Hello, everyone who happens to read this, my name is Pillowwriting101. This is my first attempt at actually publishing a Helltaker fanfic (I had ideas but I decided not to write them). Just know that this is my expansion of the lore and story of Helltaker, so please know that none of what I have written is canon to the game or comics. I hope you enjoy this prologue and that it intrigues you to read more of this fanfic.

(Also if the words are slanted like this, they are thinking.)

Chapter 1: Leo (Prologue)

A boy wakes up from his sleep, yawning loudly as he goes to get dressed. He quickly brushes his teeth, puts on clothes, and packs his belongings. He then exits his tent, breathing a sigh of relief as he heads towards a bus. Today was his last day of training with the military and he was just starting to get fond of it.

"Hey, hurry up or we're gonna leave without ya!"

The boy turned his head to face a man waving toward him on the bus. The voice who called him was Mark, the first friend he made during the time he was there.

"Yeah, come on LEON!"

This voice was his other friend- Liam, who were once rivals at a time when he met him but slowly became friends in the end.

"I've told you before, it's Leo!"

Leo ran over to the bus to board it to then came face to face with the bus driver- Felix.

"Hey, there pal looks like training is finished for you, huh?" Felix said with a laugh. "You look like a man compared to the little shrimp you were when you first came here"

"Yeah, yeah, whatever" Leo grumbled.

Leo went to sit down next to Mark, who noticed him staring at a photo.

"What's up with the photo?" Mark asked curiously.

"Oh, I never showed you before but this is my friend before I went to this camp." Leo said with a smile "He's a nice guy, before I left he said that he wants to make a harem of demon girls which I found a bit silly, but who knows if he really got a harem?"

"Just can't wait to see him!" Leo said happily.

"Wait a minute….." Mark said with confusion

"What?" Leo asked.

"You've been here for about 2 years, and you've changed a lot, do you think he'll still recognize you?" Mark exclaimed "Just saying, you been gone for a while"

"Nah, I'm sure he'll know who it is when I come knocking on his door." Leo said with a nervous laugh.

"Will he still remember me?" Leo thought panicking inside.

Meanwhile in Hell…..

The Helltaker has ventured into hell in order to get a harem, at this moment he has gotten a tired office worker whose name is Pandemonica, a lustful demon called Modeus, the gatekeeper of hell - Cerberus, a grumpy gamer named Malina, a smoker named Zdrada, an angel called Azazel, and just recently managed to sway an awesome demon called Justice.

"Yay!" Cerberus shouted in excitement. "The harem is growing!"

"Just don't let it grow too much." Malina grumbled. "The last thing we need is a bunch of girls who you can't take care of."

"If you girls don't mind, do any of you know how to exit hell?" The Helltaker asked. "I'd rather not be stuck here."

Zdrada immediately laughed and continued laughing to the point where she was on the floor. She then pulled herself together and started to smoke a cigarette.

"I think you forgot you're in the place where sinners and shiters are doomed to forever stay." Zrdada hissed. "There is no exit out of hell unless you want to start praying for god to forgive you."

"Actually, there might be a way to leave, but it's risky." Justice said.

"Well, what is it?" The Helltaker asked desperately.

"We can go talk to Lucy and if we manage to convince her, she can probably convince Judgement to let us pass onto earth." Justice explained.

"Lucy?" The Helltaker questioned. "You mean Lucifer, the ruler of hell?"

"You betcha." Justice grinned. "I've known her for a long time."

"Wait, who's Judgement?" The Helltaker asked.

"That's a surprise, for now, big guy." Justice said.

"Well shit." The Helltaker sighed. "Doesn't seem like I have many options, might as well."

"Great, follow me!" Justice said.

With that, The Helltaker and his harem followed Justice to a dark castle, which seemed to look gloomy.

As soon as they caught up to Justice, they were immediately stopped by several skeleton guards.

"HALT!" A skeleton guard shouted. "Who are you state your business for being here."

"Well you see-" The Helltaker said as he began to speak.

"Hey, hey, hey!" Justice said. "Relax, they're with me."

The skeleton guard glared at The Helltaker and turned to face Justice.

"If you insist." The skeleton guard said as he walked away.

As the guard walked away, Justice tapped on the Helltaker's shoulder to signal that he should follow her. With this, they found an elevator that seemed to look brand new.

"Sorry about the guards, they take their jobs very seriously." Justice whispered. "Also, the elevator is brand new, I've been begging for Lucy to get one, it's a lot easier than taking the stairs."

After a long ride on the elevator, The Helltaker finally reached the final floor of the castle which was the location of Lucifer's office. Before The Helltaker could even open the door he felt an overwhelming aura of evil which made him think twice before opening the door. Justice then reached for the door handle.

"Don't worry, I got this." Justice said as she winked.

"Who is it?" Lucifer growled. "If it isn't already obvious, I kinda busy-"

"Hey, Lucy!" Justice smiled as she entered her office. "Sorry to interrupt, but we need your help."

"What did you do now?" Lucifer sighed.

"I'm wondering if you don't mind if you can allow this human to return to earth." Justice said

"Human?" Lucifer asked. "What human?"

"Oh, hey you can show yourselves now!" Justice said.

With this, The Helltaker entered the room along with his harem.

"Ah, now I remember." Lucifer said with a sly smile. "You must be the one who was running around hell beating up my skeleton guards."

"I hope you can overlook that, your majesty." The Helltaker said nervously.

"It's not a problem, and please call me Lucifer." Lucifer said.

"I also hope you can accept my request, Lucifer." The Helltaker said.

