For 2022, I’ve been wanting to write more ‘creature features’ and generally improve my short story writing. My partner got me a Dungeons and Dragons Monster Manual for my birthday so I came up with the idea of writing a story every week based on a different creature from that – All There in the (Monster) Manual. Hope you enjoy!

This Week’s Inspiration: Hell Hound

Milton Masters has it all, riches, his own talent agency, a mansion and a beautiful wife. Until one morning he starts to lose everything. What’s the connection between his sudden streak of bad luck and these lapses in his memory? And what’s it all got to do with these hallucinations he keeps having of a spectral dog?


“You’re telling me I’m fucking bankrupt?”

That morning started out as a good one for Milton Masters. Most mornings were good ones in his experience. He’d woken up refreshed with no hangover in spite of his late revelries the night before. He never got hungover, never really got sick. Kylie, his beautiful wife, was in a weird mood and had acted a little cold but that was okay. Milton could just as soon arrange a nooner with his assistant, Rachael, or any one of his casual girlfriends. Kylie knew, they had an understanding. He’d gone for a quick five mile run around his massive property just for the sheer pleasure of it. He had one of those metabolisms where no matter what he ate or what he drank or what drugs he put into his body he stayed lean and fit, but he liked to run. He looked as good as he had ten years ago when in his late twenties, if not better. He’d taken the Porsche to work although the agency tended to keep itself running no matter how much or little effort he put into it.

But then Rachael reminded Milton of a meeting he had in the boardroom, which he’d forgotten. Apparently a few weeks ago some of the agency’s accountants noticed some irregularities. Milton hadn’t worried, things like that always worked themselves out. They’d hired a forensic accountant though to go through the company’s books and holdings. That morning he was delivering his report.

“It’s quite a bit worse than bankrupt, Mr Masters,” the bespectacled man in the grey suit said. “There are debts here, both in the agency’s name and in your name personally, that are astronomical. I have no idea how this has been missed or has stayed afloat for so long.”

“Do you know who we represent?” Milton said. “Some of the hottest names in the country! On the planet! They bring millions, tens of millions, back into this agency every day!”

“And then it all feeds back into this network of costs and holdings. It’s labyrinthian, I’ve been doing this for more than a decade and I’ve never seen anything like it. And basically everywhere you look you have these debts eating away at everything. They’re like termites that have been chewing at the foundations of a house for years and years, and now that house is at the point of collapse.”

“This isn’t possible.”

“I can’t understate how serious this is, Mr Masters. Your personal holdings are tied throughout all of this. You’re not just going to lose your business, you’re going to lose your house, your cars. I’m sorry, you’re going to lose everything. You could even be facing jail time.”

“It’s not possible.”

“Embezzlement is a real possibility but some of these structures go back to the very founding of your business. Do you remember who set up all these original applications and accounts for you?”

Milton stopped, and stared. It took the accountant several promptings to bring him out of what seemed like a fugue. Milton always told people he didn’t like to look back when they asked him about the start of his success, he preferred living in the present. But trying to cast his mind back to those early days, ten years earlier, it all seemed shrouded in grey. It always felt like it had happened so easily. Like one day the offices, the staff, and all the boring business stuff like accounts and legal documents were just there, and then the clients started flocking to them. No matter how Milton twisted it in his memory, he couldn’t think of who might have set those things up or how.

“This is still an informal meeting because I realised just how dire the situation was,” the accountant said. “I’ll put together a much more thorough formal report to identify your biggest risks but right now you need to stop spending. Today, this second. Don’t touch any of these accounts until we talk again.”

This couldn’t be real, this was a nightmare, Milton thought. He drifted back to his office in a daze. Windows even in the reception area outside his office offered dazzling views. His busty, redheaded assistant Rachael shot up as he entered.

“Milton, are you okay? You look pale,” Rachael said.

“Just, just, hold all my calls, don’t let anyone in to see me,” Milton said.

Milton’s office was huge but the walls were cluttered by the sheer number of platinum records, signed musical instruments, and photos of Milton with clients, other musicians, and various celebrities. Milton fell into the chair behind his desk. He knew he should call someone but he didn’t know who. He didn’t handle that kind of thing anymore. Truth be told, he couldn’t remember when the last time was he ever had to handle that kind of thing for himself.

“This can’t be happening.”

Milton buried his face in his hands for a few moments but then looked up and happened to glance towards his desktop computer screen. It was on sleep mode and black, and reflected Milton’s morose features back at him. But behind his shoulder, he also spotted the reflection of a monstrous dog. Its teeth were bared and its eyes ablaze, looking like it was about to go for his neck.

