The only thing about using telnet to test postfix, or other SMTP, is that you have to know the commands and syntax. Instead, just use swaks :)
thufir@dur:~$
thufir@dur:~$ mail -f Maildir
"/home/thufir/Maildir": 4 messages
> 1 thufir@dur.bouncem 15/553 test Mon, 30 Dec 2013 10:15:12 -0800
2 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 10:15:55 -0800
3 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 10:29:57 -0800
4 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 11:54:16 -0800
? q
Held 4 messages in /home/thufir/Maildir
thufir@dur:~$
thufir@dur:~$ swaks --to thufir@dur.bounceme.net
=== Trying dur.bounceme.net:25...
=== Connected to dur.bounceme.net.
<- 220 dur.bounceme.net ESMTP Postfix (Ubuntu)
-> EHLO dur.bounceme.net
<- 250-dur.bounceme.net
<- 250-PIPELINING
<- 250-SIZE 10240000
<- 250-VRFY
<- 250-ETRN
<- 250-STARTTLS
<- 250-ENHANCEDSTATUSCODES
<- 250-8BITMIME
<- 250 DSN
-> MAIL FROM:<thufir@dur.bounceme.net>
<- 250 2.1.0 Ok
-> RCPT TO:<thufir@dur.bounceme.net>
<- 250 2.1.5 Ok
-> DATA
<- 354 End data with <CR><LF>.<CR><LF>
-> Date: Mon, 30 Dec 2013 14:33:17 -0800
-> To: thufir@dur.bounceme.net
-> From: thufir@dur.bounceme.net
-> Subject: test Mon, 30 Dec 2013 14:33:17 -0800
-> X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/
->
-> This is a test mailing
->
-> .
<- 250 2.0.0 Ok: queued as 52D162C3EFF
-> QUIT
<- 221 2.0.0 Bye
=== Connection closed with remote host.
thufir@dur:~$
thufir@dur:~$ mail -f Maildir
"/home/thufir/Maildir": 5 messages 1 new
1 thufir@dur.bouncem 15/553 test Mon, 30 Dec 2013 10:15:12 -0800
2 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 10:15:55 -0800
3 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 10:29:57 -0800
4 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 11:54:16 -0800
>N 5 thufir@dur.bouncem 15/581 test Mon, 30 Dec 2013 14:33:17 -0800
? 5
Return-Path: <thufir@dur.bounceme.net>
X-Original-To: thufir@dur.bounceme.net
Delivered-To: thufir@dur.bounceme.net
Received: from dur.bounceme.net (localhost [127.0.0.1])
by dur.bounceme.net (Postfix) with ESMTP id 52D162C3EFF
for <thufir@dur.bounceme.net>; Mon, 30 Dec 2013 14:33:17 -0800 (PST)
Date: Mon, 30 Dec 2013 14:33:17 -0800
To: thufir@dur.bounceme.net
From: thufir@dur.bounceme.net
Subject: test Mon, 30 Dec 2013 14:33:17 -0800
X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/
Message-Id: <20131230223317.52D162C3EFF@dur.bounceme.net>
This is a test mailing
New mail has arrived.
? q
Held 5 messages in /home/thufir/Maildir
thufir@dur:~$
It's just one easy command.