When Holden Caufield leaves a bar in Greenwich Village, New York, he decides to walk the forty-one blocks back to the Edmont Hotel. Not because he feels like walking, but because he is just sick of taking taxis. It is freezing out, and Holden folds down the flaps on his trusty red hunting cap. He goes into a whole walking daydream of finding and confronting the student who stole his gloves at Pencey Prep School. Holden misses those gloves because his hands are cold. But he imagines how it would play out if he found his gloves in another student's room, hidden away in their galoshes. Holden is playing out how he would just be a coward and not dare punch the guy who stole his gloves. It bothers him that he doesn't like fist fights. He doesn't like them, not so much because he is afraid of getting hit, but that he doesn't want to hit someone else in the face. But he does not give himself any credit for his obvious kindness but insists that he is ashamed of his cowardice. This intense remunerating over his lack of bravery causes Holden to become depressed.

The fact that Holden has become so depressed leaves him vulnerable to the offer by the elevator guy (Maurice) to send a prostitute to his room. Holden tells us "Okay, I said. It was against my principles and all, but I was feeling so depressed I didn't even think. That's the whole trouble when you're feeling depressed, you don't even think." The deal for a "throw" was for five dollars. Holden goes back to his room and changes his shirt. He confesses to us that he is a virgin. He is the type of guy that when girls say "stop," he stops, whereas other guys keep going. Holden has admirable traits that make him a good guy, but he is not proud of those traits. For example, he learns through this unconsummated experience, he needs to like a girl, to want to be intimate with her. But when Holden respects a girl, like Jane Gallagher, he also feels protective of her and doesn't want to degrade her. He tells us again here that sex confuses him, but he wants some practice in case he gets married.

The prostitute, Sunny, is about Holden's age. He feels she is also very nervous even though she gets upset when he doesn't want to have sex with her. Holden tells two lies here. The first is that he tells her his name is "Jim Steele" and the second is that he tells her he cannot have sex because he has just had an operation on his "clavichord." His choice of the word, the clavichord is very amusing since a clavichord is a musical instrument! It is even more ironic because it is the second musical instrument that Holden has recently mentioned to us. The first instrument was a violin. Prior to Sunny's arrival, Holden was telling us about this character, Monsieur Blanchard, from a book he read. "He said in this one part, that a woman's body is like a violin and all and that it takes a terrific musician to play it right." Holden confesses that he would like to be able to "play it right", because a lot of the times he cannot find where anything is located on a woman. It is interesting that when he decides he cannot go through with the sex (he is too depressed), Holden chooses a musical instrument as the body part that is injured. Sunny does not realize that a clavichord is not a body part but becomes angry with him because she wonders why he asked for a prostitute if he didn't want sex. Holden assures her he intends to pay her the five dollars. Sunny says it is ten dollars. Holden says that is not what he agreed upon with Maurice, the elevator guy. Sunny takes the five dollars but calls him a "crumb bum" on the way out the door.

Now that he has the room to himself again, Holden starts to have an imaginary conversation with his dead younger brother, Allie. Then he tells us that he feels so depressed he wishes he could pray. But he cannot pray because he tells us while he likes Jesus alright, the disciples bug the hell out of him. He feels that they were completely useless to Jesus before Jesus died. Holden also says that he can't stand ministers because they all put on phony voices when they preach. We also learn from Holden that he and all his siblings are atheists, but he still wishes he could pray. He is lying in bed, smoking a cigarette, when suddenly there is a knock at the door. It is Maurice and Sunny coming to get the five dollars that they say Holden owes them.

They force their way into the room, and Holden repeats that Maurice clearly said it was five dollars for a "throw" and fifteen dollars for the whole night. Maurice backs Holden against the wall and snaps his fingers on Holden's private parts. Holden has been crying the whole time, he feels humiliated because he is in his pajamas, and because he knew something like this was bound to happen. He gets so angry at Maurice and curses at him and calls him a "dirty moron". Meanwhile, Sunny has found Holden's wallet and took the five dollars she says she is owed. Then, Maurice punches Holden in the stomach with great force. Holden is doubled over on the floor when the two take-off out of the room.

Holden then pretends he that he has been shot in the stomach and makes a dramatic move to the bathroom. He pretends he is very tough. He imagines he gets a gun and goes and finds Maurice and shoots him in the stomach. This charade does not last. And Holden tells us he feels suicidal and would like to throw himself out of the window, but the thought of all the morons on the street gaping at his mangled body on the sidewalk disgusts him.

Chapters 13 and 14 show us that Holden engages in very high-risk behavior. While he does not have sex with the prostitute, Sunny, having any dealings with her has opened up the possibility that foul play will follow. Holden suffers both physically and mentally as he is shaken down by Maurice, who comes to the room with Sunny for the additional money that Holden never agreed to pay. The interaction is a violent and humiliating experience for Holden and one that leaves him feeling even more depressed than he had been before.