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House-Owned Whores Earn Their Place at The Halloween Fuck Fest

In our final installment of the Halloween Sadists Ball, Governess Ana Foxxx is up for some serious discipline at the hands of busty Governess Aiden Starr. Ana has been a sloppy, cum-hungry slut, unable to hold her position, ask for her orgasms, remember the rules, and what's worse is that her uniform is already shredded. Aiden stares with sadistic disdain at Ana's bare feet poking through her torn stockings while Ana wiggles nervously in her tight shibari frog tie. The guests look on with much pleasure as Aiden lectures Ana about the importance of her uniform and offers her a new pair of red and black, submissive-issue stockings... at a price. Ana's torn pantyhose are stripped away, leaving her tender toes vulnerable to cropping and shocks with a zapper. Ana squeals and apologizes, but Aiden moves on to her pert nipples, pinching and biting them until they are swollen and covered with vicious teeth marks. Aiden then applies some brutal metal clamps to both Ana's nipples and labia, pulling them tightly in her hands and she teaches Ana the house rules one final time. Every orgasm Ana will have from here out will only come when she has recited the rules and has a clamp pulled off of her tender bits. Ana screams and sweats through her punishment, and eventually succeeds in delivering her recitation through the suffering painful punishment orgasms. The crowd cheers and claps as she collapses with a new pair of stockings. The party goers find themselves horny from this display and begin working each other over. One latex submissive endures a hard flogging and anal hook, while another submissive is locked in stocks and made to take a strict caning with a metal rod as swingers fuck each other and look on. Gorgeous women are tied and spanked heavily, while others suck cock and take a paddling while having their nipples clamped together in a painful daisy chain. A beautiful femme domme teases her man with a bound face sitting session, and others beg for orgasms from a hitachi as their asses and thighs are beaten red. Stefanos is perturbed to find that Ana has earned her red and black stockings before senior submissive Chloe Cherry. He bring Chloe over and demands that she find her stockings among the crowd while her pursues her with a zapper, and our guest of honor Donny Sins takes her pussy and mouth for fucking. Chloe is a sweet and desperate mess as she crawls through the party, begging for her uniform, finding sadist female party-goers who will give her each garment at a price. Her tits are clamped with wooden pins and she is given a glass to hold on a silver tray and told not to drop it, as Donny rails her from behind. Ana is a crafty little whore, and crawls over to steal the cock, almost sending Chloe's tray crashing to the ground. But Chloe holds tight and manages to keep the dick and her new uniform. Ana is sent to service Donny in an intense reverse cowgirl to earn her collar, but it is Chloe who comes out victorious with a rousing anal fuck, coaxing the cum from Donny and orgasming to the admiring cheers of an impressed party.

Nurse's Orders

Your doctor is overloaded with clients, so he sends Nurse Chloe Cherry to tend to you while you wait. It sounds like the doc's gonna be a while, so why not make a donation to the sperm bank in the meantime? Nurse Chloe can coax the biggest loads out of any man, with her cute face, tight body and secret sexy lingerie… not to mention her willingness to get hands on with her patients!

I'll Show You How It's Done

Cherie DeVille thinks she's going to have a nice relaxing day at home once her husband leaves for a business trip. Little does she know mischief makers Chloe Cherry and Ricky Johnson have broken into her house, looking to loot it! Turned on by their own bad behavior, Chloe and Ricky can't help but stop to fool around before stealing any of Cherie's things. Cherie catches the couple red handed and, instead of reporting them, decides to give them a lesson in how to fuck properly!

