SSL and TLS: Designing and Building Secure Systems, Addison-Wesley, 2001 ISBN 0-201-61598-3: very detailed.
Aside from books, depending on how you like to learn, if you like practical experience, you could go through the JSSE Reference Guide (online, part of the Java documentation) and try a few tutorials based on this. Going through the documentation of other libraries is worth it too (e.g. Mozilla's NSS or OpenSSL).
If you want to see what topics are cutting edge, go through the IETF TLS mailing list archives (or subscribe to it, of course) and follow the discussions.
Going through the examples or unit tests of BouncyCastle (in Java or C#) can be interesting too.
You could also combine this with looking at what happens with existing applications using Wireshark (you won't necessarily always be able to decipher the communication, even if you have the server's private key, since it depends on the cipher suite too).