Latest 'Strap On Sex' updates from Risque Sluts (Page 18)

Sexy MILF plunges metal objects into her sex slaves pussy before her stud pummels their holes with his huge black cock.

Summer Day is super thrilled to be interning for hot lawyer Bella Rossi. During a late night, Summer spills hot coffee all over her boss and is mortified. Embarrassed, she cleans off her boss' gorgeous tits and the mess she made on the floor. Unsatisfied with Summer's performance, Bella takes out her crop and smacks Summer's cute ass peaking under her skirt. Summer apologies profusely and lets her boss strip her of her clothes and bend her over the desk. Bella spanks and flogs Summer's ass as Summer struggles to maintain her composure. Summer has never been spanked by her boss before and she admits that her boss dominating her turns her on. She presents her pussy to Bella and begs Bella to make her cunt feel good, promising to be a good girl. Bella puts Summer over her lap and plays with Summer's hungry cunt until Summer begs to cum. After cumming over and over again, Summer is tied down. One of her tights is stuffed in her mouth and the other is pulled over her head by Bella. Bella then gets a dick on a stick and fucks her apologetic intern turned fuck doll. Summer begs to cum again as Bella fucks her tight cunt, but this slut isn't allowed to cum again until she's gotten her boss off. Bella rips open Summer's mesh hood, freeing her tongue, and then sits on her face. Summer enthusiastically licks her boss' beautiful cunt as Bella teases her and grinds on her face. After Bella cums hard, she fucks Summer to more hard orgasms. Finally, Bella straps on a cock and fucks Summer's greedy pussy before turning her attention to Summer's ass. Summer is only allowed to cum if Bella is fucking her asshole. Luckily, Summer loves feeling her boss' cock in her tight ass and begs to cum almost immediately. Bella fucks Summer in doggy before flipping her over and fucking her on her back. Summer cums over and over again under her boss' attention, and promises to be the best intern. Now that Bella's had her fill, she leaves Summer to clean up the office and prepare for their appointment tomorrow.

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Today we have our #13 ranked wrestler, Kelli Provocateur, put against our #4 ranked wrestler, Cheyenne Jewel. Kelli is a petite muscle goddess with flawless ebony skin and a sexy hot fat clit. Cheyenne Jewel is an all natural muscle-goddess with wrestling training and powerful farmer girl strength. Today it is a classic muscle on muscle match up. One wrestler is just to powerful for her opponent. She dominates her opponent with brutal leg holds, explosive power during sweeps and transitions, and good old fashioned school girl pinning. After the wrestling is done, the winner is allowed to take her prize. She ties up her opponents hands and makes her cum over and over and over again, just like she did during the wrestling. That's right y'all, We had an orgasm on the mat! The loser is turned into a useless pile of weak flesh. All her powerful muscles did her no good during the wrestling and now they do her no good in the prize round. Our champion makes the loser worship her muscles and then lifts and carries her prize off the mats.

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Today we have our #12 ranked wrestler, Charlotte Sartre, put against our #6 ranked wrestler, Daisy Ducati. Sartre is a tattooed, dark-haired beauty who started this season with an impressive match against Izamar Gutierrez, scoring several points against our top vet. Daisy Ducati, back for more grappling, attacks little Charlotte right off the bat. The size and skill level difference makes it difficult for Charlotte to gain any ground. Daisy traps Charlotte and fingers her while Charlotte squirms away reluctantly getting finger fucked. It isn't a shut out however, Charlotte gets better and better each round and she gets a feel for her opponent. Charlotte executes beautiful sweeps and reversals and gets Daisy's back and to give her a dose of her own medicine. Charlotte mounts Daisy and makes her take deep french kissing. For the Prize round, our wrestlers take the tournament very seriously. The loser herself concedes and states that losers in tournaments deserve to get fucked in the ass. The winner agrees, and even adds that losers deserve to ONLY get fucked in the ass. The winner bypasses the vagina completely and goes straight for the ass fucking then the ass fisting. The loser is left gaping open wide, wet and broken. Our chamption picks up the defeated, submitting loser and carries her gaping ass off the mats.

