If this guy finds out that you've been "working" after you and he started a relationship, he will probably not want to stay with you. One think he'll worry about is that, whenever you want some extra money, you'll resume the old life style, even after you and he are living together.

I think that if you really want a traditional relationship with a guy, you'll have to put your working days behind you. Then don't disclose your past, unless you believe that he's likely to find out anyway.