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!

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 fianc̩ and stopped by Рthe 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.

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.

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.

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 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.

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.

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.

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.

Part two of our BDSM summer soiree finds Arabelle Raphael tied down to a fuck table in tight bondage with her big nipples adorned with brutal metal clover clamps. She is faced with her teenage trainee Chloe Cherry gripping a huge dildo gag in her mouth. The governess Aiden Starr is determined to teach this little blond slut how to be a sex object rather than a selfish whore, and will start by using her as a toy for Arabelle's pleasure.

When Chloe runs for help, Mr. Pete is there for her. But when she realizes she has just run into the arms of a sexual deviant, Chloe plunges into a fantasy of BDSM and anal sex. Tall, blonde cutie Chloe Cherry has escaped a crazy boyfriend who did questionable things to her in the basement.

Chloe Cherry shows up for service with a slutty disposition and lack of regard for protocol. During her introduction to TUF esteemed attendees, she is already rubbing her cunt and grinning like mad, certain her undisciplined teenage pussy is about to be full of dick. Our long standing submissive servant Arabella Raphael sighs with displeasure, realizing how hard her job is going to be, getting this know-nothing little millennial into shape for serving the horny BDSM swingers already beginning to laugh at Chloe's obvious lack of training.

Everyone knows California neighbors do anal! Everyone except for Christie Stevens. Fresh from middle of the country, Christie is shocked to find her neighbor Chloe Cherry stripping in her backyard. Christie rushes over to let Chloe know that everyone walking by can see her, but Chloe isn't bothered.

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.