Maddy O’Reilly – Girlsway (Wrong Room)

Lexi Belle responded to an ad for a casual hook up. She instructed the girl to be in her bedroom waiting for her. When she finds Penny Pax blindfolded, in her bed playing with her pussy, she walks in and starts kissing her. Earlier that day, Maddy O'Reilly walks into her new house and wonders if anyone's home. Penny comes down the stairs to greet her and gives her a big hug welcoming her new roommate. Penny tells her if she needs anything, she just has to come find her. She excuses herself and tells Maddy she'll see her later. Penny goes back to her room and is floored at how hot her new roommate is. She's so hot that the very idea of living with her is actually turning her one. She lies down and starts playing with her pussy. Maddy who is just as attracted to her new roommate as Penny is, would love to dyke it out with her. The only problem is that she's never been with a girl before and doesn't want to make things awkward with her new roommate. Perhaps she could find someone online to help her? When she posts an add looking a casual hookup, Lexi answers it almost immediately. The thing is, is when Lexi comes to the house she goes into the wrong bedroom! When Maddy lies on her bed playing with her pussy, she finds herself waiting longer than she anticipated. When she gets up to investigate and hears moaning coming from Penny's room, she walks in to see what's going on. When she realizes that the girl she called, to get better acquainted with the female form, is eating her roommate's pussy, she realizes she has some explaining to do. When she clears up the confusion the girls laugh it off as a simple misunderstanding. Lexi goes to excuse herself but Maddy asks her to stay, stating that two girls could provide her with the experience she needs, and you know what they say...two girls are better than one!
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Maddy O’Reilly – Evil Angel (Oily Anal Big Cock 3)

Butt-blessed redhead Maddie O'Reilly, tattooed tart Kissa Sins and thickly hung Manuel Ferrara share a passionate, oil-drenched anal threesome. The natural-bodied girls wear net lingerie; Maddie has a 'SLAVE' collar and a butt plug wedged in place. Slathered slick, the trio exchanges French kissing, intense choking and slobber. Manuel fucks both mouths and shaved pussies. As one slut rides his massive, uncut meat, the other sits on his face, licks balls, tongues his bunghole, sucks feet, eats pussy and/or rims the second girl. Amid more oil, the aggressive stud fucks Maddie up the ass, slapping face and tits; Kissa gives an ass-to-mouth blowjob. Manuel drills her to orgasmic frenzy. Soaked in oil and sweat, hair matted, the kneeling ladies trade semen-slurping kisses.
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Maddy O’Reilly – Girlsway (Hold The Phone_ Conference Call)

Jenna Sativa is on the phone with a client. She's working from her office at home and is eager to get off the phone. While she explains the pros and cons of branding to her client, Maddy O'Reilly walks down to see her and she looks incredible. Wearing nothing but sexy pink lingerie, she walks up to Jenna and starts massaging her shoulders. Jenna is busy talking to the client but it's clear that Maddy just wants to have some fun. She starts running her hands-on Jenna's chest and squeezing her tits. Jenna looks at her and asks her to stop but Maddy is having way too much fun to do that. Maddy picks up a pen and starts running it on Jenna's skin as Jenna tries to push it away. She runs it down her chest and then starts running it up Jenna's leg. Jenna moans as she moves the phone away from her mouth telling Maddy how bad she's being. The client overhears her and Jenna has to correct herself as she asks Maddy to stop. Maddy smiles indicating that she's not done having fun just yet! Maddy spreads her legs open and runs her hands in between her thighs, she grabs her tits and squeezes them as Jenna gets so turned on she barely is paying attention to the client on the other line. When Maddy starts eating Jenna's pussy, it clear to Jenna that it's high time she put an end to this call and pay attention to Maddy who's got her face deep in wet pussy!
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Maddy O’Reilly – Devils Film (Don’t Tell My Wife I Buttfucked Her Best Friend 8)

Maddy is on the phone with her best friend trying to make her feel better about her asshole husband. She decides that she will take her to lunch and spend the day with her so that she feels better. It's when she gets off the phone that we realize what is really going on.
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Maddy OReilly – Sweetheart Video (Practice Makes A Happy Ending)

