Everytime I have sex with this guy, he's my first, it hurts when he first goes inside and a little bit during. Usually we do foreplay like kissing and stuff for about 20 min or more. Then when he puts it in it hurts a lot. Usually after he initially puts it in, it's easier if he comes out and goes back in. But sometimes I still bleed afterwards. I'm not sure if it's the size different that's the problem. I'm on the smaller side and he's kind of large down there. Recently I asked if we could use lube next time. Would that help a lot?