killing simon

The following is my long overdue weekly contribution to the 500 Club. I don’t know that it’s my best work, but it was sure fun to write. I have long been intrigued by the idea of assassins, but I’ve never thought to write from the point of view of one. Seeing the prompts for this week I realized it was high time I remedied that. Hope you enjoy.

killing simon

Honestly, it was Simon that did it.

He was a decent enough guy. He treated me well, no question about that. He was great in bed, handsome, charming, wealthy and he was certainly intelligent. However, he was also insecure. I have a difficult time with insecurity.

Perhaps this is because I accepted my own sexual preference a long time ago. I couldn’t care less what anyone else thinks of it. Perhaps this is because I have made a living killing people. One cannot be overly insecure when one’s chosen craft is extinguishing human life. Perhaps this is because I was growing bored of him and he sensed it.

Whatever the case, I dumped him. He was painfully dramatic about it. We had only been seeing each other for 8 months. It wasn’t like we were soulmates. But he pitched a shit-fit, crying and screaming, begging me to stay. He said that he would never love another man like he loved me.


I dismissed it and left. We weren’t living together, so I returned to my own apartment and my own life. But he began a tireless campaign to regain my attention. He called. He wrote emails and pathetic text messages. I spotted him more than once driving past my building. He even followed me out one night while I was on my way to do my job. Not that it was any trouble to lose an inexperienced tail, but it annoyed me to no end that he simply wouldn’t let the matter drop.

One afternoon I received yet another text message from Simon. It was immediately followed by an email from my handler to procure my services. I think it was the close proximity of the two that put the idea in my head. At least, I hope it was. I’m a killer, yes, but I like to think that I’m no barbarian.

Nevertheless, a solution to the Simon situation occurred to me at that moment. I could simply kill him.

I planned it out in my mind. I considered location, weapon, timing and even a couple of ironic touches just to satisfy my own vengeful nature. The idea made me smile.

That night I had a dream. I saw former marks. They spoke, condemning me. Not for murder, but for allowing my own humanity to wither and die. When I woke, I didn’t want to go back to sleep for fear they would still be there, still pointing their boney fingers while their dry voices proclaimed I’d become more than an assassin. Something worse. Someone who would kill to avoid an annoyance.

I emailed my handler at 5:37 am. I told her I was out. Out because of fucking Simon. Then I tossed and turned for nearly 4 hours.

At 9:31 am Simon sent the following text message: “miss u much. pls call when u can. i know ur busy…but i know u miss me, 2.”

At 9:32 am I turned off my phone.

And then I slept like the dead.

blind date

I couldn’t help myself. For this week’s 500 Club, I’ve decided to revisit the character I created for last week’s flash fiction post, “killing simon“. If you haven’t read that post yet, read it first. This one picks up where that one left off and is written based on the following prompt: “Your (or your character’s) best friend has set you up on a blind date. Just as you are ready the door bell rings, you open the door, and…”

blind date

After the Simon fiasco I went months without killing a soul. Killing is a bizarre profession for a variety of reasons, not the least of which being the need to create emotional detachment from what you do. This is difficult because the process of planning a kill is lengthy and engaging. It takes time to plan a death so that it appears to have been an accident or the result of natural causes.

If a person were to work any other job, weeks of preparation culminating in professional success would be worth celebrating. It would be appropriate to feel pride and joy. Not so with assassins. We try to feel nothing.

This trains the brain to approach work differently and to partition off a part of yourself for the task of killing. The months I spent not-killing were agonizing, as though that partitioned part of me was suffocating. It literally hurt me to avoid the work.

So I called my handler and arranged a job.

At the same time, one of my few good friends decided the Simon break-up had left me despondent and insisted I re-enter the fray and start dating again. “It’ll be good for you,” she said with the haphazard arrogance people tend to assume when bettering others. At her prodding, I signed up for a ridiculous online dating service which caters to professional gay men.

I sensed disaster looming in the distance the moment the account was created.

The site specializes in technology-driven blind dates, matching members based on their preferences. I was given 3 choices for my first blind date–no pictures, only short descriptions based on the other members’ profiles. I made my choice and selected a nearby Starbucks as the meeting spot.

Two days later I sat sipping black coffee when a shrill voice entirely too close to my left ear exclaimed, “Oh my god! This has to be fate. It has to be!”

I turned to find an over-excited Simon wearing a red turtle neck (as my blind date had indicated he would be wearing) and a stupid expression of raw enthusiasm. He trotted around me to take a seat and proceeded to regale me with his recent dating woes, ending his 5 minute monologue with the proclamation that the dating service’s assessment that he and I were well matched was undoubtedly “a sign”. Surely, he asserted, I would not continue to reject his advances.

