Chapter 28: The Big V

A/N: Merry Christmas everyone! I know I said I was taking a break until the show comes out but since everyone was treated to that trailer and because it's Christmas I decided it would be nice to treat you all to a little present. And what better present could you all receive than seeing the Pimp Overlord that we love to hate? That's right Mr. V is in town. What is Jenny going to do to have Valentino interested in her later down the road?

I have the first chapter of the prequel written out. If work calms down I'm hoping to have it out soon. The title of it is 'Rewrite the Stars'. Keep an eye out for that!

Oh! And I have new art work! Since everyone got a promotional poster for the show I made one for Jenny too! It's on my Deviant art account if you want to check it out!

Disclaimer: I don't own Hazbin Hotel or Helluva Boss. I just own my characters.

Merry Christmas everyone!

Enjoy!

/

Did you get my money, Angie Baby?

I'm with a John right now. Don't get why this needed to happen so soon after Extermination Day, Boss.

Just do it. No sass. K sugar

…Yes, Val

Angel felt his body grow numb as he looked at the text that was sent to him. He hadn't been at work for a while thanks to Extermination Day. Why would he bother standing on the street corner if there were Sinners trying to pick themselves up…literally.

While the rest of Pentagram City would be focused on getting back on their feet there was one Overlord who was focused on lining his wallet.

Valentino was a crude Overlord. He ruled over the Adult Entertainment section of the Pride Ring and he did a damn good job of it. From lap dances to sex tapes, anything that was crude and vulgar he made a profit off of it. He thrived off of Sinners suffering because that meant they went to him to distract themselves from their pain.

Angel sadly was one of those 'distractions'. Since he worked for Valentino that meant he was the Pimps little puppet. He had grown numb to being an adult film star. Maybe at the beginning he found it fun and exotic but lately it felt like it was eating away at his soul. Who enjoyed dancing on the pole for singles? Who enjoyed jumping into strangers cars for a quick hook up?

It didn't matter what Angel thought. If it wasn't for Val, he would be on the streets right now. As much as he hated the Overlord he had to repay him for his protection.

Stepping out of the car he was in, he quickly straightened his outfit. The driver gave him a lustful look as he handed him a wad of cash.

"That's for a great time"

Angel rolled his eyes and snatched the money.

"Yeah, yeah, now get out of here"

The driver cackled and drove off. Angel scoffed and looked at the money. The perv tipped pretty well but it wasn't enough to pay off Valentino. At this rate he would be out all night trying to get clients.

"It just had to be after Extermination Day where a bunch of people got chopped up" he muttered.

Oh well, bitching about his predicament wasn't going to get him money faster. Seeing as there was no one else on this street, he decided to try a different block for clients.

/

This street was no better than the last one. Some were interested but didn't have cash on them while others hurried off when they saw him.

Angel sighed and banged his head against the lamp post. He was only a few grand away. Why were people being so stingy?

"What the fuck are you doing?"

Angel jumped a little when he heard that voice. He spotted Jenny standing not too far way from him with a weary look on her face. He quickly composed himself and went back to leaning on the lamp post.

"What does it look like I'm doing, bitch? I'm working"

Jenny looked around them to see that there was no one in sight.

"Yeah I can tell you're really busy" she said flatly.

"You're scaring away customers, toots. People think you're asking me for my services" Angel argued.

"Oh please, if anyone is going to be drawing a crowd between the two of us, we all know it's me. Apparently my blood offers more than a quickie in the backseat of a crackhead's car" Jenny said.

"….that was cold, bitch" Angel muttered.

Jenny rolled her eyes and waved him off. She was still a bit annoyed with him. Yeah, he went to save her during Extermination Day, but he was the reason she got so mad that she left the hotel. If he wanted to sell his ass on the street then she wasn't going to stop him.

"Try not to work too hard" she said.

She walked away leaving him alone. As she left, Angel's annoyed face dropped to be replaced with a sad one. He looked at his phone to see that Valentino was asking about his money still. He groaned as he rubbed his face.

"This is going to be a long fucking night" he muttered.

Jenny heard that and stopped walking. Hanging her head, she groaned. She should just continue walking and head back to the hotel. What Angel did on his free time was his own business.

