It's actually really simple is the thing
Case 1: "You don't have to [thing society expects you to do]": Good and often important message
Case 2: "You don't have to [thing society punishes you for doing]": This is society threatening said punishment
Case 3: "It's so sad/gross/etc when people [thing society expects you to do]": Not oppression per se but you are being kind of a dick about it
Case 4: "It's so sad/gross/etc when people [thing society punishes you for doing]": You are society and you're doing the punishing right now
And then. Here's the obvious but apparently elusive fact. Society punishes trans women for being feminine, and for not being feminine enough. For every element of transition that we do, and every element that we don't do.
So when you're taking about transition options, you're never in case 1 or even case 3.
