Quoting rpgmomma8404:" Let's say all the guys you've ever had sex with have, like, I don't know, small to normal penis sizes ... [snip!] ... hurt the first time? I know this is probably the dumbest question ever. I'm just wondering if anyone has experience this. "
Depends on a lot of factors.
How excited are you?
How big is your vagina?
How rough are they?
Bigger is NOT always better. I dated someone that was about 12 inches and fatter than anyone I know...worst sex in my life.
DH is average, but sometimes it still hurts me.. :/