I wonder whether he's happy with some of the simpler things in life like, as others have suggested, a picnic, a home cooked meal or a walk, or whether he's used to a more lavish lifestyle and doesn't want to compromise.
You might not be "money driven", but money is becoming an issue in your relationship, and I don't see how it can be otherwise while you feel uncomfortable with the current situation of him wanting to pay for things a lot of the time.
To answer your question, I haven't been in this situation since I was young when, like you, I also felt uncomfortable and even embarrassed at being paid for by someone wealthier and older than me. The relationship didn't last. Relationships work better for me when I feel as though I'm on roughly equal terms with people.
I hope he respects how you feel, that he listens to you and is willing to compromise. Perhaps he needs to be shown that some of the simpler things in life can be more meaningful and that well chosen gifts and thoughtfully planned dates don't have to cost the earth. They're usually the ones that create the best memories, in my experience. In time, would you perhaps trust him more and feel comfortable with allowing him to treat you to something a bit more expensive occasionally?
I really hope you can work it out with him!
