sex for first time not working?

soooo i’m 17 and have recently (1 month ago) got a boyfriend and we have tried to have sex multiple times (around 6) and it seems like he can’t get inside of me and it just blocks off and won’t go in. as well as it not going in i also get in pain as we try and the most recent 4 times i also bled too. i feel really embarrassed and he says he doenst care and it’s alright but i really just want it to work.