Tag Archives: Bill Bailey

Burning Angel Entertainment: Joanna Angel Dominantly Submissive

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Joanna Angel Dominantly Submissive
Fall down my twisted rabbit hole of sexual fantasies with me. Whether I am submitting to my master or dominating my slave, one thing is for certain… I get what I want. This is a journey of whips, gags, leather and latex. Enjoy…
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HARDCORE GANG BANG: Jun 01, 2016 – Tommy Pistol , Mickey Mod , Mark Wood , Xander Corvus , Bill Bailey and Ella Nova

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In true Donald Trump style, not one, not two, but FIVE Donald Trumps fuck America in all her greased up holes, double penetrating her, double anal and deep fisting with gapping. Trump sprays huge loads of his fuck juice all over America leaving her wondering what the fuck just happened!
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HARDCORE GANG BANG: May 18, 2016 – Tommy Pistol , Mr. Pete , Mark Wood , Christie Stevens and Bill Bailey

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HARDCORE GANG BANG: May 18, 2016 - Tommy Pistol , Mr. Pete , Mark Wood , Christie Stevens  and Bill Bailey

In this fantastical fuckfest Christie Stevens asks fertility goddess, Maitresse Madeline, to bless her with the knowledge of true destiny. In exchange, Christie offers up her most valuable possessions: beautiful D-cup tits and a perfect pink pussy! Goddess Madeline acquiesces and bestows 4 hard cocks upon this horny, willing devotee. Watch as Christie worships their cocks with sloppy blowjobs, hard vag fucking, tight bondage, FISTING, DP, ANAL and MORE.
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HARDCORE GANG BANG: May 4, 2016 – Tommy Pistol , Mr. Pete , Mickey Mod , Owen Gray , Bill Bailey and Angel Allwood

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HARDCORE GANG BANG: May 4, 2016 - Tommy Pistol , Mr. Pete , Mickey Mod , Owen Gray , Bill Bailey and Angel Allwood

Angel Allwood is the Bionic Woman!! After a tragic accident Angel is taken by the government, rebuilt and rehabilitated into a super powered killing machine. She has the strength to crush metal with her bare hands but in a strange twist of events she also has the ability to fuck harder & stronger than any other woman alive! On her next mission instead of busting a group of five men in an anti government militia she taunts them to gangbang her and put her bionic abilities to the test! Includes double penetration, pussy fisting, DVP and a cum covered bionic bitch!
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HARDCORE GANG BANG: Apr 27, 2016 – Violet Monroe , Marco Banderas , Mark Wood , Ramon Nomar , Bill Bailey and Gage Sin

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HARDCORE GANG BANG: Apr 27, 2016 - Violet Monroe , Marco Banderas , Mark Wood , Ramon Nomar , Bill Bailey  and Gage Sin

Violet Monroe’s fantasy of being ganged up on, taken down and pounded comes true in this unspeakably high-energy aggro-fuck that never lets up. It’s nonstop fucking and sucking as she’s filled in every hole with relentless and ravenous cock, and finally rained on by showers of hot cum. Be careful what you wish for, Violet…you WILL get it.
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SEX AND SUBMISSION: Apr 22, 2016 – Bill Bailey and Lexi Lowe

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SEX AND SUBMISSION: Apr 22, 2016 - Bill Bailey and Lexi Lowe

When big tit blonde Lexi Lowe is taken hostage by Bill Bailey, she finds herself submitting her anal treasures to the big dick thief. Lexi’s fine ass takes a brutal pounding and her big beautiful tits tantalize and bounce with every thrust as Bill takes full advantage of his helpless anal hostage.
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HARDCORE GANG BANG: Mar 23, 2016 – Mr. Pete , Mark Wood , Xander Corvus , Bill Bailey , Gage Sin and Rachael Madori

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HARDCORE GANG BANG: Mar 23, 2016 - Mr. Pete , Mark Wood , Xander Corvus , Bill Bailey , Gage Sin  and Rachael Madori

Rachel Madori is one badass biker babe. She poors drinks in a biker bar every night for the same guys, and one night she decides to get them all out in the back and demand they satisfy her cock cravings. She bends over her own motorcycle to get fucked in all her holes. Chain bondage, choking, spitting, double penetration, double vag, and double anal make this hot babe happy. She finishes by begging for a very special bukkake!! This girl is AMAZING!!!
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THE TRAINING OF O: Mar 18, 2016 – Bill Bailey and JoJo Kiss

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THE TRAINING OF O: Mar 18, 2016 - Bill Bailey and JoJo Kiss

JoJo Kiss is a brand new, eighteen year old beauty that comes to to learn more about BDSM and sex. JoJo begs to come while nipple clamps pull on her tightly tied all natural tits, and her sadistic slave trainers teachers her the Rules.

