In a twist of fate, Jimmy Michaels finds his stepmom, Cherry Kiss, a luscious blonde MILF, in the throes of a private anal pleasure session. Her short hair disheveled, her breast heaving, she's lost in the throes of anal ecstasy. Jimmy, his young cock tenting his pants, can't help but stare. Cherry, embarrassed but aroused, decides to turn this into a lesson. She guides Jimmy's inexperienced hands to her slick, taboo asshole, teaching him about anal sex, about respect, and about the forbidden desires that lurk within even the most wholesome-seeming families.