I've been on both sides.. The one nervous to bring it up and the one that has the stammering woman saying "ok, so, please don't think I'm weird but...."
It all comes down to mutual understanding. I don't always like what she likes and wants to do, but I never snicker or laugh.. I always reply with something like "oh, that? nah.. that's not weird.. trust me... and, I can see how that would excite you.. " and then I follow with something from my list to show her she's not the only one with non-standard desires... One woman I was with finally admitted to liking being choked during sex and was ashamed of it, I simply countered with an "oh, well, I like electrical stim" -- which not only made her feel less of a freak, but it opened an hour long discussion in to all manner of "play time" ideas and "do you like [activity]" from both sides..
If you don't know how he'll react.. try to start with something that's non-standard but not too far out there. Most men like being dominating in the bedroom (even if it's mild).. so, start with that.. make some suggestive comment to him about how you'd like him to just be raw and take you, you can add in things like.. "I want you to do whatever you'd like to me..." then take his hand and slide it in to your pants and rub your lips with it... tack on the "fuck me eyes" and.. phew... I know that would make me throw you over my shoulder, rip your clothes off and pretty much break you.. =)
If you're talking about getting him to examine you at home, play Dr, etc... maybe ask him to come to an exam with you and see how he responds... Or, tell him that you'd like to teach him how to properly examine your breasts... I'm sure he has his hands on them a lot and it's not only a good way to break the med-fet ice, but he will be doing you a favor.
Honestly, I think more men should go to gyn exams with their spouse; or at the very least spend some time viewing the inside of her.. I mean, we spend a lot of time in there with our fingers, tongues, genitals, etc.. We should know what it is we're feeling and how it all works. I like seeing my gf with a spec in her.. there's something about seeing her cervix and inside that makes me feel a little closer to her.