IMO and its only that my opinion, I would be sitting him down and asking him straight how he felt about me, if he had feelings beyond that of SW and client and be honest and tell him you do.
That conversation also for me would need to include how he felt about you continuing to work while in a relationship with him as this is your job and you don't intend to give it up.
Only once the lines are drawn would I take the financial aspect away from the meetings, but that's me I've boon duped a couple of times and am now more cautious, I find the good looking ines tend to know they are and know how to play you to move to free sex.
I really hope this is everything you want it to be x