Latest updates featuring Maddy O'Reilly

Maddy O'Reilly in 'My Wife Is My Pornstar'

Maddy O'Reilly - My Wife Is My Pornstar

Maddy O'Reilly and her husband had a wild party. So wild that one of their guests, Chad, falls asleep in the guest bedroom. Well Maddy and her husband have a special relationship where she gets to fuck any cock she wants, so she decides to wake Chad up and have him shove his big dick into her tight asshole. Her husband loves hearing all about it!

Maddy O'Reilly in 'My Wife Is My Pornstar'

Maddy O'Reilly - My Wife Is My Pornstar

Maddy O'Reilly's husband has revealed that he has a cuckold fantasy and Maddy is more than happy to help out with that. She brings home one of the employee's from the mail room, has him get comfortable, then puts on some sexy lingerie for him. Her employee is more than happy to give Maddy the D, and Maddy tells her husband all about it!

Maddy O'Reilly in 'fucking in the living room with her piercings'

Maddy O'Reilly - fucking in the living room with her piercings

Mick comes over to his friend's house to find his friend's girlfriend doing a sexy webcam show. Maddy's boyfriend doesn't know about it, and Mick gets to sit and watch if he doesn't say anything. But he gets more than he bargains for when he whips out his cock.

Maddy O'Reilly in 'fucking in the couch with her average body'

Maddy O'Reilly - fucking in the couch with her average body

Maddy O'Reilly is supposed to watch a movie with her friend, but she's nowhere in sight. When her friend's brother comes over looking for his sister, Maddy tells him that she ditched her, so he should stick around and watch the movie with her. But she's more interested in making a movie with Giovanni ... the kind that involves a sloppy blowjob and good pussy-eating!

Maddy O'Reilly in 'Co-ed Maddy O'Reilly fucking in the floor with her tattoos'

Maddy O'Reilly - Co-ed Maddy O'Reilly fucking in the floor with her tattoos

Art student Maddy Oreilly leaves her sketchbook in the classroom, and when she goes back to retrieve it, she finds her teacher flipping through it. He tells her that her drawings of the male anatomy are incorrect -- she's got the sizing all off. Professor Glide whips out his giant cock to show petite Maddy the real deal! She thanks him for the lesson by sucking his giant cock and letting him stuff it in her pussy until he blasts a load in her mouth! Art is beautiful.

Ariana Marie in 'Best of Brazzers Pantyhose'

Ariana Marie - Best of Brazzers Pantyhose

Whether you call them stockings, tights or pantyhose, it's impossible to resist these timeless staples of feminine apparel. They can barely hide anything, yet they shroud everything they touch in mystery. Look at those ladies' legs: smooth and silky, teasing horny girls and boys alike. The only pleasure bigger than peeping at the veiled appendages is to rip a hole in the textile, break lose, and indulge in the exposed skin.

Maddy O'Reilly in 'DP Compilation'

Maddy O'Reilly - DP Compilation

Enjoy this compilation of some of our hottest girls getting DP'd! 00:03 - AppleGate DP02:14 - Double Down04:03 - Fuck My Girlfriend, Please06:19 - Casey's Double Penetration08:16 - I Need A Favor10:11 - My Boss' Wife11:46 - We Have History14:31 - Keisha's IR DP16:25 - Tiny Blonde - BBC DP


Maddy O'Reilly in 'Submissive and Sloppy'

Maddy O'Reilly - Submissive and Sloppy

Beautiful pro deepthroater Maddy O'Reilly has many miles of cock sucked. This incredible experience makes her the perfect sex toy to practice throat fucking because that is what she likes the most, submit to the shaft and let the saliva flow.

Maddy O'Reilly in 'Maddy O'Reilly: Naughty Slut Submits to The Pope'

Maddy O'Reilly - Maddy O'Reilly: Naughty Slut Submits to The Pope

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.

Maddy O'Reilly in 'Dredd 7'

Maddy O'Reilly - Dredd 7

Maddy O'Reilly takes the biggest cock she's ever seen, Dredd, up her tight asshole! Maddy's a sexy redheaded slut who likes to be treated like a filthy whore. She's wearing a fishnet body stocking with stripper leggings and high heels as she shows off her body in the bathroom. Maddy makes her way through the bedroom and out on the balcony where she shows off her sexy curves as they're drenched in the sunlight. Dredd makes his way up the stairs and admires the beauty that is in front of him before letting Maddy do some inspecting for herself. Blown away by the size of his massive BBC as she feels it through his pants, Maddy helps Dredd remove his jeans and then takes on the challenge of fitting this giant dick in her mouth. She can't fit it all the way in, but that doesn't stop her from stroking and slobbering all over that tree-trunk cock. They make their way inside where Maddy climbs on the bed and gets on all fours so Dredd can worship her ass and pussy with his tongue before joining her on the bed and letting her suck on his thick dick some more. Maddy tongues Dredd's asshole, showing just how dirty she is, before climbing on top of him and impaling herself on that BBC. She rides that cock hard and deep then flips over into doggystyle so Dredd can pound her from behind and watch her ass bounce against his balls. Maddy stops to taste all of her juices off of that giant dong, then tells Dredd she wants to feel that cock in her asshole. Dredd reams her rectum with his BBC, making her gape for the camera as he pulls his dick out and holds her ass cheeks wide open, then paints her face with all of his cum!

Maddy O'Reilly in 'Double Anal Divas'

Maddy O'Reilly - Double Anal Divas

Lovely redhead Maddy O'Reilly poses beside the pool, exposing her soft, natural tits and plump, jiggling booty. This sexy girl craves a nasty backdoor threesome with well-hung studs Mick Blue and Ramon Nomar! She gags giving the men blowjobs; their big cocks fuck Maddy's juicy pussy and thick ass. The studs treat this plush babe to a rude DP. A nasty double-anal penetration stretches her bunghole to the maximum! Ramon and Mick shower Maddy's pretty face with a messy cum facial.

Maddy O'Reilly in 'He Loves Me In Collars And Cuffs Scene 4'

Maddy O'Reilly - He Loves Me In Collars And Cuffs Scene 4

He loves when I give him control and when I let him do all of those kinky things to me that hurt so good. He teases and touches me and right when I can't take it anymore, he releases me and gives me what I really want: hot, passionate sex.

Ivy LeBelle in 'Anal Craving Beauties'

Ivy LeBelle - 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 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.

Maddy O'Reilly in 'Cable Tied'

Maddy O'Reilly - Cable Tied

Maddy has got herself into a little bit of a situation. While hooking up some electronics, she's found her cute body amidst a tumbleweed of wires. Well, sex can't solve the mess she's made, but it can at least make up for it. Especially when she strips down and shows off her round ass and perky teen tits… Wait, what mess was she talking about All I see here are potential BDSM tools…

Maddy O'Reilly in 'Wrong Room'

Maddy O'Reilly - 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!


Maddy O'Reilly in 'Free Anal 5'

Maddy O'Reilly - 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!

Maddy O'Reilly in 'The Rectal Exam'

Maddy O'Reilly - The Rectal Exam

THE RECTAL EXAM
Family doctor exploits favorite patient into anal sex exam

SCENE opens with the camera focused tightly on the exposed back of a woman with a stethoscope pressed against her skin. The camera travels as the doctor's hand slowly moves the stethoscope lower down the patient's back, which elicits a light gasp and giggle from the patient without us ever seeing her face. She exclaims that the metal is a bit cold. A close-up of just the doctor's mouth, biting his lip nervously, shows us that the exposed skin and flirty noises of his patient are distracting him. 'Sorry,' Dr. Sumner says with a bit of a dorky laugh, 'just one more deep breath please?' We watch her exposed back rise and fall slowly as she breathes deep, and Dr. Sumner stares at her mesmerized. 'Gooood,' he exclaims softly. Catching himself staring, he clears his throat and lifts the stethoscope off her back. As he turns back to stand across from his patient, we see she is a strikingly beautiful woman, Yvette. In fact, Dr. Sumner finds he has trouble taking his eyes off of her as he speaks. 'Well, your breathing checks out, blood pressure is normal, and your vaccinations are all up to date... was there anything else that's been worrying you that you wanted me to look into?' Yvette looks uncomfortable as she tries to broach the subject. Actually, yes, there was something else that's been bothering her recently, but it's a bit uncomfortable to talk about. Dr. Sumner assures her that no topic is off limits, especially not for his favorite patient, and Yvette gets a bit more relaxed. Well, she elaborates, she's been feeling some discomfort in her... well, her you know, ('butthole' she mutters hurriedly), ever since she tried anal sex for the first time with her boyfriend a couple of days ago.

Dr. Sumner is visibly taken aback, and he stutters over a response as he fidgets with his coat and tie. Yvette looks let down, she had hoped that Dr. Sumner would react more professionally than this, but he apologizes - it's simply because he's been treating her and her family since she was a little girl, sometimes he forgets she's a 22 year old woman now. But she's right, there's nothing to be ashamed of, what two consenting adults do in the privacy of their homes is not any of his business. He remarks that it's not uncommon for anal virgins to experience some pain and discomfort afterwards, and that the pain should subside after a day or two as long as she was careful, they went slowly, and used plenty of lubricant. Yvette, however, doesn't seem to have been put at ease - she's read about anal fissures and tearing and the like. Isn't he even going to take a look to make sure it isn't something more serious? Dr. Sumner starts to say that it's not necessary since her level of pain doesn't seem too severe, but then he cuts himself off. Actually, yes, she's absolutely right, he should perform a thorough examination. Just to be safe. So if she can just please lift up her dress, remove her underwear, and bend over the table...

CUT TO TITLE PLATE

CUT back to just a few seconds after, only now in a male gaze perspective from behind Yvette as we stare straight onward at her bent over ass. Her pussy and butthole are on full display as she waits patiently for her doctor to take a look. He kneels down close, placing one firm hand on each cheek to spread them wider, and stares transfixed for several seconds.

'Um... doctor?' Yvette asks timidly. 'Is everything ok back there?' Dr. Sumner snaps out of his reverie and stutters that yes, he's just making a preliminary visual inspection before he runs more extensive tests. He periodically spreads her ass cheeks wide to provide the camera with ample close-up shots of her winking hole - this goes on for almost a minute, though the doctor is now more conscious to make it seem like a proper inspection by adding authoritative sounds like 'mm-hmm', 'ok', 'so far so good', etc. to keep Yvette feeling assured.

'Well, at first glance everything seems in order, but I'll of course have to palpate the inside of your rectum next, so you should brace yourself for some mild discomfort.' 'Palpate?' Yvette asks nervously, but Dr. Sumner explains that palpate just means examining by touch. It's just a clinical way of saying he'll be inserting his finger. With lubricant, of course. He asks her to remain in position while he dons his medical gloves - as he does this, we see that unbeknownst to Yvette, the doctor's attention remains fixated on her ass on display. He smears some lubricant onto his index and middle fingers, and then gets back into position behind her.

He reminds her that as he said, she might feel some slight discomfort - and then makes a bad joke about how he's sure it will be nothing compared to how it must have felt with her boyfriend sticking it in the other night. Yvette laughs nervously, not because it was funny but to make things less awkward. The doctor sticks one gloved finger in slowly, asking Yvette to describe the sensations as he does so. She describes the initial pressure, a dull ache as his finger goes deeper in, and then finally a yelp of surprise when he sticks the finger all the way in, though it quickly subsides, and she remarks that she doesn't notice much pain now that he's all the way in. He remarks that he's going to keep his finger there for a few moments, and suggests she takes a few deep breaths. He places his other hand on her ass cheek again and spreads it idly as they wait.

Dr. Sumner begins to ask Yvette questions about her first anal experience. Though as he asks his questions, Dr. Sumner coyly pulls his finger in and out, pretending it's part of the process. Did she use lube? (Yes.) Did she work her way up to the night in question by using any smaller toys to start? When Yvette says no, the doctor suggests that if she wants to continue having anal sex she should consider it, in fact he's read about women who wear butt plugs for hours at a time to stretch themselves out, even in public. Yvette blushes and says there's no way she could be bold enough for something like that. Dr. Sumner changes the subject and asks if Yvette's boyfriend fingered her first to ease her into it, and she confesses no, he didn't. Dr. Sumner explains that that may be why she's experiencing some pain now, and that it's generally better to start slow and work her way up to bigger objects. As he says this, he tells her he'll be putting in a second finger to test her elasticity. The second finger is clearly more difficult for Yvette to handle than just the one, but he eases her into it with a sense of relish.