When Bill Bailey begins to work her tight little pussy, JoJo struggles to open up enough to let him in but Bill is persistent, and soon enough he is pounding her tight pussy into convulsive, kinky orgasms that JoJo Kiss will not soon forget.
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HARDCORE GANG BANG: Mar 16, 2016 – Tommy Pistol , Steve Holmes , John Strong , Jon Jon , Marica Hase and Bill Bailey

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HARDCORE GANG BANG: Mar 16, 2016 - Tommy Pistol , Steve Holmes , John Strong , Jon Jon , Marica Hase and Bill Bailey

You know what they say, when you give a mouse a cookie… Well, when Miss Marica Hase gives her eager Japanese students a few dirty words to pick up women, all of a sudden she’s fantasizing about shoving all five of their thick cocks into as many of her holes as possible, as much as possible, and in as fucking filthy a way as her adorable face and deliciously supple body can take! And really, there’s no one that does it better than Marica. She takes DOUBLE ANAL, DOUBLE VAG, and DOUBLE PENETRATION, writhing and moaning in unforgivable metal bondage, begging to cum again and again, covered in spit, and trying to shove three cocks in her mouth at once like the hungry little slut that she is. Ultimately, she gets what she deserves, gobbling up all five of their filthy loads with a smile on her face before waking up from the dream in her classroom, ready to teach her next group of students a lesson in how to do the best fucking gangbang you’ve ever seen….
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SEX AND SUBMISSION: Mar 11, 2016 – Chanel Preston and Bill Bailey

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SEX AND SUBMISSION: Mar 11, 2016 - Chanel Preston and Bill Bailey

When beautiful brunette Chanel Preston meets Bill Bailey on a blind date, Bill introduces Chanel to a world of dominance, submission, bondage and rough anal sex.

This update includes: bondage, gags, nipple clamps, ball gags, anal toys, gaping asshole, drooling blowjobs, bound orgasms and sexual humiliatio
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THE UPPER FLOOR: Mar 11, 2016 – Bill Bailey , Abella Danger and Zoe Parker

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THE UPPER FLOOR: Mar 11, 2016 - Bill Bailey , Abella Danger and Zoe Parker

Slutty masochist Abella Danger is a perfect slave, but can she graduate to tutoring another piece of hot slave fuck meat? The Butler finds her misusing the new girl as she cleans the lounge. Zoe has not even been taught the rules, let alone given a task aside from lapping at Abella’s asshole. Cruel metal nipple clamps and weight are applied to Abella to teach her a lesson in humility as Bill ties up the new slave trainee and shows Abella how to properly use a new girl. filling her hot mouth with cock, fucking her tight pussy, and stimulating her clit as she has the rules pounded into her, and electro zapper on hand if she can’t recite them. Abella is given a punishment orgasm, walking backwards to pull the tight metal clamps off her swollen nipples.

Second scene, Zoe is on her own as Abella has her head locked under a table and her ass tied open wide. Zoe must stand and take a deep pounding in her pink cunt while learning to plead for her and Abella’s pleasure with composure. Gracefully begging into Abella’s asshole, Zoes earns them both reward orgasms from the vibrators latched to both their clits with tight rope bondage.

Abella, having done a wonderful job with Zoe, is fed torment and rough anal fucking in bondage for the rest of her service. The look on fresh girl Zoe’s face is priceless and she soothes Abella’s cunt with her tongue and rips clamps on Abella’s insane breast zipper. Both girls get rough reverse cowgirl fucks and a hot cum on their lovely faces for a job well done.
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THE UPPER FLOOR: Feb 26, 2016 – Aiden Starr , Bill Bailey , Nikki Knightly and Charlotte Cross

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THE UPPER FLOOR: Feb 26, 2016 - Aiden Starr , Bill Bailey , Nikki Knightly and Charlotte Cross

Two pieces of fine slave flesh are up for consideration. On hand we have busty blond powerhouse dominatrix Aiden Star to run these sluts through the ringer and decide who should join the sex slave stock for good. The swinger party is packed with gorgeous women playing with their dominants and submissives. Meanwhile good girl Charlotte Cross and nymphomaniac Nikki Knightly are tied tightly to a post and made to choke on cock and lick ass while interrogated. Once Aiden has the answers she is looking for both slaves are made to cum for the crowd’s amusement.

