Latest updates featuring Vanessa Sky

Aiden Starr - Sexy Anal Submissive's Serve BDSM Swinger's Ball

Aiden Starr - Upper Floor

4th May - In part two of our raucous BDSM sex bonanza, Karlee Grey is taught to serve up her orgasms in discipline her slutty anal trainee Vanessa Sky with a firm spanking hand. Governess takes special pleasure in making Karlee squirm and beg for her orgasms, squirting uncontrollably all over her huge tits while the crowd gets horny and cheers her on. Meanwhile Ramon takes Vanessa on a fuck ride through the whole party, humiliating and fucking her deep in her ass just as she likes it. He rides her like a little slut pony all over the room, railing her on every couch and making her beg like a whore for every orgasms speared on his hard dick. The guests get overwhelmed with all the sex in the air, clapping for the house slaves and making mischief of their own. Gorgeous women are spanked by their Master's, fisted, made to suck dick on their knees, and cum in screaming sweaty piles on the sybian. One house guests is covered in tight bondage and hot wax while her latex clad Mistress keeps her under tight control, requesting a thank you with every scream. Aiden Starr joins in the fun, having Karlee lick her cunt until she sums on that little bitches face with great enjoyment. Ramon still hasn't had enough, and after having Vanessa lick his cock clean after her wild anal ride, her brings her to heel at the front the room for one final test. Meanwhile one of our guests of honor is tied in an incredible split position by her Master and has her cunt whipped red with a cat-o-nine tails and still begs her have her whole pussy filled and cums with permission on her Master's hand. All eyes turn to the front of the room where Vanessa is hung like a piece of meat in full suspension, made to recite the rules as she is fucked in the ass. Karlee squats like a good girl over a hitachi and suffers for her submissive trainee's fun with tight clover clamps on her labia and nipples, pulled off slowly and painfully by Aiden Starr until she is ready to get on her knees and get her pussy fisted, soaking the carpet with squirt and begging for Ramon's hot cum all over her face. Looks like the house is finally back in order. ...Read More
Vienna Black - Sister, Sister: Secret Anal Whore Shows Her Little Step-Sis The Ropes

Vienna Black - Families Tied

13th April - When cute little rebellious teen Vienna returns home for a surprise visit with her new creep boyfriend Smallhands, she is aiming to torment her parents, but instead finds they are gone and her older sister Vanessa is home for the week end. Vanessa is a gorgeous uptight coed and is having none of Vienna's shenanigans. Dismissing Vienna as a slut after paying Smallhands out for picking up some Hot Topic mall teen, she throws her headphone back on and goes back to working out. Determined to get under Vanessa's skin, Vienna drags Smallhands up to her old bedroom and invites him to teach her all about the BDSM sex he has been trying to convince her to try. The resulting scene is a very real first timer experience of begging for cock, intense face fucking, flogging, spanking, paddling, and submissive fucking at the hands of a sadistic top. Vienna is dragged out on to her balcony, bent over the railing, and made to have a screaming orgasm for all the world to see, with Vanessa is in the front row seats.Later Smallhands gets lost in the mansion and wanders into Vanessa' room looking for the bathroom. He starts backing out apologetically, but Vanessa makes her move, telling him if he really wants a good lay he should try someone with some more experience. Smallhands doesn't like being told what to do, and Vanessa is one hot stuck up bitch, how could he refuse? Throwing her on the bed, he starts in immediately spanking her hard with verbal humiliation, making he admit she is a greedy cum slut while paddling her round ass red, throwing her on the floor and cropping her sensitive pussy. He cuts up her nice yoga gear and throws tight metal clamps on her sensitive nipples. Face fucking her and making her cum repeatedly on the floor like a dog, she is thoroughly humbled. When she is finally in tatters and ready to submit fully, he puts her in tight belt bondage, clamps her pussy lips, and fucks her to pieces, switching freely between her ass and cunt as she screams into her ball gag and begs for more. She is rewarded with a relentless pounding and electrical shocks from a zapper. All the noise obviously draws Vienna's attention. Upset, she comes in screaming, but Smallhands reminds her that she did promise herself to him and if she really wants to done with the game so soon? Vienna has always thought her big sister was hot, so now with her all tied up and speared on her boyfriends cock, she has a chance to get in on the fun. Vienna eagerly watches and learns how to submit from Vanessa, cleaning her boyfriends cock off every time it comes out of Vanessa's ass, and waiting to cum in unison with her slut sis.The rest of the evening is spent with the girl's giving each other revenge orgasms on the sybian, clamped and tied up tight, they are both throat fucked and made to beg. Both sister's eagerly lick each other's pussy's while Smallhands takes his fill of their nubile hot bodies and covers them with the biggest load of cum we have seen in a while. ...Read More
Vanessa Sky - Honey Trap

