Kendall Karson and Bill Bailey in My Dad's Hot Girlfriend

Bill sees his rich dad's young hussy of a girlfriend Kendall Karson constantly spending all of his money, so he decides she needs a little talkin'-to. He bets her that her little pink pussy is all wet over him, but Kendall says nothin' doin'. But he pushes her buttons so much that she can't help but feel his big cock, and when she does ... she's on her knees doing some immediate ball-sucking. The sexy slender brunette fucks her boyfriend's son until he blasts her in the chin with his cum.

Kendall Karson

Bill Bailey

Naughty America · January 30, 2013

London Keyes and Bill Bailey in My Wife's Hot Friend

London Keyes is supposed to have a lunchdate with her girlfriend, but when she shows up at her friend's place, she isn't home. She finds her husband, Bill, shirtless and shaving, and she's instantly turned on. London goes on to tell Bill that his wife told her some interesting things about their honeymoon ... including the size of Bill's massive cock! The sexy Asian wants her friend's husband to share that big dick with her while his new wife is out, but will he? You bet your sweet ass he will!

London Keyes

Bill Bailey

Naughty America · January 28, 2013

Jessica Bangkok and Bill Bailey in My Naughty Massage

Bill was referred by his buddy to masseuse Jessica Bangcock, who apparently gives "special" massages when she receives the correct password. When he says the magic word, the sexy Asian transforms from skilled massage therapist to horny cock-lover! Jessica slurps up Bill's dick in the most exquisite of blowjobs, allows him to suck on her juicy big tits, and slides his massive member inside her pink pretty pussy until she cums over and over and over again. Now that's euphoria!

Jessica Bangkok

Bill Bailey

Naughty America · January 25, 2013

Chastity Lynn and Bill Bailey in My Sisters Hot Friend

Chastity Lynn's boyfriend left for college and she thinks he's cheating on her with a bunch of chicks on campus. She's so bummed she goes to her friend's house for support, but she's not there, only her brother Bill is. She tells him her issue and he tells her that she needs to stop moping about it, and that she should get back at her guy by fucking another man ... HIM! Funny thing is, Chastity's been dying to fuck her friend's brother as much as he'd been craving his sister's friend's pussy! Everyone wins!!!

Chastity Lynn

Bill Bailey

Naughty America · January 22, 2013

Allison Moore and Bill Bailey in I Have a Wife

Bill is in New York City on business, and the girl showing him to his room, Allison Moore, notices that he's not wearing a wedding ring so she hits on him by petting his cock! Shocked, Bill tells her that he just got married and isn't wearing a wedding band because they're getting sized at the moment. But Allison doesn't give a fuck anyway, because all she's doing is sizing up his giant cock to see how it fits between her tits, in her mouth and straight up her wet pussy!!!

Allison Moore

Bill Bailey

Naughty America · January 18, 2013

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

Bill is horny as fuck and is hoping to get a nooner from his wife when he goes home for lunch, but the ass he grabs that's peeking out from the refrigerator doesn't belong to his honey --- it's her friend Brooklyn Lee! She stopped by to see Bill's wife, who had to run out but asked Brooklyn to fix Bill's lunch for him. Since Bill's hungry for pussy more than he is food, he asks Brooklyn to feed him something else. She's not into it until she gets a nice look at the big dick on Bill! After that she's more than happy to play the cock-sucking housewife who's willing to fuck her friend's husband in their kitchen!

Brooklyn Lee

Bill Bailey

Naughty America · January 15, 2013

Sarah Shevon and Bill Bailey in American Daydreams

Sarah Shevon is Bill's roommate, and he's been dying to get in those panties. He mans up and asks her out on a date, but she tells him she has a strict anti-roommate-dating policy, and leaves him hangin'. Bill can only dream about what it'd be like to suck on those natural titties and tickle her butthole with his tongue. Will he ever get to slam her holes with this big dick?

Sarah Shevon

Bill Bailey

Naughty America · January 14, 2013

Puma Swede and Bill Bailey in My Friends Hot Mom

Bill lost his phone at his buddy's place, only to have his friend's hot mom Puma Swede confront him with it -- and the dirty photos she paged through on it. Bill's embarrassed and doesn't know what to say, but there's only one thing to say when the busty blonde tells him he can have it back on the condition that he sucks on her big tits and fucks her hard with his giant dick: "Yes, ma'am!"