Second trial of the evening finds the ladies tied with their legs back and hands latched down to a box in tight rope bondage. Unable to get away, they are punished and fucked in turn with hard cocks, vibrators, electrical shockers, and a pile of canes. Both ladies beg for punishment and pleasure until the whole scene devolves into a fuck pile with Aiden cumming on top.

So far both slave wannabes are neck in neck, so The Upper Floor classic is deployed: The Tray Test. Both slaves are handed their object of desire, a slave collar, and told to the hold the trays until one of them must drop it from physical exhaustion. To make the game more fun vibrators are attached to both their dripping wet pussies, and they are made to cum uncontrollably for the laughing audience. Both ladies quiver in agony, pushing their athletic abilities and self control until one drops.

Once the new slave girl had won her collar she is rewarded with a rough fucking with a hard cock while the loser gets strap on plowed and has Aiden sit on her loser face. The night ends with fisting, squirting, and lot of hot cum swapped. Well done ladies.
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SEX AND SUBMISSION: Feb 26, 2016 – Bill Bailey and Abella Danger

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SEX AND SUBMISSION: Feb 26, 2016 - Bill Bailey and Abella Danger

Abella Danger loves hardcore BDSM and rough anal sex, and is more than happy to give it up to Bill Bailey in the dungeons of Kink.com. Abella shows off her beautiful tits and ass in a skin tight latex hobble skirt and leather bondage. She begs for the whip, gags and nipple clamps, and eagerly chokes down Bill’s hefty cock. When her pussy is clamped shut and her asshole fucked hard in tight bondage, Abella’s orgasms send her into deep anal submission.
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HARDCORE GANG BANG: Feb 17, 2016 – Tommy Pistol,John Strong,Mark Wood,Bill Bailey and Kira Noir

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HARDCORE GANG BANG: Feb 17, 2016 - Tommy Pistol,John Strong,Mark Wood,Bill Bailey and Kira Noir

Kira is sick of the guys at the record store ignoring her. She finds an old book of magic spells, and casts a spell on all of them. Her spell works so well, they are compelled to tie her up and fuck her until she’s satisfied. It takes a lot to satisfy Kira Noir. She sucks cock like she is starving for it, and her holes demand to be filled. Severe bondage, double penetration, anal gaping, and suffering orgasms, cum eating and a cream pie are what this beautiful witch demands.
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HARDCORE GANG BANG: Feb 10, 2016 – Mr. Pete , John Strong , Karlo Karrera , Owen Gray , Bill Bailey and Mia Li

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HARDCORE GANG BANG: Feb 10, 2016 - Mr. Pete , John Strong , Karlo Karrera , Owen Gray , Bill Bailey  and Mia Li

Babysitter Mia Li is having a party to watch the big football game and neglecting her babysitting duties. Five dads decide to show up at her house and demand she pay them some attention. Mia gives them everything they want and more in this special football fantasy update. Blow bang, belt bondage, anal, double penetration, wet hot orgasms, cum eating, a perfect ass and big tits!!!
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HARDCORE GANG BANG: Jan 13, 2016 – John Strong , Chanel Preston , Mark Wood , Jon Jon , Bill Bailey and Jay Smooth

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HARDCORE GANG BANG: Jan 13, 2016 - John Strong , Chanel Preston , Mark Wood , Jon Jon , Bill Bailey  and Jay Smooth

Welcome back the devastating beauty, Chanel Preston to Hardcore Gangbang! In this film noir inspired XXX flick, Chanel plays the powerful black widow who destroys everything in her path to get what she wants and even challenges the private investigator and cops who get in her way. She’s captured, hooded and taken down and filled with huge hard cock! Rough man handling gangbang sex, blow banging, double penetration, wet pussy cream pie and the most perfectly beautiful face drenched in cum! Not to be missed!
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HARDCORE GANG BANG: Aug 5, 2015 – Dylan Ryan , Tommy Pistol , Barry Scott , Bill Bailey , Michael Vegas and Gage Sin

