ADVICE NEEDED ASAP!!

I’m 14 and I’m dating this guy a year older than me. I have read up about this and I know that there’s always a risk of pregnancy and std’s. I’m on birth control and he has condoms. I know I am young but i do feel like I’m ready to give my virginity to him. He’s already had sex before and he says he knows what he’s doing. I do feel like I’m ready but my main fear is that it’s going to really hurt. If there’s anything you think I should know please let me know!!