Sex and the Teenage Mind (2002)

It's a tale as old as movies being put on celluloid.  The geeky, virginal high school boy (who is actually a secretly super sexy stud) ends up going out of his way to help the super popular girl, who just so happens to be the hottest girl in school with a heart of gold and her boyfriend is the biggest asshole jock on the football field.  Welp, that's the gist of this 2002 titty comedy, Sex and the Teenage Mind!  We follow the virgin, Virgil (Jay Michael Ferguson), who is a fairly intelligent guy and ends up going out of his way to help the most beautiful girl in school, Kellie (Allison Lange), by tutoring her so she can graduate high school.  When Kellie decides that he's more than just sweet, she's kind of sweet ON him, her boyfriend goes ballistic, threatening the geeky guy with thorough beatings.  Lucky for us though, Virgil doesn't shy away from a beating, if it brings him closer to his potential lady love.  The only problem is that Kellie decides the best way to repay him for his help is to help him lose his virginity...  She's just not quite up to the task herself, so she hires a professional sex worker to come in and pop this geek's cherry.  When she grows closer to Virgil, she begins to catch feelings for him herself and just like the classic love stories of our time, she has to decide whether or not she can make a go of it with this good guy.  Lucky for us, Jay Michael Ferguson gives us a sneaky peeky of his cheekies when his oversized bathing suit falls off getting out of the jacuzzi!