When they changed my transmission oil in Bolivia before shipping my Corvair to me, they tightened the cast iron fill plug so much into the aluminum transmission case that when it got here it did not go into third gear, as the plug was hitting it. After pulling the power pack and discovering this, I put gasket shellac on the male and female threads and inserted the plug to a normal position, watching the inside of the transmission and testing the shift. After letting it set up, I filled the transmission from the top, put the cover on, and reassembled everything.
So depending on how snug the plug is, this might be a solution. But there's have offered several good solutions.