“Tell you what, Simon,” I said setting my coffee to the side. “Let’s get out of this place–it’s kind of stuffy in here and it’s a nice day out. Let’s take a walk and discuss it. Perhaps I’ve been too rash.”

Simon nodded and very nearly skipped out the door with me.

Twenty minutes later I deposited his limp body into a nearby dumpster, having removed his wallet, cell phone and jewelry to make it appear to have been a mugging gone bad.

When I returned home, I promptly cancelled my membership to the dating service.

red sweater

It’s 500 Club time again, and once more I’ve decided to indulge the same character. If you’ve enjoyed the last two weeks, hopefully this won’t let you down. For some reason, the as-yet-un-named gay assassin is just too much fun to write. This week’s prompt was simple: Write a story using “[CHARACTER NAME] never liked the color red” as the first sentence.

red sweater

I’ve never liked the color red. I suppose many people would think this to be problematic, given my profession. The truth is that there are a variety of ways to kill a person that involve no blood at all. Unfortunately, many of the easiest and quickest do involve blood. Often, plenty of it.

Even if Simon had not been wearing a red sweater that day, I would have killed him. I’d had enough. I didn’t enjoy middle school when I was 12. I have no desire to replicate the experience now that I am an adult.

Simon’s sudden (and as yet unsolved) disappearance didn’t trouble me. Despite the fact that I had, only months before, sworn I would not kill again, it’s been my experience that predators tend to prey. I am no different from a jungle cat or the great white. My mind and body seem to have been designed for what I do. I am simply allowing function to follow form.

Margaret, the same friend who encouraged me to pursue internet dating, is the only person in my life apart from my handler who is familiar with my occupation. She once said to me, “I don’t know how you do it.”

“Do what?” I asked. I do a number of things well.

“I don’t know how you kill people,” she said.

“Well, there are a number of ways. I prefer more creative methods, but on occasion I use guns. When I have more time, there’s poison, arson, explosives, contrived accidents–”

“No,” she said interrupting me and rolling her eyes. “I don’t understand how you manage it emotionally. I get the logistics.”

“I suppose I don’t think too much about it,” I said.

She frowned.

I pointed to the salmon fillet she was eating. “Your fillet, wild salmon, do you wrestle with pangs of guilt at the the reality that only weeks before tonight that meal was a living creature?”

She glanced at her dinner plate and said, “No.”

“And yet it was. It was alive, fighting for its own survival, swimming upstream to spawn, doing whatever it is that fish do. Living. But now it’s your dinner, and you feel no guilt about that.”


“And why not?” I asked. “Because you’re hungry.”

She thought for a moment before retorting. “Perhaps, but this is a fish, not a man. I wouldn’t eat a man.”

I smirked and she chortled.

“You know what I mean.”

“Of course,” I said. “I wouldn’t resort to cannibalism, either, but I need to eat. I need to survive. There will always be killers, and killing happens to be one of my more refined skills. I see no reason to feel guilt for being what I am.”

She nodded in understanding. I cannot imagine Margaret harming much of anything, but I think she followed my line of thought. Predators prey. They do not contort their nature to accommodate the weak.

Simon was, above all, weak. He chose to woo a predator. In the end, he paid the prey’s price. If you don’t want to be eaten, don’t behave like dinner.

And, anyway, he had no business wearing that god-awful red sweater.

the message

This week’s 500 Club offering is a two-fer. That’s right kids–I’ve taken on both prompts in one 500 word segment. I’ve done this because, (1) I missed last week and felt the need to offer up more the the writing gods this week; and, (2) because I’ve been wanting to write something that satisfied both prompts for a while and this week just felt like my week. But I stuck with the un-named assassin for yet another fictional jaunt. I kind of like him with no name. Perhaps I need to write more about  him.

the message

I got the message. There was no mistaking what I needed to do.

It was Tuesday after a busy weekend. Two marks. It’s ambitious, but it can be done. They were entirely unrelated but both happened to be in Chicago on the same weekend. Neither lived there. Both were Cubs fans. Really, no one should trust stadium food.

I slept late on Monday, something I rarely do, and then spent the day reading, drinking coffee and relaxing. A bottle of wine. Tuesday morning started out similarly except that I didn’t sleep late. I was just getting out of the shower when I noticed the missed call.

She had one of my numbers, but only for the most dire emergencies. All correspondence was typically done through email. She and I rarely had any reason for more personal contact than can be affected within a few lines of text.

She sounded mildly panicked. I spoke as though I did not notice.

“I require some assistance,” she said.

“Of what nature?”

She paused. One beat. “You know.”

I sighed. If I could just get her to say it…this could all go away.

“Perhaps,” I said. “Still, it would be nice to hear.”

