I used to be a bellhop at a hotel when I was younger. My friend was usually fortunate when there was a guest, but I was never as fortunate. I thought that tonight would be the ideal moment to ask Nina Elle over and play a little role-playing, finally realizing that fantasy. She tips me in her own unique style, and I get to be her bell boy.
Professor Mellanie Monroe discovers a tablet with a teacher porn website in her office. Bill retrieves it, thanks her, and leaves. However, she confronts him, giving him a real-life experience of his dream, and then fucks him.
Francesca Le~ and Kayla Carrera, without electricity, engage in a heated argument when Francesca informs them that their husbands are causing trouble on their business trips.
Brittany invites Bill to her house as an intern, expecting to see his potential and give him a raise if he shows fresh ideas for clients.
Esperanza Gomez, Esperanza Gomez's English teacher, meets Bill and expresses gratitude. She offers him a Spanish lesson, teaching him about ass and tits, and then reveals her luscious breasts for him to suck on, resulting in a sexual encounter.
Angell Summers is delivering a folder to Bill, who is dropping by her residence. Despite being told to bring it by carpool, she insists on having him present it. They are married, but their relationship is irreversible.
At the big Christmas party with boss Bill, Brandi Love, Lexi Belle, Madison Ivy, and Veronica Avluv, they discover they all fucked him recently. They plan to surprise Bill with a surprise group fivesome, including stuffing his stocking.
Karen Fisher, a curvaceous woman, shows a potential buyer art and antiques in her home. She disguises her young stud to peek up his skirt, and when her top falls off, the buyer paints his own masterpiece.
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.
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.
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.
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.
Sarah borrows her boyfriend's credit card for shopping, but her son Bill dejectedly removes her cards due to excessive spending. Sarah asks Bill to care for her private parts while his father is away.