I was tailgating at a FB game in late fall one year and the yellow jackets were out in force looking looking for food. Took a swig of my beer and one of those fuckers must have been helping himself because he stung me on the back of my tongue. Good thing I'm not allergic, I would have probably been dead in seconds.
Male athletic shorts and swimming trunks were SUPER short back in the ‘80s. I remember riding my bike and having one fly right into my shorts and getting me in my crotch. She got me a few times on the leg side. Good thing I was wearing my tightey whiteys!
Worst I had in the mouth was at Six Flags. They were closing and I had just finished riding one of their coasters when they invited the people who just rode to ride again so that it wouldn’t be too light for the few people remaining in line. I should’ve said “no” but I took the opportunity to ride right in the very front. We crested the starting hill and were reaching maximum speed when I opened my mouth to say something to my friend.
Just as I opened my mouth I felt a *smack* on the edge of my front teeth and I suddenly had a bunch of still-squirming insect legs and wings and other parts sprayed right in the back of my throat. Instead of speaking as intended it only came out as coughing and hacking. I hope the spitting that followed didn’t become a problem for anyone behind me.

I still don’t know if it was a stinging insect or not but there were a lot of June Bugs around and the feel of it cracking open against my tooth seemed like it was most likely a hard-shelled insect.