Maddy is a dirty slut, and she loves getting tied up and tormented, but we haven't had her on the pages of Kink.com for many years. That changes today when she submits to The Pope. How could anyone say no to that? We now present to you Maddy O'Reilly, bound and beaten and made to cum. Maddy begins her journey on her knees like every good whore should, in inescapable bondage. The Pope enters and we get right into the good stuff. After some flogging and cropping, we find out how playful Maddy can be. She clearly loves this more than any of us may have thought, so The Pope cranks up the intensity with some brutal bastinado. She is rewarded with multiple orgasms before moving on to the next scene, where we have Maddy face down and ass up to showcase her luscious ass. The only proper thing to do in this scenario is a double flogging scene to ensure maximum suffering. Her ass and back are berated with non-stop flogging until her flesh glows a bright red. That is followed with some heavy-handed spanking, then she is fucked and made to orgasms repeatedly. The final scene begins with Maddy spread eagle on the floor. She is as helpless as she can possibly be, and The Pope takes full advantage of the situation. Her beautiful suffering is heightened with a cat o nine tails as it whips her flesh. She squeals as he hits all of her sensitive spots. The cane stripes her body, then The Pope moves on to the brutal torment of her feet with a knitting needle. The orgasms are plentiful as the scene wraps up. It's been a while since we've seen Maddy, but we are confident in saying it's totally been worth the wait.

Dana DeArmond has two naked anal sluts held captive, each inside a clear acrylic cage. To the left is Ivy LeBelle, standing completely naked in a tall cage. To the right is Maddy O'Reilly, naked on her knees, trapped in a smaller cage. Their Mistress Dana DeArmond fingers her own asshole on a bed placed between the two, teasing them, knowing that they want nothing more than to taste her ass, and each other's asses. When Dana leaves the room, Ivy escapes and lets Maddy out of her cage. The two hurry to the bed. Maddy gets to her knees and Ivy sinks her tongue into Maddy's asshole. Maddy wants a taste and licks Ivy's asshole like she'd been starved of it, then shoves an acrylic toy inside. She pops the toy in and out of Ivy's ass and presses an Hitachi vibrator against her clit and Ivy has a huge orgasm. Maddy gets on her back and Ivy shoves a clear butt-plug inside of her and puts the vibrator on Maddy's pussy. They switch places again and Maddy gets an even bigger clear toy and stretches Ivy's ass out with it. Dana DeArmond comes back and is furious to find out that her two anal craving slaves are out of their cages and hooking up without her permission. She puts them over her knee and spanks their big round asses until they're pink. In the next scene, Dana straps on a big dildo and fucks Maddy's ass in doggie while Ivy lay on her back between Maddy's legs, ready to get face-fucked for when the dildo comes out of Maddy's asshole. Dana fucks her fast and deep and Maddy cums hard from the pounding. It's Ivy's turn to get fucked so Ivy gets on her back and spreads her legs wide. Dana fucks her ass well and Ivy has a shivering orgasm. Next, Dana flips Ivy over and slowly inserts a fat glass toy in her ass, creating a window for us to see deep down into her asshole. Maddy gets jealous of Ivy's stretched ass and wants something big in her ass too so Dana gives her what she wants and shoves her fist all the way inside Maddy's ass. And before the two get back in their cages, Dana washes their asses out with a water enema.

I don’t consider myself a prude. It’s important for a performer to set her limits and demand that they be respected. Producers, clients, customers, men never respect our limits. They push, they twist, the bargain. This time it’s gone too far. I came for a simple bondage shoot. He had different ideas. It started with a few little touches. Nothing I haven’t put up with before. I told him I was uncomfortable. That only made him mad. It all went down hill from there. I keep using my safeword. I keep calling “red”, but I think it amuses him and excites him. If he ever lets me go I’ll tell the world what he did to me. If they even believe me it won’t make a difference.

Cherry Torn runs a tough system. Even her intake processing is the most brutal known. She strips her prisoners down, does a full body cavity search then leaves them in the cage until she's ready to use them. Poor Veronica Avluv has been Cherry's toy for weeks but now she has company. Hot young Maddy O'reilly gets a new inmate hazing of a life time. Cherry's prisoners do ass to mouth, get strap on fucked, eat ass off the strap on, gape and lick inside each other gape, get fisted and squirted on all over a few parking tickets and for jaywalking.

Dana DeArmond is a fierce boss bitch and she runs a strict anal modeling agency. Dressed in a tight black dress and high heels, she demands loyalty and respect from her obedient employees. Her ASSistant, the curvy natural beauty Maddy O'Reilly know exactly how to serve her boss. She will do anything to kiss Dana's perfect ass. The new girl, petite anal newbie Vienna Black, is looking to work in the industry and needs to land this job. Her showing up late to the interview gets Dana worked up and ready to deliver a brutal punishment to her new intern. Starting with rimming, Vienna is made to use her long tongue to fuck Dana's asshole wet. Maddy then brings out the metal dildo to pop Dana's asshole right gaping open. Eager to please, Maddy is next inline for the metal dildo to show Vienna how it's done. Maddy cums hard right away from the anal fucking and it's now time for Vienna to get to work. Stuffed with a butt plug, Vienna's face is bound with a strap on dildo to fuck her new boss. Vienna has a front row view of her bosses perfect gaping asshole as she is made to fuck Dana deep. Maddy is again eager to show off and cum for her boss and she takes the first fist before both girls are stacked ass to ass ready for the bosses huge strap on cock. Both the girls get their asses rammed which causes Maddy to scream with body shaking orgasms. Looks like Dana found the perfect assistant for Maddy.

