Pain WHILE Fingering. What's Happening?

Hi, I'm sixteen and I've been dating my boyfriend for a few months and the other day he fingered me. It was a little uncomfortable but good at the same. After awhile it got a little too uncomfortable and I told him to stop, which he did. I had to pee right after and there was just a little blood, it was really only a little pink when I wiped. We just figured that he popped my cherry and everything was fine. Then he did it again a few days later and it hurt really bad. Pretty much right after started I had to tell him to stop because it hurt so bad. He was thinking that maybe he'd popped my cherry wrong or something but I don't know. It was almost like a clicking pain as well as the common pressure. I asked my friends and none of them have had similar experiences. I was ready both times, and aroused so I don't what was happening. Just so you know, I've ever used a tampon once because it was my best friends birthday party at a water park. I had to do it when I was on my first period and it freaked me out and I've been a little traumatized since. Maybe the fact that I'm not used to having anything in that area has something to do with it. I'm sorry for having to be so graphic, but any and all advice and comments would be helpful.