Very common problem with Rally II wheels. Over the decades, many wheels were removed and reinstalled, and before people began using torque wrenches, they used 4-way or factory jack crowbars to tighten the wheel nuts. I've seen wheel nuts that took 150 lbs of force to loosen, and they weren't even rusted.

There were a lot of guys, from backyard mechanics to garage mechanics, that used to feel "tough" or "strong" by tightening the living crap out of lug nuts. Unfortunately, that enlarges the hole(s) over the years. Think about it, as the lug nut is tightened and contacts the base, you're twisting metal-to-metal, at 75+ ft pounds, and putting direct pressure on the rim of the hole. It's only natural that over the years, that hole will begin to enlarge.

This was the main reason that Wheel Vintiques began reproducing classic wheels. Pontiac made over a million Rally II wheels from 1967 forward, you'd think they would be plentiful, but many have had the stud holes enlarged over the decades, and are useless.

Two options : Use non-factory lug nuts with a broader shoulder, or buy new wheels. If the lug nut is close to pulling through the wheel, don't take a chance.