I think that the adapter you show is a 25-pin to 9-pin serial adapter.
The 25-pin connector was originally developed as a serial interface, but for some reason PC manufacturers chose to use it for the parallel port.
Your adapter allows you to plug a cable with a 25-pin serial connector into the 9-pin connectors PCs use for serial ports, but the signals on the pins of a parallel port are completely different, so it cannot work and could have caused damage to the electronics on one end or the other.
Without a parallel port on your PC, your best bet, as @VojtěchDohnal suggests, is to use a USB to LPT converter, provided there is driver support for it in your OS. There may have been active LPT to serial converters at one time, but I doubt you'll find one now.