Thanks for your input and sorry for the late reply.
Yeah I'm using a real serial port on a Toshiba Satellite Pro 4300. It's a great Win 98/DOS laptop in pretty much every way except for controller support.
I did try using a terminal programme but I couldn't make head nor tail of it to be honest. I think my issue might have something to do with chipset drivers or similar as I'm not able to add ANY controllers via the control panel (I just get the same "gameport not configured" message.
I've sidestepped the issue for the time being by persisting with my USB controllers (they have a strange "stalling" issue where I lose control for a couple of seconds mid-game). I managed to get my USB working more or less by attaching the controller while the laptop is on, and then resetting. This works 80% of the time now at least.
Would love to get the Stinger going though. I'll perhaps try it without the NUSB drivers installed to see if they are causing some sort of conflict.
Thanks
Please have a look at my retro channel where I go by the handle "Retro Muel"
https://m.youtube.com/channel/UCIg73Av606GSDu89QcCBD3A