In spite of the situation, I could imagine her smiling on the other end of the phone. Most assassins have never met their handlers. I used to sleep with mine. Bad form for a gay man, no argument there.

“The day I say that is the day your obligation to me ends,” she said.

It was a game we played. A delicate dance. I had walked out on her, walked away from the job, only months before. She would have said she knew I’d come back, but the fact is she had no more idea than I did. The obligation is more like a long tease. Foreplay. The prelude to an event that will never occur.

“You do, though.” I said. “Need me, I mean.”

She cleared her throat. “I desire your assistance. Professionally. And I believe my host wishes to speak to you.”

Play time was done.

“Ten million, unmarked, in cash or the bitch dies.”

I yawned. “Yes, yes,” I said. “I’ve done this a few times before. Where shall I meet you?”

The gruff voice barked an address. “And come alone,” he said.

How else would an assassin come?, I wondered.

“Of course,” I said. “Let me speak to her again.”

There was some shuffling on the other end of the line, then she said my name and I smiled.

“Can they hear me?” I asked.

“I don’t think so,” she said.

“Are you on a cell?”

“Oh, yeah. I guess that would work.” Perfect. They were standing right there but could not hear my end of the conversation.

“Four of them?”



“I think that’s where I put it.”

“I would assume armed. Are they as dumb and poorly organized as they sound?”


“They’ll be dead by this time tomorrow,” I said.

“I know.”

the upside

Been a while, I know, but here is my 500 Club submission for this week. (I really miss writing these posts when I go a couple of weeks without contributing. I suppose I should post more than once a week. Sucks that I have to maintain a day job.) The prompt for this week’s post is: “The last thing [CHARACTER] wanted to do that day was…” I have, once again, returned to the unnamed gay assassin. Hey, if it works, it works. Hope you enjoy it.

the upside

The last thing I wanted to do that day was shoot my father. It’s not that I didn’t want him dead–I did. Badly. And it’s not that I was unwilling to do the deed, myself. I wanted very much to spill his blood, to watch, to witness his exit from a world he had made a living hell for me.

Really, I just didn’t feel like doing it on a school day. It complicated things. Considerably.

My planned alibi–a trip to library, where I would duck out a back door, kill him, and then returning to my studies–would not suffice. It would hardly make sense for me to venture to the library to do homework early in the morning on a weekday. As a result, I had to think quickly and, though I wasn’t a skilled or experienced assassin at that time, I knew theoretically that my chances of appearing guiltless decreased relative to the amount of creativity I had to employ on the spot.

But the bastard left me with little choice.

It was Wednesday morning. He was nursing a fierce hangover and, I suspect, was still slightly intoxicated. He unleashed his considerable anger on my mother, who had not made him pancakes for breakfast. She had, instead, been working the night shift at a convenience store and, exhausted, collapsed on the couch in the living room on the way to the kitchen. When I found him, he was punching her in the face repeatedly. She had already passed out. He had blood on his arms to the elbows.

I walked quietly to his room, retrieved his hand gun and crept back down the hall. With steady hands, I aimed and fired. Three shots. Two to the chest, one to the head. I had planned something more gradual, something that would look like suicide but allow me the pleasure of watching him die slowly. I wanted him to die knowing I was killing him. Me. Just a kid. It involved Drano and a funnel.

This was too fast, too easy for him, but he would have killed her, I’m quite certain, and this fact is what saved me from needing any alibi at all. The police saw it as a strange kind of self defense. It never even when to trial. Not in the courts, anyway. My mother refused to speak to me after that day, her own judgement levied against me.

It seems she loved him, even to the end. He broke her left cheek bone that day and dislodged seven teeth. She threw up blood for three days. But I was the one who took her love from her, no matter how much he deserved the taking, and she never forgave me.

After that, killing for money seemed an easy thing. People die every day. I suspect that most have it coming. God knows he did. I only wish it could have been slower.

But, he is dead, and that, I suppose, is the upside.

missed mark

I’ve decided to resurrect an old character for this week’s 500 Club. The prompt I’ve chosen is: “Write a scene that seems to send us in one direction, but switches up in a surprising way. Don’t go for the cheap joke, though. Again, subtlety is key.” If you have not read my previous short fiction stories about the unnamed gay assassin (killing simonblind date, red sweater and the message), you might want to read them first. Hope you enjoy.

mark missed

One cannot afford to make mistakes in my line of work. There is a good chance you won’t be afforded the opportunity to correct them. That fact, combined with the reality that I am a proud perfectionist, means I should have known better.

The mark was simple. Disturbingly so.

A woman. Many in my line of work won’t take an assignment if the mark is a woman. My handler knows I have no sensibilities about the issue. The assumption, I believe, is that because I am gay I lack a tenderness toward femininity. This is not the case. Rather, I will take any mark. Man, woman, child–killing is killing.

