Rachel Starr and Bill Bailey: An Ass Man's Date (HD)
Rachel Starr
All I can say is that I'm an ass man. That's why it makes total sense that I pay for Rachel Starr, the porn star, to be my date for the evening. In my mouth while I'm tonguing her very wet pussy, in my bed, in my hotel suite.
Even better is her tight asshole, which is her actual moneymaker and a pulsating, puckering beacon. And as my enormous dick pierces her, I'm going to drown her gorgeous ass in oil and see it shine from behind while it bounces up and down against my belly.
Bill finds a room for rent with stunning women Kendra Lust and Lisa Ann, who prefer a guy roommate. They humiliate him, expose their tits, and drool on his member, prompting him to decide where to sign.
Evan is exhausted and upset after fucking Alison, and Roxanne follows Bill to find a new partner for the next year. Roxanne offers Evan something Alison cannot, and he discovers steamy anal intercourse while being led back into the weight room.
Bill struggles in her course, worried about maintaining his football scholarship. Professor Sights suggests demonstrating her deepthroating skills for a high grade, as the academic year begins.
Bill discovers Holly Michaels steals sales leads while out. Bill plans to report her, but Holly's sex changes his mind. After destroying her face and spectacles, he lets it go, causing a bitch to take revenge.
Bill spots attractive Shazia applying for executive assistant job, expressing interest in a reverse cowgirl or doggystyle. During another interview, she gets hot and tells Bill to fuck her, potentially causing Secretary of the Year controversy.
Molly Bennett, a beautiful wife, expresses her love for her husband by delivering lunch to his office, giving him a blowjob, and causing him to squirt love juice on her face.
Katie criticizes Bill for not doing a good job cleaning her house, demanding immaculate conditions. Bill relaxes, but falls asleep, dreaming of Katie's tits and cock, and reminisces about housekeeping.
Tracey Sweet, a political aspirant, offers her professor a rigged election if she wins, promising to suck his cock and fuck him in the classroom, causing speculation about her chances of winning.
Bill visits his friend's house to borrow a guitar, but finds his mother, Jessica Jaymes, there. She informs him that her son has left the band, leaving her to suck her friend's dick. Bill confronts her, but she continues.
Teri Weigel's neighbor is frustrated with her dog destroying their yard, and they both confront her. Teri, being a cougar, bites into her neighbor's penis, causing her to snatch it, prioritizing her pussy over the dog's issues.
Jessie, a French girl in Bill's social studies class, is caught in a panty raid by Bill. She is enamored with the underwear he is stealing and invites Bill to pop her ass.
Gabby Quinteros is excited about a plumbing firm that hires attractive men to care for female customers. When Bill the plumber is called to fix her shower, Gabby flashes her tits and pussy, preventing him from backing up.