After he satisfies himself with having fit two fingers into her hole and wiggling them around to make her squirm a bit, Dr. Sumner pulls his fingers out gently and then tells her that while things seem normal inside, he would like to get a final deeper visual inspection using a speculum. He lays Yvette on her side on the table, ass peeking out towards him, and he pulls out a rectal speculum from a nearby drawer. He inserts it carefully and uses it to expand her asshole slightly wider. Yvette remarks that the sensation is very uncomfortable, but the doctor remarks that the sensation should pass and that he promises it's absolutely necessary. However, he is clearly enjoying himself, even inserting his finger into the opening of the speculum to tease and toy with the rim of her hole. He tells Yvette that she's lucky that a 'complete amateur' like her boyfriend didn't injure her, and that they should really take better precautions next time. Yvette, slightly weirded out, remarks that Dr. Sumner really seems to know a lot about anal sex. Like, a lot.

At this, Dr. Sumner gets very embarrassed. He takes the speculum out of Yvette and removes his hands from her, putting them between his legs sheepishly. He was just offering her some advice, that's all. Yvette asks where he even gets all this advice from, she's sure it's not stuff he learned at medical school. Dr. Sumner tries to evade the question, but Yvette coaxes him - he's been a friend of the family for years now and he's helped her through some very tough times, she won't judge him. Dr. Sumner bashfully answers that he watches a lot of anal porn. Yvette grins, it's almost cute how nervous the doctor looks. She asks Dr. Sumner if he's ever had anal sex and he admits that he hasn't but has always wanted to. Yvette gets bolder, she bets that he must get awfully tempted sometimes with all the pretty girls he must have to look at as part of his job. In fact, he's always said she's his favorite patient, is that because he likes her or is it just because he's always wanted to fuck her? Dr. Sumner stumbles over his words and Yvette takes advantage of this to coax him further. He's right that her boyfriend is a complete amateur. In fact, having anal sex with him hurt like hell. But she bets that if a real man showed her how to do it, a man who's completely obsessed with anal sex, he'd know how to do it right. She reaches for his crotch and he pulls back, it would be unethical. She gets up off the table and approaches him seductively, insisting that no other patient of his is ever going to go along with something like this, this is a once in a lifetime chance and he'd be an idiot to turn it down. She wants it, he wants it. What could be more ethical than that? She leans in for a kiss and he hungrily kisses back, his hands going straight to gripping her ass cheeks tightly as they embrace.

Vienna Black in 'Dana DeArmond's Anal Agency: Boss Bitch Trains Anal Newbie'

Vienna Black - Dana DeArmond's Anal Agency: Boss Bitch Trains Anal Newbie

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.

Maddy O'Reilly in 'Oily Anal Big Cock 3'

Maddy O'Reilly - 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.

Maddy O'Reilly in 'Hold The Phone: Conference Call'

Maddy O'Reilly - 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!

Maddy O'Reilly in 'Don't Tell My Wife I Buttfucked Her Best Friend 8'

Maddy O'Reilly - 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.

Maddy O'Reilly in 'Practice Makes A Happy Ending'

Maddy O'Reilly - 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.

Maddy O'Reilly in 'My Boss' Wife'

Maddy O'Reilly - 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!?


Maddy O'Reilly in 'Rocco and Kelly: Sex Analysts'

Maddy O'Reilly - 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.

Maddy O'Reilly in 'Undercover Pleasure - Part One: The Prototype'

Maddy O'Reilly - 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!

Maddy O'Reilly in 'Never Forgotten Scene 1'

Maddy O'Reilly - 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.

Maddy O'Reilly in 'Strap-On Stories: Strap Trap'

Maddy O'Reilly - 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!

Karlee Grey in 'Decorate My Poon'

Karlee Grey - 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!

Maddy O'Reilly in 'Survey Surprise'

Maddy O'Reilly - 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?

Maddy O'Reilly in 'Pumping My Pantyhose'

Maddy O'Reilly - Pumping My Pantyhose

After a long day, Maddy likes nothing more than to kick back and relax. Especially if it involves gorging down on Isiah's 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 won't soon forget!

Maddy O'Reilly in 'Dat Booty'

Maddy O'Reilly - 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!


Maddy O'Reilly in 'Axel Braun's Big Ass Anal Movie Scene 4'

Maddy O'Reilly - 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!

Maddy O'Reilly in 'Basking In The Afterglow'

Maddy O'Reilly - 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!

Maddy O'Reilly in 'All Stuffed Up 02'

Maddy O'Reilly - All Stuffed Up 02

Pretty, big-assed Maddy O'Reilly says, 'Nothing's hotter than getting destroyed by two guys at once.' Her slo-mo booty clap invites director Toni Ribas and hung Ramon Nomar. They spank her natural tits, shaved cunt and fleshy cheeks red. Maddy gives a slobbery, double BJ; she shrieks and blushes through straight-to-anal reaming, face slapping, gagging, double vaginal stuffing, double anal plowing and double penetration! She joyfully chokes, gives A2M head, cleans feet orally and eats spit. Ramon fingers her to an orgasmic squirt. Her own juice splashes her face, followed by two thick loads.

Maddy O'Reilly in 'Penchant For Pricey Panties'

Maddy O'Reilly - Penchant For Pricey Panties

Georgia Jones is on her way to work when she catches her roommate Maddy O'Reilly trying on her glitzy panties. Now she knows what happens to the pairs that disappear. She used to blame the washing machine for eating them, but it's just Maddy with a penchant for pricey panties. Maddy takes off the underwear and playfully shoves them under Georgia's nose to prove they're still fresh. When Georgia doesn't complain, Maddy teases her for liking the smell of her pussy. Maddy thinks the top she's wearing belongs to Georgia too. She takes it off and hands it over, stark naked. Georgia doesn't know what's gotten into her roommate. Maddy wrestles Georgia onto the bed and pries off her shirt, ignoring her protests about being late for work. Maddy wants Georgia to suck on her tits. She kisses her to encourage compliance. Then Maddy hikes up Georgia's skirt, pulls down her drawers and licks between her legs. She stuffs Georgia' mouth with her beloved panties, then takes off her bra and licks her little hard nips. She hoists her onto her lap and kisses her deeply, then pulls her in close and tribs her pussy, slowly building in speed and intensity till she cums. After Maddy rubs out another orgasm from Georgia's pussy, the lesbian stoops over Georgia's gaping mouth and rides her tongue. Georgia kneels for Maddy and lets her stuff a pair of panties into her mouth. Maddy rubs Georgia's pussy from behind until she cums on her fingers. Then Georgia licks Maddy's pussy into a frenzy using her panties to soak up the cum!

Maddy O'Reilly in 'The Rim Job'

Maddy O'Reilly - The Rim Job

While broke actress Alix Lynx is on the phone with her agent arguing over the part that someone else got, a call comes in from the auto service shop. Her car is ready for pickup, but the bill is astronomical! She heads down to the shop to find out what was wrong with her car's rims to cost that much. She meets her cranky mechanic Maddy O'Reilly. Maddy just wants the client to pay and leave. But Alix doesn't have the dough, so Maddy can't let her take the car. Alix is distraught because she needs the car to get to an audition tomorrow. If she gets the part, she'll have the means to pay her bill. Maddy wishes she could help, but Alix' sexy red sports car only takes pricey custom parts. Alix attempts to win the mechanic's favor by giving her a signed copy of her movie Artificial Intelligence on DVD. But Maddy's not interested in the DVD. She wants to have sex with the pretty girl. Alix isn't happy about it but agrees to have sex with the grimey mechanic. Maddy pulls up Alix' top and cups her firm braless breasts. Alix is utterly disgusted as Maddy puts her nipples in her mouth, but admits her tongue feels good. Slowly but surely, Maddy eases Alix out of her panties, and then licks her pussy as the actress leans up against the car. After Alix has a mad orgasm in her mouth, Maddy takes off her shorts despite Alix' objections. Maddy insists that Alix reciprocate, so Alix begrudgingly eats her pussy until she cums. Alix wipes her mouth and gets ready to go, but Maddy tells her they're just getting started. She makes Alix bend forward and lean on the car as she eats her ass from behind. Then Maddy gets down on all fours and sticks her ass in the air. Alix bravely inserts her tongue in her asshole, while massaging an orgasm from her pussy. Then, Maddy instructs Alix to lie down on the floor. The lesbian aligns her pussy over Alix' and begins to trib. The girls frantically rub their pussies together till they cum intensely! Talk about an auto body experience!

Maddy O'Reilly in 'Squirting Stories Volume Two: Mopping Up'

Maddy O'Reilly - Squirting Stories Volume Two: Mopping Up

Cadence Lux from the cleaning service comes over to clean her client's house. No one answers the door so she uses the code to get in. She's busy cleaning the kitchen when the homeowner Maddy O'Reilly comes downstairs and demands to know why the house is still filthy. She's not happy with the chemical products Cadence is using to clean. Maddy only wants organic cleaners in her home. Cadence loses it on Maddy. She's sick of her rich stuck up clients pushing her around. She saw Maddy staring at her body, she knows what she's really after. Cadence pulls off her shirt, yanks down her pants and flaunts her tits and ass. She hotly accuses Maddy of wanting to fuck the cleaning lady. Maddy kisses her on the lips and admits she does want to fuck her. Maddy plants her mouth on the maid's pussy and sucks on her clit. Cadence undresses her boss and washes her pussy with her tongue. Cadence lies down on the dining room table and spreads her legs. Maddy devours her pussy till it squirts all over. Then Cadence mops up her mess with Maddy's hair. Maddy shakes her ass over Cadence's face and rides her expert lesbian tongue. Then Cadence spins her around and they eat each other's pussies in 69. Cadence straddles her boss' face till she empties a bucket of squirt, soaking her hair with it. She sucks Maddy's pussy till she cums, then licks the pussy juice off her body!

Maddy O'Reilly in 'The Art of Lesbian Anal: Birthday Play'

Maddy O'Reilly - The Art of Lesbian Anal: Birthday Play

Maddy O'Reilly is lying on her girlfriend Jayden Cole's lap buck naked, her glistening ass covered in oil. Jayden is massaging Maddy's ass, lamenting how much she loves it and how sad she is that Maddy never let's her in there. When Jayden leaves for work, Maddy decides that anal play would be the perfect way to celebrate Jayden's birthday. It's the least she can do after their amazing year together. When Jayden comes home from work, Maddy's on the bed wearing nothing but a helium balloon. She playfully offers her ass to Jayden and Jayden can't wait to finally feast on her bubble butt. She peels off her clothes and the lesbian couple begins to make out. They tease each other with kisses on their nipples, sucking gently till they stimulate the circulation down below. Maddy treat her lover to tantalizing head, fucking her with her eyes while licking her pussy till she cums in her mouth. Then Jayden reciprocates licking Maddy until she cums. Maddy kicks off the anal birthday play, putting Jayden into position onto all fours and eating the birthday girl's ass till she howls with pleasure. Jayden returns the party favor, taking her hot girlfriend from behind. She licks her tight little butt and fills her asshole with as many fingers as she can fit, slowly fucking her ass to orgasm!


Maddy O'Reilly in 'Dredd's Interracial Anal Destruction'

Maddy O'Reilly - Dredd's Interracial Anal Destruction

Adorable, all-natural white beauty Maddy O'Reilly 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 Dredd's 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 man's anus. Dredd fills the slut's juicy ass with his giant pole and cums in Maddy's mouth.

Maddy O'Reilly in 'Craving Some Dick'

Maddy O'Reilly - Craving Some Dick

Maddy O'Reilly is back with us and is horny as hell! She can't wait to suck some cock for you and is begging for a big pounding! She makes sure to deep throat that dick and describes to you how bad she wants it! She gets it in all positions and loves licking up Damon's load afterwards!

Maddy O'Reilly in 'Happy New Rear'

Maddy O'Reilly - Happy New Rear

We're ending the year on a high note and letting Maddy O'Reilly do whatever she wants with a big cock. Lucky for us she wants it in her thick ass! Johnny gives this cutie an anal pounding that she'll remember well into 2017.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano explores the mystery and timeless attraction of a woman's asshole in this epic-length (96 minutes!) series of hot anal fetish clips. Rectal supermodel Casey Calvert and cute Gabriella Paltrova masturbate with vibrating wands, stretching their expressive sphincters with huge toys and speculums. Gabriella employs pussy clamps and pushes the wand into her ass! Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly get themselves off using various dildos, butt plugs and vibrators.

