DISCLAIMER

The following is a fan-based

FICTION

Hazbin Hotel and Helluva Boss are all owned by Vivienne Medrano + numerous amazing independent animators, music-makers, and voice actors.

Please support the official release.

Chapter 23: Feather Training, Dark Past

I was almost there when it came to get a decent grasp on using the scythe.

Training with the practice scythe was yielding increasing incredible results after putting some effort into it in the last few days.

My body, especially my arms and legs, were growing more accustomed to the increasing weight as I ended up having to double it twice now to make sure I steadily got into the next stages of training. I could cut and reap fast, but I was still lacking a serious style to use it against any good opponents. Until now I had faced the kind of foes that really didn't know much how to fight with weapons, but the stronger entities in Hell were renowned to still heavily rely on old blades such as swords, lances, and even halberds during fights. While I had yet to piss off anyone of that kind enough to come after me, that didn't mean I was going to slack off. I barely survived that skirmish with Valentino, with the boost being the only saving grace that prevented the worst from happening. I needed to get stronger. I needed to get a better understanding of fighting styles for scythe users. I had read books, pamphlets, and even tried to find anyone at the training facility that had any clear understanding of what to do as exercises to train my lack of skill with the weapon during live combat. It wasn't a quick search for an easy solution, not when most of the early attempts failed to bring any major breakthrough on the matter.

After a while, I decided to search for new alternatives and the best solution I could get was to visit 'Azzie' once again as Alastor suggested when I brought this to his attention. I remembered the curious shopkeeper and how he had in his possession some merchandise that wasn't exactly common in any other places in Hell. I didn't inquire more about the curious merchant, but I definitely had my own questions about his presence in Hell. He wasn't a sinner and definitely not a demon. I was interested in this, but at the same time I could tell that asking him wouldn't give me any answer, and maybe actually land me in some unpleasant circumstances due to my curiosity. There was just something about him that had me worried, if not frightened at the chances that he was no pushover and that he was way more powerful than he appeared to be.

Molly was out with Loona when I decided to check on Azzie and see what he could offer to solve this problem. The car had been finally fixed, so I could make the trek without having to rely on the motorbike. I felt a bit safer, but still fairly paranoid at getting rammed by another vehicle, which resulted in me being a little less at ease while driving and looking around for any possible repetition of what happened a while ago. I was spared any trouble in that regard, but the nervousness persisted even as I left the car to walk up to the shop's entrance. I could tell that the tension came from mere prospective, what could be waiting for me the moment I asked for help. Alastor told me to be careful, so I knew that what I was getting as a solid answer, it wasn't going to be fun to be part of. Or rather 'be subjected to'. The door easily moved as I pushed it inwardly to allow myself inside. The place was as desolate as last time, with the only 'occupants' being the merchandise, which had remained untouched as the disposition didn't seem to have changed much since last time, and the owner of this 'humble shop'.

"Long time no see, Alan," 'Azzie' greeted chirpily, almost uncaring of the fact that this seemed to be the first contact with another 'living' being in weeks. "What brings you here to my parlor? Did the scythe break? Do you require any replacement or… do you seek something else?"

That last bit felt unsettling, but I remained calm – or forced myself to appear calm – before replying to him.

"Good morning and… I guess you can say it's more of the latter."

His eyes narrowed in interest and I soon felt my dread tripling at his smile.

"Oh, is that so? And tell me, how may I help you this time around?"

"The practice weapon has finished its purpose. I recently got a proper understanding on how to handle the weight and-"

"You require a proper trainer."

…

"How?" I had many questions that would have been much more eloquent to highlight my unease at that awareness, but I decided to go for something simple and more general. I could tell that there were multiple answers, and only a single question could get them all out at once.

"I can see the results from your body. And magic. You have not slacked off, meaning that you have been rather 'active' when it comes to fighting," The intrigued entity replied smoothly, his voice turning to an unsettling amount of suaveness. "I heard of a fight that has happened in Valentino's core of operations. You were there, and he was so quiet about it and so unwilling to part ways with any info to the public. But I can see and I can tell, you were there and… you saw it. Through the mirror of oneself, you saw it."

This time my tension was more guarded and less fright-driven. I backed away from the counter, reaching for my pouch and my satchel with my hands, ready to pull out the shotgun and the scythe at the same time if needed to counter a sudden attack. Yet, the shopkeeper didn't rush for an attack, shifting away in mist and moving over the counter and taking a few steps towards me. A creepy smile on his face.

"I guess we can find some accommodations. But first… let's change scenery!"

Arms up!

