I use stunnel 5.41 with these settings:

client = yes
accept = 127.0.0.1:25
connect = <address-here>
protocol = smtp
protocolAuthentication = login
protocolUsername = <login-here>
protocolPassword = <password-here>

Some mail servers reject mail with an error "missing HELO/EHLO"
I think this is because after STARTSSL, you need to send EHLO again.
As it is described here:
http://www.samlogic.net/articles/smtp-commands-reference.htm
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