l33tstr33t
This happened to me too so here's what I say - roll with it. I think if you look at it from the right angle, it's incredibly comforting to know that you don't have to talk and they're cool with it, even if it is a bit awkward.
CW - transphobia
I don't know what kind of store it is for you but it happened to me at a sandwich place, and if I had a bad experience somewhere else where I felt judged because of my voice it was really nice having a safe backup place to fall back to when I needed it.
I mostly make my characters cis women but their backstory will usually have some kind of trans allegory in it. I feel like it's a safer way to interact with my feelings about being trans without necessarily having to explicitly deal with the types of things that can be overwhelming / traumatic IRL.
I'm curious... if you had money you wouldn't be depressed enough to need hormones and surgery, but do you think you would still want them? It might be one of those things where you'd be happier to be financially secure but still have that gnawing feeling lurking in the background. Money does buy happiness, but being happier in one area might not have as much of an impact on others as you might think.
I read your post and hear you. You definitely aren't alone.
Do you mean Bin Laden's Mountain Fortress, the place that's totally real?
I'm not sure it's 100% what you're looking for, but Night in the Woods is a game that's pretty explicit about "we live in late stage capitalism and it's terrible, we need unions / worker's rights / etc.". It also has an anti-fascist trans character, which is pretty rad.