@OP. As pointed out, dice itself is actually as old as it gets when talking about street gambling. Still very popular in parts of the world I've seen, still popular in modern variations in casinos, and its latest incarnation as Bitcoin dice
A coin toss is also the famous ending of an Asimov short story, where a war general reveals his legendary computing choice that led to a decisive inter-galactic war. Very interesting back notes and footnotes to the story of the die.
I don't know any stories like that but yours reminded me of a question I was wondering about: why aren't casinos making the bets in favor of the player at first? They could then turn on this house edge thing and probability, but I am pretty sure that they would profit from it more than they'd lose. Would it be considered as cheating? I mean, if the casino is at first helping one to win and then just playing fair, I don't think anyone could accuse it. And even if people knew about that, they'd probably not be able to resist the temptation to keep playing.
Actually, they do. Casino comps common in physical casinos. You come in, you get free drinks, free food, even free chips for a first timer. You're a winner from the beginning, so you're hooked.
Variations of hi-lo also let you keep on gambling, stacked against higher and higher odds, and gradually increasing edges. You're always invited to play more for double or nothing or similar, which invites the mind to think "I'm only losing winnings after all".