Innocent little Kendra Spade has been having some not so innocent desires for Sister Dana Vespoli. Aroused and confused, she takes her ass to church and asks father for guidance and forgiveness. She confesses her sinful dreams of the beautiful Dana Vespoli. On her knees and hands clasped together she worships Sister Dana Vespoli at the alter. Kendra puts her hands all over Dana's ass, grabbing and worshipping she removes Dana's clothes and puts her mouth on Dana's tight asshole. Kissing and spitting and tonguing Dana is in pure pleasure as Kendra worships her. It's now time for Kendra to confess her anal sins. Dana takes out a huge glass toy and works on spreading and stretching out Kendra's tight asshole. Kendra's demons are released with orgasm with each toy used on her ass. However Dana knows any true exorcism requires anal fucking and she brings out a huge strap on for Kendra. Kendra worships the strap one with her mouth, slobbering and spitting all over it before Dana turns it on her ass. Deep anal fucking gets Kendra ready for more orgasms. Next it's Dana's turn. Kendra uses her hands to pray inside of Dana's asshole with her fist. Dana uses the hitachi to bring out a screaming holy orgasm. The anal snake comes out next and fills up Dana as fas as she can take it. Kendra begs Dana to not tell father about what just happened.

Madame Kelli Provocateur and Betty Solace make meaty muscle boy Davin Strong prove his worth with a delicious Double Domme dungeon session that gets his cock rock hard and challenges his very core. Down on the ground and gagged Davin gets the zipper to start the day off right. Madame Kelli and Queen Betty attach the clothes-pins all over Davin’s tight skin around his cock and balls and then spank his firm ass until it turns bright red. Kelli commands Davin to do push-ups to show how strong he is. She adds an extra challenge by pressing her stiletto boot into his back and then Betty adds weight by sitting on him causing this pathetic 300-pound powerhouse of a man to shake and sweat as he works to impress his mistresses. Davin’s endurance needs work and Madame Kelli and Queen Betty are going to make sure he improves but first he must do the very important job of pleasuring these luscious ladies. Betty grabs the Hitachi and vibes her pussy as Kelli rips the zipper from Davin’s sensitive skin. This gets Betty even more wet, so she gives Davin the vibrator and orders him to make her cum. Next Davin is standing with a metal hook up his ass, bound with rope and holding two weights up creating a great strain on his muscles. Madame Kelli and Queen Betty unleash a torrent of punishment upon him with a round of brutally relentless flogging and caning that cover him with intense lash marks. If he breaks there will be hell to pay but if he works hard and holds up there will be great rewards. Davin has been such a good boy he deserves a reward. With Davin on his back and tied to a box Betty climbs on top and sits on his face. Madame Kelli jerks Davin’s cock with her massive tits as Betty writhes around making him devour her sweet pussy until she cums all over his face. Then Betty sucks Davin’s dick while Kelli gets off rubbing her beautiful Goddess pussy all over his mouth. Betty can’t resist having more orgasms so she straddles Davin’s cock and fucks him good until she is moaning with pleasure. Madame Kelli cums hard from the pussy licking and then fucks Davin’s tight ass with a strap-on. Davin Strong has proven he is worthy of being in the presence of such divine dommes so Queen Betty jerks him off until he shoots his fat load just for them.

Two of the hottest ladies in the industry devour each other’s tight assholes for the pleasure of KINK.com’s members. Hazel Moore begins her day on her back with her legs spread wide open. She offers herself as a submissive slutty treat to the vicious whims of the dominant Keira Croft. Keria wastes no time and shoves massive toys up Hazel’s ass and coerces her sub to lick her own butt juices. Hazel gapes as the long tendril-like ass toy probes deep into the depths of her willing orifice. All the while the hungry domme licks her subs as and tickles her tight pink pussy. Next Hazel is tied down to a sawhorse with inescapable bondage and is ruthlessly pegged with Keira’s long strap on cock. We peer into her gaping asshole as she has multiple orgasms that the sub is helpless to control. To end the day, the two lesbian butt lovers lie down on ground and share a double ended dildo first in their gagging deep throats and then in their lubed assholes. They take turns going ass to mouth until Keira finally finds herself on her back, rubbing her own swollen clit, while she coaxes her submissive servant to pleasure her greedy asshole with a long stainless-steel dildo. She trembles and shakes as she succumbs to a massive orgasm that leaves her panting and drooling from the ecstasy of the experience. Hazel and Keira end their day making out on a dirty mattress while exchanging their sweat and love juices. They revel in the afterglow of their secret dungeon love exchange as only two depraved sluts can.

