Penny's Fucking 40

It's Penny Barber's 40th birthday and her best friend, Ryan Keely, is about to take her out for a night of fun to celebrate. But when Ryan sees how... modest... Penny's outfit is, she's unimpressed. Now that Penny's a MILF, she has to dress the part, which is when Ryan gifts her a sexy form-fitting dress to wear instead. Although Penny's flustered, she gives in and tries it on.

When they later leave the house, they bump into Ryan's stepson, Axel Haze, and Penny's stepson, Max Fills. Max is instantly flustered and taken aback by seeing Penny in sexy attire for the first time and Penny is embarrassed, which leads to her running back into the house.

Max takes off into the house as well, retreating to his room with Axel on his heels. But they aren't alone for long before Ryan checks in on them to comfort Max. It's revealed that Max has confusing feelings about seeing his stepmom in a sexy dress, which Ryan immediately takes advantage of by coming onto him. It's further revealed that Ryan has an ongoing sexual relationship with Axel, which shocks Max. Both Ryan and Axel then work together to convince Max to have sex with Ryan and embrace his newfound love for MILFs. But little do they know, Penny's listening at the door...