Hunter's Moon
Chapter 1: A Fool's Bounty
Funny thing about Hell: many people believe it's all fire and brimstones, but that couldn't be farther from the truth. If anything, Dante had a better understanding of Hell with the seven rings, but even he, with his medieval thinking, still muddied up the details. Truth be told, each ring was a color-coated shittier version of Earth. But none of these rings were shittier than the that of the Pride Ring. The worst area of all would have to be the central city of Pentagram. The city was nothing more than a cesspool of the world's worst sinner, now free to live out their dark desires, forever transformed as demons. Or that was the case till recently.
Things changed dramatically once, not too long ago, when Lucifer failed to jump-start the apocalypse and was sealed away along with his archangel brother, Michael. Since then, Hell was put in a state of chaos and confusion without its king, with many overlords, princes, sins, and any upstart warring for the throne. All until one sinner by the name of Crowley took the throne and decided to revamp the Pride Ring. Oh, it was still a shit hole, but under him, it was now a well-organized shit hole.
Even though Pentagram City's main inhabitants were mostly made up of sinners, there were still run-of-the-mill hell-born demons roaming around. Succubi, imps, and hellhounds would casually wander the streets. One such hellhound found herself walking cautiously through these streets. Not because she feared for her life as she was more than capable of defending herself, but to hide from the other denizens from where she was going. Her destination was a building that had grown dilapidated ever since the new king took over, the Hazbin Hotel.
The hotel in question was built by Lucifer's own daughter, Charlotte, and originally intended to reform sinners into going to heaven. Charlotte, or Charlie, was allowed to run the joint with funding under her father's rule more as an ironic gesture. But, when Crowley took over, he had the place shut down, making it a bigger pariah than it already was for a multitude of reasons. One was that he saw the place, as many sinners did, as one big joke that tainted Hell's reputation, and the other reason to just stick it to the former ruler by screwing over his daughter. Either way, no self-respecting demon would be caught dead entering the place, not even ironically less they fear testing Crowley's limited patience.
But Loona wasn't like most demons, or hellhounds for that matter. From a young age, she had already learned to accept the need to be self-reliant and had no reason to have more than a little respect for authority. That's what happens when spending most of her life stuck in a hellhound orphanage only to be adopted weeks before she was going age out anyway. However, despite getting herself a 'father,' the past few years haven't been all too peachy. Sure, you can't expect luxury living with an imp, who are only one step higher on the totem pole than hellhounds, and her dad, Blitzø, wasn't the worst Loona could've landed with. The problem was that he was just a bit much. Even though she works at his business as a secretary, the guy tends to baby her constantly despite her already being in her mid-twenties. Loona was still irked by one-time Blitzø signing her a babysitter when she was eighteen.
Though Blitzø was not the reason Loona came all the way out here. No, Loona had her own personal reason to risk coming to the one place in Hell that would turn her into a social pariah. Something she must discuss with the princess of Hell herself. Even now, knocking on the door, she was urgent for an audience only to be met with a spear shoved in her face.
"We already agreed to your terms of not allowing any new occupants," exclaimed the grey-lavender demon with moth-like features and x shape eyepatch who continued to jab her spear at Loona's face, "What more does Crowley want from us now?!"
"I'm not with Crowley." Loona stated, more annoyed that she had a weapon brandished at her.
"Sure, you're not," the demoness said sarcastically, "He always sends you hounds out here to hassle us on every other occasion."
"I'm not one of his hellhounds! I work freelance." seeing she wasn't getting anywhere with this demon, Loona pulled out her phone before continuing, "Look, I've got an appointment with Charlie. We've been texting each other."
Loona held out her phone for the demon to review these text messages. Seeming somewhat satisfied, the moth demon stepped back into the hotel, shutting the doors. From the outside, Loona heard murmurs of a conversation within the building's walls. For a moment, the wolfish hellhound in gothic attire was beginning to grow bored with all this waiting. But before she had a chance to check through her socials, the doors to the hotel opened once more.
"Hello, you must be Loona." Charlie stepped out to greet the hellhound with a perky smile, "Please come in, come in. I've been hoping to follow up on our conversation."
Quite enthusiastically, Charlie led the hellhound into the hotel. Inside, the hotel's interiors were also showing signs of run down. Dust was scattered everywhere, lights were out with candles as their replacements, and even the wallpaper was falling off. Charlie, herself, looked as if she threw on her wrinkled-up red suit and tie in a hurry, along with a quick comb of her blonde hair. Crowley cutting off support clearly did a number on the princess and the hotel. But still, she managed to put on a brave face for her guest.
