Boyfriend can’t stay hard?

Okay so we started dating about 2 months ago and and have had sex a couple of times but he can never keep it hard, He’s 19 and I’m his first and I’m 20 and have had sex before him but I’ve never had it happen before? And I know it’s normal and happens a lot I just don’t know what to do about it, it seems to really upset him and I try to comfort him or tell him it’s not a big deal but it’s starting to sort of be an issue.. at first I thought it was just him being nervous about the first time but it’s continuing still. I also can’t make him finish ever, like I’ve tried every way I know how but it just sort of goes soft after a while and I feel like there’s some pre cum maybe? I’m not sure but the first time so far he lasted the longest and the most recent time we couldn’t even get it in, And the times that we have he said something about it “getting really sensitive” and not hurting exactly but he just stops ? And I thought it might be him about to finish or whatever but he just always stops. I’m not really sure what I’m asking here I guess just like, has anyone else had this issue before? And how did you work through it or figure out a way around it ?