedicating each and every orgasm to the beauty and wit of the glorious Aiden. Spread-eagle, gagged, and bound standing to a pole, Delirious is covered in no less than eleven clover clamps - crisscrossing her tits, face, belly, and cunt. With a thick, long dick deep in her cunt, Delirious again becomes deliriously lost in her own pleasure as Aiden tears orgasm after orgasm from her adorable little dominatrix-turned-submissive. Struggling against her ropes to finally get to her true prize - Aiden's delicious cunt - Delirious twists and turns, stretching and reaching, until she finally breaks free for a face full of heaven. Aiden takes full advantage, riding her whore's face and smothering Delirious in her voluminous ass until she's ready to flip her over and take Deliriousa€™ begging, spit-covered hole. Fully giving herself to Aiden, Delirious takes every inch of this dominatrix-of-dominatrixes, swallowing Aiden into her ass as she begs again and again to cum in missionary and doggy. As Delirious' eyes roll back in her head and she becomes merely a set of wet holes writhing and begging on the bed, it's clear that her clit has become completely and forever devoted to Aiden Starr. And what becomes of such a slut? Ask all the boys already lined up outside Delirious' dungeon waiting to be dominated by this queen of kink.