Wow !'stumprd the journal. Do I get a prize?
Ummm, no. You didn't "stump the journal" five hours. You even got some excellent answers but failed to notice.
The very first response was on target with your description: EDM
Later, when you mentioned plastic, you received the answer: Broaching
Broaching is the way to go but it is difficult to make a broach.
Depending on the plastic, you could make a few guided punches.
You failed to give the dimensions of the hole other than 1/4", so let's say the D will contain a 3/16" round hole. You drill a 3/16" hole, then machine a partial D shape, from a 13/64 round with more flat cut off than you want finished. You guide the tool through the hole and skim out part of the plastic. Then go to a 7/32, then 15/64, the 1/4 with the final shape.
You failed to say whether this mysterious hole was to be a blind hold. For a blind hole you do the same but relieve the inside of the tool to collect the waste material then manually clean out the bottom with a mini router.
Stump us with something hard.