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You Won't Regret This

Summary:

After dealing everything from a fellow Overlord's snooty remarks to an angelic wound capable of harming Lucifer himself, Alastor deserves a night off, right? However, his old companion-now-enemy has a different plan in mind.

or

An alternate path to how Alastor got captured by Vox in s2 e4.

Notes:

first fic, also no beta reader, but whatever we ball

(See the end of the work for more notes.)

Chapter 1: one sip couldn't hurt?

Chapter Text

It had been quite a long day at the hotel—sinners hanging up keys at the check-in after hearing what had become the talk of Pentagram City:

“Charlie Morningstar, now not only delusional, but a liar and a hypocritical bitch!” 

To say the least, VoxTek’s hit docu-series tanked the hotel’s approval, and before anyone knew it, everyone had left except for two; a lanky sinner, and a short bioengineer (who also thought the hotel was a joke, but just wanted to prove that redemption truly was not possible).

As Charlie watched the final sinner shut the door behind them, she sat and stared in despair. Her life’s work had just gone down the drain because of one poorly-worded interview. 

No—she couldn’t just allow Vox to shut down her hotel for good! She had to do something.

As the demon Princess thought, a glint reappeared in her eye—she knew exactly what to do. 

 


 

“Are you fucking insane? Vox can twist anything, live news or recording!” Vaggie said with her hand to her head. Vaggie loved her girlfriend, but Charlie's ideas never seemed to plan out the way she wanted them to.

“But-but.. Vaggie! I’ll just pop on screen for a few minutes, talk about why Vox is totally wrong about the hotel, yada-yada, and everything will be cleared!” Charlie was nearly jumping with joy as she fixed her blush. If only she knew that she was doing exactly what Vox wanted—ruining the reputation of the only place that could provide a gate to heaven. 

Vaggie sighed, and thought for a moment. She doubted the plan worked, but, really, what else could happen? You can only go up from rock bottom, anyways. If Charlie thought her plan would work, then she’d support her along every step. 

“Fine, but at least bring someone with you, babe.” Vaggie took a step forward and began to suggest herself as that someone, but was almost immediately cut off.

“Already got that covered! Niffty should be ready any second now!” 

As quick as Charlie finished talking, Niffty pushed into the room. 

“I’m ready!” Niffty smirked and held up her poorly-written sign that read: “THE HOTEL WORKS!”.

“Niffty..? But she’s..” Vaggie gestured at Niffty’s small stature, and her even smaller amount of self-awareness.

Charlie cocked her head sideways. “Oh, Vaggie! She’s only coming for support!” Vaggie rolled her eyes and smiled.

“Don’t worry, babe. We'll be back before you know it! Love you!” she said before kissing Vaggie’s cheek and running off. 

“Cya, babe.”


 

While the two lesbian love-birds bickered, another disagreement took place just a floor below—between the wicked angelic wound on Alastor’s chest, and the poorly-sewn stitches running along it. 

Alastor glared at himself in the mirror for being so prideful during the fight. What possessed him to take on the Head of the Angel Army? It’s as if he took on Satan! Perhaps Rosie was right; he was the most powerful sinner in Hell, but in Heaven? He was powerless against them.

 


 

Earlier...

 

“Rosie, my dear! Alastor’s here!” Alastor spun around, roses in hand, losing a few petals as he did so.

“Oh! Alastor! So glad to see you, dear! Warn me next time before you burst in here!” Rosie heartily laughed, and lifted her petticoat to avoid it dragging on the stairs as she came down.

“Well, I do have quite the news for you!” Alastor took a seat at a small tea table and sat the roses in an empty vase in the centerpiece. 

“Oh? Please, do tell!” Rosie took the seat across from him.

“Well, it has been a year since I started playing in the Princess’s little games, but I have gained absolutely nothing from it!” Alastor laid his elbows on the table and sat his head in his hands. “So… I left!”

Rosie dropped the teapot she carried with a glittery wisp. “Alastor, what?”

“Yes, I know, quite the icebreaker!”

“Please excuse my profanity, darling, but, what, pray tell, do you mean by that?”

“Well, I assumed since I was actually harmed by that pompous angel, our deal was no longer in action. I believe I shouldn’t stay if you can’t upkeep your end of the deal. How can the strongest sinner get hurt?"

Rosie's cheeks reddened before she laughed in his face. “Oh! I’m sorry.. I’m sorry!” she laughed harder, “Alastor, just because you are the strongest sinner does not mean that you can take on an archangel!” 

Alastor’s smile strained and his ears shot back. “Fine. Perhaps I was a tad egotistical. A little bit of pride has never hurt a soul!”

“Hurt yours!”

Alastor growled. “Yes, well.. in that case, you owe me for my service at that dingy hotel!”

“Ha! After the display you put on against Adam? You’ll have to show me you can be responsible with your power.” She sighed, “80 years later, and you still are as naive as the day we met!”

Alastor rolled his eyes and stood up with hidden rage. “Very well. Goodbye, Rosie.”

“Good day, my deer!”

Alastor slammed the door to the parlor open. She was right, and he knew it. He had been as sloppy as Adam, but he would have to be killed before he admitted that to the public. 


 

“Taking on that repulsive swine was the most foolish thing you’ve done,” he muttered to himself. He lifted his hand and placed it on the gash, wincing as his claw poked through the thread. He let out a jagged, painful sigh. As he exhaled, he came to realize that he was incredibly vulnerable in this state—a broken staff and a near fatal wound splaying across his chest. 

