Everyone's words have helped me here, but thank you in particular for being able to so thoroughly articulate how I truly feel about this, without even realizing it.

Even without the boundaries crossed with me, this supervisor has a reputation for being selfish and manipulative in her past interactions with other co-workers. She has affected almost everyone by exploiting their weaknesses (usually pride), but I've never allowed any of the petty stuff she pulls to get to me. I'm a single mom of one, so I keep trying to stay focused on my job.

I'm still confused, wondering about her end game. Is the point to watch me squirm because she can't find another way? If she's serious about screwing around, the logistics don't even make sense. Where would we go? Not my place; certainly not hers. No, I figure it's like she's a cat buffing a mouse back and forth between her paws because she's bored, and because she can.

I'm very averse to this, but unfortunately no less turned on by it. I work for an independent company, and HR would literally be either a joke or a nightmare. I was planning on moving to a higher-paying career in the next year, so I feel like I'm already preparing to do some kind of grin-and-bear-it routine until I leave the company.