Hard Torture and Deep penetration of BDSM Sex (Chloe Cherry, Rob Piper, Eddie Jaye, Jake Adams, Jay Savage, Donny Sins) - 2020 (Hardcore Gangbang) [HD/1280x720]

Chloe Cherry is instructed by her Mistress to clean the dungeon before her Mistress’ man and his friends get home. But instead of cleaning, Chloe starts masturbating with her Mistress’ dirty panties. She stuffs them in her mouth and in her hungry cunt while she rubs her horny little clit. When Rob Piper arrives home and finds this hot little blonde masturbating in a dirty dungeon, he decides it’s time to teach this insatiable slut a lesson. His friends strip her of her school girl outfit, and make her suck their cocks. Chloe doesn’t waste a second in taking their cocks in her hungry mouth and in her hands. She sucks on their cocks till she chokes and then she keeps on sucking. When they’re tired of her mouth, Rob and his friends put her over a spanking bench and start stretching her pussy open with their big cocks. Chloe loves the attention and can’t get enough. This is her first gangbang! She is overwhelmed with cock and loves it! When they turn their attention to her other hole, Chloe loses it. She is surrounded by fat cocks fucking her mouth, pussy, and asshole. With all her holes filled at once, all Chloe can do is moan around the fat cock in her mouth while her other holes take a hard fucking! She loves getting plowed and by the end, her asshole is gaping wide open. Once the men have had their fill, this slut gets 5 loads of cum all in her mouth and all over her face. Chloe loves the feeling of cum on her skin and rubs it all over her face and on her tits. Looks like the dungeon isn’t getting clean anytime soon!
Painful Torture and Enslavement (Tommy Pistol, Helena Locke, Chloe Cherry) - 2020 (Families Tied) [HD/1280x720]

With a sexy young body and an airy sense of entitlement, Chloe Cherry is any Step-Mother’s worst nightmare. Whenever Chloe needs some more money, she has no qualms about popping by her Step-Father’s house to suck his dick and get another loan. Submissive and sexually curious, this has been a long standing agreement with her and her Daddy/Master Tommy Pistol, but when she rolls up unexpected in a hot little dress looking for some good fucking and a little lipstick money, Tommy is a bit apprehensive- until Cherry get’s on her knees and put’s her greedy little hands all over his cock without permission. Clearly in need of a submissive training update, Tommy takes her through her paces with intense face fucking, spanking, hard flogging, nipple clamps, and some humiliation. What do bad girls get when they steal orgasms? They get fucked in the ass, bent over on the kitchen floor and used like a little sex doll. Enjoying both her holes Tommy gets close to cumming, but hears the sound of the front door opening and puts his cock away, demanding that Chloe get in her clothes FAST. His new fiancé and stopped by – the gorgeous and intimidating Helena Locke. She takes one hard look at Chloe and you know there is going to be trouble for this little blond minx. Once Tommy has left them alone to get acquainted Helena takes full advantage of the situation, stripping Chloe of her heels and dress, throwing her naked teen body on the floor and making her pick up her clothes while being brutally flogged, zapped, and spanked. Helena stuffs her fist in that sweet young pussy, only to deny Chloe and orgasms. As head bitch and new step-mother Helena will always get her orgasms first, and grinds her pussy on Chloe’s face as she flails and screams from her spankings. Having came on Chloe’s face, she takes her thoroughly humiliated young miss downstairs to receive further punishment and discipline. Tommy returns to a comforting domestic scene: Chloe tied down to the Syrian with a full zipper and a service gag holding a perfect scotch just for him. Only problem is, he didn’t request this, and it seems his type A submissive bride to be has gotten a little bit ahead of herself. After Chloe apologizes for her misbehavior and shakes like a whore on the Syrian while being flogged, choked, and throat fucked, she has her zippers pulled off and struggles through the mot painful orgasm of her life. She’s not the only one bound for punishment. Helena is bent over the couch and has her perfect athletic body covered with thick cane stripes for being so presumptuous as to punish Tommy’s daughter for him, and assuming a role of dominance in his hierarchy. Fucked and begging for orgasms with a pink cropped pussy and red spanked ass, Helena leads by example, and shows Chloe how to really degrade herself and beg to cum like a slut.The whole new family unit takes a fuck ride not the couch, double stuffing CHloe’s pusy and ass, and sucking Daddy’s dick real good like a team.
Hard sex BDSM Fucked Women (Chloe Cherry, Luna Star) - 2020 (EverythingButt) [HD/1280x720]