"Please excuse Vaggie for her rudeness. She's just very protective." Charlie gestured to said moth demon, who gave their visitor the 'I'll be watching you' eyes. Loona answered back by flipping her off, "Please, sit down. It's been a while since we had any visitors. Can we get anything like a glass of water? Our plumbing hasn't shut down… not yet anyway."
"Nope, I'm good." Loona sat on a rustic old chair before pulling out a pack of cigarettes.
"Um, our ventilation doesn't work anymore, so if you could not…"
But Loona lit her first cigarette and puffed it anyway, "Not sure where to start."
"Well, perhaps you can be more transparent," Charlie answered while swatting away the smoke, "You were pretty vague over the phone."
"Yeah… well… wasn't something I wanted to discuss over text where anyone could stumble on me typing," Loona admitted reluctantly, "All I know is that you're unorthodox as a demon, and I'm feeling like I might be the same as well."
"Well, technically, I'm half demon on my mother's side, and my father's an archangel…" Loona took another puff from her cigarette to show she wasn't listening, "Right, right. We're here to discuss you, not me. So, what makes you say you're unorthodox?"
"Well, I should start off in the beginning. You see, I'm the secretary for I.M.P."
"You mean those imps who go up to the human world to kill people?" Vaggie interrupted, "Don't tell us you're looking to reform because we rejected those to keep Crowley off our backs."
"First of all, we only go after whatever asshole wrong our clients, and nine times out of ten they deserved it." Loona retorted, "Second, even if I believed in your little twelve-step program, I'm hell-born. So, I'm pretty much barred from heaven no matter what I do."
"Ladies, please, let's not argue." Charlie hoped to talk down the two demons, "Loona, please continue."
"Like I said, I work for I.M.P." Loona reiterated, "Most days are just sitting around doing nothing while waiting for new clients. A week ago, we had this one client who… let's just say had quite the request."
One week earlier
Outside the confines of Pentagram City, there stood a city district better fit for the natives of Hell. Imp City was one of these. Despite its name shake, most within the Pride Ring considered this area the slums because their inhabitants were the second lower-tier demons, the imps. The city was also home to the business known as I.M.P, or the Immediate Murder Professionals. Things were quiet in the I.M.P office as usual. The married imp duo, Millie and Moxie, were working on their weapons training. Their boss, Blitzø, was currently locked up in his office, probably working through a perverted fetish of his out-of-sight. Loona found her workdays go by via scrolling through her phone to catch the latest gossip.
Lately, Loona was growing discontent with her place in Hell. Sure, she had a stable job, but she only got it from the nepotism of her 'dad's owning the business. A business that was only started up because he was fucking a Goetia on the side. But despite how Blitzø treated her as a daughter, most saw Loona as nothing more than his personal hellhound, a pet. Even her co-workers Millie and Moxie often referred to her as their boss's hellhound. Creating a social life in general hardly came easily because of this. The closest Loona ever got to was developing a friendship with a hunky hellhound by the name of Vortex. Even that was because she was hoping their relationship would eventually grow into something more, only to find out that he already had a girlfriend who so happened to be the sin of gluttony. Overall, Loona felt she didn't have a place in Hell. Still, she had a job to do, which came when a shadow cast over her desk.
The shadow belonged to a lumbering sinner resembling a scarecrow-like demon. His shoulders were broad with a raggedy old coat. A noose hung around his stiff, swollen neck like a tie tightened to the point he should be gasping for air if his actual body didn't resemble a dried-up husk of a skeleton. The witch's hat upon the demon's head really threw off the whole scarecrow aesthetic, but of course, people don't have a say on what demon they look like when they die. Speaking of, the dude stunk of the living, meaning he died just recently, and already he had an ax to grind topside.
"Hello, I'm here for…"
"Next room, dude." Loona pointed to Blitzø's office before burring herself back into her phone.
The demon was miffed at her abrasive attitude but chose to continue on why he was there. He went over to the office where a tall, curly-horned imp who looked to have scurried to hide away his current activities. Whatever that may have been mattered little to this guy. The demon had pulled a lot of strings to get himself appointed as a high-value client, and he was to make sure to get his money's worth.
