Why didn't Holden want to have sex with Sunny?
The scene with Sunny is one of the best in the whole novel. It is both sad and funny. Holden is trying to act "suave," to use his term, but he doesn't feel it. He tells the reader:
If you want to know the truth, I'm a virgin. I really am.
Most readers will not be surprised. Holden doesn't want to have sex with this tough, street-smart, tarnished girl because he doesn't feel sexually aroused. He knows he would be unable to perform. It would be a dismal experience, and it would be his first experience. He feels nervous, He is afraid. He has a mixture of chilly feelings--but none of his feelings have to do with being aroused. He keeps stalling Sunny, hoping that some slight tingle of sexual desire will make itself felt.
His biggest problem is that he equates sex with love, and he can't evoke any feeling of love for this wretched girl. What he feels is pity more than anything else. She is being exploited by Maurice and by every man who uses her body for five bucks a throw, or fifteen till noon. She has become totally desensitized to sex. Her life is ruined although she is still very young. She is like many girls who get caught up in the so-called "oldest profession," which goes on all over the world and destroys countless young lives.
Holden shows how he feels about Sunny when he says:
I took her dress over to the closet and hung it up for her. It was funny. It made me feel sort of sad when I hung it up. I thought of her going in a store and buying it, and nobody 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 doesn't know "why exactly" he has a lot of the thoughts and feelings he has. He is a gentleman, a nice guy, a sensitive young man in an insensitive world. He is ashamed of not being able to perform a filthy, vulgar action with a complete stranger in a cheap transient hotel room, when he should feel justified in having such self-respect as well concern for a fellow human being, degraded as she is.
When Sunny and Maurice come back to try to coerce another five dollars out of Holden, the little prostitute shows that she has not been entirely oblivious of his sympathy and consideration.
"Leave him alone, hey," Sunny said. "C'mon, hey. We got the dough he owes us. Let's go. C'mon, hey."