Hello. Long time listener, first time in a long time posting.
You'd had an episode was listening to recently regarding the word "simping" (which I hadn't heard of) and someone guessed it was derived from "cyberpimping" (which I also hadn't heard of). Then, a while later, I heard the old classic "Baby Got Back" on my automotive marconi, which includes the lines "Some simps like to hit and quit it, while I like to stay and play."
Now, I'd always heard this with the "simps" meaning fools. So I wonder whether this was maybe an early version of that alternate meaning. OR -- more interestingly -- what if someone heard those lines in that song and derived a meaning like the one you'd talked about on that episode? I don't remember what that was exactly, but "hit it and quit it" seems to get into the spirit.
Food for thought. In the meantime, I think I'll give another listen to Jonathan Coulton's wonderful rendition of that same song.
It's a sound theory, and one I've discussed offline with a few people. It's got the most plausability. But I have no evidence that proves that simpleton > simp > simping is the etymological path.