Can't get it in? Literally

So this is gonna sound so lame, but my boyfriend and I are both virgins and seniors in HS and we tried having sex but he literally could not get his dick in😂😂 We tried so many different positions (me riding him, missionary, etc) but for some reason it just wouldn't go in. I know I was completely relaxed so I don't think it was a matter of tightening up at all. I took my finger and showed him exactly where to put it and he just couldn't do it lmao. He said he didn't want to jam it in because he didn't want to hurt me. I don't care at all but I really want it to work. Any tips?