I say go for it!! Go out with him first before jumping in the scak (slut) and when you talking, tell him how much you dislike hair, and you actually shave your own (even if you dont) this will make him more comfortable to ask how you do it... then you can suggest that you shave it for him while scrubbing his ass for him in the shower!!
Hope it all works out there hansel.
By the by: Is that you in your avatar? Couldn't be! could it??
I think you should wait until you see where the relationship is going first. Find out if you like his personality before anything else. You can always try dropping a hint about how much you like smooth hairless skin when you're out on a "date". Hmm, hope that helps.
My wife loves my hairy chest ..doesn't like it when I trim it down ( I don't like the hair at all )
But she hates a hairy back ...I just have a little and we shave it while in the shower every now and then.
Seems strange ..lovesit on the fron..hates it on the back ...women are weird!