Those messages appear to be someone using the claim of "sexual repression" to try to get into a 14 year-olds knickers (I'm sure I've heard people use "sexual repression" as an excuse for other sex-related misdeeds too).
The whole thing comes across as very manipulative. If it is legit, and these were his messages, then he's completely done, he needs to go away and find something else to do. Unfortunately, the only thing that I can think of that he's qualified to be right now is a pimp.