To Julise...
In my limited experience the whole thing is a learning experience. I have a sub who I am totally in love with. I want to hurt her but only as much as she wants to be hurt. We are 8 months into it now and I'm finding more and more that the further I push her limits...the more she likes it. Be a little patient and maybe he'll come around.
Consider having one of those conversations over a couple glasses of wine about both of your "ultimate fantasies" Just be careful...you may be surprised where it takes you!
Good luck