Katie Kush is a nasty dominatrix and holds nothing back from her slaves! She has no shame and pisses right in front of slave draven. Clad in sexy latex and sheer stockings, he can’t help but stare. He knows what’s next! You see, draven is a toilet slave. He spends his days (and nights!) chained to his Mistress’ bathroom. Can you imagine what he sees coming in and out of her dungeon? Today is a good day. His skills are put to use on Mistress’s pussy and her ass. His face is ridden. His tongue is given a work out. He is smothered and covered as she uses him for her own satisfaction. She cums all over his face and he’s left, chained in one spot, ready for his next opportunity to serve.

Katie Kush is an aspiring actress with dreams of becoming a big Hollywood star. The problem is that her agent isn’t giving her the attention that she thinks she deserves. He’s been dodging her calls, so she decides to pay him a visit to show him what she is willing to do to make it big. Unfortunately, Katie may have bitten off more than she can chew. Her agent, Tommy Pistol is a scumbag agent and only gives his favorites clients the good roles. Katie has to play by his rules or her dreams are never going to happen. Katie is willing to suck his cock, but when he pressures her to do more, she starts to rethink her decision. Before she knows it, Katie is tied up and Tommy is having his way with her. She wants the role and told herself that she would do anything to get it. Tommy continues to exploit her for his own sexual desires which include torment and anal sex. Lots and lots of ass fucking! In the end, Katie has all of her holes violated by Tommy’s cock, she has been tormented, and all while being restrained in rope bondage.

Mistress Kaiya collects men. She finds useful information about them, confronts them with it, and then uses it to enslave them. Her latest victim is an executive named Jack who has been embezzling money from his company. She gives him a choice: he can either become her slave, or go to jail. He makes the right choice, and ends up with his face buried in her BIG ASS!! HOT ASS WORSHIP, FACESITTING, FOOT WORSHIP, AND MORE!

Leave it to Mistress Julia to completely shatter her slaveboy's psyche. After riding his face and whipping him a few times, she decides to blow her bull while sitting on the sub's face. Later on, we see her getting fucked with her legs spread. At one point, Julia even drools over her slave's limp dick, just to make this experience even more demeaning.

Mistress Jewelz slave is finally getting what he wants today..except there is a twist. He's been wanting to feel that sweet release of an orgasm for far too long after being teased and denied for months on end. He is on perfect display with his body completely exposed and vulnerable for his Mistress to have her way with. She just loves the look of a man tied up knowing they have no control whatsoever. Mistress Jewelz lubes up his helpless cock and strokes it until he is begging to cum for the 1st time in forever. If he is going to be allowed to cum it's going to be her way and her way only. She edges out a massive cum load all over the floor and scoops it all back as a boy needs his dinner. Growing boys need to eat and a big, sticky load of cum is exactly what Mistress Jewels has planned for the bitch. She knows how much he hates the taste of his own cum which is exactly why she loves shoving it down his throat.

Lily Lane and Jessica Ryan get it on for the first time in this super hot EB update. Princess Lily saunters into the dungeon in her sexy lingerie and high heels to find Jessica is all tied up and eager to please. She starts with the crop on Jessica’s butt, thighs and tender feet getting her all warmed up for a day of all the way girl on girl ass play with lots of big toys. Lily stretches Jessica’s tight hole with bigger and bigger butt plugs and then fucks her ass good with a strap-on dildo causing her to cum hard. Then Princess Lily lures her filthy little toy into her own sexy, curvy ass. Jessica licks Lily clean and then fucks her ass with a thick pink dildo and then an even bigger toy and finally stretches Lily’s ass wide open with an industrial speculum. What a fun play day!

Six years ago, Jessica Kay delivered one of the most extreme and moving sessions in Assylum history. Today, we bring it back, with 50% more footage and an entire re-mastering of the scene. This session is level 11! The faint of heart should not proceed. The painal is harsh, the punishment is hard, the degradation is deep. But this session is also a re-imagining of the great Epic of Gilgamesh--a sincere spiritual journey of a pair of modern perverts. Here we have one of the true pinnacles of Assylum with one of the most amazing and beautiful sadomasochists we've ever had here.

