Late 20s I don't have any right now. But as a teen I had a few in highschool I regularly beat it with. Then in college I also had a few guys who all had an understanding about jerking off in shower areas or when we were like in each other's rooms etc.

Not generally too bothered by medical seeing me. When I was a teenager I had to get my sports physical done by a woman that's probably the most uncomfortable I got.
I'm in general pretty cool with being seen naked by whoever.

Honestly kinda weird but I love how difficult it is to breathe when a chick sits on my face. But also when she cums it's so rewarding. Plus I love walking around with that little gloss on my face and getting to lick it off my mouth a little at a time.

14. In one of those walled enclosures for a dumpster behind a movie theatre. Just how everyone wants to lose their virginity.

Not usually. I can get a little embarrassed at first blush but usually I just kinda enjoy it.
But if I know they're younger than me and have substantially larger meat than mine... that's a little different. Like my little brother is bigger than me and that one always kinda gets me whenever I think about it.