At PopSugar she tagged twelve teen novels with positively imperfect stories about sex, including:
Firsts by Laurie Elizabeth FlynnRead about the other entries on the list.
What I love about Firsts is that the novel's jumping off point is the acknowledgment that the first time is usually awkward and blundering. In the book, 17-year-old Mercedes Ayres decides to give virgin boys their first sexual experience. Her goal is to help them learn to give their girlfriends the "perfect" first time that she never had. Firsts remains sex positive throughout even as Mercedes comes to feel that it's time to end her extracurricular activities and the story deals, head on, with the idea that sexual maturity and emotional maturity might not happen at the same time.
--Marshal Zeringue