As nbucska stated above, it is possible to use either the serial or the parallel port. If you look up serial ports (either on the net or in a decent reference book) you can find out what lines (pins) are inputs and what lines are outputs. Any input line can be read from and any output line can be written to using the appropriate software, no matter what the line or pin is called.
However, if you are hoping to write a Windoze program then you will probably need to learn something like C++ and how to write DLL files because any Operating System like NT,2000 or XP will not allow an application to interact directly with hardware (9x systems may allow some kind of access).
Other options include building external hardware to process 'normal' serial data to achieve what you want, or be satisfied with programming and using plain DOS (not under Windoze).
It may be easier to use the parallel port. Decoding parallel ASCII can be done quite easily and could be controlled using a Windoze application that simply printed to a 'Generic / Text Only' printer. If the size of a parallel cable and/or cable length limitations were a problem, you could use a USB-to-Parallel adapter cable. This would effectively give you a serial connection and be relatively easy to write software (that would run under Windoze or DOS) for.