I'm going to charge my boyfriend $50 if he doesn't make it home by 5am
How does him staying out so late make you feel?
It makes me disgusted and angry; especially because he can't seem to stop doing it.
If you feel like your boyfriend can't oblige a reasonable request you two might be incompatible. Even if you believe you are correct he might find that you are being too controlling.
So I shouldn't try to control him and do what I want?
If you boyfriend wants to stay out all night and party while you think he shouldn't, you  two might in different places in your life. It's not unreasonable to want your partner home before sun rise but clearly his obligations lie with his party life style. You might be better off finding a partner who doesn't want to be out all night on a regular basis.