the shady file I



The reaper and the hitman rode through the trails that led up the mountain. It was a beautiful sight. A light fog, illuminated in numerous places by the moonlight that pierced through parts of the tree canopy, was present throughout this part of the mountain. It wasn’t thick enough to obscure one’s vision, but it wasn’t light enough to remain unnoticed either. The arrival of fall had turned the color of the leaves, which continued to gently fall off the various trees that littered the mountain. Many had turned a bright yellow, others a dull orange or red, and some had become white and pink. The wind had picked up a little, and it made the multi-colored leaves float around in the air for a while, after they fell off the trees they were attached to, in a strangely coordinated dance, one that was as mystifying as it was serene - if one cared to notice any of it - before letting them finally touch the ground.

“The first story that was promised, dear assassin,” the reaper said.


“Ah, yes! My first kill…” the hitman muttered, softly. He looked around silently, taking in the beauty of the forest they found themselves in for a few minutes, before he began his first tale.

“It took place right there,” the hitman said, as he pointed in the direction of the slum city that lay under them. “That’s where I was born. And that’s where I grew up. My parents had nothing. They came from nothing. Every day was a struggle. Being able to go to bed every night with a full stomach was a victory. A great accomplishment. Money, therefore, was something I grew up admiring. Respecting. Craving. It seemed like a great magical force to me when I was young. This wonderful thing that could get you whatever you wanted. A house, food, clothes, electronics. You name it, and money could buy it for you. I realized that I wasn’t that far off from the truth once I grew up. Money could buy you whatever you wanted. Money, however, could not be obtained all that easily. Hard work would only get you so far. Hard work could feed you, and put a roof, or at least something that resembled a roof, over your head. But hard work couldn’t give you the luxuries you wanted. Not in that slum city down there anyway. And so, I chose a different path from my father.”

The hitman patted his horse, and continued. “I had no quarrels with any kind of labor, but I immediately knew that it wasn’t for me. It wasn’t that I was lazy. I just didn’t care for it. It wasn’t going to get me where I wanted to go. Joining a gang didn’t interest me either, despite how lucrative the offers were. That, again, couldn’t get me to my destination. There were enough gangs and gang leaders fighting amongst themselves. I didn’t want to be another fish in that particular sea. Besides, I never was a people’s person. Leading a gang requires a lot of human interaction, something that I never really cared about.”

“You’ve never talked about your childhood in such detail before, dear assassin,” the reaper said. “This is quite the change.”

“You’re right. That is odd,” the hitman said, after he took a few seconds to think about the reaper’s remark.

“I’m not complaining, child,” the reaper said. “Merely pointing out an observation. Continue.”

“And so,” the hitman said, “I waited. And waited. And waited. For an opportunity to present itself. I spent my time observing the various things, legal and illegal, that happened in the part of the slum I lived in, and in the various parts that surrounded it. I kept an eye on it all. The drug deals, the murders, the alliances that were constantly formed and broken, the multiple minor and major wars that broke out, and everything else in between. And then, one fine day, there it was. The opportunity I had been waiting for.”

“It was but a whisper. A faint rumbling that I ended up hearing as part of the things I observed. An outside gang wanted to move into the slums. They were a much larger group, with much more experience in a wide variety of all things illegal, and they were much better organized as well. They didn’t want to move into the slums by starting a war with the gang that lorded over the area. They wanted to stealthily topple its king instead. And use the ensuing chaos to move in and take over. And so, they had spread the word. A large amount of money, for proof that one particular life had been extinguished. But all assassination attempts had ended in total failure. The situation had become so abysmal that the organization was reconsidering their strategy, and seriously thinking about going to war with their target. It didn’t surprise me. I was young, but I wasn’t stupid. I knew how the slums worked. The target had a great security team, one that was as loyal as it was deadly. He also had spies that watched over all the areas he controlled, as well as in those that bordered them. Catching the target within the slums was too difficult. Catching him alone, or by surprise, was simply not possible. The slums were his domain, and he never left them. Within them, he was untouchable. Assassins from the outside were too recognizable, too inconspicuous, and therefore, immediately apparent. Assassins from within the slum were too weak to successfully execute head on attacks. Those that attempted to assassinate the target stealthily were always found out by the target’s spies, before they could even think of making their move.”

“I approached the organization, in secret. Not that I needed to worry, nobody in the slums knew who I was, after all. I asked for a few months in time, and a much higher reward. And in return, I promised to give them irrefutable proof of the target’s demise. They didn’t warm up to me at first, but I broke through their walls. In time, they agreed to give me everything I wanted. And that, was how I got my first clients.”


“So you promised them the impossible, then?” the reaper asked.


“I did,” the hitman answered. “But only because I knew that I could deliver the impossible. You see, I knew from the start that a direct assassination was simply not executable. I wasn’t even an experienced hitman, I was just a teenager, but even I knew that. And that was only because I had lived in those slums since birth. I knew exactly who the target was, and how powerful he was within his tiny corner of the world. It’s strange, you know. Back then, that was my entire world. And now, it’s all so much larger. My world, my life, my very existence. Looking back, it is clear to me that my first target was nothing but a small cog in a very large machine. And an insignificant cog, no less. But back then, it didn’t seem that way. Killing him seemed like quite the undertaking.”