But he did help her that day when he knew she was mad at him.

Spinning on her heel, she walked back up to him.

"I'll give you a hundred bucks if you walk me back to the hotel" she said flatly.

Angel looked at her oddly.

"Huh?"

"It's not safe for me to walk around town by myself when it's this late" Jenny explained.

"If you walk me back to the hotel and keep me safe I'll pay you for bringing me home"

Angel raised an eyebrow and crossed his arms.

"I charge more than a hundred bucks, toots" he said.

"…you want to be a hundred bucks richer or stand out on the street and get nothing?" Jenny asked dully.

Angel pushed away from the light post and tucked a set of hands in his pockets while the other set were still crossed.

"Let's go" he said dully.

They walked away just as a gaudy looking pink car pulled up. The inhabitant inside watched as Angel walked away with Jenny. Narrowing his eyes, Valentino was wondering why Angel wasn't busy making him his money.

/

"Why were out here this late anyway?" Angel asked.

Jenny pulled out the flyer for the audition and showed it to him.

"I wanted to find out more about this theater. Wanted to make sure it was the real deal and not one of those things where they claim that they want to make you a star but they just trick you into being a sex worker" she said.

Angel wore a smug look on his face.

"Ohhh, so you are interested in auditioning" he said.

"I'm curious" Jenny corrected.

"I wanted to know more about what was going on before I did anything. I don't want to do this only for me to fail and realize it was a waste of my time. I'm still on the fence about performing"

"What's holding you back? Don't tell me it's that loser fiancé of yours"

Jenny was about to retort but Angel interrupted her.

"He's a loser, plain and simple. He made you support his dreams and goals but he didn't think about supporting yours. Even if it was stupid and nothing came out of it, he should have let you try and give it a chance to see if it was worth it. Why do you want to give everything up to make this guy happy when he never did the same for you?"

"That's just what relationships are. Sometimes you have to sacrifice some things for things to work in the long run" Jenny said tiredly.

"No, being in a relationship means finding equal ground. You're not on equal ground with this guy, toots. You're on the ground lifting him up and he's standing over you basking in all the glory life has to offer"

He grabbed her shoulders and shook her a little.

"I've been in your shoes. You want to make the person you care about happy and you give them everything you have. But as time goes on they start to take a little bit more, then a little bit more after that to the point you have nothing left to offer. Once that happens, they toss you aside finding your usefulness over. It's not a great feeling giving and them just taking"

Jenny didn't know what to say. She didn't want to admit it but Angel was right. She gave up a lot for David. She gave up a lot for their relationship. While she was willing to make sacrifices…David never did. He didn't give up his dream job because it was 'a real job that would put food on the table'. He didn't move away from his family like she did because ' he still had family while she didn't'. Even with their wedding planning, he vetoed some of her ideas because they were too 'exotic' and he wanted something 'simple'.

Why couldn't he cave in to a few of her wishes? If he loved her he would have done that…right?

A car pulling up to the hotel pulled her from her thoughts. She knew it wasn't Charlie's car because this one was all pink.

Who was this?

Angel paled quickly and pushed Jenny towards the entrance.

"Get inside, Jen" he said seriously.

Jenny noticed the slight tremor in his voice as he spoke.

"Who is that, Ang?"

"Don't worry about that, just get inside right now"

He pushed Jenny further and stepped in front of her. The car door opened where a high heeled boot stepped out. Jenny was surprised when a very tall pimp stepped out of the car.

"Fee, fye, foo, fum. What bean pole were you dancing from?" she said.

Valentino didn't pay attention to her and just stared at Angel. The grin he put on could rival with Alastor by how creepy it was.

"Angel Baby, there you are" he said.

Angel gulped and put on a nervous smile.

"H-hey, Val. What are you doing here?"

Valentino waved his phone in front of him.

"You hadn't texted me in a while and I was starting to get worried" he said.

He gripped his phone a little too tight since the screen started to crack. He was not happy.

"O-oh! Yeah! W-well I was really busy working and didn't hear my phone buzz" Angel laughed nervously.

Valentino tilted his head to the side.

"Working, huh?"

He got up close to Angel and gripped his face with one of his hands.