He lit a cigarette. He did not smoke often, but it was a habit he had carried on from when he was alive. Mimzy had introduced him one evening after a few drinks, and he found comfort in the rich taste it left in his airways. 

He put out his cigarette and checked a small pocket watch he kept handy. 

7 p.m. 

He shrugged as he placed the watch on the vanity. He reached across the wooden top and uncorked an older bottle of rye whiskey. He was unsure as to how long it had been there, but it was one of the few things he took from his old radio tower to bring to his room in the hotel. It reminded him of one of his mother’s meals that she often cooked with a splash of rye to enhance the flavor.

As he slid his hand around on a shelf below the vanity’s top, he found himself a small tumbler glass. He pulled it out from behind a metal box and wiped it off with his shirt. It was cracked down the side, but not quite enough to be worthy of replacement. He sat the glass on the wood and poured himself a generous amount of whiskey and took a sip. It burned a bit, but the amber liquid was smooth and slightly sweet. 

He glanced at the watch again. Only a few minutes had passed before he simply set on finishing his glass. He knocked back the rest of his drink and turned to tidy himself up. Restitching his wound had gotten a large sum of blood on his shirt, and as far as he could tell, not everyone knew the severity of his wound.

Between masking his pain, arguing with Rosie, and having to deal with that foolish King, he didn’t find it too unreasonable to have a few glasses more at the bar in the hotel’s lobby. It’s not as if he had any more of his reputation to lose, especially after the entirety of the hotel watched him get his ass kicked by Adam.

He threw on his suit and bowtie. The fabric of his suit rubbed against the stitches and burned the open flesh. He put on the best smile he could muster and sauntered down the stairs, attempting to seem in control.

 


 

Alastor sat down on one of the stools, placed two seats down from where Angel Dust and Cherri Bomb were sharing cocktails as they gossiped about Angel’s boss. Alastor had always hated the triad of the Vees. They were foolish, and never seemed to have any reasoning behind their media besides producing cheap entertainment. He thought that radio simply had more thought put into it.

“Good evening, Husker. I’ll have a whiskey, on the rocks,” Alastor spoke with his usual radio-host tone and manner. 

Husk looked at Alastor with a confused expression, but ultimately shook it off and began to dig out a bottle of rye. Angel and Cherri, on the other hand, watched as Alastor took his drink. As far as they knew, the deer demon wasn’t one to drink often, and every time he did drink, he ordered a glass to sip while he talked to Husker. He had never simply ordered alcohol to drink with purpose.

Alastor’s smile softened into a small grin, showing no teeth, as he looked into his glass. He told himself he needed a break from the hotel—from Rosie and her delirious rules—but he knew nothing could stop either issue until he devised a solid plan. 

“Refill, Boss?” 

He truly didn’t notice his glass was empty until Husk spoke. Alastor slid the glass to him. Had he really drunk his cup that swiftly?

“Thank you, my dear.” 

Husk handed him the freshly refilled glass, but Alastor hesitated to grab it. Instead, he held up his hand. 

“Leave the bottle, Husker.”

Husk looked at Angel and they exchanged a confused look. Suddenly, a large, green chain appeared around Husk’s neck, that snapped back to face Alastor.

“Leave. The. Bottle.”

“Yes, boss.”  Husker sat down the bottle of whiskey next to Alastor’s glass. Alastor threw back his current drink in his cup and poured himself another glass. He paused, and looked at the label of the bottle. He read the proof in his head before he told himself, 

“Fuck it.”

And drank straight from the bottle. He didn’t really care if Charlie came back to her well-mannered host downing a bottle of whiskey like it was cold water. Perhaps it was the pain—or the prior drinks he had drank—that convinced him his current behavioral display was fine. 

 


 

An hour later, a bottle and a half of rye emptied, and a glass tumbler devoid of any ice, Alastor was decently far gone. His ears rested on his head, his coat hung on the back of his barstool, and his head nestled in the crease of his elbow on the bar. He hadn’t spoken maybe more than ten words since he had finished his third glass.  At a quick glance, he looked almost like he was asleep. In reality, if he did anything other than rest his head, he would’ve fallen off the barstool. His mind was blank as he thought about the static surrounding him. To his dull hearing, the buzzing made quite the tune.

To Angel and Cherri, it reminded them of a broken record. 

“Is he.. ah-okay?” Cherri questioned. To anyone looking, Alastor might’ve been blacked out.

“I ain't sure if I’ve seen the freak ever drink anythin’ close to that.” Angel replied.

“He’ll be fine. Did this bullshit a lot back when we were just friends. Before I lost everything to that stupid motherfucker!" Husk slammed a glass he was cleaning on the bar, shaking a few bottles in the back. 

Alastor must’nt have heard Husk’s crude remarks, as he simply shifted his head so it was still lying on the bar, but now facing Angel. He snarled and narrowed his eyes.

“Hey, Al! Ya’ know I didn’t mean all that!” Angel chuckled nervously.

Alastor’s response was rudely interrupted by a loud BANG! 

The doors to the hotel were flung off their hinges, as a rather pissed sinner walked in.

Alastor shot up in response to the door swinging open to the hotel, but he didn’t stay upright for long. He felt his head spin and he caught himself on the edge of the bar to save himself from fully falling out of his stool. The world around him spun, and it made him quite sick. He held his head still and rested his elbow back on the bar. Who had burst through the door, he had not a clue, but they were pissing him off already. The sinner stepped inside, and much to everyone's surprise:

It was Vox.