Ana Foxxx Demoted at The Sadists and Swingers Halloween Ball

The Upper Floor's Halloween Sadists and Swingers Ball is to be served by two trained house sluts, Chloe Cherry and Ana Foxxx. Governess Aiden Starr is not convinced that Ana is worthy of wearing the full uniform as Ana's service on the The Upper Floor preceded Aiden's rigorous training regime. Aiden sets a simple test for Ana: if Ana can keep the house collar on the tray in her hand through the entire first service session, then she can keep it. But if she drops it, she'll be subjected to brutal whore and service training at the very bottom of the slut pile. So Ana has her hands full, literally. In the meantime, a tightly tied Chloe Cherry can only moan and scream as she has her tight teen body punished for every mistake Ana makes. And Ana's in quite a bind! She's holding a tray, while in an athletic squat, with tight clamps on her pussy and nipples, with Donny Sins throat fucking her with his massive cock. Ana holds on tight for as long as she can while slobbering and working his dick, but gravity prevails and the tray falls. Chloe's feet are held aloft and exposed in her rope shibari, leaving her vulnerable to the barrage of electro zaps. Ana is throat fucked and then pounded from behind as she licks Chloe's cunt ad begs for Chloe to take the dick so she can request more instruction and take her flogging. The scene ends with Chloe taking a glorious pounding in her beautiful pink pussy while reciting the rules for the delighted crowd. Ana is given punishment orgasms on her knees like a filthy little trainee. The crowd is dressed in kinky Halloween costumes and having a wild party with plenty of partner swapping, asses spanked, and sluts earning their Master's cum. The Darko BDSM babes take the shiny new wooden TUF paddle at the hands of their Master Darko, leaving both beautiful masochists gasping with deep red asses. A masked red-headed bondage slut takes a brutal rope suspension, flogging, and relentless orgasms, while another party goer offers her perfect ass for a long and strict caning with a metal rod. When Ana and Chloe return to the floor, it is for Chloe's anal fucking in a doggy rope tie that makes her round ass press deliciously against the ropes. However, Ana again steals the show with her disobedience. The governess discovers Ana has rips in her stocking already, and has Ana lick Chloe's asshole as she personally zaps each of Ana's exposed toes for being out uniform. Ana is already quite sorry for her mistake by the time Donny uses her mouth as a wet service hole, but she is truly apologetic when the Steward traps her clit with a vibrator and Aiden refuses to let her cum. In the meantime, Chloe is enjoying a deep anal fucking in doggy and asking for all her orgasms like a good girl. Ana on the other hand is cumming, and falling over herself, unable to speak since she is so overwhelmed with the vibrator. Sweating, zapped and flogged, she can't stop herself from cumming without permission to the entertainment of the crowd. Aiden laughs in spite of herself and promises Ana that she will pay for each stolen orgasm for the rest of the night. Please join us for the next installment of this incredible celebration of perversion, kink and sexual service.

Pistol Whipped

Cute blonde Chloe Cherry masturbates to a farting, squirting orgasm! Next, nebbishy Tommy Pistol proposes marriage by offering Chloe a ring -- his cock ring! She gives a wet, sloppy, deepthroat blowjob, and she squats to ejaculate girl squirt onto Tommy's face. He reams her pussy and asshole. The kinky girl penetrates his penis hole with her pinky finger! Tommy fucks her drooling face through a sleeve toy, and he pushes his balls inside her sphincter! This crazy anal encounter climaxes when he cums in Chloe's open mouth.

Hard Pounding DP

Super cute blonde, Chloe Cherry, takes on two men in this hard pounding double penetration sex scene. This is gonzo style sex, including intense DP action, ATM's multiple DP positions and an explosive cum swallowing finish.

Bush League

Abella Danger and Chloe Cherry are two rival baseball players trying to squeeze in a little bit of batting practice before the big game. They're shocked to see each other on the same diamond, and soon come to blows. Once they start ripping off each other's uniforms, these two sexy sluggers slide their tongues into their pussies for a very different kind of home run!

Throat Fucks 6

Trashy blonde model Chloe Cherry loves sucking cock. As this all-natural cutie puts it, 'The more dicks, the more sloppy and slobbery!' Chloe kneels between Jonni Darkko and Jason Moody, orally servicing each stiff boner while gurgling with pleasure and drooling onto her chest. The guys fuck her pretty face in turn. This eye-watering, deepthroat, double blowjob ruins her glamorous mascara, and a cum facial leaves young Chloe covered in slobber and sperm.

Smells Like Gangbang Spirit

Cute blonde Chloe Cherry's bed & breakfast provides unusual hospitality. Showing her comely white butt and furry pubes in skimpy lingerie (or less), she treats guests Small Hands, Donny Sins, John Strong, Ramon Nomar and Mark Wood to individual customer service centered on blowjobs and hot pussy! When all five studs surround her, Chloe kneels for a circle-suck, gagging, slobbering on and stroking big, throbbing erections. An anal and cocksucking round-robin features vigorous double penetration and choking. The guys render Chloe airtight, trading off her holes and manhandling the limber girl into various, sweaty positions. She moves down the couch, parking her ass on each prick, masturbating and wailing. The DP marathon features anal gaping, ass-to-mouth head and interracial fun with Donny's big black cock. Chloe takes six cum facials/oral sperm shots; she blows spunk bubbles and swallows the semen pumped onto her tongue.

Date Delayed: Mr Pete Finally Gets Some Private Time With Chloe Cherry

Mr Pete's a little obsessed with his former classmate Chloe Cherry. He's always wanted to go on a date with her, but it's never happened, for some strange reason. Time has passed, but he's only grown more obsessed. Now he's gonna get that date, one way or another. Mr Pete ties up Chloe, straps her down and has his way with her by face fucking her, flogging her, cropping her, then fucking her tight wet pussy and her slutty, hungry asshole. He takes her to an empty classroom and starts in right away, flogging Chloe and cropping her. He puts a vibe on her pussy and eats her sweet hole, prepping her for the best part of the date, yet to come. Once she knows what she's in for, he shoves his thick cock into her mouth and face fucks her. He doesn't hold back, instead thrusting deep into her throat, over and over, while she gags and chokes on it like a pro. He may never have been on a date with her, but he knows Chloe's a cock whore who wants dick in every hole. When her throat is thoroughly fucked he flips her over and fucks her from behind, slamming her pussy and her ass until she doesn't know which way is up. He turns her over and keeps fucking her, using a vibrator on her to push her way over the top. When he's done with her, he leaves her there, so he can follow up with another round. Because he knows she wants it.

