Quick Question

So, I'm 19 and I've been with this guy for about four months and until today, I was a virgin. It's not like I've never been put in the situation before I just never felt connected with other guys like my current BF. I'm extremely comfortable with him and we've been friends for years. So, for me it was good and it wasn't even that painful. We went on and off for a few hours actually. I'm feeling pretty good but I was just wondering if I'm supposed to bleed at all. Most of the things I've read just say you can. What were some of your experiences? Also, he mention doing it again on my birthday in a week, do you think that's ok or would it probably hurt that soon?