Penis won’t fit in.

I’m really worried, me and my boyfriend have been trying alot but it never fits. We have tried about 10 times. The 2nd time it did fit but after that it wouldn’t go in again. I’ve noticed he finds it very painful to try put it in sometimes and when we do try, I always bleed a little bit, I’m not sure if it’s from it being stretched out too much or what. I’m just worried as I know we both really want too but we can’t.