The warning reinforced what my instincts were already screaming. I stopped holding on to the weapons and brought my arms to cross in front of me, tanking the punch that tried to slam onto my face and yet I ended up flung backward... through a portal. I could only blink as I could feel we were no longer inside or even near Pentagram City. The air felt incredibly tense, hostile, as if this wasn't a place meant for someone like me. Cold, so cold- and dark, so dark and yet… darker. A chill went down my spine, something that was further enhanced when I realized I was falling from a considerable height. Still, I managed to land on my feet, but I was quick to fall on my knees due to how high the fall had been and how much stress it put my legs in. It took me just a few seconds to get back up, but I could tell I would have suffered much more hadn't I reacted as fast as I did. Still, I had to wait a little more to get accustomed to the atmosphere, my breath suddenly becoming visible due to the freezing temperature of this unfamiliar place. The floor was made of cold and sturdy rocks mixed with ice and snow, mountains of white existed all around this massive clearing that I just couldn't recognize. Yet, the one element that stole my attention was the flying figure that was the shopkeeper. Lance on one hand and an open grimoire in another, the man smiled viciously as his black bird-like wings kept him floating over me.

"My full name, mortal, is Azazel. I shall be your teacher, the bestower of knowledge and experience. This place was once Lucifer's first prison, the deepest part of hell and... God's own attempt to seal away the first hint of imperfection in his cadre of loyal minstrels and messengers. You shall listen and you shall endure to become greater- or as great as your mind and soul allows you to progress into," The Fallen Angel revealed, but before continuing with this truer introduction, he landed down to set ten vials containing a transparent liquid. I frowned at the scene, but he sighed in relief once he was done with the odd task. "These shall be your rewards if you manage to commit fully to each exercise."

I was stunned by the fact that this entity was actually… Azazel. I might not be big in religion, but I knew that he was a big shot Angel that fell shortly after Lucifer did. The difference was that Lucifer became Lucifer, while Azazel still remained an Angel somewhat. But not one 'loved' by God, hence his wings being a dark black rather than the pristine white ones normal Angels were known for. How did Uncle Al manage to befriend a figure like him I had yet to understand and I was definitely going to ask him as soon as he was back from 'work'.

"What's inside the vials?"

"Phoenix's Tears," He explained with a vibrant tone. "A single drop can instantly heal any wounds and replenish any lost magical power to the drinker."

My eyes widened in surprise at the unexpected explanation. "But I thought that Phoenixes were all killed centuries ago and any tear stored destroyed."

He chuckled, as if he knew something 'amusing' that I didn't know. Something that I could tell would have left me with more headaches than not if I ended up asking about it.

"Let's just say that I made many friends through my curiosity. Some of which share my absolute curiosity to a fault. One in particular, I love and detest his success, but he was kind enough to understand and forgive me by providing me with some of the tools I sell. In this case, this is one of the many gifts he gave me," He elaborated with a sigh. "Each exercise, if you manage to not only survive but pass the test itself, you will be allowed to drink from one of the vials. Any questions?"

"Why-"

"DODGE!"

Why is he screaming like that?! Wait, is that a DBZA reference?!

Just as he shrieked that, he bolted from his initial spot right into me. I pulled out my scythe but… as I did that, he picked up speed and kicked me in the stomach, forcing me to roll on the ground for a couple of meters. I groaned at the hit, but I realized that he was already standing over me, sporting a bored and almost frustrated tone. It was clear I did something wrong, but I just couldn't think of what precisely on the spot.

"The main purpose of this exercise is to dodge. So, no weapons just yet! Or you will get punished."

Message received, I thought dryly as I narrowed my eyes at that 'new rule' he brought up. It was clear he took charge of this opportunity way too quickly and way too happily, bringing up a degree of viciousness that… I was actually familiar with it and that still left me particularly annoyed. Because it wouldn't have been easier on the two of us if he came out clean and explained this properly before throwing me into this battlefield. I still couldn't lament about anything, both because I didn't have the breathing space to give myself that edge, and because I was actually getting my body in shape even more due to the pressure I was facing. The dread, the danger- it all rallied up into my mind to the point where I was 100% active and moving around to not get hit or 'punished' for not complying to rules I wasn't even aware about to begin with. It was a long session, but not one that outright killed me. I came close to that as the exercises started to get more and more difficult, but the Phoenix's Tears proved to be as effective as Azazel said those were. They tasted bitter, but they quickly overwhelmed any sense of fatigue or pain. Almost instantly. Still, I left that place through the same portal Azazel took me through for this session, and then out of that blasted shop as I wasn't willing to concede more time to this. For today. I had other things to do, like crashing on the couch the moment I arrived back home for some rest.