Puma Swede

Bill Bailey

Naughty America · December 28, 2012

Lisa Ann, Kendra Lust and Bill Bailey in 2 Chicks Same Time

Bill is looking for a room to rent, and when he shows up to an address where one is advertised as vacant, he's surprised to find two very attractive females, Kendra Lust and Lisa Ann. And when he discovers that they'd rather have a male roommate than a chick, he's even more surprised. But not as surprised as when he watches the two push him onto the bed in his new room, pull out their big tits and slobber all over his giant member! Where do I sign?

Kendra Lust

Lisa Ann

Bill Bailey

Naughty America · December 27, 2012

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

The jig is up for Rachel Starr! Her boyfriend's son Bill saw her dancing at the strip club the other night, and he calls her out on it when his old man isn't around. At first she denies it, but eventually the sexy brunette can't keep a secret; she knows she can't hide her big ass from anyone. To keep it a secret between him and her, Rachel does to Bill what she does in the champagne room -- sucks his big dick and rides it while her jiggly ass slams against him.

Rachel Starr

Bill Bailey

Naughty America · December 25, 2012

Lexi Belle, Brandi Love, Madison Ivy, Veronica Avluv and Bill Bailey in Naughty Office

Merry XXXmas!!! It's the big Xmas party with Brandi Love, Lexi Belle, Madison Ivy and Veronica Avluv, and they're ready to party hard with their boss Bill. But while the sexy women are waiting for the bossman, they find out that not just one of them fucked him recently, but ALL of them did! But they don't intend to keep that secret buried; rather, they want to give Bill a big present and by getting naked to jingle his balls in one big fivesome ... but not without stuffing his stocking, too! The more the merrier! Happy Holidays from Naughty America!

Brandi Love

Lexi Belle

Madison Ivy

Naughty America · December 24, 2012

Brandi Love and Bill Bailey in Naughty Office

Brandi Love is feeling the pressure. Not only is she getting stress from the holidays, but the office manager is feeling the heat from corporate, pushing her to reach her deadlines with the books. She asks the big boss Bill for some help, and when she tells him that he'll take care of corporate directly, she feels more than relieved ... she feels horny as fuck! The sexy MILF straight-up tells Bill that she would feel even better if he'd fuck her. Can wild Bill fuck another one of his hot employees? You bet your sweet ass he can! But can he make sure it's kept a secret???

Brandi Love

Bill Bailey

Naughty America · December 21, 2012

Madison Ivy and Bill Bailey in Naughty Office

Get the chalk! Madison Ivy just made ANOTHER, huge sale, and her boss Bill wants to reward her! When she stops by his office he hands her an envelope with a sweet little bonus in it, making Madison ecstatic! But when she hugs Bill he takes it a bit to far and kisses the married woman. He apologizes, but apparently Madison didn't mind too much because out come her big tits, wet pussy and insatiable appetite for cock! She ends up giving her bossman a nice sloppy blowjob and letting him plunge his big dick deep inside of her. That's a bonus for everyone!

Madison Ivy

Bill Bailey

Naughty America · December 21, 2012

Tracey Sweet and Bill Bailey in Naughty Bookworms

Like any good politician-to-be, Tracey Sweet knows what has to happen in order to win an election: it has to be rigged. So, running for student president, Tracey goes to her professor and gives him an offer he can't refuse: in return for winning the election, she'll suck his cock and fuck him right there in the classroom! The sexy blonde rubs her natural tits all over her teacher and gives him the sloppiest blowjob of his life. Think she'll win?

Tracey Sweet

Bill Bailey

Naughty America · December 20, 2012

Lexi Belle and Bill Bailey in Naughty Office

When Bill catches his new hire Lexi Belle watching porn, he decides it's on. He apologizes for Veronica Avluv's bad behavior, then moves on by inviting Lexi to the Christmas party and gift exchange, but he can't wait to unwrap the present he wants -- her. The big boss tells her that Santa has a giant candy cane for her to lick, suck and devour ... all she has to do is get on her knees and she'll get it in her mouth. Lexi fits right in at the new office, especially when she rides her boss's big dick!

Lexi Belle

Bill Bailey