Casey Calvert in 'Buttman Focused 11'

Casey Calvert - Buttman Focused 11

When girls visit John 'Buttman' Stagliano's studio, they naturally expect lots of anal fun! These insanely hot tease clips showcase 55 minutes of Buttman's favorite asses, and some stunning models that enjoy making their sphincters gape open! Casey Calvert parts her adorable butt cheeks to flaunt her tender anus, Gabriella Paltrova winks her talented asshole, Jodi Taylor displays her outrageously big, beautiful booty, and Savannah Fox, Abella Danger and Maddy O'Reilly all tempt us with perfect rear views.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

When girls visit John 'Buttman' Stagliano's studio, they naturally expect lots of anal fun! These insanely hot tease clips showcase 55 minutes of Buttman's favorite asses, and some stunning models that enjoy making their sphincters gape open! Casey Calvert parts her adorable butt cheeks to flaunt her tender anus, Gabriella Paltrova winks her talented asshole, Jodi Taylor displays her outrageously big, beautiful booty, and Savannah Fox, Abella Danger and Maddy O'Reilly all tempt us with perfect rear views.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano gets as close as his camera will allow to photograph the perfect pussies of stunning models. Casey Calvert puts clothespins on her exquisitely shaved cunt. Gabriella Paltrova queefs at will while using labia clamps! Jodi Taylor strokes her sensitive clitoris and shows off her furry snatch. Savannah Fox manipulates her plump, meaty cooch. Abella Danger and Maddy O'Reilly each masturbate their sweet spots in quivering detail.

Abella Danger in 'Buttman Focused 11'

Abella Danger - Buttman Focused 11

In this series of sloppy fetish clips, dirty girls gag on big dildos to create nasty rivers of messy drool. John 'Buttman' Stagliano documents the soaking action as Gabriella Paltrova blows spit bubbles, Savannah Fox bastes her tits in gooey expectorate, Maddy O'Reilly shoves fingers down her throat and slobbers all over her chest (with suction cups on her nipples), and kinky Abella Danger thoroughly ruins her makeup, slapping her own saliva-smeared face.


Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano shoots video of insatiable young sluts using the finest in sexual technology to make themselves cum! Casey Calvert, Maddy O'Reilly, Jodi Taylor and the spit-slathered Abella Danger each climax with powerful vibrators while getting stuffed by various anal dildos. Gabriella Paltrova queefs in orgasm, fingering her juicy cunt, and redhead Savannah Fox squirts copiously while stretching her anus with a huge glass butt plug followed by a big vibe.

Savannah Fox in 'Buttman Focused 11'

Savannah Fox - Buttman Focused 11

In this series of juicy video clips, John 'Buttman' Stagliano shoots video of teasing temptresses as they squeeze, spread and stroke their sweet, plump pussies. Casey Calvert, Gabriella Paltrova, Savannah Fox, Abella Danger and Maddy O'Reilly wedge their panties between their cunt lips and tug their sensitive labia apart for our perverted perusal. Fans of these young ladies' most holy holes can bow and worship!

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

Gorgeous young ladies show off their deep-throating skills for kinky director John 'Buttman' Stagliano, using various toys and gag-inducing phalluses. Huge, wall-mounted dildos stretch the throats of Gabriella Paltrova, Savannah Fox, Abella Danger and Maddy O'Reilly, making these orally skilled sluts regurgitate rivers of slimy spit. Adorable, big-assed Jodi Taylor chokes on rubber dick while she buzzes her juicy pussy to orgasm!

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

John 'Buttman' Stagliano explores the contours and texture of several sets of gorgeous, all-natural tits in this series of teasing video clips. The director pinches and tweaks the sensitive nipples of stunning babes like Casey Calvert, Gabriella Paltrova, Jodi Taylor, Abella Danger and Maddy O'Reilly as they flaunt their sexy boobs for him. Redheaded cutie Savannah Fox gets her jiggling jugs stimulated with a pair of nipple-swelling suction bulbs.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

A true connoisseur of feminine beauty, director John 'Buttman' Stagliano trains his camera on a variety of gorgeous young ladies in his home studio. In this epic highlight reel of perversity, model-tier babes like Casey Calvert, Gabriella Paltrova, Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly sloppily suck and masturbate with big dildos, huge butt plugs, suction cups, clamps and other outrageous sex toys. See all-natural sluts buzz their sensitive pussies with vibes, teasing the director to madness!

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

In this provocative series of video clips, lucky director John 'Buttman' Stagliano gets to shove his nose into the alluring, thinly clothed butt cracks of a series of gorgeous young ladies. Casey Calvert, Gabriella Paltrova, Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly sport a variety of sexy clothes, from sheer fishnet hose and tiny thongs to butt-hugging spandex. Casey even sits right on the director's face so he can inhale the delicious scent of her ass.

Maddy O'Reilly in 'Buttman Focused 11'

Maddy O'Reilly - Buttman Focused 11

In this hypnotizing series of video clips, John 'Buttman' Stagliano closely follows beautiful asses swaying from side to side as they strut. Stunning booty teases Casey Calvert, Jodi Taylor, Savannah Fox, Abella Danger and Maddy O'Reilly stride away from the camera, providing perfect views of their gorgeous butts -- clad in fishnet dresses, taut spandex, tiny thongs, leotards or nothing at all! Abella's walking rump is festooned with suction cups, and Casey's bare booty clutches a butt plug.

Maddy O'Reilly in 'Black Snake Oil 3'

Maddy O'Reilly - Black Snake Oil 3

Captivating, all-natural fuck-slut Maddy O'Reilly adorns her light-skinned body with slinky fishnets and classic stripper heels for an interracial anal date. The lusty harlot drools over Mickey Mod's stiff black cock in an intense blow job. Hung Mickey delivers throat choking and spanking; he fingers her cunt to squirting orgasms! He douses her plump booty in oil and plunges his thick prick into her sphincter for a ravaging anal fuck. Lust-addled Maddy babbles foul-mouthed rhetoric, guzzles greasy prick ass-to-mouth and swallows Mickey's cum.


Maddy O'Reilly in 'Squirtqueen'

Maddy O'Reilly - Squirtqueen

All-natural blonde beauty AJ Applegate teases the camera with her big, curvaceous ass and small, perfect boobs. Next, the leggy bombshell dominates young brunette Maddy O'Reilly in a lewd display of lesbian lust. She rips off Maddy's dress and makes her kneel; AJ diddles Maddy's shaved pussy and squirts messy girl cum all over the young slut's face! Maddy submissively laps up the fragrant liquid. The lovely minxes grind their tender cunts together. They share vibrators and dildos, face sitting, girl kissing and female ejaculation!

Maddy O'Reilly in 'Work Is Long When Youre Wearing A Thong'

Maddy O'Reilly - Work Is Long When Youre Wearing A Thong

Maddy O'Reilly loves being the office tease. She's got a big booty and loves to flaunt her butt any way she can. Her co-workers take notice and are often distracted by her ass-tonishing backside. So, when the office boss Preston Parker realizes that the workflow has come to a halt, he decides to summon the booty-licious Maddy into his office to reiterate the dress code. Only, Ms. O'Reilly just wants to get closer to her boss--for an anal dicking, that is!

Maddy O'Reilly in 'No Panties For Me'

Maddy O'Reilly - No Panties For Me

Maddy O'Reilly loves to be ready for anything and wearing no panties we know what she is ready for as she shows us her wet pussy and begins to stroke her fingers over her hard little clit.

Maddy O'Reilly in 'Rocco's Intimate Initiations 2'

Maddy O'Reilly - Rocco's Intimate Initiations 2

Strawberry blonde Maddy O'Reilly's fleshy, all-natural body looks enticing in her fishnets-and-heels outfit as she re-connects with stud porn legend Rocco Siffredi. It's their private, very personal backstage reunion before a scene, and Maddy's excited beyond words because her last scene with Rocco was the best of her life. He teases and fingers her into masturbatory reverie. Maddy makes full, intense eye contact with Rocco's POV camera as she worships the gigantic cock she calls 'so perfect.' Her cocksucking, plus intense French kissing and brief fucking, make Maddy's cunt creamy. This backstage honesty leaves them primed to go shoot some porn.

Maddy O'Reilly in 'Anal Avenue Sluts 02'

Maddy O'Reilly - Anal Avenue Sluts 02

Beautiful brunettes Callie Calypso and Maddy O'Reilly demonstrate their love for nasty anal fucking in a three-way with director Mike Adriano. After some lewd ass licking, the girls orally pleasure the director's massive cock and ball sack in a wet, sensuous double blow job. The sluts take turns getting their sphincter stretched, each slurping Mike's meat straight from her girlfriend's gaping hole. Callie climaxes with a vibrator as her rump is reamed; finally, Maddy laps up Mike's splooge and shares it in a tongue kiss.


Dana DeArmond in 'Anal Buffet 12'

Dana DeArmond - Anal Buffet 12

Slender slut Dana DeArmond, adorable Maddy O'Reilly and gorgeous Asian sex bomb London Keyes are spotting one another in the gym. Of course, this workout is all about their round, sexy asses, and worshiping them with fingers and tongues! After a sensuous session of wanton butthole licking and anal probing, the ladies team up on Prince Yahshua and his massive black cock. Yahshua provides intense interracial reaming to their various orifices and splatters their sweet butts with hot semen.

Maddy O'Reilly in 'Up My Booty'

Maddy O'Reilly - Up My Booty

Auburn-haired slut-next-door Maddy O'Reilly poses poolside, showing off oiled natural tits and tugging her bikini bottom between shaved, puffy pussy lips. Inside, she spreads for stud Mark Wood, who spanks and rims her fleshy ass. He expands her butthole with a glass toy and a fat butt plug, which she tastes. (Maddy: 'It smells so good after it's been in there.') Mark's wood then slides straight up her booty with zero resistance. He plows pussy and asshole back-and-forth, choking her, smacking her tits and face hard. Mark pulls Maddy's red pubes as he porks her bunghole and grips her head for an ass-to-mouth face fuck with heavy spit. Orgasmic anal slamming makes her howl, buns flexing, and Maddy's butthole gapes. She swallows Mark's semen.

Maddy O'Reilly in 'Oil And Anal'

Maddy O'Reilly - Oil And Anal

Maddy O'Reilly thickly slathers her body in oil, from auburn hair to smoky eyes to natural tits to fleshy butt. She booty-claps as slick fluid sheets on her ass cheeks and floods her holes. Muscular, bearded Ramon Nomar stuffs three greasy fingers up her ass and feeds her the flavor. His big prick goes straight up her ass, pounding out moans and whines. Ass-to-mouth cocksucking makes Maddy gag. She talks dirty in a cheek-slamming anal ride, Ramon masturbating her clit. With her glistening legs pulled back, he alternates hammering butthole and pussy as Maddy blushes and cums. And she sucks his toes as he sodomizes her. Ramon pulls her oil-saturated hair and slaps her tits as he butt-fucks her. Maddy kneels for a cum facial.

Maddy O'Reilly in 'Cuckold Sessions'

Maddy O'Reilly - Cuckold Sessions

They're always up to something kind of stupid. Take Cuckold Charlie. He loves sports. The only thing he loves more than sports is gambling on sports. He calls most of his bets "locks" and "easy money". Then why does he owe the bookie 10 Large? Trust me, The Bookie is tired of chasing Cuckold Charlie around for his money. After a sound beating, it's on to Cuckold Charlie's house, where, Charlie claims, is all the money he owes The Bookie. Once there, however, there's no money. There is his girlfriend, Maddy.Maddy's shocked to see what's going on. She thought Charlie was all done betting. Charlie's such a degenerate gambler, he's going to be OK with Maddy's mouth, pussy, and ass acting as "the vig" until Charlie comes up with some hard cash. Does it really surprise you, too, that Maddy's got some skeletons in her closet? They're big, black skeletons!

Maddy O'Reilly in 'Pillow Talk'

Maddy O'Reilly - Pillow Talk

What's a girl supposed to do, when her husband is out of town and she's waiting patiently for her lover to show up and give her a hot afternoon of adulterous sex If she's anything like Maddy Oreilly, she'll get started on her own, teasing her plump pink nipples and pulling her panties aside to get a finger in her eager pussy. When Rob finally arrived, Maddy was so excited, she slid off her wedding ring and pounced right on his big black cock. After flicking her tongue over the tip of his member, Maddy two-handed the shaft and sucked Rob's cock until he couldn't wait another second to get it inside her. Maddy straddled Rob on the sofa, bouncing her big white butt on his rock hard manhood, then lay on her side so he could enter from behind, and give her a taste of his truly expert lovemaking.

