Sex life

So I did it for the first time a couple of days ago and it hurt at first like I expected, but as we kept going the pain went away, it was all fine until I tried to “do the deed” again yesterday and I couldn’t go through with it cause the pain was just to much, I knew it wasn’t because I was a virgin because of reasons explained, but I knew I wasn’t crazy cause I felt what I felt, which was a big shock of pain as he tried to shove it in deeper(sorry for the in-depth descriptions). It made me assume that I just wasn’t into it or at least not as into it as him and so my muscle were tense and I was dry or something like that. I just don’t have enough experience to tell what it could mean. I’m afraid that I have some sort of infection but I feel fine, again I don’t have enough experience to know. He was wearing a condom both times but I don’t know if I could still have gotten anything, I’m really just going on a limb.

To continue on my long story, because he couldn’t put “it” in, he put his (again I’m very sorry) fingers in, that was going fine until he went so far up that I stated to bleed a little, I don’t think that was my hymen breaking because I would assume it would have broke when we had sex the first time, after that I was done, I just didn’t want to push it anymore then I already did so I ended it there, if anyone could help explain why it would hurt that much, or what all this could mean I would really appreciate it. Because I don’t think I’m being a baby about it or that I have a low tolerance for pain because I’ve been good with pain tolerance all my life. Thank you again and I’m sorry for my TMI story, I’m just a confused middle aged teen who has no one to ask about these types of things. Any advice would help :)