Butters has made it all the way to the 4th grade without ever kissing a girl. All of his friends have been teasing him mercilessly. Butters is determined to catch up with the rest of the boys in his class. Meanwhile, one overly dedicated cop wages war on Prostitution in South Park.
The boys are beating up on Butters again via tetherball. Stan and Kyle interrupt to find out why they are bullying him today, to which Cartman explains Butters has never kissed a girl. At the same time, Clyde runs over and states Sally Darson is giving out kisses for $5 behind the school. Butters prepares himself with the other boys' encouragement (except Kyle, who claims a first kiss should be something special) and pays his dues for a kiss. Finally having obtaining a kiss from a girl, Butters finally wins the respects over the boys. That night, Butters takes things far too seriously and begins preparing to find a living as an adult.
Butters promotes to some other unpopular boys about Sally's service, and after Scott Malkinson visits, Sally and Butters enjoy the money they've amassed together, and Butters suggests turning it into a full-fledged company, recruiting more girls to fill in during times Sally is busy. It became a huge success, and Butters goes to school and tells the main boys about it. Most of the boys are disgusted by the idea, with the exception of Kenny. Kyle then declare he's a Pimp and leave. Butters then looks up the term with his girls and declares Sally his Bottom Bitch - the one girl the pimp reserves for himself, or the player's favorite girl. He then notices a pimp convention (identified by a flyer as the Players Ball) and goes to get tips from other pimps. He comes home late and when his parents inquire about his "girlfriend", and they are shocked by Butters' new found pimp vernacular.
Elsewhere, Sergeant Yates at the South Park Police Force realizes the cops need to combat the sudden rise in prostitution and chooses to go undercover, dressing like a woman and charging separately for oral sex, half and half and anal sex. Even though Yates still has a mustache, manly body hair, and a deep voice that he doesn't even attempt to disguise, a John does pick him up and offers Yates $20 for oral sex. Rather than arresting him right then, Yates proceeds to perform fellatio on the man and afterwards arrests him. He eventually goes on a group sting and gives his colleagues the code word "stretch" but waits until after he commits anal sex on the man to call it, confusing the other officers. Later, Yates prostitutes himself to an entire Alpha Tau Omega fraternity house to the tune of Peaches's "Fuck the Pain Away". Afterwards, he sharts all of their semen into an evidence bag. Some officers worry that he may be getting carried away, but Yates denies it. After his phone rings, he then informs them that "daddy" is calling, and shuffles off very quickly. Yates, unfortunately, is taking his duties too far; he has adopted the persona "Yolanda" and even has a pimp, that he often responds to booty calls for. Other prostitutes are seen gossiping about how respectful the "new pimp" in Park County is.
Back in South Park, the Recess Supervisor ends breaktime and sends everyone back to lessons. While in class, Butters solicits both Bebe Stevens and Wendy to join his operations. Both refuse after repeatedly being called bitches. Wendy calls on Stan's help. Stan tells Butters he can't call his girlfriend a bitch and a small argument ensues that is ultimately settled when Butters nonchalantly pays Clyde $100 to protect him in case Stan makes good on his threats. The next day on the playground, Kyle tries to talk sense into Butters and how he's changed but Butters explains that he is a man and that he refuses to be like other boys and listen to their girlfriends talk about their problems. Butters then visits South Park's local ACORN office to apply for housing benefits, mortgage loans, and tax-free status for his business. Butters is initially refused but when he identifies the boss as being a client of some of the real prostitutes who begin working for Butters, they are given the benefits.
Many of the real prostitutes have left their pimps for Butters, who is still under the belief it is all a kissing operation. When one of the hoes questions why Sally is Bottom Bitch, Butters settles it only for Sergeant Yates to come in, still undercover, and ask for a job making a point of how long it took him to track them down. Yates' original pimp, however, appears outside, begging for "Yolanda" back. At first Yates refuses but when the pimp proposes to him, he rushes and they make out on Butters' front lawn. Butters, feeling guilty seeing them in (what he believes to be) love, leaves the company and encourage the girls to take the money for themselves. At that point, the prostitutes smile at Butters for encouraging them.
In a final scene, Yates and his pimp are shown celebrating their first anniversary amidst photographs of their honeymoon and wedding in a small house in a place similar to Switzerland, as the pimp had discussed earlier. (Yet this seems makes no sense, since Yates is already seen to have a wife in a previous episode although) Yates asks to show him something after receiving an anniversary gift, only to bring out his badge and gun yelling "I'm a cop!" as the episode ends. Yates also seems to have forgotten about Butters since he doesn't arrest him.