+1  A: 

Show us what you got, and people will tell you how to fix it.

A link list is not very encouraging, because nobody wants to go through a list of 10+ articles to understand your problem. (explaining the down votes)

To answer one question: the point of OpenSSL (as I understand) is that you have a certificate. How else would you handle encryption?

devio
A: 

Well it seems everyone just uses stunnel

http://www.stunnel.org/

http://www.charmedquark.com/vb%5Fforum/showthread.php?t=7943

http://www.fogcreek.com/FogBugz/blog/post/Using-Gmail-%28or-any-other-secure-SMTP-server%29-for-FogBugz.aspx

The problem with this is that the user is required to download and install a service. This might not be something you want to do in which case see this question:

http://stackoverflow.com/questions/1736043/open-source-library-for-sending-emails-via-gmail-smtp-gmail-com-using-smpts-tl

Mike Trader