Add a shortcut to your Send To menu to launch a folder in IISExpress

iisexpress.bat

@echo off

:: normalize folder
SET folder=%~1
IF %folder:~-1%==\ SET folder=%folder:~0,-1%

:: random number from 8000 to 9999
SET /a port=(%random%)*1999/32767+8000

:: start the web server for the random port starting at the passed-in directory
start "IIS Express :%port%" cmd /C " "%ProgramFiles%\IIS Express\iisexpress.exe" /path:"%folder%" /port:%port% /systray:true "

:: launch the browser pointing to this location
start http://localhost:%port%/

:: To use in Send To: drag a shortcut to this batch file to %APPDATA%\Microsoft\Windows\SendTo