Should I be upset?

I’ve been talking to this guy, we’ll say Bob for a while. We agreed we wanted to wait to have sex... last night, we had a little bit to drink, not much. I wasn’t even buzzed, he had a little bit more than me but I doubt he was drunk.

Well we started making out, and he gets on top of me and rubs his dick on my vagina (I had panties on) then he asks me if I wanted to take them off. So I did. I expected him to eat me out or finger me, like we’ve done before. Well I feel him rub his dick on my vagina again, then I felt him press into it, like teasing me. So I push back and grind on him. (I thought he had his boxers on) next thing I know I feel him go deeper. I thought he still had them on because the pain definitely wasn’t expected, I was focused on the pressure, it didn’t occur to me his boxers were off.

So after him going in and out a few times it hit me that they were off. I touched his back and ass and yep.. they were down. I stopped him and he asks me if I want to stop and I say yes.

Afterward I told him I wasn’t mad that we had sex, but upset that he didn’t ask or use a condom, and I was upset that we didn’t wait. He said he felt really bad and that he’d leave if I wanted him to. I told him it was okay and we cuddled for about an hour. I told him my stomach hurt and asked him to leave. (It really did).

I give him a hug and he walks out without kissing me. I was worried maybe he’d used me (nothing against him, just considering my past) but then I get a text from him saying “I’m so ashamed of myself. I don’t know what I was thinking, I’m so so sorry”

It just surprised me because he’s the type to ALWAYS ask before he does anything. He asked for a kiss, to lay down in my bed, to eat me out, to cuddle me etc. Should I be upset?