Using USB to Parallel Port, Send an 8-bit data of Assembly Code
No, that is not possible (unless maybe if you are a guru-level windows hacker).

The reason is that such a converter creates a virtual PRINTER, and there is no windows API to send a byte to a printer.

With an usb-to-serial converter the situation is different: for this windows creates a virtual PORT and there are API calls to send a byte to such a port.

Wouter