Lily knows most of her dates can't resist her little slave's unique charms. Charlotte gets permission to worship Miss Robin's feet and lick her toes. The sight of her slave's naked ass sticking up in the air is too tempting for Lily. She spanks, slaps, licks, and kisses Charlotte's round ass. Lily tells Miss Robin to spank Charlotte's ass while she lets her slave lick her shoes and suck her feet. Charlotte soon moves up to Lily's hot, wet pussy while Miss Robin flogs Charlotte's ass. Charlotte does a good enough job to get the privilege of tonguing her mistress' asshole. Miss Robin helps by holding slave's head deep in between Lily's ass cheeks. “She's so fucking lucky she gets to taste my asshole and my pussy.” Charlotte gets her mouth back on Lily's pussy and brings her to orgasm while Miss Robin continues flogging her ass. As a reward Charlotte gets Lily's foot stuffed in her hungry mouth. Once Lily has been taken care of she's ready to watch Miss Robin have some fun with her slave. Miss Robin turns the zapper on Charlotte, then a few punches from her fisting hand. The women laugh. Charlotte cries and moans, but her pussy is dripping wet. Lily pushes her fingers deep into Charlotte's ass. She begs for more until she has swallowed Lily's entire fist deep into her ass. But one fist isn't enough, Charlotte wants a whole foot in her ass. The women suspend Charlotte and Lily fucks her slave's pussy with a strap-on. Miss Robin strips off her top and soon Charlotte's tongue is deep in Miss Robin's ass. Keep licking it clean. Taste every last drop. Miss Robin repays the slave with more flogging while she is pounded silly by Lily and her strap-on. Charlotte takes it like a champ and begs for more anal pounding. Taken down from the suspension, Charlotte straddles Miss Robin, reverse cowgirl, and has her ass filled with a strap-on dildo. Lily fucks her slave's pussy while Miss Robin fucks Charlotte's ass. Add a hitachi and some breath play and little Charlotte is done for the evening. Good little whore. Miss Robin is impressed with how much of a pounding Charlotte's ass can take. A great first date by any standard.

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Today we have our #11 ranked wrestler, London River, put against our #5 ranked wrestler, Johnny Savannah Fox. The wrestling starts out friendly but as the girls feel each other out, things start to change as we see the evolution of their tactics throughout each round. They become much more serious and cruel towards each other as they realize anal is on the line. In round 3 one wrestler completely dominates the other; trapping her on the mat and making her cum against her will again and again until she's nearly brought to orgasmic tears. The Winner then takes her Prize. She ties her opponent up in rope bondage with a vibrator strapped onto her leg so she must take it while she's getting fucked in the pussy and in the ass. The orgasms are so powerful and so frequent that the loser nearly can't handle it. She is tied up and can not get away and must take it. The winner spits on the losers face, slaps her pussy until its red and then leaves the loser on the mats a beaten and broken disgrace.

Throughout the night, Kimber Woods and Cheyenne Jewel have been playing strip poker with Aiden Starr. Both Kimber and Cheyenne sit there fully nude having lost their last article of clothing and Cheyenne wants to play just one more hand. Aiden is mildly amused with the hubris of her two naked playmates. She is willing to play one more hand, but the completely naked girls are going to have to come up with something to bet. Kimber has the brilliant idea to wager their assholes. The cards are dealt and Aiden tells the girls to show their hand. Aiden wins and is determined to show these two little losers what it means to give up their asses. Aiden bends the girls over and brutally spanks their asses until they are bright red. She pops toys in and out of their holes, making them gape wide open. The girls lick and suck each other's assholes and the toys that come in and out of them. Aiden ramps up the energy with some heavier anal play. She puts the entire two foot long slink all the way into Cheyenne's asshole. She pushes it in and pulls it out, making Kimber lick and gag on the long toy that was buried deep inside Cheyenne's ass. Kimber's asshole gets stretched wide open with the metal speculum. We see deep into her asshole, getting a glimpse of her pink asshole walls. Cheyenne gets throat fucked by Aiden's fists which makes Cheyenne drool puddles of spit down into Kimber's pried open asshole. Aiden really wants the girls to ante up more so she lays them down and ass fists both the girls hole's until they beg for mercy. Both girls have explosive anal orgasms. Cheyenne's asshole is punished the most for her being a horrible card player. Cheyenne is bent over and strap on fucked in the asshole right over Kimber's pretty face. Kimber waits with her tongue out to suck the cock right when it comes out of Cheyenne's ass. Cheyenne get's pounded good and hard until her asshole is dripping with her own anal cum and Kimber licks it all up.

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Johnny Starlight, ranked #10, is a curvy dark haired beauty who was our intermin Rookie Cup champion this season. Penny Barber, ranked #7, is everyone's favorite big mouthed MILF with a terrible gift wrap hold that gives ever girl problems. Johnny wants to squash Penny and fist her pussy. Penny wants to hand gag and humiliate the sassy little rookie. Penny Barber bullies our rookie in the first round with her signature hold, the "gift wrap" and is able to hold Johnny down. This frustrates her and get her close to orgasm. Sadly, for Penny her weakness is fingers in the pussy and once that happens, it can be game over for her. Today, that's exactly what Johnny needs to do. The winner of this match will move on in the tournament which means more money, more fame, and more fans. One girl gets trapped, fingered relentlessly and is utterly broken by the end of the match. The winner has her way with the loser. The winner hand gags, hair pulls, and puts feet in the mouth of the loser and fucks her pussy in brutal fashion.

