I also struggle with this. Its not exactly the pristine solution you want, but you can add a new site to your default iisexpress configuration via the command line:
APPCMD add site /name:MyNewSite /bindings:"http/*:81:" /physicalPath:"C:\MyNewSite"
Do you want to target appcmd.exe in c: \ program files (x86) \ iis express
After adding it, you can start iisexpress in the usual way, using iisexpress.exe, focusing on the site that you just added to the configuration.
Manipulating objects using ADD, SET, and DELETE
You need to "enable" iisexpress for ssl service.
Working with SSL at design time is easier with IISExpress
However, it might just be easier / cleaner to write your own configuration file with the bindings you want and load the site using this. More control this way.
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