I have the same issues on Mac as well. I had no issues with the Cap's route, but the option you have after Driller reveals his name leads me to the error below
I copied the error code here without the full traceback if that's what you asked for:
While loading <'Image' u'images/CG/Driller_reveal_ID1.png '>:
File "game/script.rpy", line 8948, in script
scene DrillerRevealID1 with dissolve
IOError: Couldn't find file 'images/CG/Driller_reveal_ID1.png '.
EDIT
As Mattific said the Lascivion route has the same error:
While loading <'Image' u'images/CG/Lascivion_MV_afterfuck1.png '>:
File "game/script.rpy", line 13594, in script
scene LascivionMVAfterFuck1 with Dissolve(3.0)
IOError: Couldn't find file 'images/CG/Lascivion_MV_afterfuck1.png '.