Helena Locke has high expectations of her subs, especially Syren de Mer, who comes to her ready to submit. The chemistry between them is dripping hot as Helena uses Syren in every way, punishing her when she disobeys, and rewarding her for a job well done. Syren's put in multiple positions, including an inverted full suspension, and on her back in chains, as she's subjected to anal strap-on fucking, flogging, caning and spanking. Syren arrives at Helena's dungeon to find a letter, telling her how to present herself. Helena arrives and immediately corrects Syren for her backtalk and sloppy presentation. She puts her on her knees and flogs her ripe ass, the leather swatting her hungry pussy with each strike. Helena then pulls Syren down on her boot and makes her slide her dripping cunt all over it before licking it clean. Syren is then put in an inverted suspension so Helena can have unrestricted access to her creamy pussy. She flogs Syren and eats her pussy, giving her a little pain and a little pleasure at the same time. She then canes her, swatting her legs and her cunt and her ass, before fucking her with a dick-on-a-stick. Syren can't keep herself from cumming, even as she's made to beg for permission. Finally Syren is chained by the ankles and wrists as Helena fucks her tight ass with a strap-on. She torments her at the same time with a vibrator, and Syren can barely take it. She struggles to ask permission to cum while at the same time trying not to. When Helena finally allows it, Syren cums hard, repeatedly. But she's not done yet...Syren still has to give her domme an orgasm, so Helena sits on her face and rides her tongue until she cums. She leaves Syren a used, abused, fucked mess on her floor, and Syren loves every bit of it!

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Jasmeen LeFleur, ranked #9, is a tattooed, dark haired beauty who started this season with an impressive match against our muscle goddess Brandi Mae. Bella Rossi, ranked #8, is a little disappointed to be ranked in the mid level wrestler area but is more than happy to kick everyone's ass to show the world what's she's all about. Jasmeen has been training privately and looks more ripped than ever with solid and beautiful muscle. Bella too has been training but she's been doing something a little bit different. She's been domming on Whipped Ass and other Femdom sites, whipping girls into shape and making them cum on her command. Jasmeen shows some explosive power today in this showdown. She gets trapped and fingered but is able to explode out of the positions and gain control. This is a hard fought battle for both girls but at the end of the day, only one can move on in the tournament. The winner fucks the loser's pussy and ass ruthlessly. No mercy, all holes taken! The champion then makes the loser worship her muscles, lick her sweaty armpits, and eat her pussy. She then facesits the defeated grappler and rides her face to orgasm!

Couple Eliza Jane and Pierce Paris finally have a night off together! Eliza really wants tonight to be special and orders new toys to try out with Pierce. Pierce is hesitant at first, but will try anything for Eliza. He strips for her, revealing his toned fit body. After he's naked, Eliza slaps handcuffs on him and bends him over her knee. Pierce is shocked as Eliza begins spanking him -- hard! He's even more surprised that he kind of likes it. Eliza then begins to trail her petite feet along his body. When her feet land on his cock, Eliza decides it's time to for more pain. She kicks Pierce in his balls over and over again. Pierce moans as Eliza's petite feet bust his balls, and Eliza is delighted. She's never had so much fun! She loves treating her boyfriend like a piece of meat. She sits on his face and uses his mouth to pleasure herself before sinking her pretty teeth into his big fat cock. Next, she zip ties him down and flogs him all over his ass and back. She slides her fat cock into his open mouth. Pierce swallows every inch of her fat cock, getting it all wet for his ass. Eliza splits Pierce's ass open with her strap on, thrusting relentlessly as she pounds Pierce's asshole. Once his ass is stretched wide, she fist fucks his slutty ass before stuffing both his balls into his ass. After his balls are inserted, she pushes her fist inside, fisting him while holding his own balls in her hand. But Eliza isn't done yet. She fits Pierce with a strap-on gag and fucks his face as she tugs on his nipple clamps with a leash. Once she's satisfied, Eliza uses her petite feet to jerk off Pierce. He cums hard, covering her toes in sticky cum. Eliza grabs his dick and furiously keeps jacking Pierce off until he cums again.

Tori Avano is an Army Private who is going to get the anal hazing of a lifetime. Dee Williams and Syren De Mer are two MILF commanders who are going to dish out the punishment with glorious tag-teaming action. Poor young Tori is tied up in bondage with her ass exposed and up in the air, ready to take a spanking. Syren De Mer starts the spanking. She warms up Tori's ass with spankings that turn her tushy hot and pink. Dee Williams finishes the spankings, making Tori's pink cheeks so sensitive that she jumps anytime her ass is touched. Syren grabs her flogger and goes to town on Tori's ass, back, and feet. To start, Tori's asshole gets opened up with a metal toy. These anal punishing MILFs know exactly how to open an asshole properly by giving it a good warm-up. The chemistry between all three of these anal whores is strong. Tori's asshole opens from the sexual energy, and just at the right time to attempt to take Dee William's entire fist. This is Tori Avano's very first ever anal fisting. She really wants to impress her commanders. She attempts to take the fist at first but the feelings are too intense for her. She calls mercy but then begs her commanders to try again. One the second attempt, Dee's entire fist goes in and with her ass full, Tori smashes a vibrator against her own clit and makes herself cum. Veteran ass stretcher, Syren De Mer volunteers to show Tori Avano just how its done. Syren takes a full blown anal punching from Dee Williams. Dee and Syren lick up all the gaping holes they create. Finally, Tori is released from bondage and is fully compliant to taking a good hard lesbian anal strap-on fucking from Dee Williams while Syren holds Tori's gaping asshole open and licks all the freshly fucked flesh.

