Email security made simpler
Now there's also gpg4win, a package designed to make life simpler for you, if you're a Windows user who is just getting started. While I haven't tried it, all the material I've seen makes it look like one-stop shopping (almost) for getting encryption and email signing running on your computer.
There are two pieces that may be missing (you can check out the manual after you download it): setting a passphrase and using the Web of Trust. Check out Diceware for creating a secure passphrase, and check out the GNU Privacy Handbook for information on the web of trust. Being a responsible member of a web of trust means you don't sign another person's public key to indicate it's valid unless you really have identified who that person is. If you haven't known them for a long time, you ideally verify their identity with two physical pieces of identification—a passport, driver's license, or the like.
You can browse a few links I've found helpful, too.
Now give it a try! If you want, use my public key to send me an encrypted email as a demonstration that you can do it!