Does Holden have sex with Sunny, the prostitute?

No. Holden’s depression, along with his unacknowledged issues with sexuality, keep him from having sex with Sunny. When he returns to the hotel and agrees to a stranger’s offer to send a prostitute to his room, Holden immediately regrets it. He calls the situation a “big mess,” and admits that he only said yes because he wasn’t in his right mind: “When you’re feeling very depressed, you can’t even think.” Before Sunny arrives, Holden contemplates his history of failed sexual experiences. He confesses to being a virgin and offers a vague explanation, stating that “something always happens” that stops him before consummating the sexual act. When Sunny eventually arrives and undresses, Holden shuts down. “I know you’re supposed to feel pretty sexy when somebody gets up and pulls their dress over their head,” Holden says, “but I didn’t. . . . I felt much more depressed than sexy.” Although Holden attributes his hang-up to depression, the reader can also intuit Holden’s unspoken issues with sexuality when he shifts the blame from himself to Sunny: “She was depressing.” Instead of being depressed himself, Holden insists that Sunny is making him depressed, and uses this as an excuse to shut down the encounter.