AllGirlMassage – Maddy OReilly And Jenna Sativa – Inappropriate Assist
Jenna Sativa and Maddy O’Reilly are in the living room workout out and doing some stretching. When Jenna asks Maddy to pull her from her waist as she lies on the floor, she somehow manages to grab her pussy instead. Jenna falls to the ground and hurts her back. Maddy feels so bad so she […]
AllGirlMassage – Maddy OReilly, Charlotte Stokely And Luna Star – Two Is Better Than One
Charlotte Stokely has just hired Luna Star to work at her massage parlor and is in the process of training her. One of the regulars, Maddy O’Reilly, is coming in for her afternoon appointment and Charlotte would like Luna to give her the massage. Charlotte excuses herself, instructing Luna to man the reception area while […]
Analized – Maddy OReilly, Fun With Duct Tape
Analized – Maddy OReilly, Rough As You Can Get
Red head big ass anal whore Maddy O’Reilly is not fucking around today. She shows off her booty to the camera in every way imaginable. Squatting, shaking, and crawling around the room until you just can’t take anymore. This slut is here for one thing and one thing only. Maddy O’Reilly wants to be brutalized […]
Babes – Karlee Grey And Maddy O’Reilly – 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 daz
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 […]
BigWetButts – AJ Applegate And Maddy OReilly – 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 […]
BigWetButts – Maddy Oreilly – 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 […]
BigWetButts – Maddy Oreilly – 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.
BigWetButts – Maddy Oreilly – Maddy Oreilly’s 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 […]
BlackPayback – Maddy OReilly – I Have Black Friends
Who knew such a pasty becky could turn into the best whore of all for some black dick! “I’m such a dirty Fucking slut” she squeals, as the cracker was taken by rolling orgasms during a thorough ass ramming. Whitey assumed that having ‘black friends’ means she can’t be a racist like her ancestors. Ignorant […]
DarkX – DP Compilation
Enjoy this compilation of some of our hottest girls getting DP’d! 00:03 – AppleGate DP 02:14 – Double Down 04:03 – Fuck My Girlfriend, Please 06:19 – Casey’s Double Penetration 08:16 – I Need A Favor 10:11 – My Boss’ Wife 11:46 – We Have History 14:31 – Keisha’s IR DP 16:25 – Tiny Blonde […]
DarkX – Maddy O’Reilly – Love Me Tender
Maddy O’Reilly and Ricky Johnson arrive back at Ricky’s house. Maddy is shocked at how huge the house is, she asks if it’s his or his parents. Ricky becomes confused and asks her why it would matter? She instantly shows him it’s not the house she cares about. She drags him into the bedroom and […]
DarkX – Maddy O’Reilly – My Boss’ Wife
When introducing Nat Turnher an employee of Sean Michael’s, 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 […]
DeviantHardcore – Abigail Mac And Maddy OReilly – Sexy Domme Abigail Mac uses her good submissive Maddy OReilly
Maddy O’Reilly is such a good submissive for her mistress Abigail Mac. She stays bound up for her and loves to let Abigail do whatever she likes. Abigail loves to tease her and spends plenty of time playing with her body but never giving her exactly what she wants. After Abigail unties her she gives […]
DeviantHardcore – Jenna Sativa And Maddy OReilly – Sexy Mistress Jenna Sativa dominates Maddy OReilly
Gorgeous young Maddy O’Reilly is ready to willingly take whatever her hot mistress Jenna Sativa dishes out. She takes some hard spanking, face sitting, and is teased liked crazy with her mistresses magic wand. Maddy is such a good girl and Jenna shows her a good time.