Jesse Pony is tied with her legs pulled back, ass wide open. A bejeweled butt-plug is already inside her asshole. Luna Lovely pops it out and makes Jesse taste her own ass-juice off of the plug. After that, she fingers and spits on Jesse’s asshole. Of course, eager Jesse is already gaping. Jesse loves getting her pussy and asshole slapped hard, and has a screaming orgasm while getting her pussy slapped and asshole fucked hard and rough by a long Bad Dragon toy. Jesse then gets obediently on all fours while Luna hammers a dildo into Jesse’s asshole, and Jesse screams louder and louder like the power bottom she is. Finally Luna fists Jesse’s asshole hard and rough while she begs for more, her whole body squirms in intense ecstasy as Luna slaps Jesse’s pussy and makes this submissive slut cum again and again. Then Luna gets her ass fucked with a toy while Jesse spits on her face and slaps Luna’s ass. Luna gets fucked hard and as a body-shaking orgasm. Jesse sensually fists Luna’s experienced asshole and makes her cum hard again. Craving more, Luna gets on her back and takes the slink far up into her guts as she can, while getting her pussy eaten and slapped and rubbed until she has another explosive orgasm.

Jesse Pony has Alrik Angel tied to a chair. She calls him her Slut Puppy, and he calls her Princess. He breathes short breaths inside a tight latex hood and she licks it and spits on him. Jesse makes him hold a vibrator, and she grinds her pussy against it until she cums in Alrik’s hooded face. In the next scene, Alrik’s hands are tied behind his back in a squatted position. Two flanking zippers go down his torso. Jesse smothers his lucky face with her perfect ass. She shocks Alrik with an electronic zapper and then rips the zippers off of his body. Next, Alrik is put in an inverted rope suspension. She sticks fingers in his ass and face-fucks him with her strap-on. She hits him hard with a flogger and smothers him again with her ass, making him lick her asshole until she cums. After that, Alrik is bound on his back with rope. His legs are spread apart and Jesse fucks his ass hard with her strap-on. In the final scene, Jesse wants to get fucked so she puts the hood back on Alrik’s head, spreads her legs, and commands him to fuck her hard. After a lot of hard fucking, Alrik can’t help himself and cums inside her pussy and Jesse makes him clean it up with his mouth. Its hard to believe this is Jesse’s first ever shoot as a Dom.

Jesse has always been curious about bondage, and wanted to have her first experience with Kink.com. We don’t waste any time getting this slut tied up and giving her to Johnny to have his way with. She begins tied in a squatting position with her legs spread and her mouth readily available for Johnny’s cock. Following her initial inspection, Jesse is put in a brutal ankle suspension that folds her in half, and perfect for fucking. This is one of the most grueling suspensions, so fucking her like this was impressive to watch, even if it was brief. Jesse is then tied in a doggy position with her amazing ass in the air. Johnny goes balls deep and fucks her mercilessly as she cums uncontrollably. He adds a vibe to push Jesse over the edge, and then serves up even more cock to this thirsty little slut. Jesse is so overwhelmed, but the day isn’t over yet. She is tied on her back with her legs spread super wide, and Johnny dishes out one final session of fucking until she can no longer take it.

Jane Wilde is at work, bartending. She pours Draven Navarro a shot as he goes on and on about his muscles. He tells her that she’s cute, for a brunette, and that she makes a pretty good drink, even though she’s a woman. He excuses himself to use the bathroom and when he returns, he passes out on the floor. He wakes up naked, bound in rope, trapped inside a small white cage. Now dressed in blue latex, Jane sits on top of the cage, hitting the bars with a wooden cane. He sticks his head through a small hole and Jane feeds him her toes. She frees him from the cage and torments him with her cane, hitting him all over his body. After that, she places him in a white chair and torments his nipples. She sits on his face and uses a vibrator on her pussy. In the final scene, Draven is suspended with chains and cuffs. Jane straps on a hug dildo and fucks his ass deep, making him scream and whine like a little bitch.

