A/N: For those of you who don't know, my name is Maggie Knolastname (also the name of the character in this story. She's my OC). Just a few things before we begin:

1. Some of the content here is purely headcanon that I have adopted as canon for the sake of the story (such as Angel's contract about to expire)

2. This story will have fluff but also some very sad scenes. If you can handle episode 4 of Hazbin Hotel, you should be able to handle this story.

3. If season 2 of Hazbin Hotel confirms some content from this story as untrue, I might change the story (just make a few edits, ya know)

4. This particular story will have two different endings. I can't disclose why yet

5. I will only use the Dust part of Angel's name occasionally. Most of the time, he will just be Angel

6. This is a prequel story to 'Helluva Sister' and I recommend reading at least up to 'The Harvest Moon Festival' before reading this.

If you have any questions, feel free to ask in reviews or even PM me. I don't want to spoil anything.

I do not own Helluva Boss, Hazbin Hotel or any of their characters.

I do, however, own my OC, Maggie Knolastname.

Without further ado, I present to you: 'Angel's Apprentice'

This is the story of a little imp and a porn star, and how they became friends…

Before the Hazbin Hotel…

Before I.M.P…

Before…everything…

It was a busy day at Valentino's studio. Everyone was wrapping up after a long shoot. Angel Dust stretched, ready to go up to his apartment.

"Well, I'm heading out, Val," Angel said, heading into his dressing room.

"Actually, Angel, we're working late tonight," Valentino replied, blowing some red smoke into the air.

"What?" Angel replied in irritation, "Why? Haven't we-"

Valentino cut him off, "Careful, Angel Cakes…you better not give me attitude."

Angel backed down, not wanting to piss off his boss, "Right…sorry. Why are we working late, though?"

Valentino shrugged, "We're getting a new employee, some little mafia bitch."

"Mafia, huh? I…can relate," Angel thought to himself.

"Some rich imp from the Greed ring is bringing her over," Valentino continued, "He's paying some good money for us to take her off his hands. Go check to make sure all the set pieces are in place, and maybe practice your dancing on that pole. Your last shoot was a little sloppy."

Angel didn't say anything more, and he went to practice his pole dancing. He was getting a little sloppy, and he needed to finish off strong.

"Just a little longer, Angel," he thought to himself.

Meanwhile, a limo cruised through Pentagon City. Inside the limo were two imps and some loan sharks. The little female imp had her hands folded, resting on her lap. However, she was slouching a little.

"Sit up," the older imp hissed, and she straightened her posture in fear, "I suppose y'er wonderin' why we came all the way to the Pride ring."

The little imp shrugged, and she looked down at the ground. She wondered why her father demanded her to accompany him though. It wasn't very often he invited her out of the house, but she didn't really have a say in the matter.

"You'll find out soon enough," the older imp reassured apathetically.

The little imp looked down at the floor, and then she looked at the two loan sharks sitting on her sides. She couldn't fight even if she wanted to. The limo came to a stop.

"We're here," the older imp said, and he followed two loan sharks out, "Move y'er ass, Magenta."

Magenta cautiously climbed out of the limo, and her hands rested behind her back. She stared up at the building. She didn't like the feeling she felt in her gut. Something seemed really off about this place. The older imp rolled his eyes, and he pushed her ahead. She was forced to walk up to the door. The loan sharks opened the door, and she was shoved inside.

"Ah, welcome," Magenta was greeted by a tall demon with four arms, wearing what looked like a coat, "You must be Magenta."

Magenta backed away a bit as Valentino held out his hand. There was a little moment of awkward silence as Valentino just stared at her. Magenta spent her life in silence, but her expressions were easy to read. She also was able to see into a person and read into their character. Something seemed extra intimidating about Valentino, not just because he was over twice her size.

Magenta's tail wrapped around her legs, and her father hissed, "Hold out your hand for him."

Magenta reluctantly removed one of her hands from her back, and she held it out for the moth demon. Normally, she'd expect someone to kiss her hand which already creeped her out. Valentino, however, licked her hand. Magenta quickly flinched, and she pulled her hand back. Her tail vibrated a little as it straightened out.

