Super tight

So my bf and I are each other's first everything. Well I have never been the type of person "into my body" and all this stuff kinda weirds me out. ( please don't suggest I try and change how I am). Well my bf and I have done fingering for a year and due to personal reasons haven't had sex yet. I have never been able to put a tenpin in which that may just me being scared of it getting suck. My bf has tried to finger me but legit has never ever ever been able to actually do it. He only rubs the outside which I have no issue with since it hurts so bad. Even when I want more Ik he's scared to hurt me since he has before (of course on accident but it was very painful). He always tries to do it a little mroe in the hopes that I will be more opened I guess. I have no issue at all with oral. How do I make this whole fingering thing better. Ik we both want to have sex but realistically if he can't even finger me what's the point right? I am without a doubt always turned on more than enough and we have tired lube which didn't help. I'm am satisfied with what he does and can sometimes even finish with that but still want to move on ya know??