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Chloe Cherry in Kink - Troubled Teen ReHab 2 (Sex and Submission)

When troubled teen Chloe Cherry starts a cat-fight with her neighbor, she is sent off to Troubled Teen ReHab where Derrick Pierce gives the bratty teen an anal attitude adjustment. Tied up to the wall in the detention cell with a ball gag stuffed in her mouth Derrick whips Chloe into shape with the flogger. Stinging and punishing Chloe whimpers with each crack of the flogger on her small perky tits and delicate thighs and butt. Derrick spanks Chloe bare ass and turns it bright pink-just the like color of her cute little sneakers. To keep her quiet Derrick makes Chloe suck his cock until she is subservient. But Derrick is just getting started with Chloe's rehabilitation, she has a long way to go. On all fours in doggie Derrick whips her some more with the flogger, teases her with the Hitachi and then fucks her pussy. After getting her good and warmed up he pounds her ass until she is moaning with pleasure. Finally with Chloe on her back on the cell bed, ball gag back in her mouth and clamps tight on her nipples Derrick spreads her legs wide and fucks her pussy and ass until she is begging for his cum and he shoots his load all over her face. Anal Attitude adjustment complete.
Kink 'Troubled Teen ReHab 2' starring Chloe Cherry (photo 7)

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Chloe Cherry - Troubled Teen ReHab 2 (Thumb 01)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 02)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 03)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 04)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 05)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 06)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 07)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 08)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 09)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 10)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 11)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 12)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 13)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 14)
Chloe Cherry - Troubled Teen ReHab 2 (Thumb 15)
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Angel Allwood - A Mother's Job is Never Done: Anal Assassin Trains Her Step-Daughter

Angel Allwood - Upper Floor

22nd August - 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. The blight on Angel's perfect little dream is her husband's 18 year old daughter Chloe Cherry. She is spoiled, sassy, entitled, and still lives at home. And, if there is one thing that Chloe can't stand it is being told what to do by her slutty step-mom. The simplest of requests for Chloe not to wear her ear phones in the house gets spit back into Angel's face from Chloe's bitchy little mouth. Chloe knows that there is nothing that Angel can do about it because she will always be daddy's perfect little girl. Shitty days always seem to get worse, and Angel's day has only just begun. After the spat with her bratty step-daughter the doorbell rings and her old assassin boss bursts through the door and back into Angel's life. She begs him to leave her new family alone and to respect her decision to get out of "the game." But John Strong doesn't play by those kinds of rules and with a hand of her throat he reminds Angel that there is no "getting out." In a desperate attempt to appease him from potentially causing harm to her new family she follows his instructions. He makes her strip and then handcuffs her wrists to keep her restrained. Jamming his stiff cock down her throat, she pleads with him to stop, but he makes her gag over and over. Tired of her back talking, John duct tapes her mouth shut and starts to fuck her tiny pink pussy and her tight asshole back and forth with reckless abandon. After John has had his fill, he makes Angel clean his cock off and notices step-daughter Chloe cluelessly lounging outside in the sun. His appetite quickly grows and he informs Angel that he is going to teach Chloe some much needed respect. He drags Angel to the kitchen and takes Chloe by surprise. Chloe quickly realizes that she is out of control as John tackles her to the ground, strips off her slutty hot-pants, and then scrubs her mouth out with soap. Before she can catch her breath, John thrusts his huge rod into her mouth and teaches the incorrigible bitch how to deep-throat. He then tests Chloe's little cunt and her pristine asshole to see if she is as pleasurable as her step-mom. To keep the neighbors from hearing the sound of their screams he drags them into the basement, ties them up in tight rope bondage, and stuffs their mouths with huge red ball gags, so he can further discipline his unwilling captives. First order must be established, and he has Angel teach her step-daughter the sacred rules of submission: Honorific, Eyeline, and Deportment. The girls quickly learn their place and cower at the feet of their stern and dominant man. After relentlessly punishing the smooth white skin of his slaves with hot wax and a black leather flogger, John then puts his whore submissive's on their knees. They beg their master to shower their unworthy whore holes with a hot load of his cum. John then shoots a massive wad all over their faces and makes them lick each other clean. Submissive slut Chloe Cherry and her whore step-mom Angel Allwood get tied up in rope bondage, ass fucked by a huge cock. and learn the rules of discipline!! ...Read More
Helena Locke - Gold-Digging Anal Teen Learns the Old Fashioned Way

Helena Locke - Families Tied

16th February - 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. ...Read More
Chloe Cherry - The Stinging Torment of Chloe Cherry

