Shazia Sahari and Bill Bailey in Naughty Office

Bill is interviewing for a new marketing job, and in the waiting room he sees sexy-ass Shazia. She just so happens to be applying for the executive assistant position, but she's apparently more interested in other positions, such as doggystyle and reverse cowgirl! She's so horny she tells Bill to fuck her right then and there, while another interview is being conducted in the other room. Can you say secretary of the year?

Shazia Sahari

Bill Bailey

Naughty America · September 9, 2010

Mandy Sweet and Bill Bailey in My Friends Hot Mom

Mandy's deadbeat boyfriend is breaking up with her right as Bill arrives at her house to see her son. Bill wants Mandy to know that he thinks her boyfriend was a douchebag, and she is better off without him. She thanks him for his support, and wants to show him how much she appreciates his strong arms around her.

Mandy Sweet

Bill Bailey

Naughty America · August 25, 2010

Karen Fisher and Bill Bailey in Seduced by a cougar

Busty Karen Fisher is showing a few art and antiques pieces to a potential buyer in her home.What she didn't expect was for him to be such a young stud, which is why she finagles a way for him to see up his skirt whilst he takes a close look at some old furniture she's selling. And once the voluptuous vixen shows off her bare wares, she's done doing business and is ready for pleasure. The real masterpiece is unveiled once her top falls off and out bounce her big tits, on which her customer paints his own piece..

Karen Fisher

Bill Bailey

Naughty America · August 13, 2010

Ella Milano and Bill Bailey in Latin Adultery

Ella comes over to her new neighbor's place with a gift of her famous casserole. It seems the new neighbor is still waiting to start his new job and has nothing to do all day. Ella's husband works all the time, and so she is bored during the day as well. If they are both going to be home during the day, they might as well be good friends......with benefits.

Ella Milano

Bill Bailey

Naughty America · October 20, 2009

Katie Kox and Bill Bailey in American Daydreams

Katie hired Bill to clean her house, but she doesn't think he's doing a very good job. She bitches at him to get his act together, and says that the house better be spotless by the time she come in from sunbathing out back. Frustrated with the clogged vacuum cleaner, Bill takes a break and sits down . but falls asleep, and dreams of Katie's big wet tits in his face, and his big hard cock in her mouth and pussy. Talk about cleaning house...

Katie Kox

Bill Bailey

Naughty America · October 12, 2009

Tanner Mayes and Bill Bailey in My Sisters Hot Friend

Tanner asks over her friend's brother, Bill, to fix the tv & help move her bed. She shows him the bed but where's the tv he asks. It's in the closet, Tanner says. Bill knows she has other intentions and swiftly moves in for a kiss..

Tanner Mayes

Bill Bailey

Naughty America · September 11, 2009

Ariella Ferrera and Bill Bailey in My Friends Hot Mom

Bill Bailey spent the night at his friends house to go fishing early in the morning. When Bill wakes up the next morning, he finds out Ariella, his friend's mom, sent her son fishing off without Bill so he could sleep in. It turns out, Ariella just wanted Bill all to herself to satisfy her wet pussy.

Ariella Ferrera

Bill Bailey

Naughty America · July 1, 2009

Mellanie Monroe and Bill Bailey in My First Sex Teacher

Professor Mellanie Monroe found something interesting that her student Bill left behind in her office: a tablet with a teacher porn site open! She's looking through it when Bill bursts through the door looking for his lost device. When she hands it to him, he just shoves it in his bag, thanks her and attempts to leave without confrontation. But the good professor isn't having that. She has him shut the door, then sucks his cock and fucks him to give him the real-life version of the fantasy he's been masturbating to.

Mellanie Monroe

Bill Bailey

Naughty America · April 27, 2009

Zoey Holloway and Bill Bailey in Seduced by a cougar

Zoey gets home and finds her idiot landscaper still there, watering her patio and spraying her windows, nonetheless. Fired up and agitated, Zoey calls him inside and gives him a tongue-lashing. But while doing so, the ever-horny cougar Zoey gets wet for her landscaper. She's so hot and bothered that she pulls out his hose and sucks it and fucks it until he sprays her face with cum!

Zoey Holloway

Bill Bailey

Naughty America · March 13, 2009

Tanya Tate and Bill Bailey in My Friends Hot Mom

Tanya Tate is throwing a party for her son, who just graduated from college, and his buddy Bill is helping her set things up. The sexy MILF's son and his dad had to go all the way across town to pick up the meat for the barbecue, Bill decides it's time to see if he can deliver his meat to her! Mrs. Tate is reluctant at first, but she can't deny the desire she's had to suck and ride Bill's big dick! Party on!

Tanya Tate

Bill Bailey

Naughty America · March 13, 2009

Tanya Tate and Bill Bailey in Neighbor Affair

Tanya and Bill are co-workers and neighbors. They are car pooling but have some car problems. They head over Tanya's house to look for her insurance card but Tanya wants Bill to do some pooling of his own.

Tanya Tate

Bill Bailey

Naughty America · February 17, 2009

Tiffany Mynx and Bill Bailey in My Friends Hot Mom

Tiffany Mynx carries fresh towels to the bathroom, where her son't friend Billy is showering. She's always been attracted to him, but when she catches him in the shower masturbating, she can't contain herself. Tired of living a boring life, she confronts him in the shower and tells him she's going to take what she wants: a his big dick down her throat and up her pussy, with a nice splash of cum all over her big tits. What a nice mom!

Tiffany Mynx

Bill Bailey

Naughty America · November 7, 2008

Brandi Love and Bill Bailey in Seduced by a cougar

Bill is going around the neighborhoods trying to collect donations for an inner city youth charity program that will help him get into college. But when he knocks on Brandi Love's door, he gets more than he's bargained for. She's more than happy to make a large, sizable donation, but only in return for a favor. Bill's game for anything, but when she leads him to her bedroom, then returns wearing nothing but a bra, panties and stockings, he realizes he hit the jackpot! After taking on Ms. Love's big tits, hot pussy and exquisite ass, Bill collects his donation and is ready to rule the world. Philanthropy is such a beautiful thing.

Brandi Love

Bill Bailey

Naughty America · November 6, 2008

Diamond Jackson and Bill Bailey in Seduced by a cougar

Diamond is relaxing in her yard when she catches Bill picking fruit from her trees. He's been stealing from her for weeks now, and she's ready to teach him a lesson. When he tells her he's leaving, she threatens to call the cops on him. She orders Bill to take off his shirt . then to stand on the table . then to take off his pants . then to put his penis in her mouth. His punishment? He has to fuck her until he comes on her tongue. If that's what you get for picking some forbidden fruit, gimme summa THAT!!!

Diamond Jackson

Bill Bailey

Naughty America · October 1, 2008

Faye Reagan and Bill Bailey in Naughty Bookworms

Faye is going to be cut off if she doesn't bring her grades up so her parents hired a tutor for her but she's not being very nice to him and when he heads for the door she decides she wants to learn after all and she needs lot's of human anatomy lessons.

Faye Reagan

Bill Bailey