"So," the young man in the often-cleaned fast food uniform politely asked, with body bent into a spontaneous low bow of deep respect, "you started as a student. Then you were put in charge of a library. And that eventually led to your becoming an alicorn. Do I have all that right?"
The little purple quadruped nodded.
The dark-haired youth straightened, turned, and smirked at the blonde behind him.
"Pay up."
Ashiya sighed, then passed over the bet's hundred-yen coin.
8952364
Went with the one I have.
I don't think I need to know anything else about these characters... but how specific was this bet?
8952630
There is one thing you probably should know - Sadao Maou joined the legions of Hell as a front-line redshirt and, over thousands of years, worked his way up to become Satan. His becoming a fast-food worker is step one of his new plan to become in charge once again after he gets banished to Earth.
8953858
I'd add one more point to that as there's an accidental parallel - while he wasn't trying for the specific chain of events which led to him carried away from his home to a modern Earth and eventually working as a fast-food employee, he's sticking around because he wants to learn how friendship works. (Technically, how human societies manage to default to cooperation, and how to get demonkind running in a way that doesn't depend on constant cruelty and an influx of negative energy to survive.)
The bet works on multiple levels, although I'd have gone with Urushihara as the wagering partner if you insist on a demon (and don't want one of the less familiar and clueless ones who didn't pass over). They're all basically - well, not so much "playing stupid" as "not bothering to display any level of intelligence not immediately relevant" - one way or another, but Ashiya usually defends the whole plan of fast-food assistant manager to world ruler as viable (poorly, to hide his authentic faith in it).
8953858
The best part is, his plan as a high probability of working.
8952479
..............................Oh my god you actually did it.
Thank you. This was perfect. And now I'm grinning like an idiot.