In Chapter 12, Holden gets involved with a young prostitute who calls herself Sunny and the elevator operator named Maurice. He agrees to pay five dollars for a throw, and then:
I was already sorry I'd let the thing start rolling, but it was too late now.
He waits in his room feeling nervous. He puts on a clean shirt.
I knew I didn't have to get all dolled up for a prostitute or anything, but it sort of gave me something to do.
If you want to know the truth, I'm a virgin. I really am.
People who claim that Holden is just as phony as the people he calls phonies ought to reread this chapter. He reveals himself completely to the reader as the fairly typical sixteen-year-old boy he really is, and pretends not to be. He wants to lose his virginity--but not for five dollars in a cheap hotel where the lobby smells "like fifty million dead cigars."
When Sunny shows up, Holden tries his best to appear nonchalant, but he shows his youth and inexperience in everything he says and does.
"Allow me to introduce myself. My name is Jim Steele," I said.
He is actually horrified when she stands up and pulls her dress over her head.
Sexy was about the last thing I was feeling. I felt much more depressed than sexy.
He keeps trying desperately to establish some sort of relationship with this tough, uncommunicative girl, who just wants to get it over with and collect her five dollars. When she asks him to hang up her dress so that it won't get wrinkled, he observes:
It made me feel sort of sad when I hung it up. I thought of her going to a store and buying it, and nobody in the store knowing she was a prostitute and all. The salesman probably just thought she was a regular girl when she bought it. It made me feel sad as hell--I don't know why exactly.
Holden is an incurable idealist and romantici. The "throw" turns into a fiasco. He can't bring himself to go through with it, and he makes up an atrocious lie to put Sunny off. It is ironic that after he experiences compassion for this ignorant, exploited girl, she realizes she can take advantage of his innocence to extract more money from him. She says:
"This is a five. It costs ten."
Holden refuses to pay the extra five as a matter of principle. But Sunny comes back in Chapter 13 with the tough Maurice, and together they literally rob Holden of another five dollars. He may not realize it, but he is getting more than his money's worth in worldly experience. He might have gotten beat up by Maurice if Sunny hadn't intervened after helping herself to five dollars from Holden's wallet. She has, after all, developed a certain sympathy for Holden because he was polite to her and because they are both young and, in their separate ways, are both lost souls.
The scene between Holden and Sunny is somewhat reminiscent of a scene in Dostoevsky's wonderful Notes from Underground, in which the anonymous narrator accompanies some acquaintances to a house of prostitution and meets a girl called Liza.
Liza is a prostitute with whom the narrator has sex. The narrator attempts to convince Liza to give up prostitution because it will wreck her life. He entices her, making her believe he is wiling to take care of her. Liza is the narrator’s one chance to love. She is also the only person who sees through his antics and understands how miserable he is. She knows, too, that despite the fact that he may need it, he does not know how to love. Her knowledge embarrasses and humiliates the narrator.