My Room, My Rules Bitch!

Darcie Dolce and Chloe Cherry are new stepsisters who have to share a room. The girls aren't too happy about having to bunk with one another, and that's because Darcie can't stand Chloe! While not an ideal situation, Chloe is willing to give it a shot but when her stepsister is insulting her and being a general brat, Chloe decides that she's had enough and teaches her rude, disobedient stepsister a lesson she'll never forget!

Anal Asylum: Chloe Cherry and Lexi Lore

Chloe Cherry is an orderly at the Anal Asylum. It's her job to let the anal whores out of their cages from time to time and give them their anal therapy. Today she releases patient Lexi Lore. When Lexi's cage door opens, she wriggles out feet first wearing a leather straight jacket with her perfect perky pierced titties exposed, and a ball gag in her mouth. First Chloe takes Lexi's ball gag out and lifts up her lab coat. She puts one leg up, spreads her bare ass and tells Lexi to start licking. Lexi shimmies over and shoves her tongue way up Chloe's ass and tongue-fucks her pretty hole. After that, Chloe gets a double-ended acrylic toy and stuffs it in Lexi's ass with the big side. Chloe makes Lexi's ass gape but wants to stretch it even more so she grabs an even bigger glass toy and fucks Lexi's ass with it, getting even bigger gapes. Chloe wants to go even bigger so she gets a fat dildo and plunges it in and out of Lexi's asshole until it opens up nice and big. Finally Chloe gets a big metal, hollow butt-plug and leaves it in Lexi's ass while she lets her press a vibrator against her clit and cum. After that, Chloe gets her strap-on and attaches a fat dildo to it. She tells Lexi she only fucks the good girls and slides it in her ass and fucks her deep. She flips her over and fucks Lexi's ass with her legs spread and Lexi cums hard with Chloe's cock buried in her ass. With Lexi looking like she's having too much fun, Chloe wants Lexi to play with her ass now. Chloe gets up on the exam table, ass in the air, completely naked, and Lexi shoves a big metal dildo inside her ass and fucks her with it while Chloe presses a vibrator against her pussy. After that, Chloe gets a big pink double-ended dildo and shoves it inside both of their asses and position themselves ass to ass. Before returning Lexi to her cage, Chloe gets on her back and has Lexi slide the slink deep inside her ass and cums hard with a vibrator.

Cherry Bomb

Sexy blonde Chloe parades the city in cut down jeans, seducing you with her cute looks and flirtatious ways. When she takes you back to somewhere more private, you eventually see that her innocent exterior is far from the truth.

We Have History

When an ex-boyfriend (Dillon Cox) shows up for a place to crash, Chloe Cherry is not pleased, but her current boyfriend (Rod Jackson) turns out to have a competitive side, and to figure out who was the best lover, she takes on both at the same time.

I Bet Youre Wet - S10:E7

Logan Long has two broken arms, so his sister Ms Faris is tasked with helping him out. Logan claims he's feeling dirty and wants a sponge bath. That grosses Ms Faris out, but her friend Chloe Cherry seems okay with assisting Logan. Chloe recognizes that Logan needs to be cleaned below the waist, too, so she pulls his PJs down to get started. She can't believe the size of Logan's dick! Eventually he pops a boner from all the attention. Ms Faris peeks and sees the size of her stepbro's hardon. Chloe can't believe that such a big dick isn't making Ms Faris wet, so she insists on checking it out. Lifting her miniskirt and pulling her panties aside, Ms Faris lets her.Chloe pronounces Ms Faris kind of wet and then announces that even if Ms Faris isn't interested Chloe is going to try out this nice dick. She leans forward to start sucking! Eventually Ms Faris is sick of being left out, so she joins Chloe on the bed to reluctantly give Logan a handie. She does have to admit that her stepbrother has a nice cock. Next thing Ms Faris knows, Chloe has peeled off her clothes and has slide her hairy twat down onto Logan's dick so she can ride it! Again, Ms Faris resists but she can't stand knowing her friend is having fun with such a nice stiffie. Eventually she gets naked and joins in on the fun.At first, Ms Faris rides Chloe's mouth as Chloe bangs her stepbro. Then she takes a ride on Logan's fuck stick while Chloe sits astride his face so he can eat her out. The girls switch spots so Chloe can get back on that stiffie while Logan tastes his stepsister's desire. Once they've finally satisfied themselves, the girls give Logan a double BJ until he nuts into both of their open mouths. Now that Logan has gotten some sexual relief, he's dirty again and must be cleaned by Chloe again.