Sharepoint Emails Sitting in Queue, Alerts not being sent out via email nor sms

I'm using Sharepoint 2013 Enterprise Edition on Windows Server 2008 R2. I have the mobile account setup correctly (account tested successfully) and I have the email setup for use with gmail (have configured the virtual IIS 6.0 manager to connect to gmail. 
Currently when I set alerts they take on sharepoint but nothing is making it outside of the server. I have correctly mapped the mail and mobile phone functions and synchronized the user profiles from the active directory. Configured the Forms Based authentication
(All of which work). 
When I look on the virtual smtp manager I can see a large number of connections from unknown IP addresses connecting as my public IP (Suspect bots or spammers spoofing my IP address). I have checked online and the server is not blacklisted. When I look in
the mail root file there I can find the emails / alerts sitting in the queue but going no where. If I manually move a .EML file to the drop folder after a small amount of time I see the file disappear so I know it's going somewhere. Can someone please help
me out here? 
I've attached the SMTP Service log below as you can see there are a large number of code 550 which means unable to relay. I'm struggling to understand how that can be when my accounts are all configured correctly?

Yes, it probably would be easier to use an existing relay (and easier to manage). I'd use that, instead.
You can also open one of those EML files to check the x-sender/x-receiver headers.
Trevor Seward
Follow or contact me at...
This post is my own opinion and does not necessarily reflect the opinion or view of Microsoft, its employees, or other MVPs.
Alright I'm set to relay through the internal mail server however in the EML file I'm not seeing an x-sender or x-recipient which is weird. Shouldn't SP2013 automatically populate that info?

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