A Brand New Life, a helluva boss fanfic

(Disclaimer: I do not own Helluva Boss or any of the characters, all credit goes to the creator Vivienne Medrano, aka VivziePop. Please support the official release).

(Note: This takes place long before the events of Helluva Boss episode one).

~A Brand New Life~

It was just after midnight in Imp City, but even then, the streets were still buzzing with activity.

A lone male imp was walking down the street, his head hanging low so that his face was partly obscured by his semi long white hair. The imp had a dismal expression on his face as he walked into a bar, he seemed so very depressed as he sat up at the counter.

The bartender noticed him immediately, since the bar wasn't that busy, and walked over to him. "What can I get for you, pal?", he asked.

The imp laid his head down on the counter, "Give me a...I don't know, just lots to drink...", he mumbled weakly.

The bartender shrugged as he went to go fill up a hug beer mug with some whiskey, he slid it over to the imp and then walked off to continue cleaning the countertop. The imp took the mug and drank from it, trying hard to fight back the tears that welled up in his eyes.

"What am I going to do? The rehab center gave me a year to find a way to pay for my mother's treatment, but I haven't managed to find a job at all! The little bit of savings I have is running out, and soon I won't even be able to take care of myself!", he mumbled under his breath.

Then, he couldn't fight it anymore, the tears started pouring as he put his head down on the counter. As he sat there crying, someone new walked into the bar and sat down at the counter, they noticed him and reached over to place a hand on his shoulder.

The imp looked up and his tear filled eyes widened at the sight of who was sitting next to him: it was none other than than the famous succubus superstar, Verosika Mayday!

He couldn't believe she was actually sitting next to him, "No way! Are you really the Verosika Mayday?", he asked.

Verosika smiled at him, "The one and only, hun. You look lonely, can I buy you a drink?", she said.

The imp shook his head, "I already bought myself a drink, and also I'm gay. Plus, even if I was straight, why would you wanna buy a drink for a lowly imp like me?", he said.

Verosika smiled at him as she bought a drink for herself, "Let's just say that I'm curious about you, what's got you so down? Maybe I might be able to help...", she said.

The imp sighed as he took a sip from his mug, "My Mom is in rehab now for a severe H-8 addiction, brought on by the mental trauma she endure after killing my abusive father. They were nice enough to give me one year to find a job to pay for her treatment, but I haven't been able to!

"As if it wasn't bad enough that this situation has caused me to give up on my dreams, but now I can't even find a f*cking job to pay for my Mom's treatment! I don't know what to do anymore!", he shouted as he downed more whiskey.

Verosika placed a hand on her chin, "Your dreams, huh? What were your dreams actually?", she asked.

"I wanted to be a singing and dancing drag queen, I already know how sing and dance and I love to dress up in feminine outfits. I wanted to turn that into my career, but without any connections, it's hopeless", said the imp.

Verosika smirked as an idea came to her mind, "What's your name, cutie?", she asked.

"Monroe...Monroe Montgomery", said the imp.

"Well, if you want me to, I can help you achieve your goals"

"Wait seriously? Why? What do you gain by helping me?"

"I'll be honest and admit that I do feel sorry for you and plus, that dream you have in mind...you may be an imp, but you seem to have a heart like a succubus. You wanna be a sexy singing and dancing drag queen? Well, I can make that happen"

Monroe couldn't believe what he was hearing, he had all but given up on his dreams because he had to help his mother, but here came one of the most famous people in Hell who genuinely wanted to help him.

It wouldn't been stupid to decline such a golden opportunity that was standing right in front of him.

He turned to face Verosika, "If you say you can really help me, then please do so! This may be my one and only chance, so I gotta take it!", he said in determination. Verosika smiled as she paid for her drink, "Then follow me outside to my ride, we're gonna need the rest of my posse to help us out", she said.

Monroe placed down the money for his own drink and ran out to follow her.

[Time Skip]

Twenty minutes later, Monroe found himself in Verosika's little studio office. He had already acquainted himself with her Hellhound bodyguard, Vortex, and now he was meeting the rest of her posse.

"Everyone, say hello to Monroe. Monroe, I'd like you to meet my posse: Josh, Coco, Apple, Kat, Milky, Kiki, and Ace. Everyone, I need your help with this. You see, our little friend here wants to be a singing and dancing drag queen but he can't seem to do it on his own, so he'll need our help", said Verosika.

The other succubi and incubi looked at the imp with curious eyes, Kiki walked over to him and touched his hair. "Well he's got beautiful hair and those eyes...so innocent and yet there's a hidden lust behind them", she said as she inspected his face.

Milky put a hand to her chin, "Hmm...mind taking your clothes off, sweetie?", she said.