Sexually deranged patient gets fucked hard by gorgeous nurses in this fetish lesbian trio.

Marcelo has come to church to confess his sins and seek forgiveness. When he tells Father Jim that he has been peeping through windows and watching women undress, as well as chronically masturbating, Father Jim is shocked. As his penance, Marcelo is to say 10 Hail Fathers and refrain from masturbation for a week. Marcelo thinks this is a harsh punishment and is none too happy. However, Sister Bettie and Sister Hannah have been eavesdropping on the peeping tom's confession and think that's not nearly enough suffering for such a grievous sin. They grab Marcelo, bend him over a pew and bless his ass with his belt, a paddle and canes. When his screams become too loud, Sister Bettie gags him with a Bible. They beat his ass and cock with the Bible and make him read passages as they hit him. But this still isn't enough for the sadistic Sisters. They make Marcelo bend over the altar and apply whips and floggers to his already red and aching ass. Finally, they anoint him with their "Jackhammer Jesus" dildo and their huge strap-on cocks, filling his holes to teach him a proper lesson and set him back on the righteous path! [Behind the scenes post-scene interview follows the feature presentation!]

Gas mask wearing tart is laying on a Gynochair as a ebony goddess rams her wet pussy with phallic toys. They soon are joined by a masked gimp who proceeds to fuck their wet pussies.

Nadya Nabakova works at her desk, going through papers. The tedious work makes her so sleepy and as much as she tries to stay awake, she cant and falls asleep on her desk. Her boss, Chanel Preston catches her sleeping and wakes her up suddenly by slamming a box down on her desk. Nadya says she's sorry but Chanel says some punishment is in order. Chanel picks up Nadya out of her chair and bends her over the desk, lifts up her dress and spanks Nadya's ass until it turns pink. Next, Chanel strips Nadya naked and flogs her ass and back while scolding her about sleeping on the job. Chanel sticks her fingers in Nadya's mouth getting them wet and ready for her pussy. Chanel finger-fucks Nadya's tight pussy deep, then has Nadya sit on the desk and Chanel gets out the crop. Chanel crops Nadya's perfect perky tits, then spreads her legs to get her pussy cropped making it turn pink against her pale skin. Chanel lays her down on the desk and ties her tits up and ties her wrists to her thighs in rope bondage. She then applies binder clips to her nipples and stomach. Chanel pulls up her skirt and tells Nadya to stick out her tongue and grinds her pussy against Nadya's face while cropping Nadya's pussy, and doesn't stop until she makes Chanel cum. Chanel then gets a dick-on-a-stick and fucks Nadya's pussy with it while she smashes a big vibrator against her clit. Chanel fucks Nadya's pussy on her hands and knees with a strap-on and slides a thumb in her ass to get it ready for her cock. Finally, wearing leather cuffs and a leather harness, Nadya gets her ass fucked by her boss, Chanel with her legs spread on her back, biting down on a ball gag. After cumming with a cock in her ass, Nadya wakes up at her desk, still clothed.

I just love fucking these teeny girls. Angel Smalls is a big sex pot in a little package with a huge appetite for fucking that only I can satisfy. And how am I going to do that? Well, every job needs the right tool and I have just the thing for her. After some spanking this little bitch is gonna take this hot strap on up her cunt, and I am going to give her the best fuck of her life!

