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: Demi is brand spanking new to BDSM/bondage. She has always been curious, but never brave enough to try it until now. We get the privilege of seeing The Pope walk this slut through the the day as she gets her first taste of what real bondage and domination really is. The shoot starts and you can see the apprehension in her eyes as she realizes that she may be in over her head. It's too late now, because she is in it; she has signed off on it and like a roller coaster you can't get off once it starts. Her emotions run high as The Pope begins exploring her body and invading her holes. He dwarfs her petite body as he moves through the dungeon preparing to torment her flesh and mind. She is restrained and subjected to flogging, caning, spanking, bastinado, pussy fingering, and tons of unwanted orgasms. The day is winding down and Demi is showing signs of fatigue and exhaustion. She made it thought the day, but you'll have to watch to see what she thought of her first experience.

Video Description: When cute little rebellious teen Vienna returns home for a surprise visit with her new creep boyfriend Smallhands, she is aiming to torment her parents, but instead finds they are gone and her older sister Vanessa is home for the week end. Vanessa is a gorgeous uptight coed and is having none of Vienna's shenanigans. Dismissing Vienna as a slut after paying Smallhands out for picking up some Hot Topic mall teen, she throws her headphone back on and goes back to working out. Determined to get under Vanessa's skin, Vienna drags Smallhands up to her old bedroom and invites him to teach her all about the BDSM sex he has been trying to convince her to try. The resulting scene is a very real first timer experience of begging for cock, intense face fucking, flogging, spanking, paddling, and submissive fucking at the hands of a sadistic top. Vienna is dragged out on to her balcony, bent over the railing, and made to have a screaming orgasm for all the world to see, with Vanessa is in the front row seats. Later Smallhands gets lost in the mansion and wanders into Vanessa' room looking for the bathroom. He starts backing out apologetically, but Vanessa makes her move, telling him if he really wants a good lay he should try someone with some more experience. Smallhands doesn't like being told what to do, and Vanessa is one hot stuck up bitch, how could he refuse? Throwing her on the bed, he starts in immediately spanking her hard with verbal humiliation, making he admit she is a greedy cum slut while paddling her round ass red, throwing her on the floor and cropping her sensitive pussy. He cuts up her nice yoga gear and throws tight metal clamps on her sensitive nipples. Face fucking her and making her cum repeatedly on the floor like a dog, she is thoroughly humbled. When she is finally in tatters and ready to submit fully, he puts her in tight belt bondage, clamps her pussy lips, and fucks her to pieces, switching freely between her ass and cunt as she screams into her ball gag and begs for more. She is rewarded with a relentless pounding and electrical shocks from a zapper. All the noise obviously draws Vienna's attention. Upset, she comes in screaming, but Smallhands reminds her that she did promise herself to him and if she really wants to done with the game so soon? Vienna has always thought her big sister was hot, so now with her all tied up and speared on her boyfriends cock, she has a chance to get in on the fun. Vienna eagerly watches and learns how to submit from Vanessa, cleaning her boyfriends cock off every time it comes out of Vanessa's ass, and waiting to cum in unison with her slut sis. The rest of the evening is spent with the girl's giving each other revenge orgasms on the sybian, clamped and tied up tight, they are both throat fucked and made to beg. Both sister's eagerly lick each other's pussy's while Smallhands takes his fill of their nubile hot bodies and covers them with the biggest load of cum we have seen in a while.

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: Divine Bitch Cherry Torn can't wait to break in lucky new slave Luis Long. Luis is a shy submissive with no formal training who gets to bask in the radiance of Cherry Torn for his first professional shoot ever! Cherry teaches him how to present himself -- on his knees, with his eyes forward. She teaches him how to address her, makes sure Luis knows she owns him, and breaks in her new meat with a zapper, flogger, and intense spanking! When Cherry reaches in between his legs to inspect her cock, she finds it dripping wet! What a dirty leaky slut. Luis struggles to please his Mistress and nervously scurries to obey her every command. Next, Luis is bound in rope with his legs spread. Cherry knows what this little slut needs -- a good hard fucking. She opens up his tight asshole with her cock and fucks him deep in his ass. Luis moans as Cherry plunders his ass, thrusting deeper and deeper. This slut loves getting fucked so much his cock stays rock hard and dripping while Cherry uses her new hole. Finally, Cherry decides to test her toy's orgasm potential. She rides his face, using his tongue on her glorious pussy and asshole. She cums hard on this slut's face before turning attention to her cock. Luis moans in ecstasy as Cherry pushes her cock inside her cunt and takes it for a test drive. Her voluptuous ass bounces up and down as her pussy swallows up that cock. Luis is so hard it hurts and begs to cum as Cherry has orgasm after orgasm and clenches down on her cock. Cherry know her slut wants to cum, but does he deserve to? No! Especially not after his first day of training. He may be able to follow directions but he's a long way from being allowed the pleasure of cumming. Maybe next time.

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: Raven is brand spanking new, and we weren't sure how she would respond to all of the stimulation that comes from shooting a Fucking Machines shoot. We quickly see that this little slut can more than handle this, but now we are wondering if the machines can handle this slut. Her orgasms are so fucking powerful that she loses complete control of her body. She shakes and quivers as the orgasms flow through her body. We break out the fastest machines and this slut keeps begging for more. We fuck her nonstop until we finally ensure that her hungry cunt is satisfied and that she has had enough.

Video Description: Chloe Cherry endures the brutality of newcomer Donnie Rock and his cool, sinister sadism, suffering through 4 bondage positions with flogging, cropping, spanking and nipple clamps. She starts, willingly bound to a post by the neck and wrists, with her legs locked to the floor. Donnie manhandles her, toying with her, then striking a deal with her... he'll let her breathe if she takes the whip! She agrees, and so he releases the rope around her neck and in exchange he flogs her, still locked to the floor and the post. He then clamps her incredibly sensitive nipples and face fucks her until the spit is running down her body. Fully uses, she's left there to wallow in her own drool. Next she's gagged, tied up face-down on a table with her ass up. Donnie takes full advantage of her in this position, fucking her pussy with pure, selfish intent and slapping her ass to keep her propped up. Chloe's then put in a partial suspension, fully horizontal with only one foot touching the ground. A heavy bucket is suspended from her nipples by two clothes pins, while her pussy's cropped and slapped, then fucked again! Finally, Chloe is bound to a fuck box on her back, with her legs spread while Donnie fucks her and threatens her with a zapper. He ultimately makes her cum on his cock while he's fucking her wet, desperate cunt, then blows his load all over her gagged face, demanding that she lick it all off.