All really good advice.
I think the best way to get him to smoke one of your cigars would be to say "Hey, how bout you score me one of those Macanudos and I'll bring you something I really like, and we'll have a smoke. That way if you don't like mine, we can swap."
I know that's the best way to get me to try stuff I know I won't like.
If he enjoys your smoke, great. If not, let him smoke what he likes.