What do you mean, by you got sick? Like a cold? Throwing up, nauseated? Is it normal for you to be sick so often? I would go to the doctor and ask for that to be checked out. If you are constantly getting sick, something else might be wrong.
As for the yeast infections, you still should see the doctor about them. They aren't going away from just the over-the-counter treatment or it's not a yeast infection (could be bacterial, which can't be cured with over-the-counter treatments) or you really are getting them over and over, in which case, you need to find out why. No matter what, this isn't normal and a doctor needs to check it out. You also need to tell the doctor that you are sexually active and that you need to be tested for STDs.
As for the not always having safe sex--it's pretty much the same as never having safe sex. You realize that, right? It only takes one time to get pregnant or to get an STD. Did he tell you he was tested or did you actually see a lab report? I know you think you know this guy, but I want to warn you that too many guys think they're clean and to them, that's the same thing as being tested. It's not. Again, I know you think you know him, and maybe you do, but do you trust him with your life? Because it can be that serious.
Sorry for the lecture, but I really think you need to hear it. Good luck with the doctor's appointment.