Maddy O'Reilly in 'Magic Mike XXXL A Hardcore Parody Scene 2'

Maddy O'Reilly - Magic Mike XXXL A Hardcore Parody Scene 2

Award-Winning Director Brad Armstrong brings you a 'Ladies Night' to remember! Magic Mike, Dallas, and the rest of the boys are getting the women all Hot, Horny, and very much willing to please. Girls, we know you've been waiting for this one! And guys, don't worry... there's plenty of gorgeous women in here to make you happy too! So, tonight, do yourself a favor: Let her pick the movie!

Maddy O'Reilly in 'Buttman Toy Master'

Maddy O'Reilly - Buttman Toy Master

Auburn-haired, brown-eyed cutie Maddy O'Reilly visits John 'Buttman' Stagliano for a sensual exploration of her all-natural body and lustful soul. She shows off her shapely, fleshy butt -- with her dress tugged into her cheeks for a wedgie; twerking in a thong that forms a camel toe; and naked, outdoors. Buttman tests the depth of her crack with his nose. He torments her nipples with clothespins and wicked suction devices, one of which makes her clit throb visibly. Sucking huge dildos, Maddy's drool floods her face and body. A bejeweled metal butt plug expands her anus and Buttman captures cool ass imagery through a Lucite chair. Huge glass butt plugs plus a vibe on her clit give Maddy a howling orgasm; she sucks a plug ass-to-mouth. Soaking wet, she twerks good-bye, naked cheeks clapping.

Maddy O'Reilly in 'Double Black Penetration 2'

Maddy O'Reilly - Double Black Penetration 2

Super sweet, super pretty Maddy OReilly shows off her beautiful all natural body before diving into a double blowjob with two big, black cocks. Maddy can take it all, delivering some amazing deep throat action on both men. This dirty, brunette slut loves it and gags on each cock, lubing them up for the interracial 3 way action that's only going to get hotter from here. Watch as Maddy's puffy pink pussy is revealed and she deepthroats one black cock while another slides into her from behind. She is plugged at both ends and keeps the action going the whole time. This pretty slut loves to talk dirty and does the whole time, unless her mouth is full. Spitting, slapping and spanking while each cock takes its turn on her sweet pussy, pounding away. Maddy gets DP'd, hard, and loves having her pussy and ass pounded at the same time. She sure can take some big, hot loads on that pretty little face of hers.


Maddy O'Reilly in 'Rough Malpractice'

Maddy O'Reilly - Rough Malpractice

After learning his nurse Maddy Oreilly was stripping ass-naked in the examining room and giving some of his patients hand-jobs on the side for cash, Dr. Di Sergio had to step in and handle things personally. But when the Doctor tried to fire that redheaded slut, he ran into a larger headache than he expected. While Dr. De Sergio was trying to discipline Maddy, she kept putting the moves on him, using her best seduction techniques to talk the dick right out of his trousers and into her mouth. After getting his rock hard cock sucked on, Tony pulled Maddy's pants down and spanked her big round ass, then sprawled her out on the desk so he could pound her from behind.

Vicki Chase in 'Pretty Sloppy 06'

Vicki Chase - Pretty Sloppy 06

Auburn-haired Maddy O'Reilly, Latina beauty Vicki Chase and blonde superslut Jillian Janson are nasty girls in sheer white stockings and lacy lingerie. These sultry lesbians love nothing better than to gag themselves with dildos and drool wads of sloppy spit directly into each other's mouth! Each young lady takes her turn getting her asshole drilled with a fake cock ... as her girlfriends slobber with pleasure and lewdly lick her winking anus!

Maddy O'Reilly in 'Undisputed'

Maddy O'Reilly - Undisputed

Maddy O'Reilly's Ass Devours A Big Black Cock. Sultry, sensuous and possessing an ass built for sin, Maddy O'Reilly owns this interracial offering like she was born for porn. In this slice of UNDISPUTED Maddy deep throats Prince Yahshua and takes all of his big black cock in her nasty asshole. Quality whoring from a quality whore, watch.

Maddy O'Reilly in 'Caged Ass! These girls did the crime, now they do the anal time!'

Maddy O'Reilly - Caged Ass! These girls did the crime, now they do the anal time!

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.

Maddy O'Reilly in 'Babysit My Ass 5'

Maddy O'Reilly - Babysit My Ass 5

Adorable butt-slut Maddy O'Reilly submits to a bare-assed spanking from director Joey Silvera before joining sultry blonde Carter Cruise and well-hung stud Xander Corvus in a nasty threesome. The girls double-team Xander's huge cock, orally worshiping his balls and bunghole. They take turns anally riding him, then slurping his greasy tool ass-to-mouth. Maddy even gets double-penetrated when Carter straps on a butt-reaming dildo! Using her tongue, Carter helps clean a mess of Xander's hot cum off of Maddy's pretty face.

Ava Addams in 'Rocco's Perfect Slaves 4'

Ava Addams - Rocco's Perfect Slaves 4

Young, cutie Maddy O'Reilly is really annoyed by her older housemate: Busty bombshell Ava Addams is constantly having outrageous sex! Ava enlists her big-dicked pal Rocco Siffredi to loosen up Maddy. Before long, the Euro-stud is cramming his enormous cock down sweet Maddy's throat, and both fishnet-clad sluts are riding Rocco's dick in a nasty anal three-way. After some relentless ass fucking and kinky foot worship, the ladies share a hot load of Italian cum.

Maddy O'Reilly in 'Throated Contest 2014 - Maddy O'Reilly'

Maddy O'Reilly - Throated Contest 2014 - Maddy O'Reilly

Maddy O'Reilly may not be a size queen, she's an equal opportunity kind of gal, but she does appreciate a fellow that knows how to ram his meat down her throat with energy. She's a definite contender for Throat Queen! So get out the vote!

Maddy O'Reilly in 'Anal Buffet 10'

Maddy O'Reilly - Anal Buffet 10

Adorable, auburn-haired doll Maddy O'Reilly may look innocent, but this soft, young cutie has a secret lust for huge, hard dicks. When white stud Erik Everhard and older black cocksman Sean Michaels come over, Maddy's in heaven, kneeling to worship their throbbing shafts with her mouth. The all-natural slut rides one boner while sucking the other and enjoys a passionate double penetration. Her plump ass well fucked and gaping, Maddy gets rewarded with two creamy facials.


Maddy O'Reilly in 'Lex Is Up Her Ass'

Maddy O'Reilly - Lex Is Up Her Ass

Auburn-haired Maddy O'Reilly wears a pink fishnet body suit; lush-lipped, freckled brunette Jodi Taylor sports tight, revealing leggings. The girls flirt, massaging their scantily clad, pale, all-natural bodies. Lex teases them with his huge boner hanging from his pants. He tears open the crotch of Jodi's leggings as the girls kiss, and they kneel to share cocksucking duties. As Jodi takes a doggie-style fuck, Maddy spits into her hairy ass crack. Maddy rides the big black cock, her fleshy cheeks bouncing. Lex alternates pounding Ms. O'Reilly's tight backdoor and her red-haired cunt; Jodi slurps Lex's flavored bone, gets her box bored out and eats Maddy's twat. After lots of shared cocksucking, spit play and boning, Lex creams Jodi and Maddy's faces, and they share cum kisses.

Maddy O'Reilly in 'Balls deep in that white girl ass!'

Maddy O'Reilly - Balls deep in that white girl ass!

Monsters Of Cock! White girls love big black dicks. Just ask Maddy Oreilly. She came here begging to be on today's update. All she wants is to be pleasured in the best way possible. Meaning a big black dick stuffed balls deep in that tight asshole. Big Moe Johnson was the right person for the job. He loves to fuck innocent petite women that want to be manhandled. He went from ass to pussy, pussy to ass. Pounding Maddy Oreilly just the way she wanted it. Then dropped a huge load in her mouth to swallow Enjoy!

Maddy O'Reilly in 'Epic Asses'

Maddy O'Reilly - Epic Asses

After Maddy O Reilly teased us with her juicy oiled ass and wet pink pussy in front of the office we rushed over and had cock in hand ready for pussy. She put her fine booty in the air as she went down swallowing all our swollen inches balls deep. Of course after holding those cheeks we got her doggy and fucked her tight pussy hard making that butt ripple away. Maddy's huge ass had us wanting to erupt inside, but we got lucky and covered that ass instead.

Maddy O'Reilly in 'Fetish Fanatic 15'

Maddy O'Reilly - Fetish Fanatic 15

When lingerie-clad cuties Maddy O'Reilly and Abella Danger get together, get ready for some lesbian fireworks! These young ladies love to spend the afternoon worshiping one another's plump, jiggling ass and hungrily lapping at each other's juicy pussy. After getting each other off in an intimate, orgasmic session of face sitting and lewd anal rimming, Abella and Maddy cuddle and share a passionate kiss.

Maddy O'Reilly in 'takes on a huge cock'

Maddy O'Reilly - takes on a huge cock

Maddy comes by with her big ass and hunger for cock. She ends up taking on every inch of prince's huge dong and loving it. She a bit shy but totally opposite when she's fucking. its GREAT! She sucks him off and takes a hard pounding on various angles until she takes his load in her mouth.

Maddy O'Reilly in 'Lil' Gaping Lesbians 07'

Maddy O'Reilly - Lil' Gaping Lesbians 07

For gorgeous redhead Rose Red Tyrell and adorable Maddy O'Reilly, the number one way to spend a horny afternoon is in a haze of lesbian bliss, licking and sucking... and making each other's asshole gape widely. Using a fat dildo, Rose Red invades Maddy's elastic anus and lovingly laps at her sphincter as it yawns open. Next, Maddy returns the anal favor, expanding the entrance to Rose's big booty and tonguing the winking hole. Who needs guys?

Maddy O'Reilly in 'Maddy Oreillys Bikini Butt'

Maddy O'Reilly - Maddy Oreillys Bikini Butt

Nothing makes Maddy Oreilly horny like spending the day chilling out by the pool, getting her juicy ass wet and ready for action. Bill Bailey came by to satisfy her carnal cravings, and after teasing him for a while with her big bikini butt, she gave him a sweet extra sloppy blowjob. He fucked her from behind until her she was cumming hard, and then it was time for the main event: some intense anal sex! Once he was done fucking her juicy ass, Maddy talked dirty, begging for his jizz until he busted a fat nut all over her pretty face!

Maddy O'Reilly in 'White girl ass fucked by black dick'

Maddy O'Reilly - White girl ass fucked by black dick

White girl Maddy O'Reilly bring's her amazing big butt by to be praised before it gets fucked. She bounces her ass before she starts giving this big dong a good sucking and finally fucking it. It turns out is an anal scene and she doesn't disappoint. She ends up taking this big cock deep and hard until she gets to play with his jizz before she swallows.


Maddy O'Reilly in 'Drill Her Ass'

Maddy O'Reilly - Drill Her Ass

Pale brunette Maddy O'Reilly has natural tits and a patch of ginger pussy fur. She shows off her fleshy cheeks for director Mike Adriano, and the anal marathon is on! Maddy deeply tongues Mike's bunghole, with dirty POV eye contact. In a blow job/two-hand job, she slurps spit and sloppy slobber bubbles coat her chin, tit, his balls and the lens. His cock goes straight up her ass. After some ass-to-mouth fellatio, a lighted speculum shows slimy pink intestinal walls in graphic close-up. Maddy squirts gummy candies and lube from her anus, and a close-up reveals a greasy rectal prolapse. Ass reaming makes her whimper and her butthole gape widely. Maddy swallows the cum Mike shoots on her face.

Maddy O'Reilly in 'in I Have a Wife'

Maddy O'Reilly - I Have A Wife

Karlo is running out of options to fix his marriage. The fire and passion is gone between them and he wants to know what's causing that or how to get it back. He takes a visit to Maddy who is a psychic. She hits the nail right on the head figuring out they haven't had sex in a long time and that she sees infidelity in the relationship. Karlo's a little worried about this but, Maddy says that it is on his end and is willing to give him a helping hand. Karlo isn't sure he should go through with this and Maddy assures him that the cards are always right.

Maddy O'Reilly in 'Big Black Cock POV'

Maddy O'Reilly - Big Black Cock POV

Maddy O'Reilly Is Hungry For Some Big Black Cock. Today she awoke and knew she had to get a big black cock in her ass, soon. From BIG BLACK COCK POV here's your chance to fuck Maddy O'Reilly and to have a big black cock while doing so. A whore for interracial anal sex, Maddy obviously loves the taste of her own ass. Watch.

