Latest updates featuring Maddy O'Reilly

Maddy O'Reilly - 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

13th March - 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. ...Read More
Maddy O'Reilly - My Boss' Wife

Maddy O'Reilly - DarkX

8th March - 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!? ...Read More
Maddy O'Reilly - Never Forgotten Scene 1

Maddy O'Reilly - Never Forgotten Scene 1

12th February - 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. ...Read More

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

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

12th February - 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! ...Read More
Maddy O'Reilly - Strap-On Stories: Strap Trap

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

17th December - 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! ...Read More
Karlee Grey - Decorate My Poon

Karlee Grey - Decorate My Poon

19th November - 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! ...Read More
Maddy O'Reilly - Axel Braun's Big Ass Anal Movie Scene 4

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

4th September - 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! ...Read More
Maddy O'Reilly - Basking In The Afterglow

Maddy O'Reilly - Basking In The Afterglow

31st August - 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! ...Read More
Maddy O'Reilly - Penchant For Pricey Panties

Maddy O'Reilly - Penchant For Pricey Panties

29th May - 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! ...Read More

Maddy O'Reilly - The Rim Job

Maddy O'Reilly - The Rim Job

22nd May - 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! ...Read More
Maddy O'Reilly - Squirting Stories Volume Two: Mopping Up

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

8th May - 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! ...Read More
Maddy O'Reilly - The Art of Lesbian Anal: Birthday Play

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

13th April - 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! ...Read More
Maddy O'Reilly - Craving Some Dick

Maddy O'Reilly - Craving Some Dick

9th February - 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! ...Read More
Maddy O'Reilly - No Panties For Me

Maddy O'Reilly - No Panties For Me

5th July - 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. ...Read More
Maddy O'Reilly - Pillow Talk

Maddy O'Reilly - Pillow Talk

21st July - 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. ...Read More