"You werenβt supposed to see me like thisβ¦" trying (and failing) to kick his guitar case with very few yen notes behind him out of sight. "How much to buy your silence?"
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Despite Judas' (poor) effort to hide everything, Shiro's eyes remained glued to the instrument case full of discarded coins and crumbled bills for a good long while, practically committing every detail of the scene to memory before he finally looked up to meet Judas' eyes. "There's nothing to be ashamed of."
"Have you fallen on hard times?" Although that would be a self-inflicted problem, seeing how the Order always has jobs for the taking and they cash out based on performance, there would be no judgement from Shiro if that were the case. Especially after he thought about those possible circumstances to some degree, and quickly remembered how the performance reviews can be a bit stingy.
Still - with a teacher's salary backing him up, Judas shouldn't have fallen so low like this, but Shiro didn't keep up with the man's daily life either. So, truly, who knew what was going on outside of the dormitory when the older American transfer wasn't mooching around and tutoring the younger American?