Hello there, this is in fact a pretty good question. I never attempted to test it out because I don't have any LPT printers.
Originally Posted by gospelmidi
First you can easily try it out if you have an XP VM set up. You'll just have to enable the parallel port if not already enabled. Check it in XP's Device Manager to make sure.
Printing in the VM: It might work, it might not, depends on printer and on how good the VM supports it.
For instance in VirtualBox (be it the first one mentioned and maybe the difficult one to get going) to enable LPT1 port on a VM called XP:
--> command prompt window on the host:
"C:\Program Files\Oracle\VirtualBox\vboxmanage.exe" modifyvm XP --lptmode1 LPT1
Apply that while the VM is not running.
For instance of adding an parallel port in VMWare:
--> the port might need to be added in the VM settings and then added in the VM dev Manager (if not already present).