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.

Struggling college student Gia Derza needs some extra money, so she signs up for random medical testing for a little payout. Gia finds herself up against latex nurse Aiden Starr, who runs a creepy dark medical facility. Aiden puts Gia through a battery of tests. She starts by fitting Gia with a gag, in order to do a proper inspection. She then tests Gia's senses with a Wartenberg wheel. She runs it from her sexy nipples down to her clit. Aiden then spreads Gia's hot wet pussy with a speculum, leaving it wide open for inspection. This inspection starts with rubbing her clit then fingering her hole. For further testing she adds more stimulus with a vibrator and pinwheel. She then tests Gia's pain tolerance with clothespins on her nipples and pussy. Aiden administers another dose of pleasure and observes a huge gush as Gia's massive orgasm explodes everywhere, leaving a huge wet mess. Aiden then flogs her pussy as she moves on to the second phase of trials. Gia is suspended upside down in the perfect position for Aiden to test her pleasure levels under stress. She vibrates Gia's pussy and makes her cum upside down. After a few orgasms she crops her chest for a little pain after pleasure. Aiden then makes Gia lick her ass until she has a big orgasm. For the final stages of testing, Gia is tied in pile driver where Aiden pounds her ass with her big strap on. Gia's ass is gaping so wide, Aiden goes in with her fist and does a full inspection. Then Gia is put in a doggy position where Aiden pounds her ass even harder until she orgasms again. After deep testing of Gia's holes, Aiden sends her used up test subject packing. On to the next!

Penny Pax has found herself in a precarious situation. She's in sexy lingerie, tied to a wooden column, unable to escape. She is the epitome of a damsel in distress, and with those big blues eyes, she definitely sells the part. The Pope enters and begins to inspect her body, slowly rubbing his hand across her exposed flesh, making sure to caress her big tits and sweet, slutty pussy. He slowly rips her clothes away, then shoves her panties in her mouth. The pain first comes by way of the flogger. After some impact play, her pussy is devastated with non stop orgasms. The nest scene begins and Penny is flying in a side suspension with one leg high in the air. The Pope enters with his crop and goes to town on her pussy and tits, before moving to her sensitive feet. This slut is so turned on by what is happening that her mouth opens as soon as she sees the cock. The Pope fucks Penny's mouth until the dildo is soaked with her spit, and then he moves to her pussy. The orgasms pour out of her and once she has enough of the cock, he finger fucks her into more orgasms. In the final scene Penny is on a table and sprawled out like a meal at dinner time. She is completely helpless and unable to stop what is about to happen to her. Penny is subjected to more flogging before The Pope initiates the most powerful onslaught of imposed orgasms she has ever experienced. She thrashes around trying to escape, but to no avail, as the orgasms keep coming, again, and again, and again.

The demoness Charlotte Sartre just wants two things today. To inflict pain and take balls. She wants to rip those testicles right off and put them on display on shelf. Maybe she'll wear them as earrings, anything is possible. Dressed in tight black, this slender goddess of the dungeon has some meat all tied up. Sebastian Keys, the ultimate pain slut, has no idea what he is getting his manhood into today. Tied up in fully restrictive rope bondage and gagged with a ball gag, his mistress asks a simple question, "Do you value your balls". Unable to answer through the gag and screams, Charlotte can only assume. With a staple gun she finished strapping Sebastians low hangers to the block. His cock tied up tight in rope, each testicle straining with tension pulling them down. Charlotte must first inflict the pain, she has to know if these are the right balls for her. She doesn't just cut off anyone's balls, ...well actually. She brings out the riding corp and begins to torment Sebastian, turning his testicles red. She punches his chest and slaps his face. She spits on him and humiliates this flaccid waste. Oh but she needs to test those testes more. After chocking him, she puts Sebastians balls in a vice. With each turn of the knob, Sebastian screams louder. His face is covered in clothespins as she torments his tongue with pain. Ok, maybe this pain slut deserves something, with a big black strap on cock she fucks Sebastians ass. Unable to scream clearly through the clothespin, all you can hear is pathetic whimpers as this goddess takes his ass. That's enough, this isn't about him. He needs to worship her pussy as she sits on him and smothers his face. She squeezes his balls to their breaking point while he eats her pussy. Her dripping wet lips drown his mouth. There is more for him to do. She offers her feet to be worshipped as he sucks on her toes and licks her perfect arches. His cock is now fully caged in chastity and this excuse for a man is equipped with a strap on cock, something that has the chance to please his mistress. Sebastian obeys and fucks his mistress demon with the strap on dildo. With the intense vibrations of the Hitachi she cums over and over again, taking what she needs from him. He maybe, just maybe might have done well today, but she is still going to punish his balls.

Ashley Lane is a gorgeous masochistic rope slut that has been gracing The Upper Floor with her hot body and intense play scenes for years. After repeatedly petitioning The House she has been allowed to suffer, squirt, and serve on a trial basis. Her senior submissive for the night is a selfish sexual slut, Lauren Phillips. Lauren is less interested in helping Ashley learn the rules than she is in using her giant tits and ruby red dick-sucking lips to get back on the bottom of the power hierarchy where she likes it. The first chance she gets, Lauren is groveling and licking Governess Aiden Starr's boot until she is allowed to slobber and choke on a guest's massive cock. This leaves Ashley dangling in a terribly painful spread eagle shibari suspension with her sensitive clit trapped under a hitachi and her milky skin pinned with multiple zipper lines. Aiden Starr is eager to question Ashley on how she could have possibly come to The Upper Floor for some many years and she still not know the house rules. Ashley doesn't have a good answer so Aiden and Stefanos decide she should spend her time screaming instead and set about tormenting her feet, pressing her into painful orgasms, and ripping clamps from her tender flesh. Soon Ashley is being fucked with her eyes rolling back in her head as Lauren Phillips laps at her clit and toes. Promising to get the house rules and suffer well, Ashley is made to squirt and scream and cum like a good little bitch as the crowd cheers her on. The guests are very turned on and set about spanking their submissives, and many beautiful swinger couples start to swap partners. The room is alight with moans and threesome blowjobs when Barbary Rose and Stefanos get into a long overdue play session that finds Barbary in a quick and dirty rope bondage position leaving her glorious curves vulnerable to hot wax, zappers, and cruel vibrators. Meanwhile Lauren has been tied in an inverted pile driver and is having her ass fucked deep and hard while Ashley is sweating and begging for another house rule while trying to hold chains out as so many submissives have before her. Will Ashley manage to dirty talk, learn all the house rules, cum on command, and act as a perfect oral accessory to Lauren's anal reward fuck? Watch to find out in this first installment of Ashley Lane's Initiation.