From what I'd read up getting email to send directly from Emacs was going to use up quite a bit of my life. I thought it would be worthwhile as a quick way of sending snippets to colleagues so I thought I'd give it ago. After a small amount of struggle I've got it.

1. Install gnutls

I've Macports installed so this step is easy.

$ sudo port install gnutls

Once this is installed make a note of the path to the binary

$ which gnutls-cli

2. Create an emacs readable authfile

$ touch ~/.authinfo
$ chmod 600 ~/.authinfo

Edit this file to include your own Google credentials. If using 2-step authentication you'll need to create an application-specific password in your Google Accounts-Security settings for this.

machine port 587 login password YOURPASS

3. Add the following to your .emacs file

 send-mail-function 'smtpmail-send-it
 message-send-mail-function 'smtpmail-send-it
 user-mail-address ""
 smtpmail-starttls-credentials '(("" "587" nil nil))
 smtpmail-auth-credentials  (expand-file-name "~/.authinfo")
 smtpmail-default-smtp-server ""
 smtpmail-smtp-server ""
 smtpmail-smtp-service 587
 smtpmail-debug-info t
 starttls-extra-arguments nil
 starttls-gnutls-program "/opt/local/bin/gnutls-cli"
 starttls-extra-arguments nil
 starttls-use-gnutls t

Replace the path in starttls-gnutls-program with the path noted in step 1.

Reload your .emacs file M-x load-file RET RET and you're good to go...with C-x m