Svelte sphinx Delirious Hunter has been beating up pathetic boys in her dungeon all week and needs a release! Ready to let go, submit her body completely, and choke down a dose of her own medicine, Miss Hunter texts the one woman she knows who can deliver the pain and pleasure she craves - the divine, the infamous: Mistress Aiden Starr. These two dominatrix pros waste no time, consuming each other quickly - each in her own way. Aiden teases, chokes, humiliates, and tempts Delirious, and Delirious, quite simply, can't stop fucking cumming. Stripped out of her latex into just her stilettos and thigh high pantyhose - and with the glorious tits of Aiden Starr bouncing above her - Delirious cums while being spanked, caned, and flogged with her very own whips. Wet, pink, bruised, and begging for more, Aiden easily shoves her entire hand deep into this whore's slutty cunt, extracting orgasm after orgasm as Delirious screams against her fist. Seemingly an endless well of pleasure, Delirious begs again and again of her mistress, dedicating each and every orgasm to the beauty and wit of the glorious Aiden. Spread-eagle, gagged, and bound standing to a pole, Delirious is covered in no less than eleven clover clamps - crisscrossing her tits, face, belly, and cunt. With a thick, long dick deep in her cunt, Delirious again becomes deliriously lost in her own pleasure as Aiden tears orgasm after orgasm from her adorable little dominatrix-turned-submissive. Struggling against her ropes to finally get to her true prize - Aiden's delicious cunt - Delirious twists and turns, stretching and reaching, until she finally breaks free for a face full of heaven. Aiden takes full advantage, riding her whore's face and smothering Delirious in her voluminous ass until she's ready to flip her over and take Delirious’ begging, spit-covered hole. Fully giving herself to Aiden, Delirious takes every inch of this dominatrix-of-dominatrixes, swallowing Aiden into her ass as she begs again and again to cum in missionary and doggy. As Delirious' eyes roll back in her head and she becomes merely a set of wet holes writhing and begging on the bed, it's clear that her clit has become completely and forever devoted to Aiden Starr. And what becomes of such a slut? Ask all the boys already lined up outside Delirious' dungeon waiting to be dominated by this queen of kink.

Mistress Cybill Troy loves metal toys and employs many nefarious weapons to torment her hapless sissy slave Tener Duende, who's chained to a cross and already fearing his Mistress' dark desires. First, she attacks sensitive body parts with spiky long metal nails, shades of Freddy Krueger! Then, after esconcing his balls in a metal chastity cage, she sounds him with long diabolical rods as Tener is made to hold his nipple clamps in place. Then it's time to fuck her sissy boy, so Mistress Cybill moves him to the stocks. His head and hands secured, Tener takes it at both ends as his Mistress treats him to a rough pegging and rougher strap-on blowjob.

Stepdad Jimmy Broadway was just coming in Dolly Leigh's room to ask her what she wants for dinner, and is surprised when she asks him if she's pretty, and if boys would want to fuck her. And even more surprised, when she asks if he wants to fuck her. Well, yes, but she's his stepdaughter - but you know, men are weak. Daddy enjoys fucking sweet Dolly and having her suck his dick like a champ. But then she has another surprise for him. Seems her phone has been on video record, and now there's documentation of their encounter. Dolly's mood changes from adorable to bratty and dominant as she gleefully announces that she's going to show the video to Mom if he doesn't do everything she says, she's the boss now. Dolly makes him worship her feet and crawl on all fours, and then she has yet another surprise -- a pretty pink and purple strap-on. But if stepdad Jimmy thinks the humiliation is going to end there, well, no. As a grand finale, Dolly pegs Jimmy but good in several positions, and leaves him with the humiliating knowledge that he'll always be under his stepdaughter's thumb.

Daisy Ducati catches roommate Lauren Philips masturbating to hardcore lezdom porn and using her butt plug! Lauren is so embarrassed and starts dressing, but Daisy isn't going to let this slut get away that easily. She cancels her evening plans and dominates her roommate! Lauren moans as Daisy pushes the plug in and out of her asshole. When Daisy breaks out her strap-on cock, Lauren can't wait to get fucked. Lauren's boyfriend would never fuck her up the ass! Daisy wastes no time pushing her beautiful cock into this anal slut. Lauren loves getting fucked in her ass and reaches her hand back to finger her cunt. Stuffed in both holes, Lauren is a very happy slut. She cums hard on Daisy's cock and then is tied up. Now helpless, Lauren squirms as Daisy breaks out the rest of her toys. Daisy flogs and canes Lauren all over her body. Then she teases Lauren with the zapper. Lauren's eyes widen in fear as Daisy runs it all over her body. Daisy tells Lauren she'll go easy on her with the zapper -- if Lauren licks her pussy good enough! She sits on Lauren's face and Lauren sucks eagerly at Daisy's cunt. Daisy cums hard on Lauren's face and then decides to fuck Lauren with a dick on a stick. Lauren's cunt clamps down hard around this cock, and she cums hard as Daisy slides it in and out of her pussy. Now it's Daisy's turn for more orgasms. She frees Lauren so Lauren can slip her fingers into Daisy's cunt. Lauren's fingers slide in easily and soon her whole fist is in Daisy! Daisy cums hard on Lauren's fist and squirts all over Lauren's bed. Lauren laps up her cum like a good little slut.

