If you're already at the Tao te Ching, then the Tao of Pooh is a very popular exploration of Taoism using Winnie the Pooh as an exemplar of Taoist principles.

In that vein, there are about a zillion "X and Philosophy" books, where X is a pop culture franchise, e.g. "Star Trek and Philosophy," "Star Wars and Philosophy," "Watchmen and Philosophy." All of these are collections of essays by various authors discussing philosophical subjects through the lens of popular culture. I find that it's very useful to have a set of characters and plots with which you're already familiar to use as a vocabulary to talk about heavier philosophical subjects.

I don't know as I would recommend going directly to the primary texts first off. Some of them can be read on their own merits by someone otherwise unfamiliar with the subject, but many are written in archaic or academic language that can be daunting. A class or book club can help in that regard, but just sitting down and trying to read Aristotle all by yourself may not be the easiest of going.