Billionaire Babe

Peter was never popular in high school, but now that he's a successful billionaire he wants a second chance using his secret transformation technology. This time he wants to be someone different. While giving a speech at his old high school, he finds just what he's looking for in Laura. She's his opposite in every way: Sexy, athletic, popular, and not too bright. Peter transforms himself into an exact copy of Laura, complete with access to her memories.
He then sends the real Laura on vacation at his private island while he lives her life for a week. Now he's got plenty of time to explore her life -- and her body -- at his leisure, and he enjoys the novelty of  the high school experience he never had, complete with jealousy, boyfriends, and dressing up.