What i replied to the above quote makes sense. Your post makes it look like you think we talk to someone calling them him/her.
"she tells you she doesn't like to be referred to as biological male, you keep doing it?" - i highly doubt anyone keeps using the gender in a normal conversation, you use name.
I would say the person's name, like "no Pedro, i am no going out tonight", not "no, him, i'm not going out tonight."
Since in your sentence you say "When you discuss this with a transgender woman", you'd assume you talk face to face. I've never in my life heard anyone use gender when talking directly to anyone, and i highly doubt i ever will.
So no, i'm not obtuse, deliberately or not. It fits perfectly to what you said, and if not, you worded your post wrong.