How to make sex less painful?

So I'm 18 years old and I've been in a relationship with this person for over an year. We decided to have sex when we were both ready and that happened about 2 months ago

The first time we tried, I was hot but somehow I wasn't wet, so every time he tried entering into me, I stumbled away or just painfully moaned because it was hurting way too much. He did fingered me with 2 fingers and ate me out. Didn't orgasm, didn't properly had sex but gave him oral and he jacked off 2 times

The second time, it was still painful. Maybe a little less than the first time and whenever I felt immense pain, I tried pushing away but he grabbed me above himself and showed support so we had more than half of his dick slip in but then I bled and it panicked me so he came out.

I want to have sex but I'm scared it will hurt and bleed and everything.Is there any way to lessen up the pain?