Background - I am not a virgin: I had sex once (please no comments on this) almost a year ago. It didn't last long and was from behind the entire way, but I was quite sure that he had penetrated me. I'm on the pill (for acne) if this makes any difference.
Anyway, today I was hooking up with a guy I have liked for a while, first time we were going to have sex together. We had a bit of foreplay, just enough to get me aroused, and then he tried to enter me multiple times. Every time it hurt me so much, I felt like I was in agony. Ten minutes later, he told me that he was only half-hard, couldn't get it up and that this had never happened to him before. (We weren't even using a condom as I am on oral contraception, as mentioned)
We kept on trying and he kept on telling me I was very tight. The lights were off so I couldn't actually see if he was totally hard - he felt it, so I'm not sure if he was just saying that as an excuse as to why he couldn't fit in me.
Now for the worst part.... (warning: slightly gory). We gave up and switched on the lights and there was a huge wet blood stain on the bed which had come from me. I was so embarrassed but he handled it quite well and told me not to worry as he, himself, couldn't even get hard. Which was sweet of him but I felt so bad especially as he had just gone down on me.... ergh
Why did I bleed so much when I'm sure I had been penetrated before? And secondly why did it hurt like hell when he tried to enter me? When I had sex the first time last year it didn't hurt me at all much. What should I keep in mind for next time we try? I am so put-off now by this disaster.
We were discussing what the problems could have been and he joked around by saying 'you're really tight, you bled, sounds like your first time to me'. It practically was as my first was awful and rushed, but I'm sure I had sex last year.. is it because I left it for so long that I magically closed up again? What even......? Any help? Thanks in advance