Vanessa Sky - Sex and Submission

23rd February - Vanessa Sky is a corporate spy dispatched to seduce a rival executive and steal corporate secrets. But when Derrick outmaneuvers his freshman opponent, Vanessa ends up the victim of Derrick's sadistic sexual interrogation. He ties her up to the bed flat on her back with legs spread and the Hitachi vibrating on her sensitive pussy. He punishes her with the flogger demanding to know who sent her on this mission but she claims to know nothing. This only fuels the fire in Derrick so he flogs her tits harder and with his dick in her mouth brings her to the edge of cumming but doesn't let her, not yet. One leg up one leg down bent over the edge of the bed Derrick spanks Vanessa's tender ass until it is ruby red and fucks her pussy good until she is moaning and drooling from the ball gag in her mouth. Derrick is just getting warmed up cuz this bitch needs to be taught a lesson. In doggie with a mouth gag Derrick pounds Vanessa pussy and ass until she is screaming and loving it. And finally Derrick flips her over for the grand fucking finale—with tight nipple clamps Vanessa sucks Derricks cock and gets it all wet and ready for her slutty holes and then he fucks her pussy and ass until she is begging to come again and again and again. Beware of the sweet, sticky, delicious Honey Trap! ...Read More
The Upper Floor @ Kink.com

Aiden Starr - Anal Submissive Sluts Ravaged and Squirting at Holiday Winter Orgy

Aiden Starr - Upper Floor

9th February - The night is alive with holiday cheer as hot swinger babes line up to suck dominant dick and get their beatings in this wild yule tide BDSM orgy. Meanwhile, Stefanos has proclaimed that The House will return to the basics: protocol, rules, hierarchy. But busty slave slut Karlee Grey already has the cock deep down her throat and is bouncing her tits like she doesn't remember a single rule. It will be up to newbie Vanessa Sky to get her rules through painful zipper the guests can rip off of her in exchange for hints. meanwhile Karlee is getting dicked down and screaming for permission to cum, which she is roundly denied by a cruel crowd. Beaten with her fucking Karlee howls while Vanessa tried to absorb her training with tight rope digging into her flesh and a hitachi fixed against her hungry cunt. When she is finally able to recite the rules, Vanessa is thrown onto the floor and get her anal reward while Karlee is flogged and fucked and further denied her orgasms. Meanwhile, the crowd has melted into a total BDSM orgy with spankings, rope bondage, lines of blowjobs, and our very special guests of the night playing with an electro box that denies its beautiful inhabitant any vision through its two way mirrored walls. All she can hear is the vibrator on her pussy and the violet wand closing in on her flesh. When the hatch is finally opened for her to breath, her mouth is stuffed with cock. Earning her way out of the box does not offer much relief, and she is immediately tormented with a terrifying taser and fucked with the largest candy cane anyone has ever scene. Covered in glitter like a little ornament, her master uses her like a fuck doll while she begs for cum. Vanessa learns that pain and pleasure roll downhill when she is made to hold buckets of her sister submissive squirt, her buckets getting heavier with each orgasm in tight rope suspension. the corwd is really worked up, single tailing and fucking each other, while Vanessa struggles to prove herself and stay in an athletic squat, holding her buckets proudly, and cumming like a proper whore, waiting her turn with the dick so that she may beg for each anal orgasm from the crowd. Happy Holidays! ...Read More