DevilsFilm – Maddy O’Reilly – Twisted Fantasies – Daydreams
Maddy O’Reilly surrenders to her lover’s power
DickDrainers – Maddy O’Reilly – Maddy’s Job Requires Overtime…
Lavish vacations, designer wardrobe, sumptuous food, red bottoms…Maddy’s living the good life. Hard work definitely pays off. And Maddy’s a very hard worker. It’s one of the things her boss appreciates about her. The other thing he appreciates is her asshole. And her throat. And her tight white pussy. Because Maddy’s job has a lot […]
The ladies of sorority Delta Pi Chi just moved into the neighborhood and the community is not thrilled! These sex-crazed sorority sisters party loud and screw louder with the fraternities without any consideration for their neighbors! Rush just started and a handful of horny freshman girls are eagerly waiting to pledge. The hazing gets kinky […]
DigitalPlayground – Maddy O’Reilly – Diary of a Perv S06
Maddy knocks on Keiran’s door wearing a red top and jean shorts. Her mom usually cleans his house but she’s not feeling well today. Her ass is spilling out of her shorts and she looks fantastic. Kieran follows her around and Maddy finally notices him. Maddy likes it and drops to her knees to show […]
DoctorAdventures – Maddy Oreilly – 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. […]
Drilled – Maddy OReilly, Thrilled To Be Getting Drilled
Maddy O’Reilly really desires a cock deep in her ass for complete satisfaction when she is fucking! Nothing feels better than her tight little asshole getting stretched open by a beautiful hard cock! Maddy loves having her ass cheeks turn rose red as they gets smacked over and over while Justin drills her ass hard! […]
EvilAngel – Maddy O’Reilly – The Hooker Experience S04
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 […]
FullOfJOI – Maddy Oreilly – Turning Stepmom On
I understand that you have all kinds of hormones racing, but this is a little ridiculous. I mean, I find you standing here in the kitchen, pleasuring yourself with my panties in your hand. What else am I supposed to think? Well, even though it is a little inappropriate, I cannot help but notice your […]
GirlsWay – Cadence Lux And 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 […]
GirlsWay – Maddy OReilly And Jayden Cole – 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 […]
GirlsWay – Maddy OReilly And Jenna Sativa – 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 […]
GirlsWay – Maddy OReilly, Karlee Grey And Angela White – 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 […]
GirlsWay – Maddy OReilly, Nicole Aniston, 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 […]
GirlsWay – Maddy OReilly, Penny Pax, Lexi Belle, 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 […]
Girlsway – Sara Luvv, Kenna James, August Ames, Riley Reid, Cassidy Klein, Karlie Montana And Kendra James – Missing Part Six
Lara Bradford is in the thick of her story, unaware of the future that is about to unfold. She rushes to Anita Sharpe’s door, banging for her to come to greet her. Anita Sharpe arrives quickly with her southern belle alias ready to do the talking. Lara explains the scandalous details of what she’s found, […]
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 […]
HotAndMean – Maddy OReilly And Carter Cruise – In House Whore
Carter Cruise has got a real sick crib, with a beautiful view, great pool, and decorated like the lap of luxury. But the all-out best feature is the in-house whore waiting to satisfy any of Carter’s dirty desires. Whenever Carter wants her dirty feet licked clean, she just brings them to her whore Maddy Oreilly […]
Hustler – Maddy O’Reilly And Honey Gold – Teach Me
Honey describes her first lesbian experience and how the other woman had to take control and show her the ropes. Lucky for her, and us, Maddy is there to once again guide her through a girl girl encounter!
JulesJordan – Maddy OReilly, Big Booty Slut Maddy OReillys Ass Devours A BBC
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 […]
Lesbian Encounters 2
Adriana Chechik, Adrianna Luna, AJ Applegate, Brooklyn Lee, Maddy O’Reilly, Mischa Brooks, Sarah Shevon, Sovereign Syre
LoneMilf – Maddy OReilly – Orgasmic MILF Relaxation
After a long week of hard work, Maddy O Reilly enjoys putting her feet up and watching some of her favorite scenes from the Team Skeet archives. Today, she finds a video that has her hot and bothered as she sits by herself in the living room. She gets so turned on that she reaches […]
LustArmy – Maddy OReilly – Take A Sneak Peak
LustCinema – Girl Friday (2021)
Inspired by Steven Shainberg’s “Secretary” film, Girl Friday is a thrilling lesbian psychological drama that explores the intense relationship between a dominant lawyer and her obsessed new secretary. Charlie (Lena Anderson), is a young misfit who gets her first job in a law firm and finds herself obsessing about her new boss, Olivia (Mona Wales), […]
MonsterCurves – Maddy OReilly, Rainbow Booty
Summer’s cumming so beat the heat by chicking out the curvy cutire that is Maddy O’Reilly as she flaunts her fantastic cuvres by twerking that big booty of hers while looking absolutely breathtaking in a rainbow colored bikini! She teases her body before Logan Long steps in to start oiling her butt up before eventually […]
MonsterCurves – Maddy OReilly, Twerk Tricks
Thicc stunner Maddy O’Reilly has a whole bag of twerk tricks to share, and they’re all stuffed into her tight dress along with her big booty! Maddy teases you with glimpses of that huge ass as she wiggles her hips while hula hooping, then oils up that booty and twerks for you. What Maddy loves […]
MylfBlows – Maddy OReilly – Drooling And Dripping MILF Magic
You already know that Maddy Oreilly is hungry for cock. That is because she makes sure to keep herself sharp with a good blowjob every few days or so. Today, she joins us to get her dick fix, and this MILF is literally champing at the bit to get some big sausage between her lips. […]
MylfSelects – Dripping Moms Compilation
What’s up, MYLF lovers? We know you were begging to see this collection, so the wait is over! Everyone here loves a good milf with a wet pussy, so for this amazing compilation, you’ll see Callie, Maddy, Ophelia, and Vivianne’s beavers and kissers dripping with hot cum after jaw-dropping fuck sessions.
MyWifeIsMyPornstar – Maddy O’Reilly 31506
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 […]
MyWifeIsMyPornstar – Maddy O’Reilly 31529
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 […]
Dominant Mistress January Seraph had her new specimen Maddy, caged up and ready to spread out on her fuck table. Maddy had no idea what her tits and pussy were in for and Mistress JS had all the freaky toys ready to go and took one by one to tease and test Maddy’s sexual appetite […]
NewSensations – Maddy OReilly – Maddy’s Black Bull Returns
Hotwife Maddy has been loving the lifestyle and her husband has enjoyed every story of all her sexual encounters. But black bull Jon is the stud that gets to return back anytime to slide into Maddy, since he is the one to deliver multiple orgasms.