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HARDCORE GANG BANG: Aug 5, 2015 - Dylan Ryan , Tommy Pistol , Barry Scott , Bill Bailey , Michael Vegas  and Gage Sin

Dylan Ryan is frightened of her deepest, darkest fantasies. She dreams of being dominated, fucked hard, stuffed full and drenched in strangers cum. When Dylan decides to seek a way to make her fantasies come to life, she arrives on the doorstep of an underground business who is making women’s most twisted sexual fantasies come to life! Dylan is man handled by anonymous strangers, takes 5 cocks down her hungry throat, has her pussy filled with two giant hard dicks, is DP’d and stuffed airtight. She also takes a fist deep in her cunt and can’t stop squirting all over. Watch as this depraved fantasy becomes a reality for Dylan Ryan!
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THE UPPER FLOOR: May 1, 2015 – Bill Bailey , Karmen Karma and Melissa May

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THE UPPER FLOOR: May 1, 2015 - Bill Bailey , Karmen Karma  and Melissa May

Butler Bill Bailey steps into the Master bedroom to enjoy a drink and finds a pair of hapless slaves locked in punishment bondage. These brand new girls managed to anger Governess Aiden Starr and have been stripped of their uniforms and left naked with a note requesting Bill make them earn their clothes back. Bill is not the sort of man to turn down a good time and makes good use of 19 year old Melissa and slutty cock sucker Karmen. Both girls drool and beg as he runs his gloved hands over their vulnerable flesh and shoves his cock deep in their gagged mouths. Karmen screams as bill violently fucks her in the body stocks and whips her tight body with a flogger.

Karmen is set in a predicament, holding both girls uniforms on silver trays that she must keep balanced in the air. If she drops them, innocent little Melissa will be zapped mercilessly while fucking hard dick. It’s an impossible challenge, even for a well toned slave. Karmen has tight nipple clamps and a hitachi tied tightly to her pussy creating helpless orgasms in waves. Melissa begs her to keep her arms up as she exhausts herself bouncing on Bill’s dick, but eventually gravity wins and Karmen is apologizing to Melissa’s pussy with her tongue as both slaves are zapped repeatedly.

Bill has been thoroughly amused with the whole affair, and gives the slaves back their newbie uniforms. Then he ties them both on a table with their sweet asses in the air for a proper reaming. These newbies learn how to properly serve the House with many orgasms and faces covered in cum.
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THE UPPER FLOOR: Mar 27, 2015 – Lorelei Lee and Adley Rose

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THE UPPER FLOOR: Mar 27, 2015 - Lorelei Lee and Adley Rose

An Upper Floor Feature Presentation

When the Upper Floor Governess is tasked with breaking in a brand new slave girl, the Butler interrupts and turns things around for the bossy bitch Governess.

Lorelei Lee stars as the Governess that get’s stripped, tied up and fucked hard. Adley Rose co-stars as the newbie slave girl in her very first time fucked on camera.

Bossy Bitch Governess, the Slave Girl and the Butler
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THE UPPER FLOOR: Dec 12, 2014 – Sovereign Syre,Dahlia Sky and Bill Bailey

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Sovereign Syre and Dahlia Sky compete to see who can get the most dick, and the looser must get the winner off however she wants. Both girls are put into a double pile driver and fucked silly for the amusement of the House.
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THE UPPER FLOOR: Dec 5, 2014 – Aiden Starr , Simone Sonay and Ramon Nomar

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Anal Orgy Costume Party Part 2

Penny Pax is All Anal All the Time as the House’s resident Anal Slave. Yhivi, the freshest applicant off the block, services the scene with her beautiful face and pussy as Pax takes Roman Nomar’s cock in her ass for the amusement of the House Guests. Pax must make Yhivi scream when she is getting fucked or else Pax is punished with the zapper to the clit. always delivers the hottest new girls on the scene to be trained and used like fine submissive merchandise on.
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THE UPPER FLOOR: Nov 14, 2014 – Aiden Starr,Simone Sonay and Ramon Nomar

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Halloween Orgy Part One

Slave driver of Sex, Aiden Starr, hosts the Halloween Orgy! She works Simone Sonay and Christie Stevens hard and fast, and makes this one of the best anal parties of the year!
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THE UPPER FLOOR: Oct 3, 2014 – Darling , John Strong , and Krissy Lynn

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Folsom Eve Review, Part I

It;s is Folsom Eve in the city, and The Upper Floor of the Castle fills with beautiful porn stars and slave girls for tonight’s show. The slaves are all lined up for review, and the meaning of sexual teamwork is drilled into them before they split into teams to get that dick!

