I think this might get wastelanded for illegality but Ill try:
Firstly, you'll just need the first CD to start the game up. the beauty of PC games is that all the resources are on your computer already. they just need the CD to verify that you really own the game.
So down to business:
>Put the CD in.
>Open Disk Utility.
>Select the disk.
>Click the create new image button.
>Select read-only or read/write as the format with no encryption.
>Wait.
>Next time you want to play just open up the image then start the game. It should work.
I know this works with my OS X native games. I'm unsure of your Cider wrapped game. Just wondering, how exactly do you get windows games to run in Cider? I'm unaware that that was/is even possible. I thought Cider was just a technology that can help ports (like the upcoming EA mac games).