This is a plot-outline story with no concern for logic. I'll call the two protagonists Mr. Urban Management Officer and the Peddler.
Their general personalities: an upright, cheerful, sunny top x a carefree bottom.
The plot is basically the peddler's life, in which he loses at every turn to our urban management officer.
Yeah, it's lighthearted, and the top definitely won't suffer.
It should be a short story.