Barely legal sissy boy Jake desperately wants to be feminized and made into a sissy slut, but he has a thing or two to learn first. Penny sets about teaching him that she is not just another generic Mistress and burns her name into his memory. He is pantied, spanked, pinched, and more. His eager, young cocklette is mildly and he is taught to suck cock the right way. He still has a lot to learn before becoming an official sissy, but Miss Barber decides to reward him by stroking him off in his slutty, black panties, her own over his face as he breathes in the scent of her pussy.