Unfortunately, the parallel ports fell out of popularity before 2008. I think your best bet is an add-in parallel port card.
Thanks for the add in card suggestion. That was the conclusion I had come to.
There are several such cards on the market. A very few have a driver for Server 2008 and only one has a driver for Server 2008 R2. Guess how much it costs :-( .
Mightn't Intel find it had expanded usefully the market for their desktop boards (those equipped with an onboard parallel port) were Intel to market the boards as capable of virtualising a parallet port based print server? How time consuming can it be to produce for the onboard parallel port a driver for Server 2008 R2?