Sex for the second time

today I was about to have sex for the second time. I lost my v card to someone else like two weeks ago. anyways when this current guy tried to go in me I screamed from pain and then he tried again and it was really painful and I started bleeding. 
the first time I had sex when that guy entered me it was a tolerable pain. is it because I wasn't wet enough the second time around? also when does the bleeding stop and why do I bleed. I thought the first time you have sex you bleed because you broke the hymen so why did I bleed again?