Maddy O'Reilly in 'Love Is In The Air'

Maddy O'Reilly - Love Is In The Air

When her fiancé gets sucked into never-ending conversation at a friend's party, a woman lures him to the bedroom for a passionate sexual encounter.

Maddy O'Reilly in 'Yoga Butt Sluts'

Maddy O'Reilly - Yoga Butt Sluts

Cute, natural Maddy O'Reilly loosens up on a yoga mat in brief, pink stretch fabric. Athletic Mick Blue guides her through poses and postures, her shorts riding up her crack, and her limber form puts temptation in his face. He peels off her shorts to rim her butthole and sits on a pink yoga ball for a slurpy blow job/face fuck with flowing gag spit. Maddy leans over the yoga ball, and straight up her asshole goes his meat. She whimpers and her bunghole gapes as her pussy queefs. Maddy sucks cock ass-to-mouth and masturbates as Mick sodomizes her. She swallows the thick jism he blasts onto her face.

Maddy O'Reilly in 'Sex On Wheels'

Maddy O'Reilly - Sex On Wheels

Maddy Oreilly is one of the freakiest sluts on the planet, and when she goes roller-skating, it's really just an excuse to find some big cock. So when Keiran fell into her and she got a feel of his dick, it was on. She got on her knees to give him a super sloppy public blowjob, then took him back to her place so they could really turn it up a notch. She took off his roller skates so that she could lick his feet and suck his toes, and then he fucked her up against the window so that all the passers-by could see. She licked his asshole and then jerked his dick until he gave her a nice facial cumshot!

Maddy O'Reilly in 'Alien Ass Party 2'

Maddy O'Reilly - Alien Ass Party 2

Beautiful, young alien captive Maddy O'Reilly is in a trance, completely under the mental control of director Joey Silvera. He blindfolds the stunning creature, and as he films POV-style, Maddy submissively gives the director a wet, slobbery, eye-watering, deep-throat blow job. Slurping away at Joey's stiff cock, Maddy drools and gasps, playing with the long, messy strands of spit she uses to coat his shaft. Finally, she jacks out a hot load of cum, licking every drop from her fingers.

Maddy O'Reilly in 'Heat Wave'

Maddy O'Reilly - Heat Wave

Maddy's boss may be handsome and sharp as a tack, but he's so shy and reserved. She's tried everything to entice him and tease him with peeks at her stockings and bod, but so far he hasn't taken the bait. If Maddy wants to pierce the icy cool of her Mr. White's reserve, she's going to need to hike up her skirt and waggle her plump butt, or go a step further and dip one of her breasts in his mouth. Finally, Mr. White jumped on the chance to bed his secretary, and his cock stood stiffly at attention. Lying across her boss's desk, Maddy wrapped her mouth around his cock, sucking it tip to tail while she tugged the shaft. Fulfilling a fantasy she had from day one on the job, Maddy got on all fours while Chad thrust into her from behind, pulling him deeper and deeper into her. Switching things up, Maddy sat on Chad's lap, and rode his dick until her hips bucked with the blissful feeling of orgasm.


Maddy O'Reilly in 'My Pet Pornstar'

Maddy O'Reilly - My Pet Pornstar

All in all, Bill Bailey has a pretty good life. Three meals a day, a roof over his head, and the best parents in the world. But when he finds out that they've been keeping a pornstar named Maddy Oreilly in the old spare room, he can barely believe his eyes! He peeps at her through the keyhole as she rubs her tight little twat, and then grabs the key to go get a closer look. As soon as he sets foot in the door, Maddy starts begging him to give her his big cock, and Bill Bailey aims to please. She gives that dick some nice sloppy head and then goes face down and ass up for a nice deep anal dicking. Bill fucks her ass hard and then blows a huge load all over her pretty face!

Maddy O'Reilly in 'Fetish Fanatic 14'

Maddy O'Reilly - Fetish Fanatic 14

Her leg in a cast, irrepressible brunette cutie Gabriella Paltrova masturbates with fingers and a glass toy. Enter natural-bodied brunette Maddy O'Reilly in the world's porniest nurse costume. She diddles herself on the bed near resting Gabi, then wakes her with cunt fingering, glass toy fucking and pussy eating. The girls share sensual kisses and strands of spit; they fuck each other's holes with glass toys and suck them clean, ass-to-mouth and ass-to-each-other's mouth; they trade warm, deep rim jobs and sniff assholes. Maddy sucks Gabi's good foot. The toy fetish includes glass balls stuffed up buttholes and squirted out, side-by-side. (One ball gets temporarily lost in Maddy's rectum.)

AJ Applegate in 'Stars And Stripes And Sluts Forever'

AJ Applegate - Stars And Stripes And Sluts Forever

It's the fourth of July, and Brick Danger has finally gotten his American citizenship. So how does a big-dicked stud like him celebrate such an impressive accomplishment? By fucking two of the sexiest big booty sluts he could find, of course! AJ Applegate and Maddy O'Reilly showed up in a couple of sexy little skimpy bikinis to wash down Brick's car, and as they soaped up each other's toned bodies, they made their big butts clap to get Brick ready for action. Brick fucked both those sexy sluts' big round asses, going deep in those bubble butts while AJ and Maddy came hard all over his big cock. Finally, he unloaded a big cumshot for them to share, because there's nothing more American than fucking big butt sluts!

Maddy O'Reilly in 'Anal Inferno 03'

Maddy O'Reilly - Anal Inferno 03

Adorable, sexy Maddy O'Reilly is offering her sweet young asshole to director Mike Adriano. This all-natural temptress lets the director lovingly tongue her anus. Next, she fills her colon with a fresh enema, expelling the water into a bowl. Maddy deep-throats Mike's massive cock until her eyes tear up, slobbering on his shaft so he can pound it deep inside her gaping rectum. Sucking ass-to-mouth, Maddy gets her sphincter stretched by a speculum... and swallows a mouthful of cum.

Maddy O'Reilly in 'Big booty white girl gets hard anal'

Maddy O'Reilly - Big booty white girl gets hard anal

We got a super sexy one today everybody. The beauty's name today is Maddy Oreily. When I seen her ass I started to drool. She knows exactly what angle her ass looks good in and it just happens to be all, lol. She gets pounded hard and sucks cock like she was born to do. she has that fuck me every minute and she totally said she likes it rough. So you can just imagine what is going down today on Mr. Anal

Maddy O'Reilly in 'Screaming Ass Gasms 2'

Maddy O'Reilly - Screaming Ass Gasms 2

Maddy OReilly's Ass Is Screaming For Cock. Screaming loudly too and when Maddy's ass screams Manuel Ferrara comes to the rescue. A gorgeous brunette with natural tits dressed in a see through dress and stripper heels, Maddy's hot. Cool tattoos and a cooler attitude Maddy O'Reilly satisfies......well. See her have SCREAMING ASSGASMS IN SCREAMING ASSGASMS 2. One hell of a ride.

Riley Reid in 'Rocco's Coming In America'

Riley Reid - Rocco's Coming In America

Gorgeous, young, all-natural models Maddy O'Reilly and Riley Reid are at Buttman's studio shooting a tender lesbian scene. Then who should arrive but Italian porn legend Rocco Siffredi? He takes over the scene, showing some of his groundbreaking sex techniques -- tugging at Maddy's sensitive nipples and choking her until she's in a masochistic daze of desire. He buries his face in Riley's sweet ass, and soon the adorable girls are kneeling to rim his bunghole and swallow his enormous cock. Rocco roughly manhandles these amazing sluts. They eagerly ride his giant pole and finally share a messy load of sperm.

Maddy O'Reilly in 'Super stacked'

Maddy O'Reilly - Super stacked

Maddy showed off her roller skating moves. We get to see her ass-jiggling as a bonus. As Maddy skated and told us how she needed her ass fucked, she got all hot and horny. Before we knew it, this plump sexy redhead had propped herself up on a kitchen counter and started rubbing her ass and pussy. Chris heard the commotion, grabbed that big ass, and plunged his tongue in. He cradled that ass, took her into the next room, and proceeded to fuck her ass and pussy long and hard. He made sure she got the asshole stretching she was begging for.


Maddy O'Reilly in 'in Naughty Athletics'

Maddy O'Reilly - Naughty Athletics

Maddy O'Reilly has been receiving volleyball lessons from Daniel. Since it's a bit windy out Daniel is looking to postpone his current lesson, but Maddy has other ideas. Since she can't take lessons on how to spike the ball she insist that they go back to her room where Daniel could spike his cock down her pussy.

Maddy O'Reilly in 'Maddy's 2nd Anal'

Maddy O'Reilly - Maddy's 2nd Anal

For her second anal scene Maddy needed to have twice the fun. She had to visit the city's underworld to find what she was looking for: two hung stallions to pound her ass. In a sordid warehouse the beautiful Maddy unleashes her lowest desires and gets treated the way she likes. See her perfect round butt take Ramon Nomar's reputed thick cock and the oversized shaft of current performer of the year, James Deen

Maddy O'Reilly in 'First We Play'

Maddy O'Reilly - First We Play

Bruce Venture has given himself over to his woman's ample charms, allowing himself to be blindfolded and tied up by the delectable Maddy O'Reilly. This smoking hot babe has plans for her beau, and nothing will stop her from getting what she wants!After a few lightly teasing touches, Maddy works her way down Bruce's body with warm breath and soft kisses. She settles on her knees between his legs and caresses him gently before licking and gently biting her man's rock hard cock through his pants to give him a preview of things to come. Moments later she has unbuckled her guy's belt and pulled his dick out so that she can really tease him with her smiling eager mouth.Too hot to ignore her own needs, Maddy soon straddles Bruce's lap and commences a slow seductive lap dance that presses her thong-clad pussy against her beau's rock hard cock. The lace adds a new dimension of pleasure to the blindfolded Bruce, who only knows that he loves what he feels. As Maddy gets her thighs and hands involved, her beau can't help but groan in ecstasy.This cock hungry lady can't ignore her need for too long. Slipping her thong to the side, she gives herself a small treat by impaling herself on her beau's dick. Loving the way that feels, she kicks off her panties and fills her landing strip pussy to the brim with Bruce's stiff rod.Her strokes up and down remain slow and playful as she uses her man as a personal sex toy, but Bruce doesn't mind at all. He's just enjoying the knowledge that Maddy is getting hotter and wetter by the moment as her shirt comes off and her thrusts speed up.Finally willing to let the game of restraint end, Maddy unties Bruce and gasps in pleasure as he wraps his arms around her and wildly buries his face in her breasts as his hands guide her pumping hips. His seated position doesn't offer the power he craves, so he picks his woman up and carries her to a nearby table where he delivers a hard and fast pussy pounding that leaves Maddy whimpering her excitement.Flipping Maddy over, Bruce enters her doggy style and resumes his quick pace so that Maddy's generous tits bounce and swing. That's all it takes to bring Maddy off, until her hips are bucking and her whole body is pulsing with her orgasm.Moments later, Bruce reaches the edge of his own endurance and pulls out so that he can release his load all over Maddy's lush rump and thigh.

Maddy O'Reilly in 'Tasty trio'

Maddy O'Reilly - Tasty trio

The girls had just come back from having a fun time out, and now it was time to have fun with each other. They were all looking so hot in those tight, short dresses. Maddy, Malena and Megan then began to kiss and undress each other. Maddy sat her juicy round ass on Malena's face while Megan munched on her pussy. Megan licked Malena's pussy while Maddy sucked on her toes. The girls licked each others sweet pussies and assholes until ever hole got its proper attention. Then Maddy fingered Megan's pussy while Malena played with her sweet jugs. It was another fantastic day of living together.

Maddy O'Reilly in 'Fetish Fanatic 13'

Maddy O'Reilly - Fetish Fanatic 13

With their pale, natural bodies adorned in matching ponytails and sling bikinis, dirty blonde Lia Lor and dirty redhead Maddy O'Reilly could be twins. Director Aiden Riley, an aficionado of colorful kinks and real lesbian play, pairs them for a long, extremely soaking session of mouth kissing, slobbery spit splashing, choking, pussy fun, foot sucking and fucking, ass tasting and massive, torrential female ejaculation. The girls caress titties and scissor. Lia sits over Maddy's face and squirts teeming blasts of girl juice all over her, then mops the drenched hardwood with Maddy's hair! Maddy slides Lia's little body around on the flooded floor.