"So, haven't been dead for twenty-four hours and already seeking revenge?" Blitzø confirmed the demon's brief explanation, "I appreciate someone with that kind of initiative." Blitzø stretched out his arm to the demonic scarecrow, "The name's Blitzø, the O is silent."
"Jason Combs." He answered, shaking the imp's hand.
"So…" Blitzø moved to sit behind his desk, "What can we do for you?"
"Well, back in life, I wasn't just any man. I was a witch." Jason exclaimed, "Three hundred years old, to be exact. I don't mean to brag, but I've done a lot with my witchcraft in favor of the depth of Hell by…"
"Okay, listen, I'm not interested in your three centuries-long biography." Blitzø interrupted, "I'm more interested in the asshole, or holes, who stiffed ya during your last moments of life."
"I was hoping to ease you into my request."
Blitzø let out a brief laugh, "No worries. Here at I.M.P, we do not discriminate between our clients' targets by their race, sex, or even age. Tell us who you want dead, and we'll make it happen."
"Sam and Dean Winchester."
The room suddenly went eerily quiet. Blitzø needed a minute to register what he had heard. It had to be some sort of mistake. His ears playing tricks on him or something.
"Winchesters, as in the Winchesters? The monster and demon-hunting brother duo, those Winchesters" Blitzø prayed to whatever unholy entity listening that this was some misunderstanding.
"Yep, they're the ones."
Blitzø slumped back into his chair with a heavy sigh, "On second thought, maybe you should explain this one."
"I was attempting my yearly ritual of sacrificing another soul to hell," Combs explained, "Simple thing all and all. Just conjure a spell that tricks the person's mind into wanting to off themselves."
"Wait, wouldn't that be considered cheating and kinda nulls the whole thing?" Blitzø interjected.
"Not necessarily," Combs answered quickly, "So long as the one in question does the deed to themselves, their soul goes straight to Hell no matter the outside influence." with that explanation out of the way, the scarecrow cleared his throat before continuing his story, "Anyway, I had already set my sights on a sacrifice, and have already planted a hex bag in her place the day before. I was fixing my spell when my ingredients caught fire, meaning someone had burned up my hex bag. Next thing I knew, the Winchesters busted onto my property and opened fire on me. As I was making my escape, the brawny one, Dean, I think, fired a round close to my foot, which tripped me up, falling into the noose I set up for my sacrifice, and then I woke up down here!"
"So… let me get this straight," Blitzø was trying his damnedest to stifle a laugh, "You died by… by tripping… into your own death trap?" Combs responded with a nod, "Okay, as entertai… I mean hilari… I mean… fuck! Intriguing? Yes! As intriguing as your backstory is, I'm afraid we will have to decline on this."
"I thought you said you didn't discriminate targets." Combs reiterated harshly.
"We don't, but those two are a special case."
Blitzø wasn't lying when he said this. Over the years, many have flocked to I.M.P requesting revenge against the Winchesters for their deaths. But they were all shot down. Not that the imp wanted to, for the clients were willing to pay double for the hit, but it wasn't up to him. Lucifer had long ago made the younger brother, Sam, off limits to become his vessel in bringing on the apocalypse. Dean was an exception, but the clients weren't happy settling for only half of the brothers.
One would think that the change in management would render these restrictions moot, but Crowley had his own uses for the Winchesters. It was no secret Crowley aided the Winchesters in defeating Lucifer, which eventually led him to become the new king of Hell. Still, the king's favor for the boys only stretched so far and wasn't above bartering for their deaths if the right offer was made.
"Sorry, but unless you get the all clear from the head honcho, ain't nothing we can…" an envelope slapping down onto the table silenced Blitzø. Looking it over, Blitzø's eyes fell on a devilish crest in the shape of a C, "Where'd you get this?"
"From the head honcho himself," Combs answered, which left Blitzø a stuttering mess, "I told you I did a great service for hell before I died."
Blitzø was almost hesitant to open said envelope to reveal its contents. Not once in the imp's life had he received any message from either ruler of Hell. Unsealing the envelope, Blitzø was met with a letter that read,
'Evening, Mr. Blitzo of I.M.P
If you're reading this, then you've already heard what your esteemed guest has asked of you. As gratitude for his generous contribution over the centuries, I give him my full blessing in seeking your assistance in the assassination of Sam and Dean Winchester. And, if you manage to succeed in such a task, I'll be sure to offer double on top of what Mr. Combs will be paying.
