Chapter Text
Chapter 1: Dawn of a Ploy
When it comes to surviving in Hell, there are many ways on how it could be achieved. Some relied on the family that had been there for years. Others strike it out on their own. They can find jobs, mooch, steal, or rise to power.
One way to rise to power was to become an Overlord. Gathering territory and finding a niche in marketing that can be exploited to their benefit. From media, to food, music and to one specific Overload’s delight… Porn.
The Porn industry was Overlord Valentino’s pride. He had control and pleasure of working with lustful and depraved degenerates that were desperate to shell out for getting their dicks or whatever they had wet. Yet for every degenerate that salivated at getting near the Moth Overlord, there were prudes that would rather avoid getting close to him at all costs.
This included the Spider Mafia. He’s been trying to become a client of theirs for years. But all his calls were immediately followed by being hung up on and blocked.
Rude!
They had the best drugs in all the rings! So why wouldn’t they want to take his money? He’d get drugs, they get their money, it was a win-win! But no. He was left high and dry as he tried to figure out how to get access to their newest drug.
Black Silk.
Not only was it more addictive than cocaine and heroin combined but it also was one hell of an aphrodisiac! It had this beautiful black and purple coloring that was quite alluring. How they made it, he had no idea. But he needed it!
“How the fuck am I gonna get an audience with them to approve me?”
The pimp was currently in his extravagant office. Looking out the window as he mused to himself, letting out a puff of red smoke from the long cigarette that dangled between his fingers. He knew where the office was. Who was in charge, the many family members that worked there… but they were all strictly under the orders of Henroin. The Mob Boss Overlord with his own reputation being as brutal (if not even more horrendous) than his own.
From what he recalled he had two sons and a daughter. One of the sons being…. Angel Dust. He blinked. That’s right! He had one of Henroin’s kids under his control! With a grin, he quickly turned heel to meet with his star.
Angelcakes always managed to cheer him up in the most unexpected ways. He should be getting off shortly. So he might be in his dressing room, or gossiping with one of the other workers. Didn’t matter. Angel Dust dropped everything he was doing for him. He was his boss after all.
As he was coming down the hall, he could hear his star’s voice.
“Look, I love my brother ‘nd all, but fuckin’ damn, did he have to have the worst timin’!”
Oh? The pimp paused to listen in. What's this about his brother?
"I don't give ya fuck 'bout Pops wantin' ta make amends or some shit. My Nonna can drag me kickin' 'nd screamin' but I ain't gonna ta forgive that fat bastard fer all the shit he put the three of us through! Niss needs to stop bein' a fuckin' pussy fer Pops and get his own damn life!"
Valentino raised an eyebrow. Oh? That was a bit of interesting piece of information. He didn’t hear anyone respond. Must be on the phone.
“Urg, I know right!? He knew that I had a shopping trip scheduled with you and Molls today! I swear, it’s like he knows when I’m gonna have some fun ‘nd he swoops in ta be a total buzzkill! Doesn’t help that he’s Pop’s lil’ shadow in the family biz.”
He didn’t know much about Angel’s family, not that he really cared. He knew a few basic things when it comes to the Ragno Mafia, but not much. If he could somehow convince Angelcakes to let him meet his Father…
This was a risky plan, but he needed to do it. With that, he turned the corner, smiling as he extended his arms out.
“Angelcakes! Babe! I need to have a little chat with you.”
The spider looked up at him in surprise, quickly turning to his phone.
“I’ll see ya later sugar tits. Big V is wantin’ ta talk. Laters.” Once he hung up, he turned to the Overlord, flashing a smile and shooting finger guns at him. “Hey daddy, what can I do fer ya?~”
“I just happened to overhear that your brother is coming here?”
Angel’s smile got a little tense.
“Uh… yea. Family shit ta drag me too. Why?”
“Oh nothing really. It’s just that I’ve been trying to gain an audience with Henroin and he hasn’t answered my calls. You wouldn’t mind if I… tagged along, would you?”
The smaller Sinner’s smile dropped at that.
“Uh… Gee Mista’ Valentino I… don’t know… I mean… the real person ya got talk ta is the Underboss if ya wanna meet the Don.”
“And who’s the Underboss?”
“Uh…It’s… um….”
The spider’s mind went blank. Fuck! How was he going to explain that? Arackniss was so damn private that he didn’t like anyone knowing who he was in the business! He especially hated Valentino with a vengeance! There was no way he could get them to talk to each other!
“I’m sure you can get him to agree to see little ole me. Can’t ya Angelcakes?” He purred, stroking a finger under his chin..
Angel bit his lip.
“I dunno Vee. The Underboss… we got a complicated relationship. Ya know, family drama ‘nd all.”
“I’m sure it’s nothing you can’t handle.”
The Porn Star nodded. Shit. Niss wasn’t going to like this. He’s going to have to get him into a good mood tonight. How the fuck he was gonna be able to do that was practically impossible. His brother was hardly ever in a good mood. The grouchy little shrimp. But he had to be. To get Valentino off his back. He forced a smile at him.
“I’ll do my best, daddy.”
Valentino smirked, “That’s what I like ta hear.”
Angel Dust tried to think. How could he brighten his grumpy brother’s mood? His interests were very… Specific. Certainly nothing he himself found as interesting. But maybe there was something he could find for the other during the shopping trip. Hopefully.
Course, that was also assuming it would get Arackniss to agree to meeting Valentino at all…
The spider sinner gulped and grinned uneasily at his boss, “I’ll get right on it tonight.”