Mistress Aiden Starr has invited seven of her best clients for a very special Sunday brunch. The main course- Slut Bottom Chris' ass and mouth! She leads her fuck pig out of his cage and makes him kiss the ladies' feet. He puts his tongue to work as the ladies sip drinks and enormous strap-on cocks bob above his head. Mistress Aiden commands our whore to climb up on the table as Megan Cox greases up his waiting hole and sexy young Jay Taylor steps between his legs, a large black and white dildo bobbing in front of her. Mistress Aiden mocks his teeny tiny little wiener, telling him that he has to be an ass slut because his pathetic cock isn's enough to satisfy a woman. Jay pounds his man-hole like a seasoned veteran as the other ladies verbally humiliate him. Next, beautiful blonde Maia steps between his legs, with more than a foot of black dildo dangling between her legs. She drives it deep into his waiting hole and then starts pumping it in and out as Chris thanks the ladies for their generosity. Next up is sister Dana DeArmond. While her latex nun's habit is heavenly, her bright red devil dick promises hell for the Slut Bottom. She meets no resistance when she enters his now gaping rectum. The ridges on Sister Dana's cock have Chris moaning as she thrusts into his dripping backside. The ladies make him squeal like the ass-pig he is. Sister Dana asks him how it feels to be rammed in the butt-hole by a bunch of strangers, before she asks the lord to show the sinner the way, how to be a good little slut, to be the best whore he can possibly be, in the service of our ladies! Anna Valentina and her giant flesh-colored dildo are next. She's only gentle for a moment though, before long Anna is pounding the slut like a jack-hammer while she orders him to squeal like a pig, daring him to cry. She makes him beg her to satisfy him while she spits in his face, lube and sweat leaking from his ass. Next in line is Kiki D'Aire, sporting 18 inches of rubber on her hips. While Kiki prepares to assault his anus, Dana realizes that the whore might be thirsty, and spits a mouthful of her drink in his face. Kiki teases Chris with the tip of her dildo before going balls deep into his gaping man-pussy. When she pulls out his ass practically erupts with spent lube. But only for a moment, as Megan Cox quickly fills his vacancy with her big, black anaconda. As Chris borders on tears, Dana mocks him, "poor baby got a big black cock in your ass, boo hoo!" When Megan finishes, he hobbles over to the top of the cage, so more ladies can destroy his ass! Aiden Starr slams a big black dildo into his hole and invites him to guess which famous male porn star it's molded from. As she bounces on his hips Maia and Anna double-team his mouth. Aiden pulls out and Sister Dana steps in with a rubber hand. Once it's in place, the boxing nun works out some aggression by punching it while Aiden jack-hammers Chris' mouth with her big black cock! Always respectful, Chris thanks the ladies for punching his asshole and then Kiki D'Aire comes up with an even bigger toy. How much can his hole take?!? When the giant dildo doesn't glide right in she starts to question his status as a butt slut. This motivates him and he starts backing onto her toy. Mistress Aiden asks him if he can go airtight for her, but he can only mumble an answer because Maia has a huge ebony dildo stuffed in his mouth. Finally,Chris climbs down off the cage and bends over a table so Anna Valentina can fuck his face while Maia pounds his ass! But that was just a warm-up for the monster cocks of Kiki and Megan Cox. Exclaiming that "ATM makes my pussy wet," Maia makes Chris like the plastic penis that was just in his ass like an ice cream cone! For the final humiliation, Chris is made to jack himself off. His balls drained, he crawls back in his cage and curls up with a dildo in his mouth, totally spent.

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.

Filthy Asian submissive gets handcuffed, ball gagged and fucked deep by two filthy whores.

Olive is super excited to shoot for Whipped Ass, and she wants it all: spanking, flogging, fucking, anal, pussy licking...everything! She's a natural submissive, ready to please, and with Cherry Torn calling the shots, she gets it all and more! Cherry spanks her and inspects her, teaching her how to show gratitude, and the importance of asking for permission before cumming. Every time Olive cums she has to ask, and she has to endure pain at the same time. Olive is spanked relentlessly, then paddled on her feet and desperately hungry pussy, testing her endurance. She's then rewarded by getting her wet cunt finger-fucked. Cherry hands her a vibrator and Olive cums repeatedly. Olive is then put in a partial suspension with a ball gag and her ass out, and Cherry flogs her sweet ass, tenderizing her for what's to come. She climbs in front of Olive and makes her eat her wet, slutty pussy, and her tight asshole, making her cum again and again. Olive is finally spread open while Cherry fucks her pussy with a strap on. She pounds Olive and crops her, all while using her hole in every way. She turns her over and fucks her ass, making her cum multiple times. Finally, Cherry slides her fist into Olive's worn cunt and fists her, which Olive simply can't get enough of, and she cums hard, just before Cherry decides enough is enough, and says no more!