“What the-,” Milton shot out of his seat, spinning and knocking it to the ground.

There was nothing behind him. Of course there wasn’t, for the dog to be where he’d seen it in the reflection it would have had to be hovering outside his window some twenty stories off the ground. Still, panting, Milton twisted and hunted around the office for some sign of the phantom dog. Nothing. It must have been stress or something. He’d imagined it, no matter how real it seemed.

Milton collected himself and marched back out of the office. Rachael, confused, jumped up from behind her desk again.

“Milton, what’s happening? Where are you going?”

“Home, cancel my meetings. Do I have any meetings? Cancel them,” Milton said.

Milton returned to his Porsche and tore out of the parking garage. On his way home, Milton realised he was putting an awful lot of faith in the word of just one man. Not even one of his own accountants, someone hired from outside of the agency. But somehow he knew the man had been telling the truth. He had a feeling deep in the pit of his stomach that it was all coming down. A feeling he’d been holding onto for a long time that somehow, someday, it all would end. He hadn’t forgotten the dog he’d hallucinated either. He kept glancing to his rearview mirror, pointed at the backseat, as he drove.

When Milton arrived home, he was greeted by the sight of two huge trucks parked outside his mansion. Men in dark grey uniforms poured in and out of his front doors. With them they carried furniture, rugs, paintings and other artworks. Milton screamed up the driveway and pulled hard to a stop behind the trucks.

“What the fuck is this? What do you think you’re doing?” Milton yelled as he emerged from the Porsche.

“Repossession.” A senior man came over and slapped some papers into Milton’s chest. “It’s all in here, the bank is taking it back.”

“You can’t just-, let yourselves in and start stealing all my stuff!”

“Your wife let us in,” the supervisor said.

“Yeah, she’s been very accommodating,” another nearby man said, carrying one end of an antique sofa.

The man at the other end of the sofa snickered. So did the supervisor and several other surrounding removalists. Milton ignored them and ignored the papers, tossing them aside as he ran into the house.

“Kylie! Kylie!” Milton yelled.

Milton sprinted up the stairs and headed for the bedroom, where he’d last seen Kylie that morning. He was surprised at the top of the stairs to find himself out of breath. He couldn’t remember the last time he’d been out of breath, even after a big run, but the stairs he travelled usually several times a day without issue had winded him. Milton took a moment to recover and continued down the hallway.


Milton threw the bedroom door open, and recoiled at what he saw. Kylie bent over the bed on her hands and knees, totally naked. Two removalists stood around her, one at either end, with their pants pooled around their ankles. As Milton entered they all broke apart but what he’d seen in that split-second burned itself across his brain. Kylie dropped across the bed but she didn’t look ashamed, she looked furious.

“Kylie, what are you doing?” Milton gasped.

Milton’s heart dropped into his stomach. The betrayal. They might have had an arrangement where Milton could sleep with whoever he wanted but for the last ten years Kylie had been faithful, at least as far as he knew. The two men shovelled themselves back into their pants. Staring sullenly, they filed past Milton. Kylie wrapped herself in one of the sheets and rolled off the bed.

“What the fuck were you doing?” Milton repeated himself.

“I think you should know, pretty sure you’ve been there once or twice,” Kylie said.

It was true Milton had shared women with other men like that a few times, when the mood struck him. But not Kylie, never Kylie. She was untouchable. The two of them had gone to high school together but had never hung out in the same circles. It was only when they’d reconnected around the same time Milton was putting his agency together that they’d started dating. They’d married after a whirlwind romance, their ten year anniversary was coming up soon, and as far as Milton was concerned theirs was a perfect and perfectly happy marriage.

“Is this to get back at me? You found out I’m broke and getting repossessed, and you wanted to hurt me?”

“I didn’t want to hurt you, Milton,” Kylie said. “In fact, I don’t care about you at all. I woke up this morning and I couldn’t figure out what I’d been thinking the last ten years. I don’t understand why we got together or where my feelings for you ever came from.”

“But, but, I love you.”

“You love what about me? Seriously, what? What did we ever talk about when we first got together? When did we ever fall in love? Back in high school, we never talked.”

Milton gaped. Much like when he’d been asked about the origins of his business dealings that morning, everything in his memory seemed faded. He and Kylie getting together just seemed to happen back then. But it was insane, they were in love! Kylie hung off his every word, she laughed at his every joke. She let him do whatever he wanted as long as it made him happy. They’d been distant in high school but people changed, and they’d reconnected.

Kylie slapped Milton in the stomach and snapped him out of his thoughts. Still only wrapped in a sheet, she strolled casually out of the room.