I really needed to get that nap...

My return back home was uneventful, but still as draining as I expected it to be after a five hours-long training session. Molly was already back at the manor, her date with Loona having gone pleasantly from the giddy look on her face. It was the one she tended to have when she just experienced something awesome and was waiting excitedly to tell someone (most of the time me). She gave me a look, and her surprise doubled as soon as she heard me give quite the quiet 'hello' before collapsing on the couch and groaning. She took it as a reason to probe for any information, while happily jumping on my chest for some extra cuddles.

"What's up?"

"Well, there is this fluffy girl with a cute face and personality that has been exploiting her cuddling privileges-"

"I meant your day, jerk~," Molly pouted softly, flaring her cheeks before removing my mask so she could start poking at both my cheeks with two fingers. "How did that visit go?"

"Well, I think I got my ass kicked plenty of times, now I know a bit of cool moves with the scythe and I know Azzie is Azazel."

The spider-girl blinked, taking a moment to sponge in what she just heard. "That sounded 'fun'."

"How was the date?"

"We actually decided to stay at her house. And we tried to cook!"

"Oh?" I asked with a curious tone, hiding away the worry that I had at hearing 'tried' and 'cooking' together. I knew Molly had some grasp in the kitchen, but the same didn't extend much to Loona as she was a minimalist when it came to making food. "What precisely?"

"Well, we tried to make some pasta. Nothing too big but… Loona needs some work on that."

I blinked, imagining what could have gone wrong but Molly decided to bring it up herself.

"By the way, Loona's dad might be a little more 'absent' in these few days. Something about getting hospitalized for indigestion."

That was somewhat amusing to hear, but I was actually curious about this very detail for another reason.

"Blitzo was home?"

"Yeah, he said he was fine if I was there since I wasn't 'a man trying to steal his baby girl away' or something like that."

"That's a bit-"

"Sexist? A bit. But I guess he just can't imagine someone like me being the one that steals his daughter away. Had I been a tiny bit taller and stronger-looking, he would have probably made a problem out of it."

I nodded, the accusation was a bit overblown, but, knowing the character, I could say he sure was up to go for that kind of stuff if it was convenient to him. Not like he would genuinely jump for that side, but he would do it if it came to 'save Loona from the big bad… mask man'.

"Still, that's good to hear. Did you two have fun while cooking?"

She hummed giddily. "Loona was having a blast even though she tried to hide it from me. Still, she could do better with some more practice and… we had some fun once her dad was out of the house. The kitchen is a nice place to have some kinky play."

I sighed, smiling back at her lewd grin at that last comment. "I suppose it can be. Why, are you asking me for something?"

"Maybe~?"

"Oh, I guess we can plan out something in the future then when we have the house for ourselves and Uncle Al has a long workday."

Molly huffed in minor disappointment, and I was quick to pick up what it was all about.

"You wanted to do it now?"

She nodded, not even bothering hiding the reason for her expression.

"Well, we could still do something if you want. Nothing too risky-"

"But fun," The girl concluded for me and I hummed eagerly.

Yet, as I prepared to give her some 'special cuddling', Molly tensed up and seemed to remember something.

"Actually, there was this thing I wanted to ask you about. It's something from Via. And also Loona in a way," The young woman pointed out. "Do you know what the Harvest Moon Festival is?"

I blinked, my expression morphing into one of confusion.

"I'm not familiar with it."

"It's an event that happens annually in the Wrath Ring's countryside. Stolas has hired Loona's dad to come since Via wanted to visit too and since Loona is coming."

"You want us to go too? When is it?"

"Next week."

"But we have yet to check if you can go or-"

She giggled. "Already asked Alastor. He said that it should be possible, and even easier since I'm still in Hell and I should get 'more time to wander around without repercussions'."

"Hmm," I took a moment to think about it. I had barely heard of the Wrath Ring and how part of it had started a full-fledged war to restore or assert leaderships, old and new, to redistribute the headless lands there. I could tell Stolas wouldn't bring his daughter to a warzone, so the place had to be within one of the more peaceful sections of the ring.

"I guess we could visit. Without causing any chaos-"

"If not provoked, I know," She huffed, still keeping an amused look as she pressed herself more onto me. "And now… let's get back to business, dearie~."

I could only shudder in delight before picking her up from the bed and walking up to my bedroom. It was easily becoming 'our bedroom' with how much time she spent there rather than in her room, but I don't think Uncle Al would be too fond to make it too official before I put a ring on Molly.

But looking at how things were going in our relationship, I wouldn't be surprised that it happens in a year or two from now.

1942, from the pages of Nestor XXX…

The local library held some answers.

