You need a Windows device driver for that. I doubt it can be written in Perl. It could expose a second interface that the Perl application can use. A very simple and generic solution would be a device driver that creates two virtual COM ports that seem to be connected by a crossover cable.
Some versions of VMWare allow to redirect a guest's COM port to a named pipe on the host. Named pipes can be accessed by Perl.
You could also buy a cheap dual-port RS232 PCI card and a null modem cable, insert it into your machine, and use the two real ports. There are Win32::SerialPort and Win32API::CommPort that should be able to connect to the COM port.
Alexander
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Today I will gladly share my knowledge and experience, for there are no sweeter words than "I told you so". ;-)
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