Virginnnnn

So like my boyfriend and I have been talking about having sex for a while now and I've been nervous (I'm 16) like I get nervous about everything but this is big and he's so sweet and patient but I think I'm ready I mean I'm still nervous but I trust him and everything. We're both virgins. Any suggestions bc I have multiple friends who have had sex a couple without condoms the first time and a couple with and the ones without said it hurt like a son of a and my friends that used condoms said that it doesn't hirt. Idk if I depends on size of body, penis, or anything but I'm pretty small (120ish pounds and about 5ft 6in ish) and my boyfriends penis is 8.5. Any suggestions? Like all around?