Maddy O'Reilly in 'The Family That Lays Together'

Maddy O'Reilly - The Family That Lays Together

After his mother falls ill, a woman's (Maddy O'Reilly) obsession with becoming her stepfather's (Mark Wood) wife gives way to a twisted, illicit arrangement.

Maddy O'Reilly in 'Tag team'

Maddy O'Reilly - Tag team

Logan was trying his best with his tongue to make Maddy feel some oral pleasure. She wasn't feeing it though. He needed some serious help, so she just leveled with him. She told him that she was fucking with an older lady from next door, and she did it properly. Maddy said Kendra would most likely help, and Logan said he would do whatever it took to satisfy her. They all got together, and Kendra took over from there. She pulled down Maddy's jeans and panties while she had her bent over on all fours. While her ass was in the air and cheeks spread wide, Kendra had her way with Maddy's asshole. Kendra called over Logan after Maddy's ass was primed for the taking. Kendra sucked him off to make sure his dick was as hard as it was going to be. He fucked his girl while she licked up Kendra's delicious pussy. Kendra saw Maddy come from Logan's dick, so she wanted to do the same. They finished him off with a blow job like no other.

Maddy O'Reilly in 'Strap Attack 18'

Maddy O'Reilly - Strap Attack 18

Maddy O'Reilly is especially girly in a crop-top, flouncy skirt, fishnets and a tiara -- she's the Homecoming Queen! But she hates gruff boyfriend Wolf Hudson, who said she'd never win the crown. Queen Maddy dons a strap-on, and he gags on her dong as she crams his head down. She makes him spell out L-O-S-E-R with each stroke of her riding crop to his ass and balls! She fucks his asshole with the crop and her strap-on while writing 'LOSERS GET FUCKED' in marker on his back. He sucks her dong ass-to-mouth, licks her asshole and wears her tiara as she fucks him. Her Highness fingers his asshole as he jacks off and eats his cum from her tiara.


Maddy O'Reilly in 'Puss and boobs'

Maddy O'Reilly - Puss and boobs

Dillion and Maddy had themselves a sexy seductive weekend planned where they could just get away from it all and enjoy each other. Early one morning Dillion was basking in the sunlight and getting dressed when Maddy joined her. Maddy was admiring the scene and started to get wet, as she watched Dillion's plump full breasts. Maddy quickly changed the direction of the moment, as she embraced and fondled Dillion. They kissed and rubbed each other softly, and we could see where this was going. They quickly moved back to the bed where Maddy took control, threw Dillion down and plunged her tongue deep between her pussy lips. The girls went back and forth, as they licked each others pussies and assholes until both were content. In their overwhelmed and satisfied states, the two girls laid back together and shared their warmth and serenity.

Maddy O'Reilly in 'Ass Worship 15'

Maddy O'Reilly - Ass Worship 15

Maddy OReilly Caution! Ass Demolition...Ass whore. Maddy O'Reilly is an ass whore. A natural brunette with a big round ass, Maddy starts with toys up her ass, graduates to a big cock up her ass, checks thoroughly for taste then repeats steps two and three repeatedly. From ASS WORSHIP 15 this sultry, brazen, gaping, cock monster takes it up the rear as naturally as water flows off a ducks ass. Maddy O'Reilly, ass whore extraordinary.

Maddy O'Reilly in 'Anal Perverts 02'

Maddy O'Reilly - Anal Perverts 02

Anal pervert Mike Adriano pairs cute Maddy O'Reilly (in fishnet outfit that can't contain her bubble butt) and pretty brunette Jodi Taylor (in red and black lingerie) for a spit-soaked sodomy session, and tease footage shows the girls' sexual chemistry. Mike Frenches each girl's asshole and then the other's mouth. The girls rim each other and tongue Mike's bunghole; Mike fucks their mouths and they play with stringy slobber. A marathon butt fuck makes Jodi's asshole gape for Maddie's drool and tongue, and Maddie sucks Mike's ass-flavored dick. The girls' faces get fouled with spit and spunk.

Maddy O'Reilly in 'Lex Turns Evil 02'

Maddy O'Reilly - Lex Turns Evil 02

Dirty blonde Maddy O'Reilly's tight see-through dress can't contain her meaty ass cheeks, and her collar labels her a SLAVE. A black dildo warms her up for her date with African-American pornographer Lexington Steele. When he arrives she blows him, rubbing his huge, dark dick all over her face. He fucks her doggie-style, on her back and with Maddy astride. Riding cock, she wriggles her lily-white ass and requests hard smacks. Maddy slobberingly sucks dick and licks balls, and she wallows in the spermy mess Lex sprays on her face.

Maddy O'Reilly in '1st Anal'

Maddy O'Reilly - 1st Anal

Maddy O'Reilly is so excited for her first anal sex scene. Of course so is Manual Ferrara, he is more than happy to offer his thick and hard service to Maddy tight sexy ass. She quickly spread her cheeks and is more than ready and willing to received his cock. Manual gives her some litteral deep and hard lessons in anal sex. After this ass-fucking education, Maddy wants his cum all over her cute face.

Maddy O'Reilly in 'Rear View 4'

Maddy O'Reilly - Rear View 4

Maddy OReilly Anal Who Wants To Tap This Ass? It's so nice to be appreciated and Eric Everhard is appreciated by Maddy O'Reilly for the way he fucks her ass. An all natural brunette with a big ass and a desire to be ravished, especially from behind and in the ass, Maddy is the answer to your dreams. Voluptuous and volatile Maddy is a whore not to be missed, so don't.

Maddy O'Reilly in 'Blacks On Blondes'

Maddy O'Reilly - Blacks On Blondes

We're winding down 2013 with some of the nastiest black cock sluts under the sun. Please meet Maddy O' Reilly and her killer body. Maddy is dressed in clothing that would make the most seasoned sluts blush. However, nothing else matters to her EXCEPT that she wants to please Charlie Mac and the 11 inches he's packing. Maddy lets loose by sucking on his big black cock with her amazing ass pointed directly at the sky. The worshiper of mighty black cock takes her slutiness up to level 10 as Charlie goes nuts on her tight, white pussy. Well, it USED to be tight...but that's another thing. Maddy gets then fucking of her life as Charlie doesn't give that white pussy any mercy. With each thrust Maddy's eyes gets wider and her pussy gets stretched more and more. Christmas comes early when Charlie does.....all over that pretty face of Maddy's.

Maddy O'Reilly in 'Interracial Blowbang'

Maddy O'Reilly - Interracial Blowbang

What happens when you add one dirty white girl with nearly a dozen angry black guys? Answer: you get an interracial blow bang that's completely off the charts. Maddy O'Reilly joins a huge list of white girls that are offering their oral services in order to ease the pain and suffering the black race has been facing for centuries. After an inspirational monologue by the crew, Maddy works her way down the line, teasing each big black cock before the mayhem truly begins. Maddy's mouth meets every single inch of black cock presented to her welcoming face. The gang of guys take turns treating her throat to missile after missile of militant black cock. Maddy's ordeal hits its curtain call when her beautiful face welcomes nearly a dozen cannon blasts of black gravy.


Aiden Starr in 'Orgy Masters 4'

Aiden Starr - Orgy Masters 4

More White Booty Than 3 Black Men Can Handle. Well not really, these are three of the most competent dudes in adult but there's five hotties and these whores are horny. Aiden Starr: great natural tits. Phoenix Marie; blonde bombshell. Brooklyn Chase; brunette with big natural tits. Maddy O'Reilly; sultry cock monster and Veruca James; petite anal whore. All the sluts start in silver bikinis and high heels but soon they're deep in an interracial orgy that has double penetration and more. Phoenix Marie gets DP'd as she's sucking cock (air tight) so all her holes are plugged with cock except her ears. How many times do three black cocks go into five white cunts?

Maddy O'Reilly in 'and Bill Bailey in My Sisters Hot Friend'

Maddy O'Reilly - My Sisters Hot Friend

Maddy is awaiting Bill to to take her to the airport when she finally hears a knock at the door. Bill asks why his sister wasn't the one to see her off since they are best friends. Maddy tells Bill that his sister has her finals for school and couldn't make it. Maddy is ready to go but, Bill tells her she has loads of time and that they should just relax in the house. Bill has had a crush on Maddy for a while, he realizes that she won't be coming back for some time and this is his last chance to let her know how he feels! When he tells her she lets him know that she had a crush on him too though, she never did anything about it because she didn't want it to be a weird situation around his sister. Well, his sister isn't around, and she's leaving for the semester! They skip to the courtship and get straight down to business!

Maddy O'Reilly in 'and Jessy Jones  in My Sisters Hot Friend'

Maddy O'Reilly - My Sisters Hot Friend

There's a terrible earthquake while Maddy O'Reilly is over at her friend's house and she runs to the nearest safe place she knows of....her friend's brother's arms. She feels so safe in his embrace after such a horrifying incident yet so happy that he was there to comfort her. She wants to show him just how thankful she is for his protection the only way she knows how, by riding his dick.

Maddy O'Reilly in 'Maddy OReilly Gets The Brother Load 1st Interracial'

Maddy O'Reilly - Maddy OReilly Gets The Brother Load 1st Interracial

Maddy OReilly Gets The Brother Load 1st Interracial. Look at Maddy's pictures, she's beautiful. This brunette hottie is also a crowd pleaser. In a scene from THE BROTHER LOAD 5 Maddy starts with Prince Yahshua's cock down her throat then, as she's getting fucked, she tells Prince "don't stop", "don't stop fucking me", "I love that cock". Maddy O'Reilly likes it hard. Check out the part when Prince is choking her neck while fucking her as hard as he can and Maddy loves it! After Prince nuts the Brother Loaders enter. Five black dicks to service is not daunting for our super whore and soon her face is covered in the brother's loads. Like I said, a real crowd pleaser. Do not miss out on Maddy O'Reilly.

Maddy O'Reilly in 'Maddy Sucks You Off'

Maddy O'Reilly - Maddy Sucks You Off

Slutty Maddy O'Reilly always love to give oral satisfaction. So when you whip out your hard hunk of man meat for her to enjoy, she can't wait to get to sucking. She starts off slowly talking naughty then spitting and jerking you off. She definitely knows what she's doing. She then starts begging for your cum like the little cock hungry slut she is. You gladly empty your balls of nice warm jizz all over her!

Maddy O'Reilly in 'Maddy's Naughty Twin'

Maddy O'Reilly - Maddy's Naughty Twin

This evening you want a taste of some young tattooed piece of ass. You love your wife but can't fight that lingering feeling of a fresh teen fuck. You tell her that your boss is keeping you late at the office and order up a little bit of Maddy O'Reilly . She show up looking slutty as hell and ready to perform acts your wife has never even heard of. Maddy quickly changes and returns ready to be your perfect fuck slut! You pound this young tight pussy and make her moan with every hard pump of your rock hard dick! Thank you Maddy!!

Bridgette B in 'Manuel Ferrara Gangbanged By A Pornstar Army'

Bridgette B - Manuel Ferrara Gangbanged By A Pornstar Army

This is every guys dream, one guy and a half dozen fine ass sluts and the whores all want the one dick. There's ass eating, pussy licking, cunt fucking, ass banging, face sitting, cum swapping and facials. All this group sex performed by absolute hotties. Bridgette B, Anikka Albrite, Riley Reid, Remy LaCroix, Ashley Fires, Maddy O'Reilly, Christie Stevens and six more super sluts. This is every guys dream but only one guy proves he has what it takes, Manny's that guy. Live vicariously through Manuel Ferrara and life is good

Maddy O'Reilly in 'My Sisters Hot Friend'

Maddy O'Reilly - My Sisters Hot Friend

Maddy and Marie are on their bicycles riding over to Danny's house to meet up with his sister. The speedy duo runs right into the back of Danny's leg while he's walking home. Sitting on the ground with his pants torn and his knee in pain he tells the speed demons that his sister is not even home. They help Danny up and walk him home to tend to his knee. While Danny is still angry at them for nearly breaking his leg, they ask if there's anything they can do to help and with his sister gone their imaginations run wild. The pain from Danny's knee has just moved to his dick and the tight little pussies of these natural beauties is just the cure!


Maddy O'Reilly in 'Spandex Loads 7'

Maddy O'Reilly - Spandex Loads 7

Clothing company CEO Kevin Moore does a test shoot with young photo model Maddy O'Reilly, showcasing her perfect, round ass in various styles of form-fitting spandex leggings. Wearing high heels, Maddy arches her back to accentuate every curve of her all-natural body, and soon Kevin is rubbing his stiff dick between her Lycra-clad buns. The aspiring slut wraps her lips around his boner, servicing her employer with a slurpy POV-style blow job, then gets on all fours for a doggie-style fuck. Several changes of outfit later, this fashionable, well-fucked girl kneels for a messy cum facial.

