Hazbin Hotel (and Helluva Boss) x Reader (Under Rewrite)

Sir Pentious x Reader

Second Person's P.O.V

Cherri is your best friend. You've known each other ever since that day you crashed into Hell. Being her accomplice has many perks. It's really fun, for example. And she allows you to use her awesome destructive weapons. 

The downside? Being really close to her, you're an easy target for her enemies. What better way to lure her in than to kidnap you and use you as bait? There were a few instances of this happening, and usually Cherri would have to help you escape.

Such wasn't the case, however, when you got "kidnapped" by her arch nemesis, Sir Pentious. You were busy taking over some new territory with Cherri, when he showed up and grabbed you with him and fled to his ship.

He was so incompetent at his job that simply punching him and running away would have been a piece of cake, but truthfully, you felt kind of bad for him. Maybe you could just go along with him for a bit, just to make things less painfully awkward? You turn to Cherri and wink, and she gets the hint and calls after you. 

"(Y.N), no! I'll save you, I promise!", she yells, clearly holding back laughter. Sir Pent doesn't seem to notice, and gleefully declares "I'd love to see you try! It's all over now, Missy! I have your little friend here with me, and you're never going to be seeing them ever again!" He laughs maniacally.

"Oh, joy", you drone sarcastically. These are going to be a lovely few hours.

~

"So, uh... what music do you like to listen to?"

You've been trying to strike up a conversation with him for a whole hour, but he was busy plotting something super evil. At least, that's what he's been telling you every time you asked. He ignores you. 

"I listen to metal", you say, leaning against the wall. "Pop music too, but it's been getting worse lately. It all sounds like mush now. I think the music industry is deteriorating in quality. And they aren't even making good movies to make up for it! Really, entertainment as a whole is going downhill. You didn't have movies in your day, did you? I heard movies were invented in 1888 one time. When did you die again?"

"Dear goodness, do you ever shut up?", he snaps. You shrug. "One time. My friend said I talk too much, so he bet I couldn't keep quiet for more than a few hours, and coughed up a considerable amount of money and said he'd give it all to me if I complete the challenge. I didn't utter a single word for two and a half days. That's my record so far. But other than that, no, I like to talk. Talking is a necessary thing. My ex and I never spoke to each other, and that ended with me committing arson. That's why talking to people is important. You don't talk a lot, I noticed. Do you have anything to share?"

He grows more and more agitated with each word. He's so cute when he's flustered, you think. He grabs one of his weird egg henchmen and throws him at you. "There! Why don't you talk to someone who actually wants to hear it?"

You look down at the Egg Boi. "Hm, alright. Whatever you say, Babe", you add, smirking smugly at Sir Pent. He looks up from a map. "What did you call me?", he inquires, but you're already strutting off with the egg, rambling to him about something.

~

"And that's the story of how I accidentally stole a two-hundred-thousand dollar cheque from my best friend before moving to another city. Any questions?"

The Egg Bois around you start clapping. You've been sitting on the floor, telling them various stories for nearly two hours. Cherri wasn't here yet. You assumed she must have been out partying. Perfectly reasonable, of course. Might as well be productive while she's waiting to "rescue" you. 

You notice Sir Pent was still focused on his work. He must be churning up some elaborate scheme to take over Hell. Either that, or he has no idea what he's doing and just wants you to think he is. Whatever the case, he looks a bit tense.

You get up off the floor. He's immersed in his work and doesn't notice you sneak up from behind. "Watch out, Mr. Bossman!", one of the Egg Bois warns. He looks up. "What?" You wrap your arms around his waist and nuzzle up against his neck. He gasps. "Eek! What are you doing, you idiot? You nearly made my heart stop!" He turns to stare at you, his face contorting with rage.

"Oh, you have a heart?", you say sarcastically. 

He looks just about ready to strangle you. "What is it?", he hisses. You pat his shoulder. "Calm down, Hon. I just thought you looked like you needed a small break." You lean close to him. "Is that correct?"

He looks sideways. "No! I-I don't think I do", he says, suddenly hesitant. You look him in the eyes as you gently rub his shoulders. "You sure?"

 "Uh, well, I suppose now that you mention it-"

You cup his face in your hands. "Then I think I can help with that." You lean closer to his face, sneaking your hand under his blazer as you kiss him. What am I doing?, you think as you slip your tongue into his mouth. Am I seriously making out with Sir Pentious, of all people? This guy? You begin to slip off the blazer.

Cherri would get a stroke if she found out-

Suddenly, you hear a loud crash. You quickly turn to see Cherri standing in front of the two of you with a bomb in her hand. "Hey, Old Man. Miss me?", she sneers at Sir Pent.

He doesn't respond, clearly still dazed from the fiasco taking place moments ago. Cherri looks confused. She clearly expected something more exciting than total silence. She turns to you. "Is he okay?", she whisper-shouts. 

You shrug your shoulders, trying to stifle a smile. "Let's go", you say. You run to Cherri, holding onto her waist. You turn back to Sir Pent and mouth Call me, making a gesture of someone holding a phone to their ear, before you are hoisted out of the ship by Cherri.

~

"What were you two even doing in there?", she asks as the two of you walk together, hand-in-hand. You shrug again. "He's a weird guy, I guess." She gives you a skeptical look. "You're fine though, right? He... he didn't... touch you, did he?", she asks in a lower voice.

"Oh, no, no, no. Don't worry Cher. I'm fine." You think about Sir Pent's flustered face and smile.

"Totally fine."