Six Ways to Keep the "Good" in Your Boy: Guiding Your Son from His Tweens to His Teens by Dannah Gresh. One of the most important books I've ever read! “A lot of parents are afraid of these kinds of conversations. You should be more afraid of not having them.”
A fun flowchart that includes a number of books that are on my to-read list.
The Catcher in the Rye by J.D. Salinger
The Fall of Rome by Martha Southgate
The Lake of Dead Languages by Carol Goodman