losing it.

So me and my boyfriend have only been together about a week and a half, but we've been very very close friends for three years. Before we started dating we made out and then after we started dating we went full on fingering and handjobs and such. I'm pretty positive I'm ready to have sex with him, I'm just worried about the pain. When he fingered me I let him at it for about 5 minutes before it just became too uncomfortable. Anyone have any suggestions to help ease it? We have lube just didn't think to grab it in the moment. He is not a virgin but I am.