Maddy and Scarlett are college students, hanging out in Maddy's dorm room. Scarlett is trying to do homework while Maddy is devising how best to fake her massage certification so she can start doing massages through the 'Relax' app. Scarlett wants her to be patient and get through massage school so she can be legit, but Maddy just wants to make money to go to Ibiza during spring break. Scarlett relents and agrees to take a break from her own homework and let Maddy practice techniques on her. Maddy is paying special attention to Scarlett's perfect hips and butt, to alleviate sciatic pain. Scarlett starts to get hot and bothered during the massage and finally admits that she is very aroused. Maddy is excited, realizing she might have found a way to really cash in doing happy ending massages through the 'Relax' app. Maddy happily gets Scarlett off with her fingers and mouth and Scarlett returns the favor.
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Maddy O’Reilly – DarkX (My Boss’ Wife)

When introducing Nat Turnher, an employee of Sean Michaels', to his stunning wife Maddy O'Reilly he notices how Nat is mesmerized by her. Sean catches him off guard when he gives Nat the okay to fuck her. He quickly declines, until Maddy tempts him by sucking her husband's cock right in front of him luring him to join in on the fun. How can he resist a woman like Maddy who is craving double penetration? All she wants is two big black cocks in her at the same time is that too much to ask!?
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Maddy O’Reilly – Evil Angel (Rocco and Kelly_ Sex Analysts)

Legendary Rocco Siffredi and his classic muse, buxom British blonde Kelly Stafford, explore the freaky, psychosexual crosses they bear. A visually striking orgy in a European mansion features Rocco, Kelly and porn rebel James Deen harshly dominating fishnet-clad sluts Maddy O'Reilly and Dahlia Sky. The girls provide slobbery oral worship amid gagging, choking breath play, slapping, spanking, hair pulling and foot sucking. Collared, leashed Maddy rides James' dick as Kelly rims her. The scene starts with Kelly dramatically splayed on a cross; by the end, she has naked Rocco bound to the cross as Dahlia sucks his load into her mouth.
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Maddy O’Reilly – Girlsway (Undercover Pleasure – Part One_ The Prototype)

Agent 069 (Carter Cruise) has been selected to work on an important assignment. She's been instructed to infiltrate Aniston enterprises, which have been suspected of working with North Korea. Her mission: to enter the premises, sedate the receptionist (Maddy O'Reilly), and use a new technology to extract her DNA and temporally assume her identity. Having 60 minutes before she shapeshifts back to her former self, Carter needs to extract the files before her time is up. After sedating Maddy, she wastes no time storming the office and looking for the file. When the CEO, Nicole Aniston, comes back from her workout, she surprised to find her employee - Maddy, who is really Carter - rummaging through her office. When Carter makes up an excuse about a canceled afternoon appointment, Nicole reminds her that her back is sore and she wants her massage. Knowing that she needs to play this right, Carter does what she's told as she bides her time trying to figure out how to get out of here. When Nicole complains about upper body soreness, Carter isn't sure what she's getting at... but when Nicole grabs Carter's hands and puts them on her tits, Carter gets the message loud and clear. Carter realizes pretty quickly that she needs to get this over with but can't be too obvious as to not blow her cover. She complies with all of her boss' demands and gets it on with her. When they finally finish she's got about 3 minutes to go. When Nicole comes out of the office with the briefcase, Carter asks if she needs to volunteers to take it off her hands. Nicole declines but Carter insists, stating that she wants to help her. She pulls it out of Nicole's hands just before her times runs out but Nicole knows something is amiss. Will Carter get out of this mess? Will she escape without being found out? Can she extract the briefcase containing the secret file without blowing her cover? Find out in part 2!
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Maddy O’Reilly – Wicked (Never Forgotten Scene 1)

Robert and Elizabeth were young sweethearts in the 1940s with a picture perfect romance. Then a silly argument set off a chain of events altering their paths for eternity and leaving Robert's heart to spend decades longing for the one true love it simply cannot forget.
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Maddy O’Reilly – Girlsway (Strap-On Stories_ Strap Trap)