Monroe was surprised and a little embarrassed, but if it meant they would help him out, then he would have to oblige. He slowly took his clothes off, starting first with his hoodie, the his shirt and finally his pants. He stood in front of Verosika and her posse in only his underwear, which were black with frilly lace.

Ace licked his lips as he gazed at Monroe's body, "Mmm, he's got such a delicious looking body, huh?", he said seductively.

"Yeah, but even though he's a guy, he's got such a curvy figure! You sure you're not really a hermaphrodite?", asked Kat.

Monroe shook his head, "No. I'm a guy and I identify as one, but I always did like the fact that I have such a small and feminine shaped body. It means I can wear women's clothes without worrying about being too big to fit in them", he said.

"I know! Let's give him a makeover! We have some spare outfits for him to wear, and we could do his makeup and give him some extensions to make his hair longer", Apple suggested.

Verosika nodded in agreement, "That's a perfect plan, let's do it!", she said.

Monroe was a little bit nervous, but he was also very excited. He hadn't mentioned it yet but he was one of Verosika's biggest fans and he had always looked up to her, wanting to be almost as beautiful as her. So, he stood by and allowed her posse to make him over.

While Milky and Kiki were looking for the right outfit to put on Monroe, Coco, Apple and Kat did his hair and put on extensions. Then, Ace and Josh helped with his makeup. While this was going on, Verosika was on the phone with someone.

"Yeah, that's right. I've got an imp here who'd love to perform at one of your clubs. No, he's not interested in that type of work, but he can sing and dance. I think he's better suited for stage performances...", she said.

"Okay, cutie pie, try these on for size!", said Coco as she thrusted a set of clothes towards Monroe. He caught the clothes and began putting them on; soon, he was wearing a black satin dress with long sleeves and an opened revealing back and two red hearts on the breast area. He also wore a pair of black knee high heels.

The dress on the short side, but it did go down past his waist so his underwear wasn't showing. His hair was much longer now, thanks to the extensions; his eyelashes were more pronounced due to mascara, and he had light blue eyeshadow and light blue lipstick.

"Hey, Verosika! Check it out!", Ace called out.

Verosika ended her phone call and turned around to see Monroe's new look, she smiled in satisfaction as she went to grab a medium sized square mirror.

"Take a good at yourself, cutie. You look pretty sexy if I do say so myself", she said.

Monroe looked at himself in the mirror and gasped in shock over how beautiful he looked, he had always wanted to doll himself up like this but his family never had that much money, so he couldn't even buy a tube of tinted lip balm.

"I look so gorgeous! Thank you guys so much!", he said excitedly.

Verosika set the mirror down, "Oh, we're not done yet. Now, we gotta get you some work flaunting that sexiness of yours. I just got down speaking to someone who can help with that", she said.

Now, Monroe was confused, he didn't know who she was referring to exactly.

"Wait, who?", he asked.

"First, tell me something: you can sing, so do you know any songs?", asked Verosika.

Monroe walked over to where his hoodie was hanging on a chair, he reached into one of the pockets and pulled out a small notepad. "I've actually written my own songs. If this person you're talking about can make the music for them, I'm more than happy to perform a demonstration", he said.

Verosika's posse took the notepad and flipped through it, looking at the songs.

"Wow, there's a lot in here!", said Kiki.

"Yeah, and they're pretty good too. You should hire him as your song writer, Verosika", said Apple.

Verosika herself grabbed the notepad and looked through it to read the song lyrics, "Hmm, not bad. These are pretty good, alright then, it's settled. You'll be giving us all a little show when we get there, Monroe", she said.

Monroe smiled as he started getting as giddy as a schoolgirl, but he was still confused about something. "But wait, where we going? And who is this person who's considering hiring me?", he asked.

[Time Skip]

Monroe sat in silence in the main sitting area of Ozzie's, one of the biggest and most well known clubs in the Lust Ring. It was named after the embodiment of Lust himself, Asmodeus, even though he owned practically every club in Lust.

Monroe was sitting at a table and waiting while Verosika was talking to Asmodeus off to the side, praying that his nervous sweating didn't mess up his makeup as he read over one of the songs in his notepad so he could memorize it.

Just then, he and Verosika's posse were approached by Fizzerolli, who would host any live performances that were ever held at Ozzie's.

"So you're the guy they're talking about, huh? Gotta say, you're a real looker, that's for sure! But...do you really have want it takes to be a sexy force to be reckoned with?", he said with a slight jeer.

Monroe said nothing as he tried not to let the fact that he was nervous be known, he just continued trying to memorize the song lyrics. That was when the group was approached by Verosika and Asmodeus.

"So, Monroe, Asmodeus has agreed to let you perform. He's going to watch and then afterwards, he'll decide whether or not to give you a job", said Verosika.