NubileFilms – Girls Vs Guys Orgasm Compilation
Are you ready to settle in for a compilation of some of the hottest orgasms we’ve featured on Nubile Films? This girls vs guys competition isn’t just about the sights and sounds of real climaxes. It’s also about who can make the ladies cum harder and longer! We start out with the girls. This collection […]
OfficeObsession – Maddy OReilly – 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 […]
When newlywed Gabi Paltrova confides that her husband never made her orgasm, sister-in-law Maddy O’Reilly tells her she needs to experience a proper G-spot orgasm, if she wants her marriage to work. Maddy helps her sister-in-law locate the elusive G-spot, lifting Gabi’s dress and showing her where to touch herself down there, and how to […]
PureTaboo – Maddy OReilly, 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 […]
PurgatoryX – Maddy OReilly – Permission E1
Maddy (Maddy O’Reilly), is much younger than her husband (Steve Holmes). She has a constant thirst for fucking young handsome studs (Nathan Bronson). Fortunately for her, her husband understands her needs. Better yet, he actually enjoys jerking-off as he discretely watches his wife getting plowed by her temporary lovers. Maddy informs her husband that she’s […]
PurgatoryX – Maddy OReilly – Permission E2
Maddy (Maddy O’Reilly) and Steve (Steve Holmes) are lounging in bed, talking about last night’s erotic adventure. Maddy loves having sex with young studs, especially knowing that her voyeur-loving husband’s secretly recording the action while stroking his cock. The perpetual perverts get horny as they replay their homemade x-rated video. Mutual masturbation soon turns into […]
PurgatoryX – Maddy OReilly – Permission E3
Maddy’s (Maddy O’Reilly) going to a local Happy Hour and her husband, Steve (Steve Holmes) knows exactly what that means. He gets to jerk his cock while he watches his wife getting abused by eager young studs. Only this time, he’s in for a real treat. Maddy brings home two chiseled black dudes (Jon Jon, […]
ScamAngels – Gina Valentina, Karlee Grey, Maddy OReilly, Group Sex
Wild American beauties Gina Valentina, Karlee Grey and Maddy O’Reilly decide to play another hot sex scam on a well-hung stud. The dirty talking babes ride Logan Long’s cock, suck him off and play with his cum then get paid for keeping quiet.
ScamAngels – Maddy OReilly And Chloe Cherry – Two sexy beauties and a big dick – Double The Stakes
Having two girls pleasing your cock is a wet dream come true for any man, but these gorgeous girls take things a little to far. There is something evil and mischevious about them that the poor guy is not suspecting. Watch Maddy O’Reilly and Chloe Cherry having their way with Ryan Diller in a premium […]
SevenSins – Sluts MaXXXed Out! (2021)
Things are getting rough again in the Seven Sins studio. The hottest pornstars drop by for a day of going wild. All the hard cocks present disappear deep into their throats, pussies and asses. Let your ass gape wide open, so we can fill this hole with cum! Seven Sins gonzo at its hardest, so […]
Cute brunette Maddy O’Reilly is the adorable star of episode five of “Girls Love Sex – The Lost Tapes.” The sweet 23-year-old admits she is a little shy as she responds to questions from director Bo Llanberris and his gorgeous redhead assistant Elle Alexandra. This reprise of the classic SexArt series created by legendary auteur […]
SinsLife – AJ Applegate, Karmen Karma, Katrina Jade, Kissa Sins And Maddy OReilly – Leaving Las Vegas Orgy
When we moved to Hawaii from Las Vegas we knew we had to have a going away party… and the best way we could think to celebrate was to have a GIANT REVERSE GANG BANG ORGY!!!!!!!
SisLovesMe – Maddy Oreilly, Its Called The Cum Treatment
Maddy O’Reilly isn’t a the brightest stepsister in the world, but she is fucking hot and gullible! She is distraught over having two zits on her face. Her creepy brother tricks her into thinking that male cum will clear her problem up. He gets her to suck him off so he can pump his bro […]
SweetSinner – Maddy O’Reilly – Infidelity 3 Scene 2
After her masseuse kisses her one day, married woman, Addison can’t stop thinking about him. But, she is determined to stay faithful to her husband. When she arrives for her next massage though, the temptation is just too much. Despite her attempts at resisting her masseuse’s advances, Addison eventually gives in – resulting in a […]
SweetSinner – Maddy OReilly, Risk
TeamSkeetSelects – Cassidy Banks, Liv Wild, Maddy O’Reilly And Linzee Ryder – Feelin’ Green, Feelin’ Irish
Top of the morning to you, and happy St. Patrick’s Day from all of us at TeamSkeet. For this joyous day, we’ve put together a hot, sloppy compilation of some of the greenest, most thematic St. Patrick’s fucks we’ve ever enjoyed. From Ashley Adams to Maddy O’Reilly and back to Cassidy Banks and more, we […]