"Such a pretty little one," Valentino said in a suggestive voice, "Cute too. She'll definitely bring in a nice crowd of clients. People love the shy, quiet type."

Magenta shrunk back a little, backing away in discomfort.

"You think you can break this…" the older imp struggled to find the words, "pussy asexual phase of hers?"

"Oh, for sure," Valentino answered, giving Magenta a toothy smile, "We'll have no problem breaking her."

"Good," the older imp answered, "cuz she ain't no use to me like this. Her last candidate had no interest in her after finding out that she wasn't going to fuck 'im"

Magenta winced at the word, being disturbed by the thought of anyone taking away her virginity. Her father glared at her, and she resumed her posture again.

"Whatever ya gotta do to break her of this, do it," the imp said, "even if ya gotta force her."

Magenta's eyes widened in horror, and she started shaking. She met the eyes of her father, and he rolled his eyes, "I don't care what it takes. Just do it."

Valentino smiled maliciously, "Oh, don't worry…uh…sorry what the fuck was your name again?"

"Crimson," the older imp answered, "and you better be serious with what I'm payin' ya."

Valentino took out a piece of paper that glowed a bit. The other workers at the studio gasped, for they knew what that meant. Crimson was signing over Magenta's soul.

"She's usually pretty obedient," Crimson said, signing the contract as a red chain, made of red smoke, formed around Magenta's neck and extended to Valentino's palm, "Just threaten to beat her if ya have to. If you have to actually beat her, go for it. She'll eventually submit."

"That's what I like to hear," Valentino said, and the chain disappeared, "We'll have our best star mentor her."

Maggie shrunk back again, terrified. She was used to being scared and silent, but something just seemed really off and unsettling about this place now. Now this psychopath owned her soul. She realized she wasn't going back to the mansion tonight…if ever.

"Angel!" Valentino yelled, and Angel looked Val's way, dismounting from the pole.

"Uh…yeah, Val?" he answered as he approached. He knew that when Val called, it meant to come over, "What's up? This that new chick ya told me about?"

Magenta was incredibly intimidated as another tall four armed demon approached. He wasn't quite as tall as Valentino, but he still towered over her. He wasn't wearing anything but tall black heel boots. He was almost twice her height, and she shrunk down, bringing her shoulders past the top of her neck. Her tail wrapped around her legs again, and she trembled a bit. Crimson stared apathetically at her with his hands folded behind his back. He rolled his eyes, shoving her forward.

"This is Magenta. You're going to mentor her," Valentino said, "show her all the ropes and…how things work here."

Angel shuddered a small bit, tightly shutting his eyes and wincing as Val placed his claws around his shoulders. He looked down at the ground hoping it was only a moment. Luckily it was. He furrowed his eyebrow, unsure what to think of the little imp in front of him. She didn't look like anything special, so this would probably be an easy job. He wished it was a hot guy though.

"You, uh, know how I am with girls," Angel stated, "I charge extra."

Crimson handed Angel a huge wad of cash, and stepped back, "I trust that will be enough."

"Angel, here, is my best employee. He'll get the job done. Just show the little bitch to your dressing room, and we'll start working with her tomorrow," Valentino said, "I know you're tired, baby."

Angel shrugged, "Alright, then, this way…uh…Magenta."

Angel began to escort Magenta to his dressing room, but Crimson spoke up, "Oh, and, uh…I wouldn't expect a word out of Magenta. I taught her well what her place is."

Crimson walked away with Valentino to discuss more business, leaving Angel with a bewildered expression. What did he mean…'taught her well what her place is'? He didn't really care to analyze the situation for the moment. He was getting paid a lot to mentor this little mafia bitch, so who cares if she don't speak? He knew some sickos would actually like that kind of shit. He opened the door to his dressing room, and he followed Magenta inside. Magenta was slightly shocked he didn't shove her in. She hugged herself as she stepped forward to stay out of Angel's way. However, as she heard the click of his heels behind her, she panicked. She backed away so suddenly that she tripped over the chair at the vanity table. Angel rolled his eyes as she stumbled.

"Oh for fuck's sake, calm down," Angel said coldy, "just do ya job, and don't fuck anything up. My contract is almost up, and the last thing I need is to piss off Val."

