what I know ""plunge milling""
3d surfaces roughed out with a short drillbit, that don't flexing, for more efficient roughing..
if you like to simulate this in 2.5 D and you don't have solidworks or similar program, then I think the simplest is filling the pocketing area with circles like the drill bit diameter..
if you want to make overlaps between drills, then you need an offset from the area inside with value the half of offset..