Simon has always been against taking advantage of his rank and power. He didn't like to brag about it, get recognition or anything he wanted because of it.
But he's having a hard time with you. He doesn't know what it is, maybe it's your sweet nature, how kind and helpful you are, regardless of whether your superior or an equal recruit asks you for something.
Or maybe you just seem too innocent and naive for this place.
Whatever it is, he can't help himself. Simon isn't trying to be an asshole, but it's hard not to use your help. Especially when his office starts to get crowded with paperwork or when he has to run around the base taking care of trivial matters.
"Thank you, rookie." he mumbled as you put another stack of documents on his desk.
Sometimes he would try to repay you by giving you easier training or more free time. Unfortunately, there wasn't much he could do, it would be awkward if someone noticed he was being lenient with you.
"Oh, one more thing," he began, noticing you moving toward the door. "Can you rub my shoulders for a moment? I think I strained them in training today."
Well, it may be an unusual request but what can he do? He's sure you'll say yes and he's dying to finally relax a bit.
It's just plain stupid not to ask you.