Magenta shrunk back, letting Angel pass by her.

"The name's Angel Dust," Angel continued, "As ya probably heard, I'll be mentoring ya, Magenta."

Magenta nodded, and Angel scoffed, "The fuck kinda name is Magenta anyway? Do you even like that name?"

Magenta shook her head. She much preferred a different name, but only one other person called her it.

"We gotta change that. I ain't callin' ya Magenta," Angel said, "How about Maggie?"

Magenta responded with a spark of the eye. How did he know that was what she preferred? She looked away from Angel, down at the floor again before nodding.

"Alright, Maggie, we start tomorrow. I guess you'll be stayin' with me too," Angel continued, oblivious to the terror in Maggie's eyes.

Maggie began to shake and silently cry. She fell to her knees hugging herself so hard her claws dug into her. Her pupils dilated as she had a breakdown. Her tail wrapped around her body for comfort. Reality was catching up to her that this was happening. She may never see her brother again. She may be a sex slave for some pompous abuser. As a child, she was told that was probably her purpose, but it never hit until now. She was alone with some porn star that was more than likely going to force himself onto her if it came to it. She let out the quietest whimper as tears formed in her eyes.

"Val ain't gonna hurt ya so long as ya do ya job," Angel continued, but he gave a small gasp as he saw the little mafioso on the ground, "Hey…it'll…It's…You'll be…uh…"

Angel couldn't find the words, and he bent down. He was still much taller than her, but at least he wasn't quite as tall and intimidating.

"Hey…I…I can't lie and say everything is okay," Angel consoled, starting to feel bad for her, "but I can tell you that…I won't hurt'cha."

Maggie looked up, and she stared into Angel's eyes. Something in his eyes told her that he was sincere. Her glowing yellow eyes glistened with a spark before she looked down. She was able to stop shaking, and relax her claws. Angel frowned sympathetically.

"I've…never seen one of Val's new employees act like this. Sure, they're nervous, but…nothing like this," he thought to himself, "I dunno why, but I can read this girl. Why the fuck do I care, though? It's my last job, and then I'm out of here for good, finally…Still…something about her seems…different. Why did her father even bring her here?"

"I ain't gonna hurt ya," Angel repeated as he gently placed one of his hands on her shoulder, "And I know it's scary, but…it's not so bad once you let loose a little. How about…I talk to Val about maybe taking baby steps? Maybe we can work with ya gradually until you're comfortable."

Maggie said nothing. Wow, Crimson wasn't kidding. That made Angel think. What did he mean? How did Crimson teach her to be…well…silent? He shook the thought. He couldn't afford to really care.

"Look, we can talk more about this tomorrow. Right now, I wanna go home," Angel said, regaining his slightly apathetic demeanor, "and don't even think about making a mess in my apartment."

Angel then put on his clothes, but Maggie looked away from him as he did so. She didn't like to think that he was naked the whole time. Angel didn't feel like getting all the way dressed since he was just going back to the apartment. He threw on his custom made trench coat, and that was it.

"Let's go," Angel said, "We got work to do tomorrow."

Maggie nodded, and she followed Angel to the apartment. It was small and not very inviting. She was shocked, once more, when Angel allowed her to enter at her own pace. Maggie was unsettled to be in someone else's apartment, a porn star's apartment at that. She never watched Angel's videos, but she saw posters for him all over on her trip to the studio.

"Nuggs!" Angel called out, "Daddy's home!"

Maggie's eyes lit up when a small pig popped up from a blanket. The pig approached the pair, and he stared up at the little imp. Who was this new person? Was it a friend? Maggie wanted to pet him, but she was hesitant.

Angel chuckled a bit at the cuteness, "This is Fat Nuggets. You, uh, can pet him if ya want."

Having permission, Maggie reached out to pet Fat Nuggets. Fat Nuggets oinked adorably as he nuzzled his head into her hand. What he did next, Angel and Maggie didn't expect. He nuzzled into Maggie affectionately. Maggie's eyes sparkled adorably.

"Huh, Nuggs doesn't usually do that to anyone but me," Angel observed, "He must really like ya, toots."

