LOL not to worry.
an ENGINEER designed the two plug system so that when changing the oil,
it all falls into the golden plan of marine motor maintenance.
get your new tube of lube at the ready, loosen the top plug but don't remove it just yet.
then, with one hand, remove the bottom plug and drop it on a clean cloth or newspaper.
then quickly insert the tube of lube. then, with your other hand, remove
the top plug. with two hands, squeeze the tube of lube and try to fill it until
it starts to run out of the top plug, then, with your spare third hand, quickly
put in the top plug that creates a vacuum so the oil will not run out the bottom hole.
then, remove the tube of lube and with another hand, quickly put in the bottom plug.
tighten everything up and you are good to go.
go to YOUTUBE and you will see several methods of how to change your lower unit oil.
pick one or two that might suit your skill set.
but on the serious side, the lube is so thick that very little will be wasted.
once you do it a couple of times, you loose less than a teaspoon full.
Since you are having a little problem with this - - - remove the top plug and practice
putting it in quickly and turning with your fingers to get a quick grab on the threads.
I think this where most folks get frustrated. Just can't get it threaded quickly enough.
Once you understand that part - the rest should fall into place rather cleanly.
good luck.