Just as a matter of interest, where are you getting System 7.5.5 from to install on the VM?
If you are using something other than the original installation disks, I suggest that you go find them and install the OS from them. That way you will have all the required support for System 7.5.5 and will be able to install programs, including Stuffit Expander, and get that application running.
You have not mentioned what virtual machine you are using so the actual process of moving files into the VM remain a mystery.
Sorry, but I am not going to take a giant leap backwards to attempt to install 7.5.5 onto my computer. I left that version of the Operating System behind a considerable number of years ago.
As you have a machine that is capable of running System 9.x, why not use Stuffit Expander on it to unpack the files you need for this game?
P