Sherman Maus and Kacie Castle are supposed to be sitting silent, in bound punishment, imposed by the fierce and sexy Isis Love, but Sherman can't keep his mouth shut. He mocks Kacie and calls her a brown-noser and a kiss-ass since she's generally an obedient little slave. They bicker back and forth until Isis Love catches them in the act. Startled by her presence, they blame each other for the disturbance. Isis has no choice but to punish both of her subs. She begins with corporal punishment just to warm things up, flogging and whipping them into redemption. Then she clamps these two little slaves together with their tongues and nipples so they learn to get along. After all, "teamwork makes the dream work". Kacie then gets a little imposed pleasure with the vibrator as Sherman is made to watch. Tied up and with his cock in chastity, poor little Sherman can't do anything but helplessly watch Kacie orgasm. Isis then pulls out a huge strap-on for Kacie to suck on. Kacie gets it nice and wet so Isis can pound Sherman's ass with it. Sherman then gets pounded hard by Isis's huge dildo as he eats Kacie's pussy. He gets flogged and pounded and close to orgasm but he is denied. Isis then makes Sherman fuck Kacie's hot wet pussy. This steamy punishment gets hotter and hotter as Isis makes Kacie lick her pussy too, so she doesn't forget who is in charge. Isis then uses the vibrator on herself and squirts all over Kacie, as Kacie gets pounded by Sherman. Now that the team is coming together, Isis lets Sherman bust his load all over Kacie's wet mouth. Now that these little slaves have been taught a lesson in teamwork, they are ready to serve.

Izzy makes her chastity slave crawl into the bedroom. She wants to sit on his face and make him lick her to an orgasm. Princess Izzy loves using the chastity slave’s tongue. Fully nude, she straddles and rides his face. Izzy makes her slave lick her pussy and ass. After she cums on his face he must clean her. She can use his mouth whenever she wants for as many orgasms as she wants while he is kept in chastity and denial.

Hazel is one of the most innocent looking girls we shoot, but don’t be fooled by her looks. Hazel is slutty as hell, and loves to do really dirty things like get tied up and used like the little slut that she is. She has never experience anything like this before, so we pair her up with Johnny Castle, and sit back and watch as he takes her on this new journey. Hazel begins on all fours as Johnny explores her body and begins testing her abilities. It’s not long before he has his cock buried deep inside of her mouth and pussy and she begins to moan with pleasure. next, we have Hazel tied with her legs together and in the air atop a wooden box. Johnny gets right back to the torment and fucking, and Hazel is more turned on now than ever. Orgasm after orgasm pour out of her as Johnny power fucks this slut. The final position has Hazel’s arms box tied, and the rest of her body is free for Johnny to manipulate however he sees fit. He rotates between her mouth and pussy for fucking as well as incorporating more corporal punishment along the way.

Gwen Vicious is late to meet and interview with Febby Twigs about the possibility of joining her and Avi Love for a hot anal three-way. Febby calls her stupid, grabs Gwen by the hair, and brings her to meet Avi. In her short purple latex dress, Gwen crawls on her hands and knees to Avi who sits at her big red leather throne. Avi tells her to stand up and strip naked. Febby and Avi agree that although pathetic, she'll do. They tell her to get on her knees and spread her ass. She grabs both of her big round ass cheeks and spreads them wide. Avi grabs a ribbed glass toy and slides it into Gwen's tight little asshole and fucks her deep with it. They switch to a bigger glass butt-plug and slide it in and out of Gwen's asshole, stretching it even further. They have Gwen get on her back and spread her legs and they see if she can handle one more toy. They get a big long purple butt-plug and try to fit the entire thing in her asshole, but her pathetic ass can only take the tip. They feel sorry for her and let her cum with a vibrator but they're far from done using her for their own pleasure. Avi strips from the waist-down and gets up on her throne. Febby shoves Gwen's face into her girlfriend's asshole and makes her lick it. Avi presses a big Hitachi vibrator against her clit and cums hard with Gwen's face buried in her asshole. After that, Febby makes Gwen get underneath Avi and lick her pussy while Febby fucks Avi's ass with a big pink dildo. After Avi's ass gets warmed up with the pink dildo, Febby straps on her biggest cock and shoves it in her girlfriends ass, fucking her deep and hard. Next, Avi gets on her back and has Febby shove the Slink as far as she can up her ass, and cums hard while filled up with almost two feet of toy. When its Febby's turn to take a big toy up her ass, she gets face-down, ass-up and gets fucked deep and fast with a monster of a cock. Stretched out by the large dildo, Febby commands Gwen to slide her entire fist up her ass. Gwen gets it in Febby's ass with ease and fist-fucks her ass until she cums hard.