Dang... giving you advice was easier when all we had to discuss was ... how bad you really wanted a subway ...
1. Before telling him anything...find out a little about him... "Wow, so how long have you been in Vice....?"
2. Exactly what constitutes "Dating". My son tells me people his age don't really "date" until after they have "hooked up" with someone a few times and decide they really like them. Do you "hookup" ... or do you charge him? If you don't charge people you date, what happens if hobbiest (a lot are single) asks you out?
3. So now he's your BF, covered or no? Uncovered and telling him later you are in the business but you are "careful" may not sit well with him (actually, you may want to get legal advice regarding that one).
4. Where do you find people to date that are what you are looking for but (1) Do not read BackPage or (2) Do not cruise the internet?
5. If you date someone and he knows what you do, along with all the other insecurities that go with dating, don't you have to wonder if he's doing it for the free ride.
Just go find some wrinkled old guy with major bucks, marry him, give him the best sex of his life literally... take your new inheritance , retire and date till your hearts content.