If I fully understand what your saying, the only way to truly produce what you’re asking for is to do XYZ 3D point to point moves following the hole edge profile. (No cutter comp) It’s kind of like looking at a round potato chip from the side.

However, you can also cheat and do it with line arc move in a XZ arc or YZ arc depending on the puck orintation.

This can be done with a end mill that has a 90 degree tip. The last time it wrote a program to do this was for a prototype part in plastic. It was done on a Haas indexer but the actual moves were done as I stated above.

There were multiple holes and I had to do a radius on them. I can post a picture as I still have a sample part but you would have to wait a week and a half as I'm out of town on vacation.

Steve