The biggest tips I can give you are to relax and use lots of lube. Also, make sure your fingernails are trimmed and you've "cleaned" yourself down there before you do anything else. Nobody wants a poopy penis. Take things slowly because rushing is only going to hurt you. Good luck! 

Definitely eyes closed for sure. I find kissing open eyed is creepy….

This one's a tough one. I would never jeopardize my relationship with any of my friends, but if he's a 10/10, I'd go straight for it. (pun not intended)

If I'm in a committed relationship and my partner has gotten tested, then bareback.
Otherwise, condoms.