The pain and the swelling reaction are highly variable. You will have a better idea after you have been stung 100 times.

But as for me, I don't seem to get used to the pain. It always hurts.
I'm hypersensitive to bee venom (as in anaphylactic type reactions) so I take regular shot of venom from an alergist. That has made a huge difference in my local swelling reaction as well.