It's like being shamed for having something, and not being allowed to be anything other than completely happy because of it.

That's so true and so frustrating! When a friend who has something I don't (like a nice job for example) complains/is depressed about it or about something else they're not happy about, I often catch myself thinking "OMG shut up! You have this thing I wish I had and you're still not happy? FFS, spare me the whining!" and a while later I feel bad because having A also means having to deal with the problems that come with A, and it doesn't cancel other problems like the lack of B or how overwhelming C can be, etc. Sometimes people just need to vent.

How would it be a privilege though if I'm expected to be an entertaining date at the minimum or put out at the maximum? It's not a privilege then, it's a trade right?

Yes! Being treated with kindness because others expect sex (for example) from you isn't a privilege nor a 'treat', it's annoying and objectifying! I want peple to treat me with kindness because they genuinely like me and/or are polite. I think men consider that to be a good thing because most of them would have sex with people they aren't even that interested in because they're desperate to get laid. So if someone is kind to them, that's a bonus. I could be wrong though. I don't know, it's what it seems to me. In general, men and women have different expectations about sex and our culture socializes men to be very sexually active and persue sex as much as they can.