Teachers Tramp Carmen Caliente is on the phone with her friend talking about how epic her weekend was. She ended up hooking up with all sorts of girls and cant wait to start college and find some new pussy. When her friend tells her that a new massage parlor opened up, Carmen asks her if thats the one that Maddy OReilly is working at. Her friend tells her it is and that she should go check it out. Carmen hangs up the phone and starts thinking about how hot it would be to dyke it out with her old teacher. Now that shes 18, shes 100% sure she could seduce her. When she gets to the salon, she asks Maddy if she remembers her. Maddy tells her she looks familiar but isnt 100% sure where she knows her from. Carmen tells her she used to be one of her students. When Maddy confirms that shes 18, she takes her in the back and asks her to take off her clothes for the massage. What Maddy didnt expect is for Carmen to start taking off her clothes in front of her. She lies down on the table and cant believe how good Maddys hands feel on her body. Maddy massages her back and legs but Carmen keeps telling her to get closer to her ass and pussy. Every time they do, Carmen moans a little louder. When Carmen turns around and lies on her back, she motions for Maddy to massage closer to her pussy. Eventually Maddy does exactly that but Carmen wants her fingers inside her. She grabs her hands and puts them on her pussy. Maddy thinks she could provide some additional relief and she gets up on the table and starts eating Carmens pussy. She returns the favor in kind as she eats her old teachers pussy. When she starts college, she knows exactly where shes gonna go to blow up some steam when she gets stressed right here at this salon with her old teacher

Puke Snorting Sluts What better way to kick off the new year than with pukesnorting sluts Tori Avano and Maddy OReilly

Maddys 12 Guy Blowbang Lucky Maddy OReilly has a very special surprise waiting for her in a big garage. Its actual emptiness has being filled of guys ready to fucking her sweet young face and let any kind of sexual juicy cover her. As she takes cocks after cocks, she gets manipulated like a sexual doll and fucked in every way, until she get covered like her birthday cake

Anal Craving Beauties 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 OReilly, 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 others 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 Maddys asshole. Maddy wants a taste and licks Ivys asshole like shed been starved of it, then shoves an acrylic toy inside. She pops the toy in and out of Ivys 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 buttplug inside of her and puts the vibrator on Maddys pussy. They switch places again and Maddy gets an even bigger clear toy and stretches Ivys 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 theyre pink. In the next scene, Dana straps on a big dildo and fucks Maddys ass in doggie while Ivy lay on her back between Maddys legs, ready to get facefucked for when the dildo comes out of Maddys asshole. Dana fucks her fast and deep and Maddy cums hard from the pounding. Its Ivys 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 Ivys 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 Maddys ass. And before the two get back in their cages, Dana washes their asses out with a water enema

The Bartender Waitress Darcie Dolce is sick of her boss haranguing her. She quits her job on the spot and drops in at the allgirl spa for a massage. Masseuse Maddy OReilly gives her a lastminute appointment. The second she sees the bodacious brunette she wants to release all her tension. Maddy escorts Darcie to the massage room. When Darcie gets undressed she is reticent to take off her pantie but Maddy makes her feel comfortable enough to receive her massage in the nude. Darcie lies down on her tummy and Maddy rubs her back and shoulders. Thanks to Maddys pampering touch, Darcie begins to feel better about walking away from her job. Darcie turns over and Maddy massages her heavy breasts. Darcie is so relaxed by the time Maddy reaches her legs and thighs, she doesnt realize that Maddy has leaned in close to her clit. She isnt lubing her with oil anymore. Now shes using her spit. Darcie feels a strange wetness on her pussy and questions the masseuse about what kind of spa this is. Maddy looks her in the eye and demonstrates with her frisky lesbian tongue. Once Darcie blows off steam she reciprocates on Maddys tasty pussy. They finish off their sexy massage with a languid session of tr

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Maddys Interracial Anal Destruction Adorable, allnatural white beauty Maddy OReilly craves interracial thrills she loves getting her thick, soft booty fucked by enormous black cocks! Stretching her sphincter with a glass dildo, she eagerly sucks on Dredds massive meat pole, barely able to fit the head in her mouth. She mounts his monster dick and slides her pussy up and down the throbbing shaft. Dirty Maddy rims the black mans anus. Dredd fills the sluts juicy ass with his giant pole and cums in Maddys

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Free Anal 5 Maddy O’Reilly hates it when guys come in to her bar not knowing what they want, but Xander Corvus is here for the secret menu, the one with FREE ANAL! Xander heard about this place from a friend, but getting blindfolded and taken to a backroom to find out he’s free to anally fuck Maddy any way he wants is more than he expected! With this busty redhead ordering him to stick it in her ass or get our Xander does as he’s told! Bending her pale ass over, spreading it wide and filling her to the brim with big dick, Xander pounds her tight little ass as hard as he can!

Pumping My Pantyhose After a long day, Maddy likes nothing more than to kick back and relax. Especially if it involves gorging down on Isiahs gargantuan meat stick. All that she asks is he rips into her pantyhose, and gives her ass the pounding it deserves. Isiah is more than happy to oblige, rubbing her rump with oil before giving her a pantyhose pumping she wont soon forget!

Maddy OReilly Naughty Slut Submits to The Pope Maddy is a dirty slut, and she loves getting tied up and tormented, but we havent 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 OReilly, 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 nonstop flogging until her flesh glows a bright red. That is followed with some heavyhanded 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. Its been a while since weve seen Maddy, but we are confident in saying its totally been worth the wait.

Double the Stakes Having two girls pleasing your cock is a wet dream come true for any man, but these gorgeous girls take things a little to far. There is something evil and mischevious about them that the poor guy is not suspecting. Watch Maddy OReilly and Chloe Cherry having their way with Ryan Diller in a premium XXX scene thats worthy of remembering.