Maddy O'Reilly in 'Tongue In Cheek'

Maddy O'Reilly - Tongue In Cheek

Mature personal trainer Kendra Lust gives adorable, young Maddy O'Reilly a lesson in stretching and proper posture. These sultry, glamorous ladies are packed into form-fitting spandex, their shapely bottoms outlined as they share a sensuous workout. Next they put on wicked platform pumps, and Kendra eagerly massages the young girl's soft butt cheeks before burying her face in Maddy's juicy ass. Maddy probes the busty brunette MILF's anus with her tongue. They enjoy a lewd session of butt licking pleasure and slippery, well-oiled ass grinding.

Riley Reid in 'Going Rough on the Muff'

Riley Reid - Going Rough on the Muff

Whenever Riley Reid gets into one of her nympho moods, one partner isn't enough to satisfy her cravings for the deepest, hardest fucking possible. She calls over Keiran to join in all the naughty fun banging her big-booty fuck buddy Maddy O'Reilly on the sofa. Face-sitting, finger-fucking, cock gagging, these hot babes don't leave anything out in their hot threesome, captured in all its HD porn glory!

Maddy O'Reilly in 'Maddy O'Reilly'

Maddy O'Reilly - Maddy O'Reilly

Maddy O'reilly may be young but she is one of the finest deepthroaters in the game. We had a lot of fun with this little devil…She was so excited to take the deepthroat challenge, and oh boy did we enjoy giving it to her!

Jada Stevens in 'Locker Room Hijinks'

Jada Stevens - Locker Room Hijinks

Jake loves spying on the cheerleaders in the locker room. Those perky little tits bouncing as they pull on their sexy uniforms! But when Jada, Kennedy, and Maddy catch the peeping tom in the act, they decide to strip him down and show him just how their pussies taste!

Maddy O'Reilly in 'Tanlines 03'

Maddy O'Reilly - Tanlines 03

Super-sweet, young Maddy O'Reilly is a sun worshiper; her skin is a light caramel hue, but flawlessly pale inside her bikini tan lines. This gorgeous slut teases director Kevin Moore's camera, peeling out of her bathing suit and spreading tanning oil all over her glistening skin. Kevin films POV-style as Maddy wraps her lips around his hard boner and slurps hungrily. She straddles his dick and rides, then lures him indoors; he slides his prick inside her hairless pussy, fucking her from the rear. After a hard dicking, Maddy gets her tan-lined ass decorated further with some hot splooge.

Kirsten Price in 'I Dont Need A Babysitter'

Kirsten Price - I Dont Need A Babysitter

Maddy is psyched that her parents are going out of town for the weekend, until she finds out that dyke Kirsten across the street is going to be keeping an eye on her! At first Kirsten is a real bitch, making her clean and scrub the bathroom, but then Maddy realizes the advantages to having a hot sexy lesbian in her shower...

Francesca Le in 'Facial Vi0lation 2'

Francesca Le - Facial Vi0lation 2

Suburban pornographer Mark Wood is shooting some sexy photos with big-assed blonde beauty Anikka Albrite. She starts giving him some attitude, so Mark's dominant wife, Francesca Le, teaches the bratty model a lesson - shoving her fingers down Anikka's throat and making her swallow Mark's huge, throbbing cock while he films the slutty action POV-style. Francesca pinches the poor girl's nose shut, yanks her by the hair and stretches Anikka's lips wide to shove her hubby's meat to the back of her throat. After a wet, nasty facial violation, Anikka takes a messy cum load in her open mouth.


Maddy O'Reilly in 'Suck Balls 3'

Maddy O'Reilly - Suck Balls 3

Gorgeous, all-natural Maddy O'Reilly is a glamorous, young slut with an insatiable hunger for hard cocks and swollen ball bags. This slender, sensuous dicksucker goes right to work on director Jonni Darkko's raging boner, giving him a lewd POV-style blowjob with plenty of nasty ball-sucking action. Maddy deep-throats the director's meat with professional skill and wetly slurps on his testicles, gagging with submissive delight. She kneels and buzzes her pussy with a vibrating wand as Jonni splatters her pretty face with hot, messy sperm; already dripping goo, the beautiful girl sucks out the last drops of Jonni's cum.

Maddy O'Reilly in 'Beyond sexy'

Maddy O'Reilly - Beyond sexy

After a couple hours at the mall trying on new outfits and teasing each other because we weren't wearing any ting under our dresses, we had to get back to our little get away hotel spot. We were so turned. As soon as we got into our room, we stared kissing. We continued onto the bed and stripped down. We slobbered on each other pussies for some afternoon ecstasy. Maddy wanted to please me even more, so she had some extras. She tongued my ass for what seemed like hours. She got me so wet and excited. After we heated up the bed, we had to take cool off a bit in the shower. We didn't leave the action in the bed though. We continued our pussy munching in the shower until we couldn't keep our legs from shaking with pleasure anymore.

Maddy O'Reilly in 'and Johnny Castle in Naughty Rich Girls'

Maddy O'Reilly - Naughty Rich Girls

Dainty little rich girl Maddy O'Reilly is going on a blind date with a friend of a friend, but when he shows up dressed down all casual and dirty from his motorcycle ride, she's appalled. When he goes to the bathroom to clean himself up, she desperately calls her friend back and tells her that she's scared for her life. But when he cleans up well, Maddy's pleasantly surprised ... but it's too bad Johnny heard the spoiled, ungrateful rich girl's conversation with her friend, because now wants to bounce out! But Maddy pleads for him to stay ... by getting on her little rich knees and hands and sucking his dick! Turns out she's dirtier than he is ... especially with a faceful of cum!

Maddy O'Reilly in 'Obedience School Part 1'

Maddy O'Reilly - Obedience School Part 1

Auburn-haired girl-next-door Maddie O'Reilly sends her husband to work. Out shopping, she feels she's being watched. Later, an intruder breaks into her home, spies her as she sleeps in thong panties, then binds and blindfolds her in a closet. He touches her with a knife, thrusts his cock into her face ... and she's into it. Maddie promises to be good and gives up control through choking, spanking and a hard fuck. 'Tell me I'm dirty,' she whimpers, and he jerks off on her face. The intruder is her husband, and Maddie calls this, 'the best role play ever.'

Maddy O'Reilly in 'Wet Food 4'

Maddy O'Reilly - Wet Food 4

Dolled up in a pink bikini with matching high-heeled pumps, stunning Maddy O'Reilly masturbates with a vibrating wand, getting warmed up for a nasty party with nine of her closest male friends. There's nothing this adorable slut enjoys more than wet, slobbery blow jobs! Soon Maddy is surrounded by a crowd of enormous, throbbing cocks; the guys take turns brutally fucking her pretty face, making her gag and drool; smearing her make-up into a sloppy mess. After this nasty deep-throat party, the gorgeous girl kneels for a series of cum facials that leave her dripping with spit and gooey sperm.

Maddy O'Reilly in 'Sticky And Sweet'

Maddy O'Reilly - Sticky And Sweet

Dressed in matching black lingerie, Maddy O'Reilly and Natalia Star exchange a lingering kiss over their man Giovanni Francesco. Giovanni is content to watch as both of his women flirt and tease each other above him, slowly removing their matching lingerie until they are both nude.Rising to his knees, Giovanni switches places with Maddy. He positions himself so that Maddy can kiss his erection as she lies on the bed, and so that Natalia can join in the fun by leaning over from above. The two girls take their time worshipping their man's hard cock, sucking and licking.Soon, the lovers reposition themselves so that the pleasure they are generating is distributed equally among all three of them. Maddy remains on her back with her face buried in Natalia's warm juicy pussy and Giovanni's dick deep inside Maddy's tight sheath. As Maddy grows closer to her climax, Natalia drops to her hands and knees beside her friend to tease Maddy's hard nipples with her mouth. Giovanni follows suit, sliding down his belly and using his tongue to eagerly lap at Maddy's tender nub and send her falling over the edge.Natalia climbs to her hands and knees to present her luscious ass to Giovanni. He takes her invitation, sinking into her plush warmth and thrusting with long sure strokes. As Maddy recovers, she is eager to take part in her lover's pleasure. She reaches out to fondle Natalia's tender clitoris, inching steadily closer until she can suckle her friend's big breasts as well. With such devoted attention, Natalia is soon moaning and gasping her ecstasy.The trio takes a moment to catch their breaths and reposition themselves before things heat up again. Starting at Natalia's sensitive feet, Maddy begins kissing her way up her friend's body. She doesn't get very far before Giovanni takes advantage of her open position and anchors her hips so that he can slide into her warm wet channel.Stymied in her climb up her friend's body, Maddy reaches forward to slide a finger into Natalia's tight twat while Natalie takes charge of her own pleasure, massaging her clitoris as she watches her lovers move together.After a second body-shaking orgasm, Maddy finally reaches her goal of nuzzling and licking her friend's weeping pussy. Giovanni is ready to help Natalia cum again, lying down on the bed so that his woman can crawl on top of him and slide down so that they come together in reverse missionary style. Maddy is there to help both of her lovers feel incredible, licking Giovanni's balls as he thrusts in and out of Natalia's warmth, and then massaging her friend's hanging tits as Natalia climaxes again. Satisfied twice over, the girls fixate all of their attention on helping their man cum. They help Giovanni to his knees and take turns sucking and pumping his pulsing erection until he is on the edge of ecstasy. With a few quick flicks of her wrist, Maddy helps him finally achieve his climax all over Natalia's ample bosom. Never one to let a delicious treat go to waste, Maddy leans forward to lick Giovanni's essence from her friend's chest. When she has lapped her sticky treat up, the two girls exchange a long kiss as they share their man's flavor.

Maddy O'Reilly in 'My Amazing Girlfriend'

Maddy O'Reilly - My Amazing Girlfriend

Maddy O'Reilly is intent on giving her new boyfriend Johnny Castle an afternoon to remember. Dressed in sheer lacy lingerie, she gets things started with a hot, intimate blowjob. Things ratchet up a notch as Maddy removes her filmy bra and brings her tits together to rub her man's cock in the valley of her cleavage before taking him back between her plush eager lips.When Maddy stands and turns around to allow her guy to remove her panties, she shows him that she's not done teasing yet by bending forward and allowing him to slide his erection through the split in her luscious ass before he buries himself deep in her welcoming heat.The lovers soon shift to doggy style with Maddy supporting herself on the coffee table. As Maddy grows closer to her ultimate culmination, though, they return to the couch so that she can ride her man while maintaining intimate sensual eye contact as her orgasm pulses through her.When she has taken a few moments to recover, Maddy lays herself out beside Johnny and resumes her interrupted blowjob. Under such a pleasurable assault, Johnny cannot last much longer before emptying himself into Maddy's waiting mouth. She swallows every drop of her man's essence, taking her time licking her fingers and lips with a contented smile.

Maddy O'Reilly in 'The Kinky Cafe'

Maddy O'Reilly - The Kinky Cafe

Hot girl locked inside a kinky cafe and sexually dominated.


Cassandra Nix in 'Snail Trails'

Cassandra Nix - Snail Trails

When sexy, young girls play together, there's no telling what nasty mischief they'll get into! Slender, all-natural beauties Cassandra Nix and Maddy O'Reilly, dressed in seductive bras and panties, kiss passionately; the gorgeous lesbian lovers lick each other's perfect tits and finger their sensitive pussies. Dipping into a vat of sticky lube, they coat each other with the stringy, clear goop and inject their pretty twats with the sloppy mess. Slathered in slime, they indulge in an intimate session of Sapphic lust. Finally, Cassandra and Maddy swap mouthfuls of girl glaze and grind their slick pussies to climax.

Maddy O'Reilly in 'The Hooker Experience'

Maddy O'Reilly - The Hooker Experience

Young stunner Maddy O'Reilly is a brand new call girl nervously easing into professional escorting. When a respected out-of-town client lures her with the promise of a large payday, the beautiful rookie agrees to schedule a discreet meeting at his hotel room. At his request, Maddy wears red lipstick, high heels and sexy lingerie that emphasizes her adorable, all-naturally petite figure. She leans back and spreads her thighs, stroking her pretty pussy, then sensuously sucks her customer's hard boner. Soon Maddy's riding his stiff dick in several positions, then kneeling to receive a hot cum facial.