Chloe Cherry - Brutal Sessions

9th May - 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. ...Read More
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Chloe Cherry - Chloe Cherry Gagged and Bound

Chloe Cherry - Training Of O

10th October - Chloe Cherry sits, gagged and bound to a wooden chair in a red pleated skirt that's been pulled up to show that her hairy pussy has had an hitachi vibrator secured directly beneath it. Chloe's wrists are bound behind her back with rope and her milky thighs tied to the chair with leather belts. Black rubber pads are stuck to her upper-thighs pulsing electricity into each muscle. James Mogul has some questions and stands wearing knee-high black leather boots at the helm of this interrogation holding two potentiometers. One knob controlling the electricity and the other knob controlling the strength of the vibe, depending on her answers. Next we find our adorable blonde damsel squatting with her thighs bound to her ankles wearing only white thigh-high stockings, balancing on her tippy toes, her tits bound with rope, tied to the ceiling. Tommy pistol gets his cock ready in the background as James Mogul makes Chloe zap herself with electricity while he flogs her. Soon after, Tommy Pistol walks up and stuffs his cock deep down her throat covering her face and tits with her spit. Unhappy with her open-mouth blow job, Tommy strictly reminds her to keep her lips tight as James Mogul applies the nipple clamps once again. In the next scene we find Chloe on her back with her legs spread eagle bound with rope. Mogul attaches two clothespins to her pussy and rips out an orgasm with an old fashioned vibrator pressing it on her exposed clit. Tommy comes in and fucks her pussy and ass deep and hard going back and forth. In the final scene Chloe is placed on her knees with her thighs tied to her calves and her ass is fucked fast and hard until she begs for his cum. ...Read More
Chloe Cherry - Lazy Submissive Gets Taught a Lesson by Mistress' Studs

Chloe Cherry - Hardcore Gangbang

20th September - 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! ...Read More
Chloe Cherry - The Drifter

Chloe Cherry - Sex and Submission

3rd November - Blonde beauty Chloe Cherry, Bar maid of the Dry Gulch Saloon, needs to make $15 by the end of the day or it's her ass! Those are the threatening words from her husband who goes into town to buy a new axle for their wagon. When the husbands away the wolves come to prey...Roaming through the Southern California mountains drifter Xander Corvus stops in the saloon to get a refreshing beverage and some relief from the blazing sun. When Chloe overcharges him for beer things go wild! Xander isn’t gonna let some dame short change him plus her sexy ass is looking pretty good in that skirt.He grabs Chloe by her pale delicate neck and wrangles her to the ground, tightens a belt around her wrists and throat fucks her until she is begging to get her pussy fucked. It seems her strict husband never gives her the time of day so she is hot and horny for some hard cock. First he rips Chloes shirt open to play with her perfect natural tits and then on all fours in doggie Chloe gets a deep fucking in her wet and ready cunt. Outside in the bright afternoon sun Xander ties Chloe to a hitching post with one leg up and disciplines her with the flogger. The ball-gag in her mouth makes her drool and drivel but no one can hear her screams. After fucking her pussy some more he gets inside that tight ass and pounds her the fuck out until her hole is stretched and gaping. She loves it and can’t get enough. Xander makes her clean his cock with a blowjob and then takes her inside to finish her off. Corporeal punishment with the flogger and crop get Chloe excited and eager for some more hot action. Xander hammers her ass and pussy back and forth till her eyes are rolling back in her head. She’s never been fucked like this before. With her tongue wagging for Xanders cum he shoots his load all over her tits and then hits the dusty trail because he is...The Drifter. ...Read More
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Chloe Cherry - Teach Me to Twerk

Chloe Cherry - Teach Me to Twerk

18th May - Chloe Cherry has recently joined a twerking team and is hard at work on her routine. Practicing in the mirror, she makes sure her sexy little booty moves in all the right directions. When Nia Nacci walks into Chloe's room, she has no idea what she's up to. She clears her throat and Chloe turns around laughing. Slightly embarrassed, she explains that she just joined a twerking team and has to get in all the hours she can before the next gig. Nia has no idea what twerking is, but is definitely intrigued. She might not want to admit it but she's definitely never noticed how hot Chloe's ass is, especially now that she's shaking it in every direction. When Chloe asks Nia to try, she gets the rhythm down almost immediately. Who knew she was a natural! Chloe puts her hands on Nia's hips and ass and directs her on how to move. Chloe gets up and shows her how to do it while she tells her about the time she twerked on a girl's face. Nia tells her that she never knew she was into girls. As a matter of fact, so is Nia. When Nia asks if Chloe would be willing to twerk on her face, Chloe happily agrees. The girls start kissing and taking off their clothes as they ravage one other's bodies. The girls don't know it yet, but they'll both be twerking on each other's faces until the next morning. ...Read More
Alyce Anderson - Bare