Maggie flinched a bit at the nickname, but she continued petting Fat Nuggets. She gave him scritchies, and he nuzzled his snout into her face. She almost let out the faintest giggle, but she stopped herself. Fat Nuggets gave her one last affectionate nudge before allowing Angel to pick him up.

"Did ya make a new friend, Nuggs?" Angel cooed the pig, and Maggie was caught off guard how his demeanor changed so much. He was so sweet and baby talky to the pig.

Maggie found it adorable even.

Angel looked to the side crossing one set of his arms, "If ya want, I guess I can let ya snuggle with him if he chooses to. I'll, uh, show ya to your 'bed' I guess."

Angel guided Maggie to a couch. It didn't look very comfy, but it was better than nothing. It wasn't the first time she didn't sleep in her bed. It was the first time she slept on a couch, though. This was all so new to her.

"Sorry, Val hasn't really given me anything else besides my bed, and I ain't lettin' ya sleep with me. I may be teachin' ya about this shit, but I don't sleep with bitches. Not that you asked, but I'm gay. Maybe someone else would be into, uh, that, but I sure as hell ain't," Angel said as he changed into his pajamas. Just a little set of shorts and a comfy shirt.

Maggie looked away as she realized he was taking off his coat. She didn't say anything, but she crawled onto the couch. It wasn't very comfortable, but she curled up. She looked back at him, and she couldn't help but note that he kept his heels on.

"Yeah, I sleep with my heels on. It ain't none of ya fuckin' business," Angel barked and Maggie looked down apologetically.

"Uh…are ya sleepin' in that?" Angel asked, and Maggie looked down at her dress, "I s'pose your dad didn't have ya pack anything."

Maggie shook her head, fighting tears. She was given no warning what was happening. She might as well just consider herself kidnapped. Angel walked over to his closet, and Maggie noted a lot of feminine clothes with a few hints of masculinity. She looked away when he turned back to her, feeling it was wrong to stare or snoop. Angel rolled his eyes, and he went through his clothes.

He pulled out a very basic t-shirt, "Here, why don't'cha wear this. A t-shirt for me is a nightgown for you. Sorry about the extra sleeves. Maybe once you earn your first check we can go get ya some real pajamas."

Maggie took the t-shirt, and she looked around. She didn't really wanna change in front of this stranger. Angel could read her.

"Oh, uh…right," he stammered, "I'll turn around so you can change."

Angel turned his back to her, and he covered his eyes for good measure. Maggie took off her dress, and she slipped the t-shirt on. Never had such cheap feeling fabric touched her skin. Crimson may not have treated her well, but he did always buy her the most expensive clothes. She didn't know why, probably an image thing. The t-shirt was…comfortable. The extra sleeves made it slightly drafty on the sides, but it was better than sleeping in her dress.

"Ya good now?" Angel asked, but he didn't receive a response, "Imma turn around now."

He turned, and he had to admit Maggie looked kinda cute wearing one of his t-shirts, "Heh, look at that, fits like a glove. Guess you're not used to such cheap fabric, eh, princess?"

Maggie cringed. Sure, her life seemed like a princess, being the daughter of a mob boss, but it wasn't at all what it looked like. Angel realized even that was a bit too harsh of a comment to make. The damage was done, though. He'd said it and hurt her feelings. No turning back now. Maggie then started to shiver. It was a little drafty in this apartment. Angel then grabbed her a blanket. It wasn't super comfortable, but it was something.

"Get some sleep," Angel said looking away from her, and Fat Nuggets hopped onto the couch with her, "Guess Nuggs chose you tonight. Ya thirsty? I got some wine or booze."

Maggie shook her head, and Angel shrugged as he downed a bottle of booze. With that, he turned the light out, and he headed to his own bed. He hugged a very uncomfortable pillow, letting his thoughts drift him off to sleep. Maggie couldn't help but stare at the darkness. It was terrifying to her. Even her room at home was never this dark. She began to shake a bit, but Fat Nuggets nuzzled her. She hugged the pig, burying her face, before bursting into a silent sob.

A/N: Not much to say I guess except, uh, leave a review if you like it so far.