Crazy director Joey Silvera creates some of porn’s best pegging action, and the scenes collected in “The True History Of Strap Attack #2” show the nasty glory of hot chicks impaling male wimps upon menacing strap-on dongs. Busty Asian London Keyes dominates her slave, spitting in his mouth and jamming his face in her big ass cheeks. She leaves red paddle welts alongside his gaping backdoor. Latina minx Kristina Rose plants her buttocks over her boy-toy’s face as he struggles to breathe. She sodomizes him and jerks him off twice. In a scout uniform, Dillion Harper is prepared to fuck her teacher up the ass! Gorgeous Chanel Preston, as a cold-hearted psychiatrist, prescribes humiliating rectal ravishment for her muscular patient. A submissive pervert worships adorable, young Remy LaCroix and takes a relentless ass reaming; she milks his sperm into his mouth. Buxom Tanya Tate and 19-year-old Cassandra Nix take turns face-fucking a slave and ramming his rear; striving to be crowned Miss Teen Strap America, Cassandra drools his cum into his mouth! Curvaceous Tasha Reign issues a brutal pegging. Maddy O’Reilly corn-holes a bitch-boy’s ass, coats her fake dick in his sperm and makes him suck it clean.

Mia sprays the stage once again!Wherever Mia goes she ruins things. It's that slippery pussy that always gets in trouble. As her livefeed continues we try to come up with the best names for her and her drippy pussy. The ropes go on as Mia giggles about her wet cunt. We add more fuel to the fire so to speak as Mia drinks more water. The verbal torment begins as we make her say YASSSSS! A word she absolutely hates. Once Mia is tied up nice and tight the table is slid out from under her so she's flying. The vibrator goes on her pussy and rips more juice out of her. OT ties her toes back to further expose her. All Mia can do is hang there with her drippy little twat. OT flogs her all over including her tender little asshole.

The rope between her legs has been rubbing at the sides of Maddy O'Reilly's clit for what feels like forever. Her bondage barely lets her move, but she can shift her weight just enough to get the rope to caress her just a little bit more. When Cyd waves a rubber cock in her face she sucks at it greedily. She knows the value of a little bit of lubrication. Cyd is going to drive that dildo home and she wants to make sure it is nice and wet before he does. It fits perfectly in her hole. The crotch rope she enjoyed so much holds it securely in place and makes a great point to attach his Hitachi to. Feeling full and vibrating is enough to get Maddy off. What comes next is enough to put her fully into subspace from the overload. Nipple clamps pull her tits up toward the ceiling while a leather strap around her throat constricts her airway. The intensity of her orgasms is enough to make her shudder and gasp. The extra effort behind every breath has her on the verge of passing out in ecstasy. The crotch rope she loves so much is going to be a real pain. A line between her legs has knots at regular intervals. She has to slide her pussy along it as she tries to make her way to where Cyd tells her to stand. It felt good when it was rubbing against her gently but now, as it scratches and digs, she is wondering why she thought this was a good idea. Of course all of her concerns melt away when she receives her reward for a job well done. It only takes a few seconds with the Hitachi before the last act of torment becomes the thought that fuels her next great orgasm. A little bit of pain and humiliation go a long way for a girl like Maddy.

I no longer need Maddy to prove anything to me. I am all too aware of how she feels. She loves me. She wants to serve me. And I will give her that chance. She is so natural in how she obeys. Her devotion to pleasing me is pure, just like the outpouring of emotion that my attention elicits. She holds nothing back, screaming, moaning, and crying freely as the moments, and my canes, hit her. That is real freedom. It doesn't matter that her arms and legs are bound by rope or that her will is broken by mine. All of the caning, crying and cumming sets her apart from the mundane and makes her free. And she can only achieve it through submission.out sets the stage perfectly for the vibrator. It is true that if you vibrate anyone long enough they will scream for mercy, but if you get them wet with pain first it becomes that much more intense. Sister Dee knows that, and Star is about to learn the hard way.

Sometimes I just lose interest in people I’m talking to. London was a great kisser and super hott. I was really feeling it, but I just sort of moved on. She didn’t! She didn’t at all! She has become obsessed. I can see now that ghosting on her was a big mistake. I could have had her sexy body on me without all the pain. Oh the pain!! She is so cruel. Does being ghosted on really hurt this much? I promise I’ll never leave her! Why would I want to? I should never have ignored her messages. I was so mean. I’m the cruel one! London is only helping me to be a better person. She’s so good to me!

I have put together a 55 minute edging compilation challenge. Can you follow instructions and hold back long enough to make it through the entire challenge? This video is great for stamina training your cock for better orgasm cum control. Are you up for the challenge?