Signed: Your King
Crowley
"Well, who am I to say no to the big man himself?" Blitzø crumbled up the letter and tossed it aside, "Okay, you got yourself a hit!"
Blitzø jumped on his desk again, offering his hand, which Combs accepted, "Glad to hear you see it my way."
"Of course, not only will we have to charge for two assassinations, but also extra on top due to the high-profile nature of our targets." Blitzø exclaimed with much excitement.
"I'm good for it," answered the demon scarecrow, "So long as you can make the kills."
"Oh, don't you worry. This will be, without a doubt, the…
"…worst job we've ever taken, Sir."
Some time had passed since Blitzø's meeting with Combs, and afterward, Blitzø had called everyone into the staff room to express excitement over their next hit. His adopted daughter, Loona, sat at the far end of the large table, once again more preoccupied with her phone. On the other side of the table, much closer to Blitzø, sat Millie and Moxie. Of the two of this couple, Millie was the most ecstatic about having another job to work and another person to kill. Her husband, Moxie, did not share the same enthusiasm.
Of course, Moxie was a complete buzz kill of the whole situation. His nasal whining was enough to grain on Loona's sensitive ears, but what could she do? The little guy was a good shot when it counts. The best that could even be done about the little imp's constant complaints was to partake in the semi-tradition of making Moxie the office punching bag.
"But of course, Mr. Smooth-brains can't help but stare a beautiful horse in its mouth," Blitzø jabbed back, "Seriously, Moxie, this is the hit of a lifetime. We get this shit done, and we'll be swimming. The fuck is your problem? You suddenly hate money now!?"
"Sir, these aren't just any targets we're being sent after," Moxie exclaimed, "We're being sent after the Winchesters for fucks sake. Do you have any idea how many sinners have gone up topside to kill them?" Blitzø hummed in confusion, "And how many of them have succeeded?" before Blitzø could respond, Moxie continued to cut him off, "And now, we're being asked to deal with them? How in Hell are we going to accomplish what so many couldn't?"
"Well, unlike those undead assholes, I've got a flawless plan to guarantee our success." with a marker, Blitzø illustrated said plan upon the whiteboard that stood behind him, "Step 1: we portal up to Earth, of course. Step 2: I intercept them pretending to be an old friend from high school. Step 3: I treat them to a night at the bar. Millie, you'll go as the wait staff and secretly liquor them up with the strong stuff. Step 4: After they're good and drunk, we step outside. They 'accidentally' trample a cute innocent animal, which is actually Moxie dressed as a possum. Step 5: While they're bawling their eyes out over what they've done, I sneak back behind them, I blow their brains out, and we collect the biggest payload in our fucking lives. Are there any questions before we go up top?"
"Yeah, why am I the one who gets trampled in this scenario!?" Moxie asked, his voice nearly becoming shrill in response.
"You gotta admit, you do have an opossum figure." Blitzø just answered without a second thought.
"But what makes you think they'd even care about accidentally killing a little woodland creature?" Millie asked in a rare act of questioning her boss.
"They move around the country to kill demons for the cause of 'saving people,' Blitzø stated with actual air quotes, "Aren't all people like that supposed to care about the plants, animals, and other shit like that?"
"According to the I-Survived-the-Winchesters subsinnit they're just a couple of flannel-wearing gun-toting douchebags." Loona chimed in, all the while continuing to scroll through her phone.
"And that still doesn't address the bigger issue," Moxie carried on, "Did you forget who we're dealing with again? The Winchesters have gone up against multiple sinners. Sinners who possess human bodies and are granted powers while on Earth. Not to mention, they're also the ones who sealed Lucifer in the first place. So, again, I ask, how do you expect three imps with bad wigs and costumes to have any chance of killing them?"
"Look, we don't have time to dick around with all the minutiae of the plan!" Blitzø exclaimed in frustration, "That scarecrow-looking motherfucker convinced Crowley to pay us double on top of the pretty penny he's paying, and to sweeten the deal, I gave the offer to get the kills for free if we don't succeed in a certain time frame. We have one week to kill these guys, or we won't see dick all of that money!"
"What happened to that deal being twenty-four hours?" Millie asked at this sudden change.
"I had to bump it up after Moxie fumbled that camp counselor job."
"Good job at screwing us over, dickhead." Loona again chimed in.
Moxie growled at the hellhound's remarks, "Do you have anything better to do than make senseless insults at my expense?"
