The novel begins with a definition of "Portnoy's Complaint" describing it a psychological disorder in which a well meaning person feels at war with his or her powerful sexual kinks.
We then meet a young Jewish man who is dealing with exactly that predicament. This entire novel is one scene, one continuous dialogue where the young man explains to a therapist about his life during a session of psychotherapy.
He begins by telling his therapist about his family, and about his private battle with obsessive masturbation, an area in which he was sexually adventurous. He also recounts stories of various times when he had sex with girls from his classes. He used to know a model named Monkey, and they would get real weird together.
As part of his Jewish heritage, the boy recounts his pilgrimage to Jerusalem. The boy explains the tension between his moral commitment to do good and his sexual desire to do evil. This dilemma comes at a great price, and this therapy session is filled to the brim with expletives, obscene stories, and unbridled self-hatred.