So... I totally had an open conversation with my mom about sex when I lost my virginity and asked her for some advice...

Lady, I would not recommend kegels for your problem. Part of the problem might be that you don't know how to fully relax your body and if you're doing kegels, especially if you're doing them wrong, you might not fully relax while doing them, which will just make your muscles stronger and tighter, and that will just add to your problem.

You will probably need more than just a visit to PP. You might eventually want to invest in vaginal dilators and physical therapy (yes, they really do have physical therapy for your sex life). A vibrator might also help distract you while you're having sex and make it feel less painful.

Personally, I would not recommend alcohol for two reason. One, you're underage and that can just lead to bad decisions. And two, it can cause you to dry out causing more pain.

I'd also recommend two forms of birth control in case a fear of pregnancy is lurking in the back of your mind, also not letting you fully relax. And your doctor was definitely right about the cycle... you expect pain, you tense up, there's pain, so you expect it next time. It's kind of a hard cycle to break, though.

Good luck!