very nervous virgin

ok so I have a few different things that are terrifying me.
the first being I'm afraid of getting pregnant. now protection isn't an issue, my boyfriend knows it's not going to happen until after I've started taking birth control and it would definitely be paired with a condom, but I don't know why I still get so nervous that with this 99% effectiveness I'm going to be that 1% so for that I more or less just need words of encouragement.
I'm also very afraid of how much it will hurt. I know my boyfriend isn't a virgin and that's ok with me (it actually makes me more relieved because at least one of us knows what we're doing) and I know he's willing to be patient and gentle, but I'm a baby when it comes to pain so is it really that bad?
though I'm glad my boyfriend is experienced, it makes me nervous at the same time because we're not in the same boat. He's experienced and I'm not, and though I'm happy he's so educated about sex (and actually a bit impressed, he actually reads up on it) I feel kind of like I'm not going to compare to what he's had before. i mean the chemistry in our relationship is there, and he's told me that I mean more to him than any girls he's dated in the past (and yes I'm with you, I'm kind of the first person to call out how corny that is, but I genuinely do think he means it) but I know he wants to (and he's not pressuring me at all, he's 100% fine with waiting until I'm ready) but when the time comes I'm afraid it's just going to be terrible compared to the last person, I mean he would never say if I was but it's an insecurity.
there's more but I don't want this being too lengthy so I'll hold off on the rest for another time