Then, the Lord of Lust bent down to Monroe's level in order to inspect him. "Well, little imp...you look the part, but can you walk the walk? We shall see, head backstage. The stage crew will help you with whatever you need", he said.

Monroe took a deep breath to steel himself as he got up and went backstage, there was a crew of other imps back there working some sound equipment.

"What do you need us to do?", one of them asked.

Monroe walked up to them, showing them a page from his notepad that he had pulled out. He turned it to the back to reveal sheet music, "Do you think you can replicate this melody? I've only practiced this on a flute, so I'm not sure how this would translate to electronic music", he said.

The stage crew took the page and looked it over a few times, "No sweat, we can make this. Did you memorize this song first? Because we're gonna need to hold onto this paper", one of them said.

Monroe nodded, "Yeah. I read it over a few times during the car ride here and just now while waiting, I know the lyrics like the back of my hand now", he said. Then, he looked back at the stage, which was dark and covered by a curtain, an idea forming in his mind.

"Do you guys have any props?", he asked.

"Lots in the backroom, why? What do you need?", asked one of the stagehands.

"Do you have anything that resembles a giant bottle?", asked Monroe.

Back in the seating area, Verosika sat with her posse, Asmodeus and Fizzerolli, all of them waiting for Monroe to go on.

"Sweet Satan, what's taking so long?! When is this kid gonna come out and show us what he's got?! Did he chicken out", complained Fizzerolli.

"Don't be such an impatient asshole! Give him some time to get ready, and besides, he wouldn't chicken out. Not after all the time we spent dolling him up!", said Coco.

Just then, the stage lights suddenly came on, white and dark pink strobe lights fluttering around the stage as some sensual Indian style music started playing. The curtains opened up, revealing Monroe sitting in a sexy pose in what looked like a giant genie bottle.

Then, the music's tempo suddenly changed as he finally started singing.

"When you're ready come and get it

Na-na-na-na

When you're ready come and get it

Na-na-na-na

When you're ready

When you're ready come and get it

Na-na-na-na

Na-na-na-na"

Monroe stood up and started dancing around the pole that everyone just realized was inside the bottle.

"[Verse 1] You ain't gotta worry, it's an open invitation

I'll be sittin' right here, real patient

All day, all night, I'll be waitin' standby

Can't stop because I love it, hate the way I love you

All day, all night, maybe I'm addicted for life, no lie

I'm not too shy to show I love you, I got no regrets

I love you much too, much to hide you, this love ain't finished yet

This love ain't finished yet

So baby, whenever you're ready

[Chorus] When you're ready come and get it

Na-na-na-na

When you're ready come and get it

Na-na-na-na

When you're ready

When you're ready come and get it

Na-na-na-na

[Verse 2] You got the kind of love that I want, let me get that (let me get that, yeah)

And baby, once I get it, I'm yours, no take-backs

Gon' love you for life, I ain't leaving your side

Even if you knock it, ain't no way to stop it

Forever you're mine, baby I'm addicted, no lie, no lie

I'm not too shy to show I love you, I got no regrets

So baby, whenever you're ready"

During the more upbeat and energetic parts of the song, Monroe performed some gymnastic level dance moves on and around the pole. During the slower parts, he made slow deliberate movements and hand gestures that drew attention to his curvy body, chest and butt.

"[Chorus] When you're ready come and get it

Na-na-na-na

When you're ready come and get it

Na-na-na-na

When you're ready

When you're ready come and get it

Na-na-na-na

[Verse 3] This love will be the death of me

But I know I'll die happily

I'll know, I'll know, I'll know

Because you love me so"

During this particular part of the song, Verosika could've sworn she saw tears forming in Monroe's eyes. And she wouldn't have been wrong, because these particular lyrics were referring to the love Monroe had for his mother and how he'd do whatever he could to help her be happy again.

But then, he blinked the tears back as he got a rather excited and mischievous look on his face.

"Yeah!

[Chorus] When you're ready come and get it

Na-na-na-na

When you're ready come and get it

Na-na-na-na

Na-na-na-na (I'm gonna get it, yeah, yeah)

Na-na-na-na

When you're ready

When you're ready come and get it

Na-na-na-na

Na-na-na-na"

On the last note, Monroe did a front flip, landing in a sexy and alluring pose on his knees. The room was silent for five seconds before everyone started clapping and cheering, Monroe smiled in delight at the standing ovation he was getting.

The stage hands came out and helped him exit the giant bottle so he could take a bow, then he was approached by Asmodeus. "Little imp, that was amazing! Verosika was right, you may be an imp but you've definitely got the heart of a succubus. And you're definitely worthy enough to work in one of my clubs!", he said.

