Jim, a handsome, all-American athlete, has always been shy around girls. But when he and his best friend, Bob, partake in "awful kid stuff," the experience forms Jim's ideal of spiritual completion. Defying his parents' expectations, Jim strikes out on his own, hoping to find Bob and rekindle their amorous friendship.

Along the way he struggles with what he feels is his unique bond with Bob and with his persistent attraction to other men. Upon finally encountering Bob years later, the force of his hopes for a life together leads to a devastating climax. The first novel of its kind to appear on the American literary landscape, The City and the Pillar remains a forthright and uncompromising portrayal of sexual relationships between men.