“You’re getting fat by the way,” Kylie remarked on her way out.

“It can’t have all been fake, it can’t,” Milton said as she left, but in his gut he knew it was.

Milton still felt out of breath, and his heart was pounding. He crossed the room to their walk-in wardrobe. Kylie was right about his weight, and that suddenly felt important. Milton stripped off his shirt and stood in front of one of the wardrobe’s full-length mirrors.

Somehow, Milton had developed a paunch that hung over his waistband. His chest and arms had softened as well. He still wasn’t in necessarily bad shape for a man of thirty-eight but Milton remembered admiring his lean physique in the mirror just that morning. The hard lines of muscle that he never really seemed to work on. Could stress cause the body to break down so quickly? He felt heavy, and old. Like years of alcohol and drug use were suddenly catching up to him.

Then, suddenly, behind him, Milton saw the dog. Clear as life, it looked similar to a rottweiler with a huge, muscular frame, a giant of a canine, and totally black. Its lips were drawn back from fangs that could easily rip him apart. Its eyes were blazing red, as if lit by some internal fire. Milton heard it let out a chainsaw snarl that rippled up his spine.

“Jesus!” Milton whirled around and crashed into another mirrored closet door.

Nothing, there was nothing behind him. But it had looked so real, Milton could picture individual strands of fur rippling down its back. See the shine of drool on its teeth. He’d heard it growl! But the carpeted patch behind him was empty. He checked the mirrors and found them empty as well.

“What the fuck is happening to me?”

Milton’s heart thundered. His whole body felt like it was covered in a cold sweat. He pulled his shirt back on, feeling vulnerable, and raced out of the bedroom. Looking for Kylie, he couldn’t find her. All the removalists seemed to be concentrated at the front of the house. Milton snuck down the back instead, feeling like a thief in his own home.

Behind the house was Milton’s enormous pool, clean water glittering in the sunlight. It had an irregular shape, like a natural lagoon surrounded by gardens and shady cabanas. At the other end of the pool was the pool house. Two stories with several bedrooms, bathrooms, and its own bar, the pool house was bigger than plenty of peoples’ actual homes. When they weren’t entertaining and the mansion started feeling a little too big and empty, the pool house was Milton’s private oasis.

Milton let himself in. At least the repossessors hadn’t gotten to the pool house yet. The front room, with big glass doors and windows facing the pool, was full of more music memorabilia. A jukebox and a dozen guitars occupied one wall, tens of thousands of dollars worth of instruments. Milton hadn’t picked one up in a while but he used to play all the time. When just how much his life had changed started to overwhelm him and he got struck by fears it would all somehow be taken away, he’d play guitar for a while and lose himself. There was no time like the present to start again. Milton slipped one of his favourites off the wall, plugged it into an amp by the jukebox and sat down to start playing.

Milton’s hand froze over the neck of the guitar. He strummed but he had no rhythm, his fingers just falling against the strings. He tried to twist his left hand into the right shape but he couldn’t remember any chords. His mind was blank. He couldn’t even find a comfortable position to hold the instrument, like he’d never picked up a guitar before in his life.

“No, no, it’s not possible,” Milton said.

Milton couldn’t remember a thing he’d ever learned about playing guitar. Sure, it had been a while but not that long. He frequently pulled one of the instruments down from the wall and played a little bit at parties. His guests often told him he was good enough to pick up a music career of his own, had he ever wanted to deal with all that recording and touring. Some of it was no doubt flattery but Milton was genuinely good, he knew he was good! But suddenly he could no longer access the memories or ability to play. The strings hurt his fingers, as if he’d never built up any calluses. All that came out of the amp was noise.

Milton heard another chainsaw growl, rising to a snarl. Looking up, he saw the dog again, its reflection ghostly but very much present in one of the pool house’s glass doors. Its fangs were exposed and its eyes on fire. It opened its mouth and barked, the sound so deep and loud Milton felt it in his chest.

“You! You did this to me, go away!”

Milton ripped the cord out of the guitar, stood up, and pitched it toward the dog’s reflection. The glass pane shattered. The guitar flew right through it and cracked against the pavers that surrounded the pool. Knifelike shards continued to tumble out of the frame and break apart.

“Mr Masters, I don’t think you’re in any position to be treating your assets like that,” a voice said.

The bespectacled accountant from that morning strolled into view and stopped in the middle of the shattered frame, right where the dog’s reflection had been. In his grey suit and red tie, he was such a small and unassuming figure that even after he’d started Milton’s downfall it still took Milton a few moments to recognise him. Shoes crackling on broken glass, he stepped through the frame.