Maddy O'Reilly in 'Playing Footsies In The Girls Room'

Maddy O'Reilly - Playing Footsies In The Girls Room

Two cute co-ed's seduce teacher with their sweaty socks and feet and end up in a kinky threesome with feet, wet soles, fucking and a 4 foot foot job!

Maddy O'Reilly in 'All I Want'

Maddy O'Reilly - All I Want

Maddy O'Reilly has waited in just a sheer bra and panties all day for Marco Rivera to come home, and now that he's here she's intent on seduction.Dropping to her knees in front of her man, Maddy helps him out of his shirt and pants and then leans forward without breaking eye contact to lick her way up Marco's long erection. Settling in for a long, thorough exploration of her man's cock with her mouth, Maddy alternates between sucking and licking at her man's penis in an amazing blow job. As Marco nears the end of his endurance, Maddy stands up and slips out of her panties so that she can climb atop her man's erection and sliding him home into her tight wet sheath. She rides him slowly, bending down to kiss him before guiding his hand up to cup her sensitive breasts.Climbing off of her stud, Maddy takes a moment to re-lubricate her man's cock with her mouth before she mounts him again reverse cowgirl style. After a few hard thrusts, Maddy switches places with Marco, positioning on herself on her hands and knees with her ass high up in the air as a supplication to her man to take her. Marco pushes himself into Maddy's luscious warmth, but then pulls out and kneels down so that he can eat his woman out from behind.As Maddy moans and writhes in pleasure from her man's ministrations, Marco once again rises to his feet and takes her doggy style. The action is fast and furious as Marco pounds in and out of Maddy's pussy.The passion between this couple truly ignites as Marco leans forward while he thrusts to kiss passionately at Maddy's neck and back. Maddy responds instantly, moaning and whimpering at the seduction.When her orgasm is nearly upon her, Maddy turns over to lie on her back so that she can make eye contact with Marco while he pushes her over that last little cliff. Her climax rocks through her, and she moans and quakes as pleasure overcomes her.The moment Maddy stops shaking from her pleasure, Marco reaches the end of his endurance and pulls out so that he can cum all over his lover's slender belly. Sated, the lovers come together for one last kiss as they bask in the afterglow of their encounter.

Maddy O'Reilly in 'and Mick Blue in My Friend's Hot Girl'

Maddy O'Reilly - My Friend's Hot Girl

Mick comes over to his friend's house to find his friend's girlfriend doing a sexy webcam show. Maddy's boyfriend doesn't know about it, and Mick gets to sit and watch if he doesn't say anything. But he gets more than he bargains for when he whips out his cock.

Maddy O'Reilly in 'Strap Attack 17'

Maddy O'Reilly - Strap Attack 17

Trim, all-natural Maddy O'Reilly challenges skinny boyfriend Kade to a pole dancing competition. After his predictable defeat, Maddy decides to add to his humiliation by making him eat her asshole, worship her spiked heel... and take her strap-on dildo up his wimpy butt! This kinky, young beauty licks Kade's pucker and works a fat vibrator up his rectum while he strokes his dork with his trembling hand. Soon Maddy's corn-holing his tight bottom and jacking hot semen out of his shaft; she scoops up his goo, coats her fake cock with it and makes her bitch-boy suck it clean!

Maddy O'Reilly in 'Hardcore'

Maddy O'Reilly - Hardcore

Petite sex fiend Maddy Oreilly warms up her tight pussy with her fingers before an intensely passionate fuck on her hands and knees


Maddy O'Reilly in 'Maddy OReilly Likes Cum Before Coffee'

Maddy O'Reilly - Maddy OReilly Likes Cum Before Coffee

Maddy O'Reilly Likes Cum Before Coffee. From BED HEAD AND MORNING SEX here's a portrait of a girl who'd rather wake to a cock in her mouth than the smell of fresh coffee. Maddy O'Reilly, a teenager of ill repute, no sooner than upon awakening dives on the first dick she sees, good girl.

Dana Vespoli in 'Slutty and Sluttier 17'

Dana Vespoli - Slutty and Sluttier 17

Petite, fashionable Maddy O'Reilly finds herself watching a hard-core video and getting hot and bothered. In walks stunning brunette Dana Vespoli, who immediately dominates young Maddy: bending her over the couch, exploring her pretty pussy, smothering the sweet girl's pretty face with her shapely ass. The ladies are joined by well-hung businessman Steve Holmes; he grabs Maddy by the hair, shoving his huge cock down her throat. Dana orally pleasures the brown-haired beauty. Maddy rides Steve's hard pole and sucks his shaft directly from Dana's flavorful asshole. When he finishes, Maddy laps his spunky load off of Dana's butt.

Maddy O'Reilly in 'Maddy OReilly, Tanya Tate Kitten Vs Cougar'

Maddy O'Reilly - Maddy OReilly, Tanya Tate Kitten Vs Cougar

Maddy OReilly, Tanya Tate Kitten Vs Cougar. Tanya Tate's the cougar, Maddy O'Reilly's the kitten and the cock is Michael Stefano in this slice of COUGARS, KITTENS & COCK 2. A three way volcanic in it's execution and gifted by Maddy O'Reilly an incredible whore in training. Hot stuff.

Maddy O'Reilly in 'My Sisters Hot Friend'

Maddy O'Reilly - My Sisters Hot Friend

Maddy O'Reilly is supposed to watch a movie with her friend, but she's nowhere in sight. When her friend's brother comes over looking for his sister, Maddy tells him that she ditched her, so he should stick around and watch the movie with her. But she's more interested in making a movie with Giovanni ... the kind that involves a sloppy blowjob and good pussy-eating!

Maddy O'Reilly in 'G Spot O Face'

Maddy O'Reilly - G Spot O Face

Sexy, brainy Maddy is the undefeated Wurdzz championship winner. This year's tournament is off to a rocky start when she suspects Johnny, another contestant, of smuggling letter tiles in. Furious, Maddy demands Johnny be strip-searched. He agrees to it, claiming he has nothing to hide - except his giant dick.

Maddy O'Reilly in 'Nothing is Hard Enough for Maddy O'Reily......Until Today'

Maddy O'Reilly - Nothing is Hard Enough for Maddy O'Reily......Until Today

James Deen sticks his cock deep in Princess Donna's ass and shoves it right down their slut for the day, Maddy O'Reily's, throat.

Maddy O'Reilly in 'Sexy Maddy OReilly Hard Pussy Pounding'

Maddy O'Reilly - Sexy Maddy OReilly Hard Pussy Pounding

Sexy Maddy O'Reilly Hard Pussy Pounding. Born to be bad. Maddy O'Reilly may still be a teenager but this glamorous brunette dwells on the dark side for sure. In this filthy fraction of YOUNG AND GLAMOROUS 3 check out Maddy's natural body and watch how well this slut sucks dick. A star in the making, Maddy O'Reilly

Maddy O'Reilly in 'Ryan's Teen Slut'

Maddy O'Reilly - Ryan's Teen Slut

There's only two things on Maddy's mind, school and cock. She comes over to the Madison's knowing that she could get pounded by Ryan's hard dick and gets exactly what she wanted. Ryan fucks her teen twat until she keeps cumming on his cock and leaves her with two loads of cum deep inside her warm pussy.


Maddy O'Reilly in 'Crack Fuckers'

Maddy O'Reilly - Crack Fuckers

Adorably petite redhead Maddy O'Reilly is dolled up in high heels and a tight white dress that hugs the curves of her cute, little booty. Maddy teases the camera, wiggling her soft buttocks until director Kevin Moore is totally aroused. Kneeling on the bed, this gorgeous young lady sensuously sucks his hard dick, oils up her ass and lets the director slide his erection between those round, firm buns. Finally the beautiful slut lies facedown on the bed; Kevin humps her rear groove until he spurts a load of cum right into the sexy cleft of Maddy's butt!

Maddy O'Reilly in 'Naughty Bookworms'

Maddy O'Reilly - Naughty Bookworms

Art student Maddy Oreilly leaves her sketchbook in the classroom, and when she goes back to retrieve it, she finds her teacher flipping through it. He tells her that her drawings of the male anatomy are incorrect -- she's got the sizing all off. Professor Glide whips out his giant cock to show petite Maddy the real deal! She thanks him for the lesson by sucking his giant cock and letting him stuff it in her pussy until he blasts a load in her mouth! Art is beautiful.

Maddy O'Reilly in 'Sex Tape 5'

Maddy O'Reilly - Sex Tape 5

We frequently get some nice amateur submissions on a weekly basis. Yeah the majority that's sent to us is usually sub-par, but the few that are good we throw up on the site. Every now and then, however, we'll get a killer video; an instant classic. I got a submission in the mail a few days ago; a DVD labeled 'Sex Tape #5'. Being burn out on amateur submissions, and not so impressed with the naming/presentation, I set it aside. To be honest, I wasn't even going to bother with it, but let me tell you, thank GOD I did!! This video has to be the hottest amateur sex tape we've ever received. The DVD had multiple footage on it. The guy playing with his girl in their hot tube, getting ready to go out on the town. The shit gets magma hot though when he wakes her up with one hell of a good morning, followed by some amazing sex. Who ever this girl is, her man better put a ring on that finger! Her moaning alone is enough to make you bust a nut. Other than this guy's girl, the only other thing I keep thinking of is the fact that it's called Sex Tape #5. Where are the other videos at?!?! PLEASE SEND THEM IN!!!


Scenes from other sites featuring Maddy O'Reilly

Maddy O'Reilly in 'is sexually brutalized by cock and bondage. Deepthroated and fucked while helpless.'

Maddy O'Reilly - is sexually brutalized by cock and bondage. Deepthroated and fucked while helpless.

Welcome back the beautiful and very dirty Maddy O'Reilly, this girl loves her job, loves rough sex and breath play and it shows!Bound and helpless in three different positions, Maddy soons remembers just how exciting and fun Sexaully Broken is. It doesn't take long for our sexy slut to be in subspace, while drool runs down her face and body as the cocks penetrate her throat over and over with our mercy. Not many girls can even handle the intensity of Sexaully Broken. Maddy handles it, and does it with grace, even when broken she bounces back quickly and with a smile.

Maddy O'Reilly in 'Redheaded Maddy O'Reilly is ball gagged, tightly tied and ragdoll fucked by two big dicks!'

Maddy O'Reilly - Redheaded Maddy O'Reilly is ball gagged, tightly tied and ragdoll fucked by two big dicks!

The curvy redhead Maddy O'Reilly is back for another serving of Sexuallybroken. She just can't get enough. And who can blame her? Bondage cock and orgasms are always a great way to spend the day. Let's give this cock slut exactly what she craves.Bound in strict rope bondage that perfectly displays Maddy's juicy all natural breasts and sporting a big black ballgag that seals up her face pussy, our starlet is ready for a test drive. Let's see exactly what this fuck toy can take.Pussy, meet dick. Dicks, meet pussy. Get acquainted you three. Maddy is ragdoll fucked all over our well used bed as the cocks run a train on her tight pussy. Judging by the noises that are leaking around her ballgag, Maddy is enjoying herself immensely. As are we.Maddy is fucked every which way from every possible angle as the dicks turn her into a sex sandwich. The tight rope bondage turns her into the perfect fuck pet. We use her until we have had our fill for the day. We will try another round when the urge arises...

Maddy O'Reilly in 'Redheaded Maddy O'Reilly bound and drooling in strict bondage as she is dicked down by BBC!'

Maddy O'Reilly - Redheaded Maddy O'Reilly bound and drooling in strict bondage as she is dicked down by BBC!

Today we are happy to welcome back that lush pale redhead Maddy O'Reilly to the pages of Sexuallybroken. Maddy is one of those that was simply built for sex. She craves it. She needs it. And we are here to provide. As we do.The set up is simple but effective. A pillory, a hot porn star and two hard cocks. Mix up and let the fun start. Once we have Maddy bound in place, all we have to do is walk up and make full use of that luscious bubblebutt. Which is exactly what we proceed to do.The drool pours out of Maddy's ballgagged mouth as the dicks pound out her pussy. The harder we fuck her the bigger the puddle of drool grows around her feet. This is hole training at its best. All Maddy can do is take the dick we dish out. She loves every single minute of it.We fuck until we have had our fill, two hard cocks tag teaming our starlet down into a drooling undone mess. Maddy clouded eyes stare off into the distance and we do the only logical thing...stick a leather hood over her head and vibrate her to another orgasm. Good times, good times. Until we meet again...