If this sounds cold, you do well to check yourself. I’m an assassin. I’m not meant to be gentle.

She lived in a nicer part of town. I’d been tailing her for days, learning her routines. She was painfully predictable, and I felt the time had come for me to make a move. Each evening, after a quiet dinner alone, she read for a while in the bath and then went to bed. Her bath time presented me with a prime opportunity to manufacture the illusion of suicide.

I broke in quietly and crept upstairs. Though I had been watching her, I had never employed video surveillance in the bathroom itself. It hardly seemed necessary.

Assassination is often a simple act, the tried and true producing the most consistent successful results. I was planning to walk in, use her surprise to my advantage and simply hold her head beneath the water until she expired.


I open the door and heard her yelp in surprise. I approached, walking quickly across tile and bath rug, and placed my hand on her head, driving it beneath the water. She kicked and pushed, but was easy enough to hold her down.

I watched her hair, a tangled wet mop of brown thrashing in the water, and allowed my eyes to move down her body toward her feet. But I never made it that far. At her pelvis, I saw something that shocked me. Shocked me so much, in fact, that I recoiled and stepped back.

A penis. She was, in fact, a biological he.

The alarmingly passable transexual before me rolled forward coughing up water and suds. I stared at her chest, surgically augmented. At her face, pretty if simple. And at her crotch, starkly utilitarian by contrast.

“What the fucked?” she exclaimed.

I was still in shock, having been taken quite off guard. I shook my own head and said, “Sorry. Didn’t expect that.”

Then I casually withdrew my pistol and, with her watching, took aim and fired. There was a lot of blood, but she was in the bath so it was almost entirely contained.

I left in a hurry, fairy displeased at the messiness.

But, my God. Who would have expected that?

held back

He’s back. I really should consider writing more about the unnamed assassin. Something more than 500 words. I find him disturbingly comforting.

This is, however, is another flash fiction piece for the 500 Club. The prompt is: “Often times we write stories where our main character rushes in to save the day. Write 500 words where your main character can’t stop the inevitable.” I enjoy turning the prompts on themselves, interpreting them with liberty, and this is no exception. After all, what’s inevitable for you and what’s inevitable for a gay killer are likely two different things.

held back

“I held back. That is the simple truth of the matter.”

My handler said nothing, short breaths whispering across the phone line.

“Held back?” she asked. “You were supposed to use a gun. It was supposed to be a shooting. What you did, that was you holding back?”


An few hours earlier I had been crouched outside the mark’s hotel room, hiding behind a large planter. Assassination can’t always be sexy. I had contorted myself into a foot and a half of space, wedged into a darkened corner, the leaves of a ficus masking my presence. I prefer elegance in my craft, the kind that makes it looks as if I was never there. I like to leave no evident, save the corpse, of course.

However, the client made it quite clear that he wanted a message sent. Not typically my bag, a mob-style hit. It’s considerably more likely to get you caught, for one, but it also deviates significantly from what has become my calling card within the professional community.

Three times my usual fee persuaded me to make an exception. That, and the idea of seeing the mayor dead.

Johnny Whitman laughed from around a near-by corner, his voice loud, obnoxious and overly confident. He was in a hotel without his normal security, here in secret to meet and mingle (in a particularly intimate fashion) with one of our fine city’s voters. Despite the clandestine nature of his errand, he was chattering excitedly with his lover loud enough for me to make out his voice a good 40 feet away.

It’s bad enough that he insisted on always meeting in the same room, a ridiculously sentimental gesture. He didn’t need to advertise his whereabouts further by subjecting everyone on the floor to his guffaw, as well.

But then again, he wasn’t a subtle man.

He came into view, his companion hidden from my sight by the greenery, and I tensed. A keycard was inserted and extracted. The lock whirled and clicked open. The door swung and I made my move, pushing against his back and then closing the door behind me in a single maneuver.

That’s when I saw him. Mayor Whitman’s lover.

My eyes narrowed. He choked on his words, his hands up before him in a gestured plea for me to stop. He looked from my masked face, to my gloves, to the gun in my hand, and then back to my eyes.

“Whatever you want,” he Mayor Whitman said. “Whatever! I can get it for you.”

“You seem quite outspoken on the gay marriage issue,” I said. “Very against it, as I recall.”

He looked to his lover and swallowed. I pocketed my gun and reached for the pewter vase on the entry table to my right. I took two steps forward and calmly beat them both to death with it, crushing their skulls until the bone crunched like gravel. The vase held up nicely.

“Held back?” my handler asked again.

“Yes,” I said. “You have no idea how much more I wanted to do.”

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