Super sexy Madeline Monroe licks asshole and sucks cock while Crissy Lynn is double penetrated. Both beauties are fucked hard and used well, and they earn a huge load of hot come all over their pretty faces while the crowd cheers and jeers.
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PUBLIC DISGRACE: Sep 26, 2014 – Ariel X , Bill Bailey and Mona Wales

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Mona Wales humiliated at Folsom Street fair. Attention whore degraded!

Ass fucked in a filthy bathroom, paraded naked through a crowded fair, made to perform a degrading pissing act and trapped in a glass box for all to humiliate. Pissing, face fucking, anal, electricity, bondage, extreme emotional humiliation.
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Jun 20, 2014 – Ariel X , Bill Bailey , and Alina Li

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Innocent Asian slut humiliated and fucked in convenient store

Sweet little slut Alina Li gets dragged through a convenient store full of unsuspecting shoppers. They join in the spanking and fingering her tight hole after they watch her swallow Bill Bailey’s huge cock. He takes care of her tight fuck hole with a good pounding in the aisle. She likes it too much and gets punished for cumming without permission. The crowd yells for shoe licking, verbal humiliation, rope bondage and fucking with items off the shelves! Clean up in aisle 5!

Format: MP4
Duration: 68 Minutes
Size: 751 Mb
Resolution: 960×540
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Jun 6, 2014 – Ava Devine and Bill Bailey

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The Mad Scientist and his Cheating Wife: Unique Bondage Device and Anal Fisting

Format: WMV
Duration: 83 Minutes
Size: 913 Mb
Resolution: 1280×720

Bill’s suspicions of his cheating wife Ava turn out to be true. For punishment, he takes her back to his laboratory and straps Ava down to a futuristic sex chair where she receives extreme sexual domination. This erotic role-play also includes anal fisting, rough sex, humiliation, bondage devices and face fucking!
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May 30, 2014 – Aiden Starr , Christie Stevens , and Bill Bailey

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Slap Fighting Anal Fucking Foursome

Hostess Aiden Starr deftly handles house slaves Clair Robbing and Christie Stevens as Bill Bailey thoroughly pounds their pussies and asses with hard cock. This is an awesome update of nasty foursome sex on the Upper Floor, the web’s best live action sex site!

Format: WMV
Duration: 62 Minutes
Size: 678 Mb
Resolution: 1280×720
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Sep 27, 2013 – Juliette March,Lyla Storm and Bill Bailey

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Format: MP4
Duration: 78 Minutes
Size: 570 Mb
Resolution: 1280×720

Two Slaves Fight for Cock

When two slaves are pitted against each other they fight for the right to suck and fuck the hardest cock in the House.

Two slutty slaves fight for the right to serve horny cock on the Upper Floor.

Slave Lyla’s Anal Return, and the Order of Authority

Lyla Storm is an alumni slave trained by Stefanos. Juliette March is also an alumni trained by Mogul. Each thinks they should be the Boss.

The Order of Authority establishes who is the Alpha slave, and who is the bitch. We know of no better way to determine this than by letting the sluts fight it out. With one hand fastened to her opponents, and the other with double ended dildos attached, the first one to get fucked is the bitch. Let the games begin.

Once that is settled, the party moves to the Lounge where the bitch slave fucks the Alpha’s pussy with a dido gag while getting her own pussy reamed by Mr. Bailey’s huge dick. Orgasms ensue and before long the guests are groping and fucking each other silly in a beautiful, hedonistic orgy of lust.

The boy / girl / girl action heats up when both slaves take it in the ass like the accomplished, trained sluts that they are. They lick and suck and fuck all afternoon in all sorts of bizarre positions until they finally drain that thick cock of all the come it has and feed it to each other.
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