dozens of times, and it's not that bad. It's alot like a shot, actually, unless you happen to be very allergic. It surprises you, but like a shot the pain is gone pretty quickly. If the stinger gets left in, go ahead and pull that sucker out.
It's not a big deal, but it's not pleasent hence why people don't like bees.
Wasps, too. Depends on the wasp, and the person, I guess. I got stung a few times by them, also, didn't really think it was different than a bee sting, except the wasps didn't die as a result, so I hated them more.
Haha, a friend of mine has a dog that likes to eat bees and wasps. He'll jump around like crazy until he catches one, yelp and run off and hide somewhere when he does, then he's back to chasing them in a few minutes.
That dog also likes to sleep in the middle of the road.