Alyce Anderson - Bare

13th January - Chloe Cherry and Alyce Anderson are studying for a big exam but can't seem to stay concentrated on their notebooks, instead they keep checking each other out as the sexual tension between them builds. When Chloe gets ready to leave, Alyce asks for a goodbye hug which quickly turns into more... After making sure that no one else is home, the girls start to explore their bodies together. Chloe's more experienced and starts off by licking Alyce's perky teen titties before slowly making her way down to her young pussy. They strip off each other's clothes and Alyce flicks her tongue against Chloe's nipples before Chloe goes back down between Alyce's legs to pay more attention to that pretty little pussy. Alyce gets more confident and they 69 so they both can get the taste of teen pussy in their mouths. Chloe brings out a dildo and asks Alyce to use it on her tight little asshole and only gets better from there... ...Read More
Alena Croft - The Fuckerfly Effect

Alena Croft - Brazzers Exxtra

2nd July - Reminiscing about an old boyfriend she never should have broken up with while masturbating sends MILF Alena Croft back in time to fix her sex life! Meeting up with a younger version of herself, Chloe Couture, teen Alena and her mature counterpart make things right with Xander Corvus by sucking his big dick. As Xander's huge cock is pounding his blonde teen girlfriend's tight pussy, future Alena returns the favor by serving up a mouthful of her own pussy! There's no telling how bad the timelines are getting scrambled, but right now there's a threesome with two versions of Alena Croft to take in. As both babes get glazed in a fresh load, they lick up every drop off each other's firm bodies, returning Alena to the future and lifetime of fucking Xander! ...Read More
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Holly Hendrix - Bratty Teens Holly Hendrix and Chloe Cherry

Holly Hendrix - Bratty Teens Holly Hendrix and Chloe Cherry

25th January - Holly Hendrix and Chloe Cherry were hanging out and her annoying roommate Seth Gamble came in gushing about his girlfriend with cringe-worthy lovey dovey bullshit. When he left to get ready for his woman, he forgot his phone in her room - BIG MISTAKE! Being the brat she is, Holly decided she'd heard enough about his not-even-that-cute lover and enlisted Chloe to go along with a devious plan to break them up! By the time he got out of the shower - it was too late. If he wasn't going to marry the girl of his dreams, at least he could have a threesome and punish-fuck someone in the ass! It was for the best. ...Read More
Chloe Cherry - Goth Anal Whores 2

Chloe Cherry - Goth Anal Whores 2

19th June - Oh dear! Twisted blonde brat Chloe Cherry was a naughty girl and ruined all her dolls! What's a troublemaker to do? The only thing left to have fun with was her sweet pink twat! Daddy Small Hands was disappointed in her actions, but he would use his big cock in her pretty ass and pussy to correct her misbehavior. It's not really a punishment for a girl who loves to fuck, but she's very sorry for being a bad girl- she is, after all, a very good goth anal whore determined to make her daddy smile. Wanna play with her toys? You'll have to retrieve them from her butt! ...Read More
Keisha Grey - Fauxmance

Keisha Grey - Fauxmance

22nd December - Keisha Grey is on the phone with her boyfriend who has to work late again, but Keisha is no sucker. She knows something is up and calls him out on it, he's been cheating on her and she'd had enough. He tries to defend himself, but she breaks up with him, hanging up the phone in disgust. Chloe Cherry can't help hear arguing coming from Keisha's room. She opens the door to find Keisha in tears. Having planned a day with him, Chloe suggests that since the day is young and that Keisha looks super hot in her outfit, they should take full advantage of the day and spend it together. Lounging in the bath, they take in the suds, as Chloe washes Keisha's chest and plays with her tits a little. Keisha can't help but thank her for the fauxmantic day they set up. Chloe gets lost in the moment and can't help but lean in and kiss Keisha who looks confused and doesn't know how to react. She runs out apologizing for making a mistake. When Chloe goes to her room the next day to apologize for her behavior, the truth is, she also has a confession to make, she's a lesbian and she really likes Keisha. Keisha isn't sure what to say but the fact is, she's been having the same thoughts as Chloe. Chloe is relieved but also a little worried because she doesn't want the friendship to get ruined. Keisha however, isn't worried. Smiling, she tells her that it could only go up from here. They start kissing losing themselves in each other's arms. ...Read More