I thought about asking the priest, but I felt like not even he would be willing to help me with this question. Who or what was Furfur? The books I got hold of told me a truth I would have preferred to remain unaware of. A demonic entity, a Grand Earl of Hell, the ruler of twenty-six legions of demons- he was somehow tied to all of this. At first I thought the situation reached only Alastor, but the presence of this entity in town had been tracked since its foundation. There had been some theories back a while ago, mostly in high school's circles, where professors admitted that the first Mayor was shunned and then executed for practicing witchcraft. While for some times that event was chalked up as one of the many errors of the 'Salem Trials', the truth was that there was some sense to it as bizarre events unfolded and were all meant to benefit the first mayor. Upsetting opposition, revolts, and people thinking he was embezzling money- every single one of those was removed by some lucky coincidences that ended up favoring the mayor. In the end, the high tension and the tidal wave of trials born after Salem's case led to his ultimate demise. No amount of luck could have prevented that from fully unfolding, but he went out without leaving a single proof behind to confirm his execution to be a warranted one.

The reason that was possible, I learned by digging through a couple of old books of the family that were written by an old descendant, was because 'monstrous Imps' were mustered to remove the proof under their Lord's demand. The Lord bore the name of Furfur. It was now evident to me how this was a problem, how this was where everything started and why Alastor was targeted. What really worried me and yet admitted about the truth behind Alastor's own downfall was a detail that I almost missed at first reading: This demon was a compulsive liar, to the point where he would be forced to make deals to be honest to someone he spoke to. And that didn't exclude the possibility that he could lie while making the contract, hence making it impossible for a human or a demonic entity lesser than him to have him speak as honestly as possible.

What were the chances he tricked Alastor?

High, pretty high. So high that I knew I had to dig some more in the library, only to… discover that someone had bought all the books on the topic. It was a bit of a stunning discovery that the Librarian gave me, but she also went out of her way to bring up how the purchase had happened right.. the day I came back home. It was too much for me to call out as a coincidence and I now knew that I wasn't the one searching for a monster, it was the monster that was waiting for me to unwittingly make my way to his lair. I knew it was a trap, so much that I felt compelled to bring with me my old M1911. Like the shotgun, the gun had served me well, and I had used it the most during my wartime service. The address listed in the librarian's papers listed an old house in the rich side of town. Or at least, that was what I could remember of the place before I left.

Instead of that, I found myself standing in front of a manor slightly bigger than the one I once lived in. I had a name, one Alfred Bran, which was an unfamiliar one considering I would have heard anyone rich bearing that name or last name. Surnames were also important in town and if it was someone from the founding families, then I would have known of him or any relatives of his. Yet nothing and I could only guess what was going on in here. Quite dark, the rooftop was made of black bricks while the walls were dark-gray. Quite ominous, but not a sight that deterred me from keeping my investigation going. So I walked through the gates, knowing that I was venturing in dangerous places. I had three crosses on myself, and a bottle of holy water that should by all means beat any kind of demonic entity with a body. When I arrived at the entrance and was about to knock at the doors, I froze when someone opened the way for me inside. An old man, balding, looking weary and incredibly drained. Wrinkled, hands and face. He spared me a look, a silent gaze that pierced my whole soul in a single moment.

"I suppose you are here to see my Master… am I correct?"

I tensed up, the unsettling voice just added more to the creepy atmosphere surrounding this place. Still, I wanted answers and I knew I couldn't back away now that I was inside.

"Yes."

Solid, determined- I was met with a nod and led inside. It was a bizarre scenery, way different than anything that I had ever seen in town but definitely reminding me of the time I saw in Los Angeles. Rather expensive, it stood out but… this was the first time I ever saw this building, and I had been wandering the town for a while ever since my return. Maybe I was too busy looking at the family's situation to care about what changed in town. But still… this all felt particularly off for a place like this town. There were many rooms, some having been used recently, others having been left to rot to the dust. I didn't care much, but I could tell the place didn't have many occupants on a regular basis and I was proven correct just as we arrived at the office, right where the butler's Master was finishing sipping a cup of coffee.

The man was wearing an expensive outfit, a dark-blue jacket and pants, a white shirt underneath and a red tie to make things even 'fancier' than expected. His dark hair was slicked back, making him appear as the standard rich man that I had seen in Los Angeles. For a moment, I thought he was a congressman or a politician of sorts but… I could tell he wasn't. There were many books that weren't tied to politics, and there was a general 'lack' of what I knew politicians' offices had nowadays. This was an intellectual, and from the paintings on display, I also knew he was a collector of Hell-related relics. There was a skull of a deer with a pentagram engraved on its forehead. There were horrible portrayals and paintings that would have been impossible to watch but that I could after seeing much more in that horrible war in the pacific.