Monroe squealed in excitement, "Oh thank so much, my lord! Thank you, you have no idea how happy this makes me!", he said.

Asmodeus smiled at his enthusiasm before turning to Fizzerolli, "Fizz, get in touch with Sophie at Club Déviant. Tell her we found a new star for her stage. Also, make sure she prepares the right accommodations for our sexy little friend here", he said.

Monroe smiled so brightly that his cheeks began to hurt, he hadn't been this happy in his life and it all felt like a dream.

[Time Skip]

An hour later, after getting acquainted with the owner of Club Déviant, a French succubus named Sophie who worked directly under Asmodeus as a model, Monroe followed up a set of stairs in the back of the club.

They stopped in a hallway on top floor, though it wasn't that long of a walk since the building was only three stories tall. Sophie led Monroe down the hallway, passing a series of doors until they stopped at one that had his name on it on a golden plaque.

"This is where you'll be living from now on, darling. I'll let you in to look around before you fill out the lease agreement", said Sophie. She took a set of keys and unlocked the door, revealing to Monroe that it was a penthouse apartment.

His jaw practically hit the floor at the sight of the luxurious apartment, he sprint around the place looking at everything it had to offer. There was a living room area with a flat screen TV, a white leather couch and a round bed on an elevated platform a few feet behind the couch.

Then there was the bathroom: it had a standing shower, a bathtub that looked more like a jacuzzi, and a sink and toilet with golden fixtures. Next was the kitchen, which was fully complete with a large fridge stocked with food, stove and oven, a sink with a dishwasher, several cabinets stocked with dishes and a little countertop island with bar stools.

Next was the walk in closet filled with flashy outfits for Monroe to wear during his performances and casual clothes to wear to go out, there was also an assortment of shoes, jewelry and underwear, and drawers filled with pajamas.

And finally, there was the guest bedroom which had a simple full sized bed and a small dresser for whenever Monroe wanted to invite someone over.

Monroe looked around and that's when he spotted the black sequin curtains, he walked over to them and pulled them aside, revealing a large set of windows that led to a balcony. He opened the window and walked out onto the balcony, getting a good view of the city.

He smiled as he felt the breeze blowing through his hair, but then it got too chilly so he went back inside. That was when he saw Sophie wheeling in a luggage that held the few meager belongings he had in the old shabby apartment he used to live in. And she also had a small pet carrier with her too.

"Verosika's Hellhound brought over your things for you, and the thing in the pet carrier is a gift from Asmodeus. Once you sign the lease agreement, I'll leave you be. You'll start working next week", she said.

Sophie handed Monroe a clipboard with a few papers on it, he read through each one and signed his name in the appropriate spaces. Once that was done, she handed him the keys and left, leaving him alone in his new home.

Monroe smiled happily as he took in his surroundings, that was when he heard some scittering coming from inside the pet carrier. He opened it and out popped a small bird/rodent like demon animal with six red eyes and a blue collar around its neck.

Monroe picked the critter up and looked at its tag, seeing that it's name was "Monty". He smiled as he petted the little critter on the head, "Well aren't you the cutest house warming present ever? I'm gonna have to buy you a litter box soon though", he said as he let his new pet run around and explore his apartment.

He then opened his luggage and unpack all his stuff, putting them in the necessary places. When he was done, he placed something on the side table next to his bed. It was a framed photo of himself and his mother.

Monroe looked at the photo fondly, "Everything's gonna be alright now, Mom. I'm gonna pay for your treatment until you get better, then I'll make sure you have a front row seat to all my shows", he said.

He then decided to enjoy himself by breaking in the new apartment. He took a long and relaxing bath whilst enjoying some smooth jazz and a glass of wine, then he helped himself to a slice of cheesecake inside his fridge while watching movies on his flat screen TV.

Finally, it was really late so he decided to go to bed. As Monroe made his way to his bed, he heard and felt something crinkle under his foot. He looked down to see a small note under his foot, he bent down to pick it up and unfolded it to reveal a short letter from Verosika that looked like it was written in lipstick.

The letter read as such:

I've never done as much as I've done for you, cutie. So, the way you're gonna pay me back is by being the best singing and dancing drag queen in Hell. Don't disappoint me, you better give it your all!

Also, my phone number's at the bottom so call me if you ever wanna talk or hang out. Remember you can always come to me for anything, after all...what else are friends for?

Have fun!

Love,

Verosika

Monroe smiled as he folded the piece of paper and placed it in the drawer next to his bed, then he climbed on top and crawled under the covers. Monty climbed onto the bed and curled up into a ball next to him.

Monroe gave him a little pet on the head before shutting off the lights and getting comfortable under the blankets, a content smile on his face.

His life had finally, officially started...and he was gonna enjoyed every part of it!

[The End]