I wanted to make some special tee nuts for the compound on the Smart & Brown model A and a friend of the museum who did cutter grinding put the required taper on the end of a 1/2" four flute endmill. If you have a suitable donor cutter, then a small engineering firm could probably modify one for you cheaper than a special.
Emgee's suggestion of parallel slots with a tapered plunger would work very well if the plunger included angle was about 2 degrees.