The busty and beautiful Ivy Lebelle is caught stealing Chanel Preston's hidden stash of cash! Ambushed by Chanel and woman-handled into submission, Ivy is terrified - stammering and beading with sweat - but still unwilling to give up the name of her boss. That's not problem for Chanel, who knows how to extract information from tough whores like Ivy. Trussing the determined slut up with duct tape and ripping every shred of tight clothing off of her body, Chanel buzzes a taser in Ivy's face and grazes it over her thighs, making this terrified thief scream and beg for mercy. Spanking and flogging Ivy's juicy ass, caning her feet, squeezing her puffy nipples, and slapping her ripe tits finally gets Chanel the intel she wants! Still shaking with fear and guilt at having given up her boss, Ivy begins to moan as Chanel rubs her swollen clit, sensitive from the interrogation. Sinking slowly deeper into Chanel's mind games, Ivy's tight cunt gets wet with pleasure as orgasm after orgasm is ripped from her body, struggling against the duct tape that binds her. But Chanel isn't going to let her toy go so soon! She binds Ivy onto her back, splaying the dripping lips of her pussy wide open with clothespins and fucking her with one hard cock and then another, in missionary and doggy, continuing to tear orgasm after orgasm from this hungry slut! Chanel rides Ivy's face, smearing her makeup with cum and cunt as she gets her own pleasure before flipping Ivy over and fucking her deep in the ass. This little thief whore can't stop cumming as Chanel fucks her tight asshole in missionary and doggy, screaming from the overwhelming pleasure of constant orgasm. Finally spent, little Ivy is thrown back to her boss, who's even more devious and twisted than Chanel...

Kendra Spade and Isabella Nice are potential new members for the Pi Cum Louder Sorority. Today, the house mother is putting these two natural nineteen year olds to the test to see if they can be sisters in the sorority. Since true sisterhood is a group of women who appreciate each other for their strengths as well as their faults, Casey is going to be accepting of the fact that these two girls have no anal experience, limited lesbian experience, and little to no bondage experience. As a matter of fact, today is little Isabella's first time ever doing bondage and only her third time trying anal. Casey's first instruction for these two stunning nineteen year old girls is to have them lez out together for her amusement. Kendra and Isabella are both stunning all-natural brunettes with flawless young skin, long slender legs, tight round butts, and cute natural breasts. Kendra and Isabella really start getting into their instructions. They deep french kiss each other passionately and take each others clothing off until Casey interrupts them and gets the spanking and anal play started. Casey puts Kendra over her knees and starts popping toys into her ass until Kendra is gaping. Kendra and Isabella's gape aren't good enough for Casey, so Casey ties them get up in bondage and uses the speculum on them both to make sure their assholes stay open the way they should stay open. We get a nice look deep into Kendra's pink asshole. Kendra writhes and undulates with pain and pleasure as her asshole is stretched beyond what she knew it could do. Poor little Isabella can barely take the speculum. She takes it one notch wider and asks for mercy. Kendra is then rewarded with some heavy anal strap on fucking while Isabella is also rewarded for pushing her anal limits. Isabella is rewarded with licking Casey's big beautiful gape.

The stunning Nikki Darling hasn't been able to achieve orgasm with any of her partners. She has been working extremely hard at it, but nothing he does is working. She is able to reach intense orgasms through solo masturbation but has not reached that level of intimacy with her partner. The brilliant and beautiful Dr. Helena Locke has been working with Nikki Darling through her Orgasm Clinic and today's appointment is ready to go to the next level. Dressed in tight black clothing Nikki patiently awaits her doctor on a medical exam table. Helena Locke walks in and commands attention in her doctor's coat and thigh high stockings. Helena has a few questions for Nikki, has she been doing her homework? Has Nikki had any experience with bondage, discipline? Has Nikki experienced same sex attraction. It's timne for an intense hands on session. Helena tears off Nikki's clothes before spanking her round ass. Helena must work Nikki's ass hard to bring the correct blood flow and sensitivity to Nikki's body. After turning her ass red, Helena works on Nikki's perky perfect breasts and torments her nipples to arousal. Is Nikki ready to orgasm with Helena? A Hitachi is brought out for Nikki to use which brings a huge squirting flood orgasms. Helena's hands pound Nikkis engorged vulva to orgasm again and again. After fisting that tight perfect pussy, it's time for round 2. Tied up in tight rope bondage suspension, Helena brings out the flogger to do more sensitivity work on Nikki's ass and body. Nikki must also learn how to give orgasms before she can truly receive them. Her mouth is used to suck and fuck Helena's pussy, getting it dripping wet. Finally a dick on a stick comes out to fuck Nikki's pussy to orgasm. For the final round of treatment, Helena brings out her big cock strap on. Nikki's pussy is pounded hard while clothespins are clamped to her tight body. For her final orgasm treatment Nikki's ass is fucked hard with deep anal. The anal penetration causes Nikki to scream in pleasure over and over and over again.

