Chester High School is a school in Fluvanna, near Stoolbend.
After Cleveland Brown Jr. agrees to be Daisy's prom date when she believes him to also be a lesbian in "All You Can Eat", the school principal threatens to shut down the entire dance rather than let two lesbians dance together. Junior enlists Roberta to pretend to be his lesbian date. As they arrive, the principal threatens to shut down the dance. Junior comes clean about being a guy with his own sister. Daisy arrives and admires Junior for standing up but wants to leave. Roberta talks her into a dance together and she also invites Junior to join them.