Create a cutter and follow a cutter path

I'm searching for a manner to let a cylindrical cutter follow a cutter path with two radii and remove material as it would be in 'the real world'.

For example, a tapered shaft with a keyway, start along a radius then parallel and ending along a radius.

Indent give me the option to create a tool and cut a part, now I like to move the indent to make it more dynamical.

Swept cut is not real enough because of the cylindrical cutter.

Anyone ?

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