South Park (1997)

S13E9 Butters' Bottom Bitch

Butters has reached the 4th grade without ever having kissed a girl, and his friends won’t let him forget it, teasing him relentlessly. Eager to keep up with the other boys, Butters sets out to change his luck. At the same time, an overly zealous police officer is on a mission to crack down on prostitution in South Park, leading to chaotic encounters in the town.