Pulling on Underwear to get in and Pressure when thrusting

I was with a guy and things got hot and heavy and he tried to take off my underwear but I was pulling for it to stay on. I said no, but he kept pulling and eventually relented. Then he snuck his fingers in, which I allowed.

Is this normal behavior? I just remember my underwear stretching a lot because he was pulling for it to come off and I was pulling it to be on. Is it selfish to allow them to pleasure me with fingers but I’m nervous about doing PIV? I asked if I could use my hand instead and he’s like I don’t like it because I know my own body better. The underwear thing has happened to me 3/4 people.

Also he put his penis in and I was in pain and I said ow ow ow ow, and I thought he’d stop and pull it out but it just kept it in there. Is that normal? This happened on a first date. I was drunk/tipsy. I’m sort of ashamed that I went up to his place, but I really thought if someone as in pain they’d stop and ask me how I was. Are guys too horny to hear me? Or register that I’m in pain?

Also question to people with vaginas, do you feel a lot of pressure when they thrust? It hurts and feels like a lot.