"Considering how much your harem has grown and how much of a waste it would be to kill you, I'll accept your request." Lucifer said. "But, what will I get in return?" "You want something, you must give me something in return."

"Uh, I make pancakes." The Helltaker said.

"Are you playing with me, Taker?" Lucifer asked as her body and eyes began to glow a red aura. "Is this a joke to you?"

The Helltaker began to sweat, panicking that he made a huge mistake.

"Shit, Shit, Shit." The Helltaker thought. "I'm dead, I'm dead, I'm dead-"

But all of a sudden, Lucifer's body and eyes stopped glowing.

"You're lucky that I'm a fan of pancakes." Lucifer said with a sly smile. "I'll do my part of the deal and I'll even join your harem to sweeten the pot"

"Thank you, Lucifer." The Helltaker said.

"Don't mention it." Lucifer said. "I'll teleport us to the Sin Machine to make our lives a little easier."

With a snap of her fingers, Lucifer teleported everyone to the Sin Machine.

"So, this is what the Sin Machine looks like." Malina said. "I've heard many rumors about it, but I never expected it to look like this…."

"So, we just have to pass by this and we're home free?" The Helltaker asked.

"Not exactly, the last thing we have to deal with is Judgement." Lucifer said.

"Who's Judgement?" The Helltaker asked.

"She's the current High Prosecutor, the successor of Justice." Lucifer said.

"Then, where is she-" The Helltaker said before being interrupted by a loud voice.

"WHO DARES ENTER THE REALM OF THE HIGH PROSECUTOR?" A loud voice roared.

Walking out of the shadows, a dark-skinned demon appears with a very revealing outfit, glowing white eyes, and white hair which seemed to float on its own. She gave off a wicked smile and turned to face Lucifer.

"MY QUEEN, WHAT IS IT THAT BRINGS YOU HERE?" Judgement said with a booming voice.

"Judgement, dear, I have a human with me who would like to go back to earth." Lucifer said. "Would you be ever so nice and let him pass through?"

"NEVER, I HAVE SEEN HIS SINS AND HE MUST BE PUNISHED!" Judgement shouted.

"ALTHOUGH….." Judgement said.

"IF YOU INSIST ON GOING BACK TO EARTH, YOU MUST DEFEAT ME IN BATTLE!"

The Helltaker began to sweat, defeating one of the most powerful demons in hell? He might as well give up and let the Sin Machine take him away. But, he then remembers about his harem that he worked so hard for and his confidence renews.

"All right, Judgement, you asked for a fight and you'll get one!" The Helltaker shouted as he began to charge at Judgement.

"He's so dead." Zrdada thought with a chuckle.

"Just when I finally found someone to play games with." Malina thought.

"This will be interesting…." Justice thought with a smirk.

"I just want my coffee….." Pandemonica thought exhausted.

"Don't give up!" Cerberus thought.

"Even if he dies, I'll revive him and have him forever make pancakes for me." Lucifer thought gleefully.

"I knew I should have kept him to myself…." Modeus thought.

"Glorious!" Azazel thought. "This fight will greatly help my research!"

Judgement summoned her white chains and directed them towards the Helltaker, who he himself was barely dodging the chains. This cycle continued for several minutes along with some flirting, until eventually, Judgement stopped attacking.

"WHY….." Judgement said gritting her teeth. "WHY WON'T YOU GIVE UP?"

"BECAUSE I CAN'T GIVE UP ON MY HAREM!" The Helltaker shouted. "NOT AFTER I WORKED SO HARD TO GET THEM!"

"Look, I don't want to do this." Judgement said in a normal tone. "But your soul is sentenced to eternal damnation."

"But, I could temporarily suspend your punishment if you promise never to enter hell again…."

Judgement said. "SO, GET OUT OF MY SIGHT!"

"..."

"..."

"..."

"WHAT?" Judgement growled. "YOU WANT ME TO JOIN THIS HAREM OF YOURS?" "I WOULD NEVER!"

"We could always have someone like you join." The Helltaker said.

"W-Wait, really?" Judgement questioned in a surprisingly soft tone. "I guess I could join, I could use a break from my job….."

"Alright!" The Helltaker shouted in relief. "The harem is complete."

"Finally, it's about time." Malina grumbled. "When are we leaving here?" "I swear it's been ages waiting for you two to finish fighting."

"DON'T WORRY I KNOW THE WAY OUT!" Judgement said. "FOLLOW ME!"

With this The Helltaker and his harem follow Judgement to a gate we led out to Earth, The Helltaker who had not seen the sun for a few hours had to cover his eyes with his hands.

"Yeesh, the sun is trying to blind me." The Helltaker muttered as his eyes began to adjust. "Anywho, welcome to my house!"

"Not bad." Pandemonica said with a small smile. "I half-expected you to have it worse."

"You overestimate me." The Helltaker laughed.

With this, the harem entered the house and found it quite tidy as everything was clean and where it was supposed to be.

"Damn, I haven't seen a clean house in ages." Zrdada said. "I must be in heaven."

"The house isn't always this clean, it's usually Leo cleaning every few months." The Helltaker said, moving a few books.

"Who?" Lucifer asked.

"Oh, I guess I haven't talked about him yet." The Helltaker said. "He's my best friend, he recently went to a training camp."

"How long has he been gone?" Lucifer asked.

"About two years." The Helltaker said nonchalantly.

Some of the girls reacted a bit surprised at The Taker being so relaxed about it, while the others didn't really react at all.

"I do wonder when he's coming back." The Helltaker said. "It kinda sucks without him being around."

"I'm sure he will come back, sooner or later." Lucifer said as she looked around the house.

"Yeah, yeah." The Helltaker said. "When are you going to come home, Leo?"