Ricky Spanish is sulking in his bedroom, and his stepmom Caitlin Bell asks him what's wrong. Ricky explains that his girlfriend broke up with him just before prom to go with a different guy instead. Caitlin tries to console him. He asks Caitlin why girls think he's not good enough for them, he's just as good as those other guys, just in different ways! Caitlin agrees and coddles Ricky, saying he's sweet, sensitive, kind - all those things would be plenty good enough for HER! Caitlin keeps insisting that he's a real catch - those high school girls don't know what they're missing out on. Ricky feels a bit better but is still sad and pouting - he even had a special surprise planned, with a limo and hotel for the girlfriend and they were going to... He stops himself from continuing. Caitlin gently encourages him to continue, she thinks she knows what he's about to say and won't judge. He admits they were going to have sex for the first time and both lose their virginity. Caitlin consoles him, holding him in her bosom and saying it'll be alright, he'll get his chance some day. He whines that he doesn't know when that will be, it could be YEARS from now. Caitlin is sympathetic and wants to cheer him up, and suggests a bold idea. If he really wants to lose his virginity that much, maybe... she can help? He's shocked that she would suggest it. After she assures him she's not joking and wants to do this for him to cheer him up, he's ecstatic and grateful. She says maaaaybe they shouldn't tell anybody about it, though. He eagerly agrees to keep it a secret, and Caitlin lovingly guides Ricky through his first sexual experience.