I currently have Implementing SSL / TLS Using Cryptography and PKI Joshua Davies. It is very recent and covers even newer TLS version 1.1 and 1.2 and ECC. It is based on many C sample that are dedicated for this book and apply more for people wanting to develop or extend a tls stack understanding deep internal crypto, OpenSSL is mentioned but openssl usage sample is limited to 3 pages ( book is 663 pages ).
SSL and TLS Designing and Building Secure Systems from Eric Rescorla which is the best book i could find about the subject but it is outdated. It covers to TLS 1.0 ( 2000 ). It contains general SSL TLS description with some history and cover general Security Concepts and TLS from basics to advanced with details. BUT still imited to TLS v1.0 It give hints to develop with ( but not only with ) OpenSSL over 40 pages ( Coding with SSL ) but with very old openssl ( prior to 0.9.7 ).
And the openssl 'reference' : Network Security with OpenSSL from John Viega, Matt Messier & Pravir Chandra, It covers openssl 0.9.7 then up to TLS 1.0, it is too old. It comes with many samples and many hints. It cover usage of openssl tools to generate certificates, sign , crypt . Coding with openssl server and clients I had more difficulties to enter in this book that for the others, its writing is less fluent.
Still i didn't find a book giving up to date advice to code securely using openssl for latest known TLS threats addressed by various extensions.
I wonder if an up to date book dedicated to coding with OpenSSL describing latest API and covering TLS 1.1 and 1.2 ?
[ Still i didn't yet read 'Bulletproof SSL TLS and PKI' or other references given in answers ]
[ And yes some opinion can be based on quality of book, but not on coverage ]