Angela White is stretching after her afternoon jog in the park. Maddy O'Reilly approaches her pointing out how hot she looks in her outfit. Maddy makes it pretty obvious that she's hitting on Angela. She asks her out for a coffee, but Angela lets her know that she has a girlfriend and there's no way she's going on a date with her. Maddy is overly aggressive telling her she's going to regret it. Annoyed, she leaves abruptly. Angela goes back home to her girlfriend, Karlee Grey, and tells her what happened. Funny thing is, Karlee confesses that the exact same thing happened to her. The girls are stunned as they describe the culprit to each other realizing it's the same girl! Karlee informs her that she even has her number: Angela can't believe someone tried to pick up her woman. The girls start thinking of a plan to get back at her. They give her a call and the trap is set. She's on her way to the house not knowing that she's gonna get more than she bargained for. Angela surprises her and before Maddy realizes what's happening, they shove her to the floor and pulls out their strap-ons. Maddy tells the girls she's not into that, but if she wants both of them she's going to have to play it their way. With two straps-on in her mouth, the tough girl act disappears. Slapping her tits they fuck her throat, shoving them deep in her mouth as she gags and spits. As they double penetrate her they finally get to show her who the boss really is!
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Karlee Grey – Babes (Decorate My Poon)

You never know when inspiration will strike! When sweet redhead Maddy has to strip off her shorts after spilling nail polish on them, it gives her BFF Karlee an idea! She grabs her girlfriend's nail gems and begins decorating Maddy's bare pussy with a dazzling array of shiny jewels. Next, it's Maddy's turn to give her artistic side free rein as she uses the gems on Karlee's beautiful big tits. The pair sit back to admire their handiwork, and Maddy finds herself drawn to playing with Karlee's bedazzled boobs! Soon, the babes are kissing passionately, letting their adornments guide their hands and mouths to each other's breasts and pussies. Before long, they find themselves pressing their slender bodies together in a hot tribbing session!
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Maddy Oreilly – Reality Kings (Survey Surprise)

Nobody likes answering surveys, but when a hot teen redhead like Maddy O'Reilly comes knocking on your door with a clipboard in hand, how can you say no? And what if this shy slut comes to your door with cum dripping down her chin? Brad Knight and his wife think they should let Maddy in so she can get cleaned up, and when Brad's wife leaves the room, this homewrecking harlot starts cockteasing by rubbing her pen on her lips and around her busty bosom. Brad is left wondering what kind of survey question “do you want to spank me?” is supposed to be, but at least he knows the answer is “absolutely!” Next thing Brad knows, Maddy is sucking cock in her purple sundress, stripping to her sneakers, and getting her pussy licked. Then she lets Brad give her his dick in doggystyle and fingers her pussy when Brad gives her a second helping of jizz on her face. So what will Brad's wife think?
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Maddy Oreilly – Reality Kings (Dat Booty)

Maddy O'Reilly is one sexy minx! She's got a lot of curve appeal with perky tits and a nice plump ass. She loves showing off her perfect body but the real treasure to this sexy slut is that she loves to take it deep in her butt! You're in for a treat as Maddy teases her ass-ets in an intro that is guaranteed to make you hard! Then, she hops on the massage table to get some much needed stress relief from Jessy Jones. After rubbing oil all over Maddy's curves, he rips open her fishnet stockings and plays with her butt plug before giving her an internal massage by fingering her dripping wet pussy! Grateful, Maddy sucks Jessy's big hard cock, but the horny slut only has one thing on her mind: getting Jessy's big cock deep in dat booty! Of course, Jessy is more than happy to give her the fuck of a lifetime before spreading his man juice all over her perfect round ass!
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Maddy O’Reilly – Wicked (Axel Braun’s Big Ass Anal Movie Scene 4)

It's the BIG ASS ANAL EVENT OF THE YEAR! Legendary director Axel Braun assembled an all-star cast of stunning girls with seriously huge butts, and masterfully filmed them enjoying some totally awesome anal sex. So go ahead and make it your duty to bang a big booty!
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Maddy O’Reilly – Girlsway (Basking In The Afterglow)

Darcie Dolce is smitten with Maddy O'Reilly and misses her lover very much. Basking in the afterglow of a passionate night, she lounges in bed and begins to stroke her pussy. She pulls off her bra and fantasizes about their explicit encounter, filled to the brim with longing. The girls have just arrived home from their date and they are ravenous for each other. Maddy pulls down the top of Darcie's dress and exposes her huge natural breasts. Then Darcie pulls up the bottom of Maddy's dress. She grabs her ample booty and slides her fingers inside her wet slit. Darcie kisses Maddy's pussy and lets her ride her tongue to orgasm. Maddy dives between Darcie's legs and slowly sucks the cum from her clit. Darcie shakes her tight little ass for Maddy as she rims it. Then Darcie lies on top of Maddy and the lesbians cum together in 69. It's no wonder Darcie's in a fog of post-coital bliss and can't stop masturbating!
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