"Speaking of working, you get my money yet?"

Jenny could see Angel's hand tremble slightly and his face breaking out in a cold sweat. He was scared.

Not taking her eyes off of them, she slowly backed towards the entrance of the hotel and reached for something.

Angel gulped as he tried to calm his nerves. Even though he had been working for the Pimp for decades, he still felt like a scared boy in front of him.

"I almost got your money. Was just about to take on another client when you got here. I'll have it by the end of the night"

Valentino sighed as his grip on Angel's face tightened.

"Oh Angie. You know I hate waiting" he said.

"I think I've been going soft on you lately. When you get back to the studio we're going to – OOF!"

Jenny swung a metal bat into Valentino's stomach and made him let go of Angel.

"Back off Slickback! I saw him first so I call dibs!" she barked.

Angel gasped in horror. What the fuck did Jenny just do?!

"Toots!"

Jenny held a finger up to silence him. She stood in front of him with her bat aimed at Valentino.

"Quiet Ang. I paid for you first. He can wait his turn"

Val held his stomach and growled as he glared at Jenny.

"You little bi-"

Jenny pressed the bat to his lips.

"Watch what you say. You're at the right height for me to knock some teeth out" she warned.

Val pushed the bat away and stood up straight to make himself look intimidating.

"I'm not a client, bitch. I own this Spider slut's ass" he snapped.

Jenny raised an eyebrow.

"Do you now?"

She looked at Angel over her shoulder.

"Hey Ang, turn around will you?"

Angel was puzzled for a moment but turned around. Jenny looked at his ass and hummed in thought.

"I don't see your name anywhere on his ass so you're obviously a big fat liar"

Angel covered his mouth to cover his laugh. He spotted Husker near the entrance and secretly waved him down. The cat spotted movement out of the corner of his eye then did a double take when he saw what was going on outside. Pressing his face to the window, he saw Angel mouthing for help while Jenny had a bat to Valentino's face.

"You got to be fucking kidding me!"

He ran off to get help from a certain someone.

Meanwhile Jenny continued to have a stare down with Valentino. The pimp was getting annoyed with this little pixie.

"Do you know who I am?"

Jenny looked him over and raised an eyebrow.

"You're a huge fan of the Rocky Picture Horror Show" she said dryly.

Val growled and got in her face.

"I'm fucking Valentino!"

Jenny stepped back and held a hand up.

"Whoa now! I don't need to know that you're fucking some guy name Valentino. What does any of that have to do with anything right now?"

Angel grabbed her and tried to pull her away.

"Toots, stop!" he said.

Jenny looked at Angel out of the corner of her eye and gave him a reassuring look. Even if he was an asshole most of the time, she wasn't going to let anyone harm him.

"I got your back" she whispered.

She turned her attention back to Valentino.

"Listen Dr. Frank-N-Furter. I took Angel to this hotel so we could have some fun" she said as she gestured to the hotel.

"I really don't care that you're his boss. Angel charges by the hour and thanks to you wasting my time I'm now past my budget. Now unless you plan on giving me a discount for being a buzzkill I suggest you beat it before I beat you with this bat again. Okay?"

Valentino growled. He just about had it with this little pixie.

"You think you can mess me up with that?" he taunted.

Jenny pretended to think it over.

"Yeah I probably wouldn't…but I can mess up your car"

She walked past him and headed for his car. Valentino grabbed her and brought her up to his face. He didn't care that she was paying for Angel. He needed to teach this bitch a lesson.

"Listen here you little bitch, I'm going to –"

"Is everything alright here?"

Alastor walked up to them with Charlie close by. His eyes glowed as he looked at the group.

"Val old chap! It's been a while. Didn't realize you were in this part of the city. I see you've met Jennifer"

Valentino gave Alastor a disgusted look.

"Is this your brat?"

"…You could say that" Alastor said.

"She's quite the firecracker isn't she?"

Charlie pushed her way in front and glared at Valentino.

"Put her down right now. She works for me"

At the mention of working for the princess, Valentino gave in. He was ballsy but not ballsy enough to mess with the Royal family. He dropped Jenny to ground where she landed on her ass

"You mother fu-"

Alastor quickly appeared behind her and covered her mouth with his hand.