“What the fuck are you doing here?” Milton asked.

“We had a deal, Mr Masters,” the accountant said. “I’m here to see you fulfil it.”

“What deal? I didn’t sign anything!”

“Oh, but you did, and in blood no less.”

The accountant took off his glasses and cleaned them with his tie. He went to put them back on but then seemed to think better of it and tossed them aside instead. With every step, the planes of the accountant’s face subtly changed along with the way he held himself. A devilish grin split the man’s face.

“I know you don’t like to think about the past, too busy living in the present, right? But think back,” the accountant said. “You were a nobody in high school, pathetic, and then after you graduated things didn’t get any better.”

“People change! I built all this from the ground up!” Milton said.

Milton’ head jerked as he heard the dog snarl and its jaws snap. He couldn’t see it, couldn’t see its reflection, but it was somewhere in the room with the two of them. Invisible, but he could feel it.

“You bounced from one minimum wage job to the next, no aim, no girlfriends. You didn’t even have the drive to actually learn how to play guitar like you always wanted.”

“God, no.”

Milton backed up toward the pool house’s bar. He started to remember those shiftless, aimless years, waiting for a break that never came. Something that would magically put him on the path to greatness.

“As you approached thirty you became more and more desperate,” the accountant said. “You’d heard the story of Robert Johnson, the blues musician who sold his soul for his unearthly skill. Not true, by the way, he was never one of ours.”

“No, no.”

Milton started to remember. All that grey in his memories began to lift, and he remembered the night the man in grey described. He heard the dog in the room with them again. Something heavy and hairy brushed against Milton’s leg but he couldn’t see it.

“You went to the crossroads at midnight. You drew the signs, you said the words.”

“I didn’t know it was real!”

“And you signed away your soul when I appeared to you. You’d been thinking about the contract for so long, everything you wanted, no loopholes. But such small, petty dreams. To be rich, to hang with the cool kids, to fuck the prom queen. You wanted abs without having to work for them, and to play the guitar without practising. Petty, petty, but it was yours for ten years, as per our agreement.”

“I didn’t know!” It had all come back to Milton now.

“Oh, and one other thing, very interesting. You wanted to forget. So you could really enjoy all your pleasures, you wanted to forget how you got them so you wouldn’t spend the next ten years worrying about what was to come. We could spare you that, what’s ten years against an eternity?”

“There must be some kind of deal we can make now! A new deal, if you give me time! If you give me more time!”

“I’m afraid your time is up, Mr Masters. You called the tune, you danced to the music, and now, as they say, it’s time to pay the piper.”

Milton heard the dog bark and something seized him by the leg. He looked down and saw invisible fangs shred through the lower part of his pant leg and draw blood. Milton screamed and threw himself backward. Teeth like knives ripped through muscle and meat. Lashing out with his other foot, Milton met something solid even though he couldn’t see what he’d hit. Blood flew, the invisible hound savaging his calf for a few more moments and then letting go.

“Jesus! Jesus, God!” Milton grabbed the bar and hauled himself up to try to get away, leg gushing blood. “Please! Okay, please, I’ll come with you but call it off! Please, call the dog off!”

“Oh, Mr Masters, if I were you I’d savour this moment. Compared to where you’re going this is no more than a gentle hazing.”

Invisible, the hellhound came around the bar and hit Milton from behind. Teeth ripped open his arm and yanked him down from on top of the bar. Milton fell, screaming. He felt its hot breath on his face, smelled his own blood, as the creature fell on top of him and began to bite.


Sean: This one really grabbed me and wouldn’t let go, it took me a couple of days to write but only because I came up with the idea really late in the evening on the first day. I just had to see it to the conclusion so I just went ploughing through it as quickly as possible. I think it’s a pretty good twist but I’m guessing the title and the monster probably gave it away early to some people. Damn it, it’s a good title too though! Titles are hard.

This hellhound is a lot less friendly than the last story I wrote involving a canine monster from the afterlife.

Keep your eyes on my website for more in this series, I fully intend to release one every week across 2022 – totally free. And for more updates you can find me on Facebook and Twitter.

Next Week’s Inspiration: Grell

2 thoughts on “Crossroads

  1. Love it. Not really in keeping with the hell hound but I would have enjoyed it if the dog and the accountant were the same character – as in he’s just a big dog in a suit but no one else notices or think it’s strange

    • Hahah, see the problem is I feel like I already telegraphed the ending too much. If the accountant was a dog in a suit I wouldn’t be able to resist writing all his dialogue like Scooby Doo and giving him away as well.

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