You will likely need a old PC with a real parallel port, but if you are lucky it could work.
VMWare does support passtrough for for parallel ports. So you probably would want to run DOS under that. Its not perfect DOS emulation but its good enough to make most things run. Also you could probably get FreeDOS running natively on your PC, tho getting the LPT port working inside of it might be a challenge.
The problem however is that any method of adding a LPT port to a modern machine ends up being quite far from the CPU. The way LPT ports work is pretty much like a GPIO register on a MCU, it simply outputs whatever value is written to it. This means that the timing of the write operation arriving at the ports controller is critical. Back when this was simply a latch sitting directly on the CPUs data bus meant that you could get pretty predictable timing on it. But in a modern PC the Parallel Port PCI card might have a whole chain of stuff between it and the CPU. That PCI slot might go to a PCI bridge chip that converts it into a diferent bus that goes into the motherboards southbridge, this connects to the CPU socket via a PCIe bus, then inside the CPU this connects to the memory controller subsystem (formerly a northbridge on older PCs) and this controller finally connects to the actual CPU cores where the Windows multitasking kernel runs and interrupts its work all the time. Phew... that's a long way.
So because of all this extra crap in between the timing really gets messed up. To make things worse the LPT driver might have some extra functionality to fix this timing, but that functionality is designed to work with LPT printers, so it might make things even worse for other use cases.
So its all a question of how bad timing your device can tolerate and how much your modern PC messes up said timing in the first place.
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