Portnoy's Complaint, by Philip Roth
The book starts with a clinical definition of Portnoy's Complaint: "A disorder in which strongly felt ethical and altruistic impulses are perpetually warring with extreme sexual longings, often of a perverse nature." That should prepare you for what is coming next: a hysterical tale of guilt, shame and lust as told by protagonist Alexander Portnoy to his psychoanalyst Dr. Spielvogel. Portnoy's Complaint takes place in 1969 — the apogee of the sexual revolution — but there is nothing free about Portnoy's love. He is frank and vulgar about his desires yet, conversely, racked by guilt over them, often due to the baggage associated with having been borne of a conservative Jewish immigrant family from Newark, New Jersey. All bets are off when he meets Mary Jane Reed, a.k.a. the Monkey, one of the only women who can go libido to libido with him. Politics, identity, culture — everything is viewed through the lens of sex, often in unsparing detail and crude language, which led to the book being briefly banned in Australia and some libraries in the United States.