However, the complexity of the OpenSSL library has me stumped. (Plus, it's Unix-centric. I'd like to turn it into a Visual Studio port so I could compile without needing cygwin, gcc, etc., but that's another story).
You might look at NSS. It's the Netscape implementation of TLS, used in Mozilla among other things. You might find it easier to follow than OpenSSL. It's also Windows-friendly, running on top of NSPR, the Netscape Portable Runtime (another useful piece of code, but not on topic for this list).
Where can I learn about SSL?
If you just want to know how the protocol works, for example to implement it, read RFC 2246. If you want the rationale as well, read one of the books that others have pointed out.
The protocol is actually being revised, if you want to look at the bleeding edge, try:
http://ietf.org/internet-drafts/draft-ietf-tls-rfc2246-bis-05.txt
-- Pete
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