While magical things can happen between an escort and a client, for every one that does, there are a thousand stories of poor fools being taken in by handsome young hustlers. I very seriously doubt you're one of the lucky rare ones...
Who knows what happened to the money you gave him? Maybe he spent it on drugs, maybe he bought clothes and toys, maybe he just put it in the bank and lied to you and said he spent it all so you'd give him more. So far, his strategy of telling you he needs money seems to be working since when he asks, you give it to him.
He was working in a bar where he exchanges his sexual favors for your money. It wasn't you he wanted, it was your cash. He may be a nice guy, he may like you, but don't mistake the nature of the relationship.
If you stopped paying your mechanic, even if you liked each other, he'd stop helping you.
I think the problem is that lots of us who hire have an emotional need that escorts can fill. That's ok as long as we're very honest with ourselves about that. If we aren't, then we can fool ourselves into believing that the escort's act is real. It isn't.
I think you're letting your emotions cloud your judgment. It has happened to all of us at one time or another. But step back and examine the escort's behavior dispassionately. It sure looks to me like he's taking you for your money and doesn't give a damn about you. Either that, or he's a complete train wreck and you are better off staying well away.
If he's into drugs and trouble, you aren't going to save him. The only person who can save him is himself.
Good Luck.