"Do you have anything better for me to do than pointing you to the nearest dessert buffet?" Loona shot back, finally looking up from her phone.
This backtalk struck a nerve with the short imp, "For the last time, I am not fat!"
Loona had herself a little cackle from this response. It was true that Moxie was far from being considered fat, but that fact mattered little to Loona. She and Moxie have never gotten along for as long as she's known him. The little imp's pompous attitude and his high-pitched voice grained on Loona's nerves the second of the two's meeting along with him with her standoffish demeanor, and thus, a rivalry was born. Words were said, and insults were thrown about all until Lonna stumbled on that one that seemed to get under the imp's skin. For whatever reason, Moxie became so insecure over it that he would, at times, proudly brag about how much weight he lost as if anyone cared. Loona certainly didn't, only that this one insult lived rent-free in Moxie's head gave her so much joy.
With her fun had, Loona returned to her phone while the meeting continued around her. Thanks to each of them poking holes in Blitzø's main plan, arguments broke out between Blitzø and Moxie on how they should best kill the Winchesters. There were discussions of said topic ranging from using knives to poisons and booby traps. Honestly, it all became white noise to Loona. Especially when each suggestion was shot down over how they'd even get close to the brothers without them catching on that they were demons.
"Well, we have a hellhound with a proper human disguise." Millie said, "Maybe we could have her enact the kills."
Loona heaved a sigh over the prospect of being able to do something for a change, "Not like I have anything better to d..."
"Absolutely not!" Blitzø hollered before rushing over to secure Loona in a protective embrace, "No way is my baby girl going anywhere near those demon-killing maniacs!"
With a growl, Loona shoved Blitzø off her. See this; this was why Blitzø annoyed her so much. Despite her being fully capable of defending herself in case of a pinch, Blitzø never skipped a beat to play overprotective dad any chance he got. It didn't even matter that she was a well-trained assassin like the rest of her three co-workers; her being daddy's baby girl was the role Blitzø couldn't see past.
"Great, so our best means of getting close is off the table. What now?" Moxie asked though with a snide tone with the prospect of Loona being left out.
With a frustrated groan, Blitzø answered, "Okay, fine, we go silent assassin and snipe them from a distance." he then proceeded to quickly doodle this simple plan on the board, "This is not nearly as satisfying for what those assholes deserve for screwing over Hell, but we're on a time crunch. M&M, get packing on supplies, and Looney…
"Let me guess, I'm on portal duty again." Loona huffed while pulling out the Grimoire, their only link to the human world.
"Aww, look who's showing some initiative," Millie said in a condescending tone before waving a dog treat in front of Loona's face, "Someone deserves a treat."
"Do that again, and I'll be sure to give you some fucking treats." Loona growled.
So it was that the I.M.P crew geared up for their trip to the world of the living. Loona, for her part, prepared the portal spell. One would think the hardest part would be figuring out where the Winchesters currently were, as they were known to travel around, but that part was easy. The spell was particular to one simply needing to think of where they wanted to go, and the portal would make it so, even if one was thinking about finding specific people. The hardest part was finding the proper page from the book, and Loona's whole workload was done.
The second the portal opened, the three imps jumped through, leaving Loona behind to await their return. Might as well get comfortable while she waited by at the desk scrolling through her phone. Looking back, it might be a blessing to not have gone. From the look on the other end of the portal, it looked like they were going to be in some hick town in some mid-western state. Dull building that haven't been updated in twenty years, shit reception, and probably just one bar. Yeah, Hell didn't seem too bad right now. Still, this routine was growing quite stale as of late. Just sit around to open a portal to Earth twice in one day and wait for someone to pay to do it again.
For once, Loona wished something interesting would happen, something to get her out of this rut. But that might as well be a fleeting dream. Loona was never so lucky to have such a thing in her near future.
End of Chapter 1
A/N: Thus, this is the start of a new story. At the time, I'd been wrestling with the idea of a Helluva Boss crossover for some time but had difficulty placing which series to do until I was binge-watching Supernatural on Netflix, and it just clicked. Surprised no one else has attempted this crossover yet. It was fun finding workarounds to mix both together despite how their systems work so differently.
Speaking of which, I should clarify that this will take place in an AU timeline where the events of season 7 of Supernatural were avoided, for it's not where all my favorite characters from the show are still around, but also because I really don't care for that season. Hope you all enjoyed it so far, till next time.