Help!

Hey guys! Okay, so I’ve been seeing this guy for about two weeks now and we’ve been getting to know each other and it’s been going great. We’ve also been having sex, and I actually lost my virginity to him two weeks ago when we first started talking (I’m 20 - I know, a late bloomer). I had the stereotypical pain the first time, but I’m the two weeks we’ve been involved we’ve had sex five times and it’s still hurting each time we have sex. After a minute it starts to feel okay but I end up bleeding afterwards anyways. From what I remember we had one experience where it worked out well because we engaged in a decent amount of foreplay and everything went smoothly, however we’ve consistently utilized foreplay in order to prevent the pain/bleeding from happening and it’s still happening. So what I’m trying to figure out is if I need to visit a gynecologist? Or if I just need to have him step his game up lol