Always discomfort, sometimes blood

Jae
I've only been having sex for about a month now (just swiped my v-card), but I feel discomfort every time we go at it. Usually not enough to stop but after a long time of fooling around, it turns to pain and we stop and almost every time, I end up bleeding. Sometimes I think he's fingering me too hard but shouldn't I feel more pain when I start bleeding?