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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 "tight ass". 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.
4 years ago
926
4:00
In lavender lingerie, holding a bejeweled butt-plug in her ass, Ella Nova hurriedly cleans the bathroom at the request of her Stepmother, Dana DeArmond. She gets on her hands and knees to scrub the floor when her Stepmother stomps in. Dissatisfied with the job she's been doing, Dana takes Ella and bends her over the countertop and spanks her ass hard. She pulls Ella's panties down and lifts one of her legs up onto the counter, exposing her pussy and bejeweled asshole. Dana tugs on the butt-plug, pulls it out, and tells her that her punishment will be taken out on her asshole. She grabs a double ended acrylic toy and plunges it in and out of Ella's hole, getting little gapes. Dana grabs a Bad Dragon dildo and shoves it down her own throat, covering it in her spit just before ramming it into Ella's warmed up asshole. She fucks Ella's ass with it while she presses an Hitachi vibrator onto her Stepdaughter's clit and lets her cum. Dana lifts her dress and smothers Ella's face with her ass and makes her lick her crack from the bottom to the top. Dana puts the vibrator to her own clit while Ella licks her asshole and cums hard with Ella's face buried in her big beautiful butt cheeks. Next, Dana straps on a huge dildo the size of her own arm. Ella gets on her hands and knees and her Stepmother slowly pushes her big cock inside Ella's asshole. She fucks Ella deep in her ass and Ella cums hard while getting fucked. After that, Dana shoves a rainbow colored cone plug in Ella's ass. She pulls it out and sticks her whole hand inside Ella's ass. She fist-fucks Ella's hole until she cums hard and after Dana licks Ella's big gaping asshole. After that, Dana wishes to punish her asshole even more and so Ella gets on her back and receives two extra large anal beads inside her stretched out hole. Finally, Dana shoves the entire Slink toy up Ella's ass and clean it out with a water enema.
4 years ago
1926
4:00
Lauren Phillips sweeps into her new McMansion with her giant suitcase and her hourglass figure, ready to charm her new step-daughter with a day out on the town. But her petulant teenage charge, Maya Kendrick, has already worked her way through seven step-mothers. She's also already fought her step-brother Seth over who will have to deal with Mommy number 8, her or him. Maya and Seth are a twisted duo that spend their time playing power games and fucking when their parents aren't looking. Maya has just had her ass beaten red and fucked on the living room couch in belt bondage when Lauren shows up for some wholesome family fun. The way Maya's eyes roll back in her head as she slobbers and moans with Seth's cock in her mouth make the whole premise of a chore trade seem a farce. Maya screams and begs as her nipple clamps are pulled on her tiny little tits and she is flogged, but it's only to beg for his cock in her slutty pussy and ass. Maya is surprised when she gives Lauren lip and Lauren changes tack, grabbing Maya by the ear and locking her in her room. Satisfied by her take-charge attitude, Lauren gets cocky when the maintenance man comes by. She invites him in for some afternoon delight, only to find him filming her while she's giving him a blowjob. Upon demanding he erase the video, Seth introduces himself as her new step-son and the fun really begins! Locking Lauren's arms behind her back in metal handcuffs, Seth flogs her huge tits, degrades her with her new name "8" written on her chest with lipstick, and electrifies her, then makes her squeal like a little piggy and crawl around the living room. Releasing his little sis and outfitting her with a huge strap-on, the two siblings take Lauren down with a double fucking, each taking turns with her ass and mouth while they continue with a litany of humiliation and corporal. Lauren is placed in a pile driver with clamps all over her tits, with cuffs locking her in place. A dildo is placed in her mouth for her to hold while Maya uses it to get herself off, and Seth fucks his new Mommy's ass. Lauren squeals and begs to cum, but to no avail, the twin sadists just continue to enjoy her body until they decide it's time to cane her stretched-out calves. Lauren can only watch helplessly and her sore muscles have 8 red stripes placed upon them with a heavy bamboo cane. Tied on her stomach and ball-gagged, Lauren serves as fuck furniture, getting railed in the ass and pussy until Maya wants to have another orgasm and her brother switches to her holes. She teases and spits on Lauren until she reaches climax and her pretty eyes roll back in her head. Having been properly trained in her maternal duties, Lauren is released and allowed to service her step-daughters clit. Seth fucks Maya and steps on her vibrator mercilessly until Maya begins to wonder if her orgasms are punishment or reward. Both new mother and daughter team look perfect on their backs, taking a hot load of cum together. Perfect bonding day!