“Impossible as it all seemed, I knew what I was doing. Desperate as I was back then to get out of my measly, poverty filled existence, I don’t think I would have put myself in such a situation otherwise. I think, or at least I like to think, that I had more sense than that. I had this one thing that nobody else did, you see. I had this one piece of information that not even the target’s spies were privy to, something the target kept well hidden. I had come across it by accident a while ago, and I wasn’t entirely sure about what to do with it. And thus, I had ended up sitting on it. But this taught me my very first lesson. Many weaknesses can be found in every person, no matter who they are. They take steps to protect themselves against all these weaknesses. However, there is always one weakness that they aren’t aware of. And that one weakness is the primary ingredient an assassin needs to succeed in their mission.”

“My target’s weakness was his affinity for young men. Back then, homosexuality wasn’t as accepted as it is now, and especially not in places like the slum city I was born in. It was not just frowned upon. It was punishable by death. The best one could hope for, if they were found out, was to be turned into a social outcast. The target knew this, and that is why he kept his secret all to himself. He kept his promiscuity in check, and always stuck with one lover for months, before killing them and moving on to the next one.”

“And how long did it take for you to get noticed by the target?” the reaper asked, as the hitman paused to catch a white leaf from the group that danced past them.

“Not long. He noticed me almost immediately. I was young, and unspoilt, just the way he liked his lovers to be. It didn’t take long for him to approach me, or rather for me to get him to come my way. Before I knew it, we’d begun to meet in one of the slum’s brothels. The brothel’s landlady knew the target’s secret. She had known and kept it for years, in fact. She was paid well to do so. It was the ideal place for an assassination. The target’s bodyguards always searched the room first, and then waited outside it. The landlady entered the room with the target, an elaborate hoax to show the world that the target was the landlady’s oldest regular, and still enjoyed devouring her body. The landlady always left the room from its secret exit, which the bodyguards did not know about, just as I entered it.”

“Getting in place was the easy part. Getting the target to trust me, to let his defenses down when he was with me, was the real challenge. He didn’t drink or get high around me for the first few months. He was always alert when he was with me. He didn’t fall asleep, or even close his eyes for a few minutes for that matter, in my presence. But I was patient. I didn’t give away my true purpose.”

“I learnt a lot of things about myself during those few months with him. Money was important to me, but that first job showed me how important it really was to me, and how far I was willing to go to get it. It showed me how much I loved money, and how badly I wanted the finer things in life. I understood myself.”

“I realized that things like morality, ethics, a clean conscience and so on meant nothing to me. Neither did family, or friendships, or relationships and the like. I didn’t really care for any of these things. I realized that I was willing to do whatever it took, if it meant getting the things that I had always dreamed of possessing since I was a child. I had no financial troubles. I was in a position to get a job that would pay me enough to earn a decent living. I could get married in a few years, have kids in a few more, and give them a better life than the one my parents had worked hard to give me. However, I didn’t want a decent living. I didn’t want a family. I had no interest in love, or in emotions in general, unlike the other kids in the slums who were my age. What I wanted was something else entirely. And I was willing to go any distance to get the things I wanted, even if it meant being penetrated, and licked, and kissed, by an ugly, sweaty, stinky man who I had no interest in. Even if meant orally servicing him every time we met for hours on end, and having to bear the disgusting, ungodly smells that emanated out of his crotch. I wasn’t homosexual. I wasn’t attracted to other men. And yet, I was willing to pretend to be someone who was. I partook in all sorts of sexual activities I had no interest in during those few months, all to gain the trust of my target for a few seconds, so that I could strike a killing blow, and finish my mission.”

“I must confess, there were times when it all felt completely futile, when it felt like that day would never come. But I persevered. I continued playing my part, despite my disinterest in it. And finally, my moment arrived. It was a small moment, but I knew that the hard part was over as soon as I experienced it. My target shared a joint with me after one of our sessions. It was a single joint, nowhere near enough to make him unaware enough to be dealt with, but it was the start of something.”

“Over the next few weeks, I continued playing my part, and his trust in me kept growing. Soon enough, he began spending the night with me, and began allowing me to prepare his drinks and meals, the ones he consumed after he had exhausted himself by playing with my body. I did nothing for a while. I let the target get even more comfortable with me. And then, one day, I slipped the remotely triggered poison my clients had given me into his drink, and watched as he swallowed it whole. I informed my clients about my success the second I was away from the target. They triggered the poison two days later, and I received my payment shortly thereafter.”

“That was the last I saw of this slum city for a while,” the hitman said, as he concluded his first story. “My clients were very happy with me, and they put me in touch with a few of their friends. The rest, old friend, is history.”

“So that’s how he died,” the reaper said, thoughtfully. “Let’s turn here, dear assassin. This trail should take us higher.”