I don't think Moe Kare!! fits. I mean, her first boyfriend was as less experienced as she was (only maybe, a little more dense than her in terms of love), and the second guy was definitely NOT unexperienced. He had a lot of (sexual) relationships. It's true that Hikaru (the heroine) may very well be his first love, but he is still far more experienced that her.
"In a world where most people would be crazy, then it would be normal to be crazy and crazy to be normal... but then again, if you were normal, then you would be crazy... isn't it crazy what a paradox a little craziness can create?"