4 years ago
31281
4:00
London River enters the yoga studio of Alexa Nova and right away they start a breathing exercise. Alexa is unsatisfied with London's breathing, so she positions her in "downward dog" and tells her to breathe through her ass. Alexa leans in to London's ass and sniffs through her yoga stretch pants. To get a better view, Alexa rips open London's pants, spreads her cheeks, takes another whiff, and sticks her tongue down her hole. Alexa tells London that she has to open her ass more to get the deepest breath so she has her get into "child's pose", grabs some rope and ties London's legs together so she cant move. Alexa gets a large metal toy and sinks it into London's asshole to begin stretching it. She pops it in and out to make London's asshole gape. Next, Alexa lies on her back and spreads her legs wide to demonstrate a more advanced yoga technique. London cant help but stick her face next to Alexa's asshole and tongue fucks her. London gets a large metal butt-plug and slides it slowly into and out of Alexa's ass. When her ass is good and stretched, London starts slowly putting each of her fingers into Alexa's ass until all five are inside. When London's whole fist finally gets inside Alexa's ass, Alexa cums hard. London gets inspired and wants Alexa's fist now in her own ass, so she puts herself face down and her ass in the air and Alexa lubes up her hand. Alexa's fist gets instantly swallowed by London's hungry stretched hole and with a vibrator pressed onto London's pussy she has multiple huge orgasms while getting fisted. After that, London gets on her back and Alexa gets her leather strap-on with a huge dildo attached to the front. She fucks London's ass deep and hard and they end the session by pressing their assholes together and trib-fuck.
4 years ago
676
4:00
Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! Today is the moment you've been waiting all summer to see. We have had 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Today we have our #4 ranked wrestler, Cheyenne Jewel, put against our #1 ranked wrestler, Mistress Kara in the season finale. Cheyenne "The Wrangler" is an all-natural, muscular, big assed, brunette hard-body. Her wrestling skills are very good, but she has taken on Kara many times and has never been able to figure out how to stop Kara's signature move. Kara "The Queen" was originally ranked #2 behind Ariel X, but Ariel has had to pull out of the tournament due to injury. Kara is the Queen for a reason. She easily dominates her opponents and then turns them into servants to please her after each victory. She has one move that every single wrestler seems to get stuck in. A move that enables her to keep control while burying fingers deep into her opponents' pussies. She has landed this move on every girl in this tournament. Today, Cheyenne Jewel is able to stop Kara's move. This is her most technical match EVER against Kara. The girls are so even in the arm wrestling that they end up dragging each other all over the mats trying to gain an advantage. The wrestling is the same way. Zero points are scored in the first half of the first round. The girls circle each other and push each other, trying to catch each other off guard. They are tentative and patient. Each girl knows that one mistake can land them in hot water with fingers buried in their pussies. The match ends with a very low score on the board. The winner gets her hand raised and then drags her opponent to the center of the mats for brutal domination. The winner slaps the losers face and hand gags her as well. To show her dominance, she puts her loser into a head scissor and denies her orgasms while she punches her belly. The loser will only be allowed to cum when the winner allows it. Finally the champion allows the loser to cum and then makes her come again and again and again making her have orgasm overload. The loser is weak from the orgasms which makes her prime for putting into brutal submission holds. The winner takes advantage of this and puts the loser into one submission hold after another. She puts her in a choke, a boston crab, a baby swing and a camel clutch. The loser taps out each time. The winner then takes her strap on cock and fucks the loser until she cums more and more. Finally the winner wants her prize. It is her time to cum. The winner rides the losers face until cum is dripping out of her beautiful winner pussy. This is a winner take all match. The winner lifts and carries the loser off the mats and tells her that every night from today on, she is going to fuck the loser just like she did until the fucking loser can finally beat her in wrestling. This punishment is on going until these two meet again on the mats and settle the score there.
