Alyssa Dutch and Bill Bailey in My Friends Hot Mom

Bill hears that his buddy's mom Alyssa Dutch is taking him to Lake Tahoe for a vacation this winter, so he asks if he can tag along since he would go on trips with them when they were little kids. Alyssa knows that Bill isn't so good at winter sports, but she has heard that he's fantastic at picking up on women, which she mentions. When Bill admits that he wants to hunt for snowbunnies, the blonde MILF grabs his big dick and tells him she wants him to plunge down her rabbit hole and fuck her like the MILF she is! She gets white stuff all over her face before she even hits the slopes....

Alyssa Dutch

Bill Bailey

Naughty America · October 17, 2012

Dana Vespoli and Bill Bailey in My Naughty Massage

Bill's got the big championship football game coming up, but he pulled his groin in his last game so he visits a massage therapist for some healing. His masseuse, Dana Vespoli, is good with sports injuries, so she knows all the right places to rub Bill. She also knows how to make him feel better by pulling his dick out of his boxing shorts and shoving it in her mouth! The sexy massage therapist sucks her client then rides his dick until his groin is all better!

Dana Vespoli

Bill Bailey

Naughty America · October 4, 2012

Brooklyn Chase and Bill Bailey in My Girlfriend's Busty Friend

Brooklyn Chase is pumping some iron in the gym when she runs into her friend's boyfriend Bill. She can't help but notice how big his arms are getting from working out, and he has not problem showing them off to her. In fact, he does more than show her his guns ... he shows her his big dick and gives her a sweaty workout with it! Watch the sexy brunette bang her friend's boyfriend in the gym!

Brooklyn Chase

Bill Bailey

Naughty America · September 27, 2012

Kendra Lust and Bill Bailey in Housewife 1 on 1

When Kendra Lust finds her sleepy husband still in bed after she steps out of a shower, she decides he needs disciplined because they're supposed to be going out and having fun! Lucky for him, her version of discipline involves her big fat ass bouncing off his big dick as she fucks it, her huge tits flopping in his face as she rides him. Why can't every wife discipline her husband like that?

Kendra Lust

Bill Bailey

Naughty America · September 19, 2012

Ashli Orion and Bill Bailey in Naughty Office

Ashli Orion is ready to start her new copy editing job, but her co-worker Bill, shows up and pretends to be her boss and tells her that she was hired more for her nice big ass than her brains. Ashli starts for the door but Bill reminds her of her $50,000 annual salary, and she heads back to him and gets on her knees to show her qualifications! After a nice blowjob and some raw, hard office sex, Bill shoots his cum all over her face and leaves . just as Ashley's real boss walks in!

Ashli Orion

Bill Bailey

Naughty America · September 13, 2012

Holly Michaels and Bill Bailey in Naughty Office

Holly Michaels really wants to stay aboard at her new job, but her boss has to soon make the decision of who he's going to keep as his assistant, so it's possible she may be out! She's diligent to work extra hard and fast, and even goes so far to tell her boss that she'll go the extra mile to fulfill all of his needs, even when it comes to getting the best blowjob he's ever had! The brunette beauty gives Mr. Bailey a taste of what she means with some office sex that includes hot pussy-eating and some big tits tittyfucking, and ends with a hot creampie!

Holly Michaels

Bill Bailey

Naughty America · September 11, 2012

Mia Gold and Bill Bailey in Latin Adultery

Mia Gold hauls her husband's employee Bill out of his concrete-pouring job to talk to him about something important: her man cheating on her. Bill tries to escape by telling her he doesn't have time for nonsense, but when the spicy Latina pushes suspicious restaurant and hotel bills in his face and starts asking questions about they're so-called "job" in San Diego, Bill clams up. He eventually relents and tells her that her husband is cheating on her with a stripper! Mia isn't having it, but what she is having is Bill's big dick, in her mouth and tight pussy!

Mia Gold

Bill Bailey

Naughty America · September 10, 2012

Yurizan Beltran, Ella Milano and Bill Bailey in 2 Chicks Same Time

Ella Milano is a horny-ass sorority chick who meets a random stud at the bar and brings him back to her house for some fun. He tells her he wants to go to the after party with her, but she tells him that the after party is in her room. When he follows her there, he finds Ella's horny roommate Yurizan Beltran sitting on the bed, awaiting his hard, big dick. Everybody gets naked and the lucky stud gets two chicks on his cock in a hot, wet threesome!!!

