There are probably very few people trying to do this, but I have my Mac talking to my Bridgeport S1 with TNC 151B. Works like charm.
Running Heidenhain TNCserver on Windows XP on top of Parallels Desktop on top of OS X 10.4, using a Keyspan USB-serial adapter with drivers on the Mac side talking to Windows through a serial socket emulator called SerialClient. Hardest part was figuring out which buttons to push on the control - I had to actually read the manual.
Now if I could just figure out how to save the machine parameters....