Need tips on losing virginity…

So me (21) and my boyfriend (21) have tried to have sex a couple of times now but it literally won’t work…I feel completely comfortable with him and we both really want this. He says that I’m extremely tight to the point of where he’s hurting himself trying to get into me. It also hurts me as well at certain points. We tried missionary but the problem we keep running into is that it feels like his dick is going upwards which causes me discomfort. Do I need to guide it in for the first time? And how much pain/blood should I expect? Whenever we have gotten further than usual, it feels like a ring of fire and then I can’t go any further. The pain makes me want to scream into a pillow so we immediately stop trying. Are we doing it wrong? Is there a specific position that would make this easier?