So for this idea I'd like to cross a lot of taboo lines! And that's before we even get to the dirty part. Obviously pretty niche, but having chatted with a few guys into this stuff: it can be WAAAY hot. Basically aunt/neighbor/friend's mom (my character) catches younger male (your character) or finds out his secret of wearing panties. I'm thinking dubious consent, though she may get a little forceful from time to time.
This can be light or get pretty heavy. If you're interested send me a PM and lets see where that rabbit hole dumps us out.