4 years ago
3482
4:00
Penny Pax is a naughty little house slut that loves being bent to the will of her dominant, cocksure boyfriend, Seth Gamble. She knows and loves her place in Seth's world, crawling towards him and begging for his cock with just the sexy sway of her hips. Looking up from his reading, Seth answers the call of Penny's body, grabbing her throat and gorgeous, flowing red hair as he restrains her and tugs at the clamps on her nipples. Seth spanks her, zaps her, slaps her pretty pussy until it's pink with pain, and tugs at the clamps again. Penny moans and writhes with the desire to please her master as Seth pushes himself on her, parting her lips with his thick cock. Penny gags and spits, choking as Seth pumps in and out, taking her throat as he pleases. He then does the same with her cunt, taking it for himself, making his pretty pet beg to cum as he fucks her until her eyes roll back in her head. Bing bong! The doorbell interrupts Seth and Penny's kinky tryst, and Penny crawls obediently to open the door. Seth's stepmom, Chanel Preston, shoves her way past Penny, who's shocked - Seth has never told her anything about his family or past. Hot and bothered, Chanel scolds Seth, demanding that he return home to his large inheritance and lavish lifestyle. Scoffing, Seth sends her away, but before she leaves, Chanel offers Penny a deal: she leaves Seth, and Chanel pays her handsomely for her trouble. Penny refuses at first, but the temptation is too great - she betrays Seth, whose stepmother returns the next day to gloat over her success at turning yet another of Seth's slutty subs against him. Seth lunges at Chanel, grabbing his stepmom's throat and pressing her face against his dirty feet. She licks between his toes, relishing her stepson's surge of power, and begs for his cock in her mouth. Seth makes his stepmother earn it - slapping, choking, and flogging her until she deserves to gag and spit on her stepson's thick dick. With clamps on her tits and a thick set of canes against her thigh, Chanel cums hard, bucking against Seth's hand. He then ties Chanel up, legs akimbo, and he canes her beautiful arched feet as he fucks her and press the vibrator hard against her clit - making Chanel scream and beg for more. With Penny's return imminent, Seth straps his still shaking and cum dripping stepmother to the Sybian. Returning to this torrid scene, Penny knows Seth has heard about her betrayal, and that she's in for a brutal punishment. Seth strips Penny of her clothes, slapping at her face and body as he shoves his cock deep into her throat and then Chanel's. As his stepmother licks his balls, his girlfriend chokes on his cock, both gazing up doe-eyed into his stone-cold face. Now Seth wants more. He takes all of Penny's holes - fucking her cunt, into her ass, right into Chanel's mouth, back and forth again and again until both are moaning in ecstasy against Seth's cock. Used up and dripping wet, Seth's girlfriend and stepmother beg for his cum, and he delivers - all over Chanel's face and Penny's round pink ass. That's what you get for betraying Seth Gamble.
4 years ago
4012
4:00
When little Kendra's step-sister Natasha shows up unexpectedly at her door, all that the submissive princess can do is pout and whine because her Master, Tommy Pistol, has other plans for the two sisters... Only moments before Natasha's arrival, Mr. Pistol's cock was deep in the wet, hungry asshole of his personal slut and wife, Kendra Spade. Collared and cuff, Kendra jingled into the dining room to bring her Master his breakfast, forgetting Tommy's one requirement - her tits must be presented to him and available for fondling at all time. As punishment for a fully-buttoned blouse, Tommy smears Kendra's face in his buttered toast, clamping her pussy lips together, and spanking his whore for being so fucking greedy for his cock so early in the morning. Kendra soaks up every drop of attention, gagging herself on Mr. Pistol's cock until she's gurgling up strings of spit and cumming over and over again as he fucks her fast and hard in her tight pink asshole. Interrupted all too soon by Natasha, Tommy sends Kendra off to do some shopping for a welcome dinner so that he can have a private moment with Kendra's step-sister to teach her the rules of the house. Shocked by the kinky relationship between them, Natasha is reluctant to accept Mr. Pistol's requirements of discipline and respect, but caves quickly knowing that she'll be allowed to dominate her submissive whore step-sister as well.... Tommy tears Natasha's dress off, revealing her supple tits and round, tantalizing ass. Next he tears into Natasha herself, flogging and spanking her, fucking her tits and mouth before finally fucking her dripping, beautiful cunt - giving her a lesson she won't forget on what it means to be a Master. When Kendra arrives home from shopping, the two are ready to pounce, convincing their sweet submissive that she needs a dose of domination from family. While Natasha spanks, paddles, and slurps at her asshole, Kendra chokes herself on Mr. Pistol's cock before riding it, bouncing up and down as she begs her step-sister for more. Natasha then brings Kendra's face hard against her cunt, rubbing against her step-sister's tongue as she cums while Tommy continues to fuck his favorite little toy. Mr. Pistol fucks Kendra faster and faster in cowgirl and doggy, both in her pussy and her ass, while zapping Natasha with an electric wand. As Kendra cums over and over again on his cock, her asshole gapes and Tommy gives Natasha a taste of her own step-sister's sweet asshole. But Tommy also wants a taste of something different.... The two step-sisters swap, and now it's Kendra that has to beg for her husband to fuck her step-sister as her step-sister buries her tongue deep in Kendra's pulsating pink pussy. As Natasha cums on Tommy's cock, Kendra feels a wave of new submission wash over her, and she eagerly shares her Master's dick with Natasha - the two sucking on his balls and cock until Mr. Pistol covers both sister's faces in cum.
4 years ago
36123
4:00