“Good, that’s my star,” Valentino released him and started heading out, “Enjoy the rest of your day, Angelcakes. I look forward to meeting the Underboss soon.”
A pit of fear buried itself in Angel Dust’s gut. He could only imagine what was in store for him if he failed. And unfortunately, it was a high possibility. Much higher than he liked. He had to appeal to Niss somehow…
With a light groan, the porn star gathered his things and left feeling more apprehensive than before.
Unlike Angel Dust, however, Valentino was in high spirits. Well, as high as they could be considering nothing was official yet. But he knew he could count on his star to get what he wanted. A little family drama surely meant nothing when it came to making important deals. The Underboss, whoever he was, couldn’t pass up the opportunity. Not when it likely meant a huge payday for them.
“No.”
Angel groaned, flopping against his brother’s lap in an exaggerated way. They were currently in Henroin’s office. Much to the younger demon’s annoyance. At least Nonna was there to keep them from ganging up on him.
“Nissy pleeeeeaaaasssseee???? If ya don’t talk ta him, he’s gonna up my workload ‘nd be a real piece of shit ta me!”
The small ebony spider frowned, taking a look at the Wild Pegasus Whisky and the Star Wars’ Millennium Falcon Lego set that his brother got him after insisting they stop by a store real quick. Said they were gifts for “being an amazing brother.”
He knew it was bullshit. But he had a really shitty week so he had overlooked it. Now he knows it just to get on his good side. He snorted, taking a drink from the whisky.
“No. I ain’t talkin’ ta the rat bastard.”
“Niss! C’mon!!”
The little spider pretended to think, then shook his head.
“Nope. Ain’t doin’ it.”
Henroin frowned, eyeing his youngest.
“What is he wantin’?”
“I don’t really know. He jus’ said that he wants ta talk ta ya. I guess maybe ‘bout some drugs? I told ‘im no one talks ta ya except after goin’ through the Underboss.”
Arackniss crossed his arms.
“Probably to get his digustin’ hands on a case of Black Silk. Not happenin’.”
The only female spider in the room hummed. Henroin looked over at her. Sofia “Nonna” Ragno, his mother, had known how their business worked long before he was even born. She was a black widow spider, wearing a blue blazer and white blouse with a frill collar, with a matching blue pencil skirt, with red-skinned deer gloves. Her red hair was up in a bun. She was about the same height as Angel, with two bright red eyes, with the remain six looking like a trio of freckles just below the large two.
She was a well-known member of the family. She had even gotten her hands dirty working for them plenty of times in the past. Even if women weren’t supposed to do the nitty-gritty of the business, she insisted. Making sure that women in their family got their dues. She was as sassy as she was quick-witted. She was now an elder in their council.
“You got something on yer mind, Ma?”
“I think we should see this as an opportunity.”
Angel and Arackniss looked at each other than her. The smaller of the two raising a brow at her.
“What are ya gettin’ at Nonna?”
She went over, placing her hands on Angel’s shoulders.
“We know that Valentino has Angel’s soul contract. ‘Nd now that things are better for the Family acceptin’ him, he can come back to be with us. But that can’t happen with Valentino still bein’ his Overlord.”
Henroin nodded.
“We could take this as a chance ta get Angel’s contract so he can rejoin the family.”
Angel Dust’s eyes widened. He looked between the three as if to make sure he wasn’t hearing things. Using the meetup as an opportunity for his freedom? As much as he wanted to believe it could work, he had his doubts. And they weren’t unfounded. He knew there were two ways to get out of a contract with Valentino. One way was if their popularity plummeted, and thus weren’t worth keeping around anymore. And the other way… Couldn’t exactly work if they were exterminated.
Being Hell’s biggest porn star, well his popularity wasn’t exactly decreasing. There was no way Valentino would let him go. Not even to get whatever it was he wanted. It’d be a pointless attempt!
But the look on Henroin’s face told him everything.
“Think it’ll work?”
Nonna crossed her arms, “If he’s desperate enough. We should at least hear him out, make him think we’re interested. If what he wants is doable, we ask for Angel’s contract in exchange. Otherwise, no deal.”
“Hold on!” Arackniss suddenly exclaimed, “We can’t jus’ give him whatever! The scarafaggio ain’t worth doin’ business with! Else he’ll start thinkin’ he’s got us where he wants us! Who knows what else he’ll ask for down the line!”
“He won’t have anything worth tradin’ for,” Henroin interrupted, “We got somethin’ he wants, ‘nd he’s got somethin’ we want. Once yer brother’s back with us, there won’t be nothin’ else he can hold over our heads.”
The small spider sinner gaped at his father, hardly believing that dealing with Valentino was being considered at all. It’d no doubt lead to more trouble than it was worth. Why couldn’t any of them see that!?
“Unless you got another idea on how ta get yer brother back.”
He blinked. He glanced around trying to think. But nothing came to mind.
“That’s what I thought. Meet with him ‘nd approve a meeting with me.”
Arackniss frowned, biting back any refusal. He knew better than to argue when Henroin’s mind was made up.
“What if it don’t work?”
The three looked at the porn star, who held a worried expression.
“I know Valentino. He ain’t gonna let me go jus’ like that. Not for drugs or whatever he wants. I’m too valuable fer him ta lose.”
Henroin and Nonna looked at each other. The elderly black widow bent down and placed a kiss on the top of his head.
"Just leave that to us, angelitto."