Petulance Training: Juliette March

The adorably bratty Juliette March is the Queen of all Pain Sluts and is super excited to be back for her fifth brutal round on The Training of O. James Mogul knows just how rough Juliette March likes...

Captive Slut

Pretty Penny Pax is all tied up with nowhere to go. Somewhere out there in a desolate, dark dungeon poor Penny is being held captive by John Strong. He is convinced she has stolen something from him ...

VIP anal with Lea Lexis and Moka Mora

Moka Mora is a bottle service whore who will do anything to hang out with the elite crowd at a pool party. Lea Lexis is a classy cabana babe who knows how to get what she wants. When Moka comes over ...

Tough Electroslut Dylan Ryan Returns!

Tough electroslut Dylan Ryan is in a predicament inside Chanel Preston's lesbian electro-dungeon! If Dylan puts her foot down, the plug inside her pussy will shock her. Dylan struggles to maintain he...

One Bad-Ass Bitch – Mona Wales

Monas back and it has been far too long. Very few models can take it just as hard as they can give it and Mona sets the standard. Her tight pale skin shines, her body squirms, and lips pout as The Po...

Off The Record: Anal Media Whore Gets Her Story

Lauren Phillips creeps into the Upper Floor bouncing her gorgeous tits, just brimming with questions for The Upper Floor staff about the move from The Armory. The only problem is that she scored the ...

Pay to Play

Sexy Casey Calvert is living the good life in her big fancy mansion. She spends her days lounging topless by the pool drinking chardonnay and napping in the sun until one day she gets a call from an ...

Fear Training: Stella Cox

James Mogul and Bill Bailey double-down on training the beautiful pain slut Stella Cox to not be afraid and to keep bouncing those big natural titties. Bill Bailey sends his fat cock balls deep into ...

Rogue FBI

Sexy FBI agent Veruca James is caught up in some dirty business with the Russian mafia. When she tries to drug her partner Tommy Pistol things do not go as planned and Tommy goes capital R Rogue on h...

Anal Queen Contest

This is based on Actual Events! Luna Panda was a participant in a Miss big booty anal queen contest not to long ago. This is a reenactment of what she endured to win her crown. The two contestants, L...

Cherry Torn Trains New Lesbian Electro-Slave

Pain slut Mercy West is wet with anticipation before Mistress Cherry Torn even gets started. Mercy is bound spread eagle with electrified copper pipes attached to her legs. Mercy gets flogged, zapped...

Fresh Meat – Sadie Santana

Sadie is new to us, but not new to bondage. She is very familiar with the ways of domination and submission. Today she will be schooled in pain and torment. Her entire body is The Pope's target and h...

Duties of a Submissive Anal Wife

Dahlia Sky is a fucking dream wife: submissive, gorgeous, and a voracious anal slut. Plucked fresh from the sex slave stock of The Upper Floor, she finds herself back again a year later with her Domi...

Nikki Thorn Rammed in Public

It's Nikki Thorn's turn to be publicly embarrassed, walking through the streets with her ass on display lead by Tina Kay and Ram to a nearby bar where the two meet Steve Holmes. Nikki Thorn begs for ...

Anal Psycho 3

In Anal Psycho part 2 after fucking thug Tommy Pistol, Mona Wales and Penny Pax chain him to the bed and take off with a suitcase full of lottery money. Now Tommy has tracked Mona down at the Hotel M...

Casey and Dahlia Suffer Together in Brutal Bondage

Casey and Dahlia are both known for being tough girls who really love bondage and torment. For the first time ever, we have them both at the same time. The predicament bondage devastates them in the ...

Domestic Training: Arabelle Raphael

What is to be done when an ungrateful wife steals money and lacks the respect that the man of the house deserves? Mr. Pete knows exactly how to fix this problem and calls upon the services of James t...

Immigration Authority

Voluptuous British Bombshell Stella Cox loves her naughty sex toy business but when she gets a visit from Federal Agent Mickey Mod asking for her legal paperwork she gets a dirty lesson in Immigratio...

Buttfucking is the best Birth Control

Rosie and Audrey Holiday are step sisters who need to see a doctor for birth control. The Doctor order the two slutty step sisters to do her bidding so that she doesn't have to tell their parents abo...

New Electroslut Bombshell Gets Shocked!

New electroslut Missy Martinez is bound in Goddess Daisy Ducati's lesbian electro-dungeon. Wired with e-stim pads, Missy gets shocked by the violet wand all over her beautiful body and stocking clad ...

A Rose By Any Other Name

After a long time of not seeing her on our sites, the incredible Kristina-Fuckng-Rose is back to suffer. She is locked into the devices and the torment begins. Watching her suffer, and the extreme le...

Squirting Step-Daughter Punish Fucked

Angel Allwood is a hot busty MILF wth it all: A mansion and a younger boyfriend on the side. It all comes crashing down when her cute little piece of ass step-daughter comes to visit. Angel's Dominan...

Blind Date

Luscious Lily LaBeau is tied up spread eagle against the wall in a dark, cold dungeon. She doesn't know how she got there or who tied her up. With clothespins on her hard nipples and a vibrator on he...

Cock Thirsty in Hungary

Tina Kay buys two Hungarian whores, Lia and Laurita, for Steve Holmes do do with what he pleases. Steve and Tina lead them both by leash and collar through a sketchy neighborhood in the hot weather t...

Holiday BDSM Slut Orgy turns Fangirl to Sex Slave

The decks are stacked for sexual deviance in this Holiday Upper Floor affair. Aiden Star has a greedy TUF fangirl Kimber Woods in her clutches, and that fit little bitch is going to earn every inch o...

Polite Obedient Slut Takes It

Mandy Muse experiences The Training of O for her first time but is no stranger to Kink. James Mogul stretches the limits of Mandy's ass, pussy, and mind using single-tail whips, floggers, zappers, an...

My Slutty Cousin

When beautiful, chaste bride to be Lyra Law leaves the house to pick up wedding invitations her visiting step cousin Chloe Cherry can't keep her slutty ass off of her fiance's Steve Holmes huge, hard...

65 Minutes of Hell!!

Roxanne is known for being a little brat, especially to The Pope. Today she will be put to the ultimate test with a non-stop, no cuts, and no holds barred shoots. She is put in a spread eagle on the ...

Scared Tough Electroslut Comes Hard on Electricity!

Scared Electroslut Juliette March is bound, gagged, electrified, and at the mercy of the gorgeous Bella Rossi. Juliette submits to a thorough flogging while her abs are shocked with e-stim pads and h...

Used and Left Behind

Amarna begins with her head in a two way mirrored deprivation box. Her arms and legs are belted in leather to guarantee her helplessness. The Pope floats in and out of the darkness with flogging and ...

The Nymphomaniac’s Anal Apprentice

The insatiable wonder that is our sex slave Veronica Avluv takes on her greatest apprentice yet: The gorgeous Amara Romani. This shoot is all chemistry as Ramon Nomar takes hold of these two hot anal...