Luna Star’s “A” Student Blonde cutie Chloe Cherry is making bad grades so she has to prove herself to teacher Luna Star by getting her ass fucked, stuffed and stretched. First assignment is to wear a jewel topped butt plug in her ass in order to get it ready for their study session. Luna inspects Chloe’s ass and pushes the plug in and out of her tight hole and lets Chloe taste it. This gets Ms. Star excited so she sticks her curvy ass in Chloe’s face and makes her lick her asshole round and round in and out while she vibes her clit with the Hitachi and grinds around on Chloe until she cums. Luna and her strap on give Chloe a deep and thorough throat fuck to get her cock all wet and ready for the fuckin’ thats about to ensue. Now Chloe on her back with legs spread wide open Ms. Star fucks Chloe’s ass with gusto. Her big tits are framed in a black strappy bra that matches her leather strap on and her high heels give her leverage to pound Chloe hard and fast. Flipped over on all fours Chloe gets it in the butt with that thick dick until her little hole gapes. They rotate around into all kinds of crazy upside down positions so Luna can hammer Chloe’s ass in the best possible way. Then Chloe climbs on top of Ms Star’s cock and slides it in her slutty hole reverse cowgirl and with the aid of the magical vibrator Chloe takes a great ride to fuck town until she cums hard. Chloe is on her way to being student of the month if she can handle all the toys Luna wants to play with. First the see thru cylinder fills Chloe’s ass and stretches her real good, then she stuffs a rainbow colored tapered butt plug that looks like a unicorn horn in Ms. Cherry’s butt and fucks her until she cums. Finally the impossibly long slink is pushed deep inside Chloe’s butthole and she takes it like a champ. Now its Lunas turn to get fucked so in doggie position Chloe fucks her ass with a long stainless steel rod while Luna uses the Hitachi until she orgasms. Ms. Star wants the slink so Chloe slowly but surely rotates it in her sexy ass and jiggles it all around driving Luna crazy til she cums hard. Chloe has learned so much today and turned her F into an A by fucking Luna’s A.
House-Owned Whores Earn Their Place at The Halloween Fuck Fest (Aiden Starr, Maestro Stefanos, Ana Foxxx, Chloe Cherry, Donny Sins) - 2019 (THE UPPER FLOOR) [HD/1280x720]

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.
Ana Foxxx Demoted at The Sadists & Swingers Halloween Ball (Aiden Starr, Maestro Stefanos, Ana Foxxx, Chloe Cherry, Donny Sins) - 2019 (THE UPPER FLOOR) [HD/1280x720]

The UF Halloween Sadists & 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.
Anal Asylum: Chloe Cherry and Lexi Lore (Chloe Cherry, Lexi Lore) - 2019 (EVERYTHING BUTT) [HD/1280x720]

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.
Scandalous Anal College Admission For Bratty Step-Daughter (Rob Piper, Chloe Cherry, Michele James) - 2019 (FAMILIES TIED) [HD/1280x720]

Rob Piper is just trying to be a good father, math professor, and track coach. But the teen college sluts surrounding him would rather suck dick than do their homework. At home he has to manage his hot teenage nightmare of a step-daughter Chloe Cherry, and at work he has posh, cocky college admissions brat Michele James. Michele’s father has paid her way into a fake sports scholarship in Rob Piper’s department, so she thinks she can just throw 20-grand on Rob’s lap and give him a 10-minute blowjob to avoid training. He is here to show Michele that regardless of how rich and untalented she is, she is still going to work for her education.
Job Hunt (Seth Gamble, Chloe Cherry) - 2019 (SEX AND SUBMISSION) [HD/1280x720]

When nosy parker, Chloe Cherry, goes on a job interview, she cannot keep her hands to herself. Seth catches her snooping through his office, and decides she knows too much. So with a nice fresh piece of rope Seth wrangles this blond beauty into his lair to find out if he can trust her and to have his way with this long legged cock sucking anal loving wench.
Be My Butt Lovin’ Valentine (Anna De Ville, Chloe Cherry) - 2019 (EVERYTHING BUTT) [HD/1280x720]

Anna DeVille and Chloe Cherry are butt lovin’ roomies in this weeks EB update. Anna is secretly attracted to Chloe and gives Chloe a special Valentine’s Day gift of a long glass dildo! Chloe doesn’t have those kinds of feelings towards her roommate but that doesn’t stop Anna from convincing her she will love every minute of the kinky, juicy ass play that is about to happen.
College Girls Lose Their Anal Virginity to Experienced Woman (Chloe Cherry, Jane Wilde, Norah Nova) - 2019 (EVERYTHING BUTT) [HD/1280x720]

Chloe Cherry and Jane Wilde are just two adorably cute college freshman. They love to sneak off and experiment with each other. These two perky young tight bodies have no idea what to do with each other and usually just end up making out. They of course both want to remain a virgin. Lucky for them their sexy professor Norah Nova knows exactly how they can get what they want and still be virgins. ANAL. The girls minds are blown by this idea and can’t wait for their asses to be blown wide open as well. First Norah shows them her beautifully jeweled butt plug which they remove and start sucking on to taste Norah’s anal juices.
Chloe Cherry 2019 (DEVICE BONDAGE) [HD/1280x720]

We finally have Chloe here on DB, and we couldn’t be happier. She is tall, blonde, and sexy as hell. She is willing to suffer in bondage and be made to cum against her will, so why wouldn’t we want to shoot her. She begins in a standing back bend position which exposes her body to the sadistic torment of The Pope.
Chloe Cherry and Donnie Rock 2019 (BRUTAL SESSIONS) [HD/1280x720]

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.
Angel Allwood , Chloe Cherry and John Strong 2019 (THE UPPER FLOOR) [HD/1280x720]

Angel Allwood always thought the good life would be sweet. No longer tied to her old life as an assassin for hire, she decided to get married to a rich man and retire to a life of leisure. Little did she know that nothing is as perfect as it seems.