Jake Grand, a crossdressing pizza delivery guy, faces an unusual dilemma when he's left with a pizza debt. His customer, Dolly Dixxxin, suggests a kinky barter - fuck him, and the pizza's free. Jake, in a lacy bra, panties, and stockings, blushes at Dolly's lewd propositions, but the thought of fucking a guy while dressed as a woman gets him rock hard. He eagerly agrees, dropping to his knees to service Dolly's stiff cock before Dolly bends him over, fucking him silly while Jake moans in high-pitched ecstasy, his sissified fuck proving to be the best tip Dolly's ever received.