Losing virginity help!!

Alison
I'm 19 and I tried to lose my virginjty with my boyfriend a couple of weeks ago. He's not a big guy, but it hurt so bad I started crying before he even got the tip in. My doctor just thinks I'm...small...down there, if that makes sense, and that I just have to keep trying.
Problem is, both me and my boyfriend are terrified to try again. I'm scared of the failure and he's scared to hurt me. Has anyone else ever been in the same boat? Does anyone have any ideas how to make it more comfortable (besides lube)? Thanks!