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Hot AF Maddy O'Reilly and Marie McCray fuck the shit out of their friend's brother
Naughty America · January 4, 2026

Hot AF Maddy O'Reilly and Marie McCray fuck the shit out of their friend's brother

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
Maddy O'Reilly
Marie McCray
Marie McCray
Danny Mountain
Danny Mountain
Two hot babes Jillian Janson and Maddy O'Reilly know how to party
Naughty America · March 23, 2025

Two hot babes Jillian Janson and Maddy O'Reilly know how to party

Jillian Brookes & Maddy O'Reilly are over at their friend's house and ready to party since their friend's parents are out of town. Their friend's brother is trying to put a stop to it though. Well, these two hot chicks think they can change his mind because there is a party in his pants and they're going to make sure he is cumming. Jillian and Maddy take his huge load and get to party down afterward. (Original release date: 12-6-2013)
Jillian Janson
Jillian Janson
Maddy O'Reilly
Maddy O'Reilly
Will Powers
Will Powers
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Maddy O'Reilly in I Have a Wife
Naughty America · September 22, 2014

Maddy O'Reilly in 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
Maddy O'Reilly
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Maddy O'Reilly and Bill Bailey in My Sisters Hot Friend
Naughty America · December 12, 2013

Maddy O'Reilly and Bill Bailey in 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
Maddy O'Reilly
Marie McCray, Maddy O'Reilly and Danny Mountain in My Sisters Hot Friend
Naughty America · October 11, 2013

Marie McCray, Maddy O'Reilly and Danny Mountain in 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
Maddy O'Reilly
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Maddy O'Reilly and Johnny Castle in Naughty Rich Girls
Naughty America · April 24, 2013

Maddy O'Reilly and Johnny Castle in 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
Maddy O'Reilly
Maddy Oreilly and Giovanni Francesco in My Sisters Hot Friend
Naughty America · October 16, 2012

Maddy Oreilly and Giovanni Francesco in 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
Maddy O'ReillyGiovanni Francesco
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Maddy Oreilly and Billy Glide in Naughty Bookworms
Naughty America · December 14, 2011

Maddy Oreilly and Billy Glide in 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
Maddy O'ReillyBilly Glide