"I ask again, why are you here and not with your…significant other" he spat out the last part.

"I'm here because Angel is late on his payments. He owes me quite a bit of money. And that one"

He pointed at Jenny with his cane.

"That one is being a real pain in my ass. I'm half tempted to take her off your hands and make her work for me to pay off her hitting me with a bat"

Jenny's remarks were muffled by Alastor's hand. He pulled her close with his other arm and held her still as she struggled to get away.

"Come now, Val. Can you fault her? A large intimidating Overlord that she's never met before suddenly appears before her and is demanding money? It was merely self defense"

"I don't give a flying fuck what it was. I either leave with my money or I'm dragging Angel's ass back with me" Valentino threatened.

Charlie sighed and held the bridge of her nose.

"Angel" she said slowly.

"How much do you owe him still?"

Angel wrung his hands together.

"Ten grand" he said.

Charlie groaned. She didn't know if she had that much money locked away in the vault of the hotel.

Jenny tried to pull Alastor's hand away from her mouth to no avail. She spotted her ring and remembered something. David said that this ring was passed down through his family for generations. It went so far as the late 1800 to early 1900's. Jewelry like this was very rare to find and very expensive. While it didn't look great it was still worth a lot of money.

She bit Alastor's hand which caused him to let her go. Running from him, she went up to Valentino.

"Hey bigfoot"

She pulled off her ring and showed it to him.

"Will this cover the rest?"

Charlie and Angel panicked when they saw what she was doing.

"Toots no!"

Jenny ignored them and waved the ring.

"Come on, my arm is getting tired"

Valentino took the ring and looked at it close.

"This is some fine bling you have here. I'm surprised"

"Yeah, yeah, I have a pretty ring. Will this cover the rest or not?" Jenny snapped.

Val examined it more making sure it was real. After careful looking he tucked it into his pocket.

"This should cover Angel's ass…for now" he said.

He gave Angel a dangerous look.

"You got off lucky, Angie. Next time you better not keep me waiting"

Angel gulped and nodded.

"Yes Val"

Val looked at the group in disgust. His eyes lingered on Jenny for a while. What an odd yet annoying person.

"Keep your brat on a leash next time, Al"

Jenny went to jump him but Alastor grabbed her by the back of her shirt and held her.

"I'll keep an eye on her when you keep an eye on that annoying television punk" he spat.

Valentino scoffed and went back in his car. The driver drove off leaving the group out in the front of the hotel.

Charlie sighed with relief. Valentino was one of the nastier Overlords in the Pride Ring. He wasn't one of the strongest but he was one you didn't want to mess with.

She looked at Jenny sadly. She had to give up her engagement ring so things didn't get worse. Angel had angry tears in his eyes. He wasn't angry that Jenny helped him. He was angry that he got her into this mess and she had to bail him out.

"Why did you do that?!" he snapped.

Jenny just shrugged. It hurt that she had to give up the ring. Yeah, she was having different thoughts about David right now but she still cared for him. But it was just a ring.

"It's no big deal. It's just a ring" she said.

"But it was your engagement ring!" Charlie said.

"I can always get a new one. I'm just glad it was able to help Angel out" Jenny reasoned.

"You didn't have to do that, toots!"

"And you didn't have to help me on Extermination Day. We're even"

Angel bit his lip. Jenny had every right to be mad at her. He was pointing out how flawed and messed up her relationship with David was. She could have let him suffer but instead she went out of her way to protect him from Valentino.

He didn't know how he was ever going to repay her for this.

The somber mood was ruined when the static around Alastor buzzed louder.

"Oh Jennifer" Alastor sang.

He got close to her face with glowing red eyes. Even his smile seemed to glow as he looked at her.

"We need to talk"

Jenny gulped at the look he was giving her.

She was in trouble now.

/

A/N: Uh oh. Is Jenny in trouble for biting Alastor or for picking at fight with Val?

Hope Val's intro to the story was fun. He and Jenny got off on a rocky start, but like he says in the future, he loves it when Jenny plays hard to get.

Angel is going to owe Jenny big time for this. Wonder what he'll do to repay her?

Hope you enjoyed this!

Please review and tell me what you think!

Take care!