"Nestor. I heard of your return- a Hero comes home to see his family… or what is left of it."

"Spare me the 'pity', sir. I'm not here for courtesy."

His smile widened despite my rough tone, almost expecting me to react like this.

"Indeed, you are here for answers. You want to know what happened to your brother- or what is left to your brother and what is now filling up to replace what was sacrificed," The businessman said while standing up, walking around his desk and taking just a step towards me before stopping. "You lost something yourself, but what you gained was… so much better than what Alastor begged. You did it without help, you lived by your sheer strength alone and I guess that's why you were always the best of the two-"

"Shut up! Who the hell are you to say this crap?! Some cultists? Is this some shit to draw a demon on Earth? I will stop you before you can hurt others!"

"Oh dear, aren't you truly a piece of work? That scar, I bet it hurts a lot. But no, you can't stop me and I can't summon someone that is already there, my dear Nestor," The man took another step, and this time I pulled my gun and aimed at it.

"Fuck off. Stay where you are, you bastard. Don't get any closer!"

Another chuckle. "Nestor, Nestor… I thought you would have listened to your instincts. After all those spared you from worse fates than losing an eye to the enemy."

"I said fuck! Off!"

"You are not in control, Nestor. Just like Alastor, you are but a meat puppet for me to-"

BANG!

The bullet soared and slammed onto the man's head. I blinked, shock filling my brain as I didn't see him fall backward as a dead man should. He remained still, if not recoiling by the impact, the massive hole in his head slowly closing down, his skin reforming and the blood drying out into nothingness as he healed back to normal before my own eyes.

"I guess you caught a lie. Sure, Alastor was easy to manipulate but he was no follower. The same extends to you Nestor, you follow orders only when those benefit you and those you care for," He hummed as the bullet fell on the ground as if his body had just rejected it. "A good example of a family man in the line. What a fascinating thought and yet… and yet so dangerous. You truly are unique in your own way, dear boy."

I couldn't stay. Not with these odds. A handgun wouldn't do, I could tell by now I had to leave. I turned around, ready to run away from the dangerous individual but- I froze, his hands were now grasping at my face from behind, cupping over where my eyes were and he whispered a solemn sentence in old language. There was no explanation in English as I was suddenly swept away from the home and brought out of it as if magically moved back to the streets. The hands vanished and I was finally freed to look around with my good eye… only to discover something was wrong.

Yes, something was incredibly wrong when I felt that not only my good eye was working as it should but- but then I realized something was wrong with my sight. It felt...

"W-What?" I muttered in shock as I removed my eye patch, freeing my now restored eye from the cloth-induced blindness.

I-I could see. I could see from both eyes. The wound that had pulled me out of service was now gone and I could… Oh God.

I glanced back, seeing the doors now closed, but my gaze saw someone watching from the office's window. Horns atop his head, and a blue-colored smile that reminded me of Alastor's own smile staring right at me. It felt horrible, I felt the bile and- and I knew I had to now set the preparations for this upcoming fight. This wasn't something a monster could defeat in a battle, but I had seen war and I knew that in the end, all that matters was to find the right way to make the other bastard lose regardless of me winning or not.

Even if it meant dying trying to do the right thing. For my family, for Alastor, for my wife, for our future.

AN

I would say Nestor's diary has roughly three to four 'mini-chapters' to it before it concludes. The Final Battle is about to come but it will also bring out a few questions for the main story to solve.

REVIEW Q&A!

Guest 1 (Chapter 26):
1) He might have a rival, maybe;
2) Maybe;

Guest 2 (Chapter 26):
1) Dante… Alighieri from Dante's Inferno;
2) As of now no, but I wouldn't say no to hear any ships' names for the possible combinations.

Coldblue2015:
1) Maybe;
2) Yes, kind of;
3) Maybe;
4) Not really, they took all the winnings for themselves;
5) Yes;
6) I dunno, I never watched that series and I will probably watch it now. Still, I kind of have plans for a story's sequel and a Helltaker story to take priority rn. Let's just say that the Helltaker one will be as long as this one too;

RandoFox: Can't answer that just yet.

Marshman101: Thanks and there is a plan to include a male or two in the harem, but I will probably have to use double warnings to alert some of the readers that aren't into that stuff.

JustAFan123:
1) Yes for first and maybe for the second one;
2) Yes, and yes, Charlie has two familiars;
3) I have plans to start one once this story is wrapped up. I already have a few chapters ready but it will be shorter than this but easier to update frequently.