Well, I was asked to make this thread multiple times by my fellow Grill War role-players, and since I had some time on my hands, I figured that I might as well fulfill that request while I had the time.
This first snippet "Airen's Despair," was actually continued by Merry, so the only part I'm gonna post here for now is the part that I myself actually wrote.
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Airen's Despair - The Steadily Emptying Wallet
"Man Lancer, how can you eat so much food, you're a freaking spirit!"
Airen grumbled various phrasings of this particular sentence as he made flipped through the resturants menu, seated at a table alongside the casually dressed Servant members of his alliance, each item he bought placing an almost physical weight on his already unbalanced bank account.
"I apologize. If you do not wish me to eat at meals than I shall not."
...A slight amount of guilt.
Airen sighed, "No it's fine, I don't mind paying for my own Servant's meals, BUT-" he turned to glare at Assassin and Breaker, "WHY AM I PAYING FOR YOU TWO?!"
"Because I know where you sleep."
... Assassin always had been a convincing person, so convincing in fact, that Breaker didn't even need to defend herself from his question, but she did anyway.
"Because I think you're a nice guy."
"You tried to kill me when we first met!"
"You're still alive though," she smiled, "That's proof enough that I think you're nice!"
...Well that sounded kinda ominous.
"I may be mistaken, but you all appear to be threatening my Master for food," Lancer said with a deceptively feminine smile, "That wouldn't be the case would it?"
"Maybe."
Assassin again, that man was too brave for his own good.
To the despair of both Airen and his wallet, (due to possibly having to pay property damages) things looked like they were on the verge of violence, Lancer's hand was twitching, as if he was indecisive about whether or not to smite his ally, and Assassin was standing with that cold look he got whenever a battle approached...
"Wait, no fighting! There are still people around!"
This honestly hadn't been his best plan, neither Enigmatic nor Satehi were here to keep their servants in-line.
It was all up to him.
"Calm down Lancer, Assassin wasn't being serious about planning to assassinate me. Right Assassin? Right?"
He needed to know. They were using Enigmatic's base as their own temporary one at this point in time, so if shit was gonna hit the fan sometime in the near future, he needed to start planning for it as soon as he got back.
...He honestly should have been planning for it already.
The black clad servant laughed a bit at the serious, but hopeful look on Airen's face, before he locked eyes with Airen, and in his usual serious voice said, "No promises."
If it was possible to see images of another world, Airen may have had a vision of a world where he was assassinated in a helicopter by this particular Servant.
Unfortunately, he had no powers of the sort. But since he ended up being bros with Assassin in this timeline, it was a moot point.