The only way I know how to encrypt SMTP is tunnel it via SSH.
I personally use Tunnelier (
http://www.bitvise.com/tunnelier.html) as my SSH client. I configure Tunnelier to forward both imap and smtp. Then all I have to do is configure my mail client (ThunderBird) to use Localhost for both imap and smtp and everything is encrypted. (This also provides me with a console and SFTP of course)
My setup is actually a bit more complicated than described because I use multiple concurrent instances of Tunnelier to simultaneously access multiple servers. This is easy to do because Tunnelier will listen on any port you specify and forward it to any other port you specify. Because TBird requires each email service to have a unique servername/username combination, I had to set up a localhost alias in my Windows hosts file for each server I access.
If you give your client SSH access, I suggest disabling the SSH SFTP capability for security reasons.