Ella Milano

Yurizan Beltran

Bill Bailey

Naughty America · September 7, 2012

Rachel Roxxx and Bill Bailey in My Dad's Hot Girlfriend

Rachel Roxxx is sick and tired of looking after her boyfriend's new dog, so she bitches to his TV-watching son Bill about it and tries to get him to watch Rover. Bill laughs in her face . until she proposes a deal that involves her sucking his big cock and taking it right up her tight little asshole in exchange for him feeding and cleaning Fluffy. Deal or no deal?

Rachel Roxxx

Bill Bailey

Naughty America · September 6, 2012

Sheena Shaw and Bill Bailey in I Have a Wife

Sheena Shaw is looking at an apartment, and she recognizes the landlord Bill as the guy who introduced himself as "Steve" at the club where she's a stripper. he doesn't catch on until she waves her big ass in his face and rubs it all over his crotch. Bill doesn't know what to do because he's married, but the sexy blonde knows exactly what to do: she rubs her natural tits in his face, pulls out his big dick and sucks and fucks it until he cums on her face! Looks like somebody scored an apartment...

Sheena Shaw

Bill Bailey

Naughty America · August 31, 2012

Lisa Ann and Bill Bailey in Seduced by a cougar

Bill is the new grocery delivery boy for Lisa Ann, and he soon finds out why all the guys at his shop fight over who gets to deliver her groceries to her. The brunette with big tits welcomes him warmly, and when she finds out she doesn't have enough cash to give him a tip, she decides to help him out by taking the tip of his cock and inserting it into her mouth and pussy! The cougar fucks the delivery boy good and hard, and works his big dick so well that he pours his cream all over her face and tits. Who knew he'd deliver meat, too?

Lisa Ann

Bill Bailey

Naughty America · August 27, 2012

India Summer and Bill Bailey in My First Sex Teacher

Professor India Summer talks to her student Bill about his recent poor performance in class, and questions whether it's because he's become more popular with the ladies on campus. Bill eventually admits to his teacher that he's been tutoring his female classmates in exchange for sex! Rather than being disappointed, the sexy brunette professor is turned on . so much so that she offers to give Bill's waning GPA a boost . if he fucks her better than he does the girls in class!!!!

India Summer

Bill Bailey

Naughty America · August 22, 2012

Jacky Joy and Bill Bailey in I Have a Wife

Jacky Joy is the president of her building's homeowners association board, and Bill's wife is a member of it. Jacky knows three things: 1) Bill is good-looking; 2) Bill's wife is on vacation in the Bahamas with her girlfriend; 3) Bill's address. What she doesn't know is that Bill has a big dick, so she's at least in for one surprise after she goes to his home and propositions him to cheat on his wife with her and her big tits and wet pussy.

Jacky Joy

Bill Bailey

Naughty America · August 14, 2012

Brooklyn Chase and Bill Bailey in My Wife's Hot Friend

When Bill finds his wife's friend Brooklyn Chase in their bedroom, rifling through his woman's jewelry box, she lies and says that his wife told her she could borrow a bracelet. Bill knows his wife, and he knows she wouldn't ever do such a thing, so when he calls the sexy brunette on it, she knows she's caught. But she and her big tits have certain ways of getting what they want . by sucking her friend's husband's big dick and letting him creampie in her moist, wet pussy.

Brooklyn Chase

Bill Bailey

Naughty America · August 9, 2012

Holly Taylor and Bill Bailey in Fast Times

Bill is helping his classmate Holly Taylor study for their organic chemistry exam, but she's totally clueless. The blonde thinks their course is about good-looking people hooking up, and she's not joking. Bill tries to talk to her seriously about the subject, but she insists that they fuck in the classroom first, and to show she's not joking, she lets him play with her pierced nipples and clit before she sucks his big dick and fucks him until him cums on her glasses! Now that's orgasmic chemistry.

Holly Taylor

Bill Bailey