Francesca Le has come home from a long day of work to tend to her house Pet. Alana Cruise is said house pet who has been tied up in rope bondage and left in Francesca's Living room to wait patiently until Francesca returns. Alana has been bound with rope wrapped around her nude body, her pretty brunette hair left loose. Francesca enters the living room in her beautiful MILF business attire. Under her blouse and skirt she has a sexy set of lingerie. Francesca is very pleased to see her house pet obediently waiting her return. Not only is Alana bound and waiting in a very submissive position, she is waiting with a jeweled buttplug in her ass which pleases Francesca greatly. Francesca spanks her pet as a reward for waiting like perfect slut. Alana's legs and ass undulate and thrust towards each of Francesca's blows. Alana is enjoying her spanking so much that she farts her butt plug out while francesca is playing with it. Francesca pops the toys in and out of Alana's ass all the mean while giving her the greatest spanking of her life while farting toys out of her asshole. Francesca wants to test her pet's anal skills out. She is not an experienced Anal slave which is why Francesca is moderately gentle with her but still pushes her limits since that is what the anal slave wants. Francesca fingers Alana's asshole with 5 fingers working her way up to an anal fisting until Alana can take no more. Then Alana takes the 2ft long slink as much as she can into her asshole until she must call mercy to her anal trainer. Francesca the rewards her anal slave in training with her own big beautiful asshole while she face sits Alana and makes her lick and sniff her beautiful butthole. After Francesca cums she rewards her pet with a big anal strap on. She fucks Alana's asshole until its Raw. Francesca pulls, Alana's hair and bondage chest harness so that she can thrust deep into Alana's nearly Virgin Asshole. Once Francesca has had her fun with her slave, she ties her back up and leaves her there until next time.

Gorgeous redhead lesbian pain slut Emma Heart is dressed in a tight pink mini skirt and all tied up in restrictive rope bondage, waiting for her new beautiful Mistress Bella Rossi. But, long time house slave Violet Monroe in her house stockings, garter and leather harness wants to get her devilish taste first. Violet Monroe cuts and tears off Emma's tight clothes revealing her perky nipples before grabbing Emma's milky tits and shoving her fingers down her wet gagged throat. Violet tries to get her hands all over Emma's tight red pussy but is caught by Bella. How dare Violet just take what she wants in Bella's Dungeon. Both slaves need to be taught a brutal corporal punishment. The flogger, whip and cane come out to turn these white asses red! Both slaves scream in pain before orgasming in perfect harmony. Bella spits in Violet's shocked face, and chokes Emma heart into orgasm. Both slaves get fucked hard with huge strap-ons and eat each others tight wet pussy. Emma is a foot slut and loves sucking on violets painted toes. This pleases their demanding mistress and she decides it's time for Violet to give up all her holes. Deep anal strap on fucking gets Violet singing. But that's not the finale. Emma strapson again and fucks Violet's pussy hard before Bella goes for the ass again. Deep hard double penetration gets all the women screaming!

Delirious Hunter is a Tall blonde all Natural bad ass. She's long, lean and very flexible and she's hoping her flexibility will help her defeat Bella Rossi. Bella Rossi is our Vet for this match. She's an all natural curvy redhead with years of wrestling experience. With Two very flexible, tough girls on the mat, it's sure to be a fun match. These girls flip all over the mats trying to avoid fingers and orgasms. However, try as they might, they can't stop it from cumming. One girls is completely stuck on the mats. Her legs locked up in the dominant girl's legs. She is immobilized and fingered close to orgasm. The ref sees that there may need to be some extra help needed so she hands the dominant wrestler a vibrator and she uses it on her opponent until she is weak with orgasms and made to surrender. The winner ties up the loser with her own bands then spreads her pussy open and fingers and fucks it. The the winner face sits the loser's face and rides it until she cums.

Loser internet Troll Marcelo has irritated his mistress for the last time! The stunning busty brunette femdom goddess Chanel Preston will need to deliver severe punishment to this pathetic man loser. Tied up in restrictive rope bondage, Marcelo's face is gaged and covered. He is humiliated in sexy sheer women's stockings. His tiny cock pathetically hangs there as he is tormented with corporal punishment. The cane comes out and inflicts severe pain to Marcelo's saggy body. Clothespins are applied to his sensitive skin as he screams. He'll scream even louder when they are violently removed. Chanel delivers sharp pain to Marcelo's scrotum with the crop. This loser like's it! He is willing to do whatever it takes, whatever humiliations is needed, to please his mistress. Spread out on all fours and his ass in the air, Chanel Preston brings out a HUGE cock strap on. Marcelo's greedy man hole takes all of her packed heat deep in his ass. This anal whore will take a fucking for his goddess. Well if the strap on wasn't enough, Chanel Preston has more. Her fist! She punch fucks Marcelo's ass with her fist. He takes a deep anal fisting. All these screams is getting Chanel Preston hot. It's time for her to take true pleasure from this worm. A strap on cock is tightly positioned over Marcelo's face and he gets a front row view of his queen fucking his head. Tied up in tight rope bondage there is nothing he can do but pleasure his mistress to orgasm. After satisfying all her needs Chanel crushes her pathetic troll and stomps all over his body with her beautiful feet. Her black long stockings are gorgeous on her nude body. Finally extremely hot candle wax is poured all over this troll until he screams.