Author's Note: This will be an interesting idea. Now, I've dabbled in self-insert stories before. But, they've been mostly for video games. This story, will be my first time adapting a show. An adult show on YouTube no less. So, just letting everyone know right now, this IS a self-insert fanfic involving Helluva Boss. But, there will be some new things added, if this first chapter is anything to go by. So with that being said, I don't own Helluva Boss, it belong's to Vivienne Medrano aka VivziePop. I hope everyone enjoys this! Please read and review!

Chapter One: Waking Up In Hell Part 1

Xandar's P.O.V:

I felt the cold ground as I woke up. It was very painful and above all, irritating as hell. I opened my eyes and looked around. Seeing a ton of red, and strangely named buildings, my brain finally woke up.

This was an odd looking place. Where the hell was I? I stood up finally and felt my back pop. "Ah!" I gasped loudly. "Shit, that fucking hurts..." I hiss n in pain. I tried to remember what had happened the night before. It seemed fuzzy.

I sighed. Taking a look at my surroundings I growled in frustration. I must be far from home. Oh, right. I almost forgot. I'm Xandar Lee.

I'm just your average human with a bubbly personality and a kind mindset. But right now? I was in pain, hot, due to the environment, and pissed of beyond all belief. Why, you may ask am I pissed? I don't know, maybe it's because I had no fucking clue where I am?

I decided to try to think back to last night. Try to remember. I remember attending another day of college. I spent the day studying, reading and writing. I had dinner...

Why can't I remember what happened past that? I decide to take a look around. As I walk along a shady looking sidewalk, I am acutely aware of light footsteps behind me. It sounds like the clicking of shoes. I decide to walk faster, only for the footsteps to increase.

I hope to dodge this person and duck into a nearby alleyway. Sadly I come across a dead end. "Brilliant Xandar," I scold myself. "You get followed, and what's the first thing you do? Ya walk into a dark alley with a damn dead end."

I turn around to see...nothing. Looking around in confusion I shrug. I try to walk back the way I came until-

"Gotcha!" A voice shouts as I'm grabbed by the back of my neck. I feel cold metal against my throat. The voice laughs. "Oh this is too easy! Thanks for your stupidity human! Now I can get a hefty payment for my troubles!"

I take in what he said. Human? Well of course I'm human? What else would I fucking be? I try to turn my head, only for the grip to tighten and the cold blade to push in further causing pain, and a trickle of blood to drip down my neck.

"Shhh!" The voice hissed. "It's alright idiot! Soon you'll be sold off, and I'll get my big reward!"

"Yeah? What reward fucker?" I challenge. "As far as I know you're a human too-" I'm cut off as the grip tightens further causing the last word to become a gasp.

"Don't tell me you don't know what Hell looks like?" The voice mocks. I feel my blood run cold. Did he say Hell? As in...THE Hell? The ever continuing punishment for sins?

"Wait," I begin in shock. "I'm in Hell!?" I shout in surprise

"Shut it!" The demon scolds. "One more quip outta you, and I'll slice your fucking neck! I really don't want to. I mean, a dead human is less the reward. But you are so damn irritating, I'm almost considering killing ya here and now."

I stay quiet. Hopefully someone will help me. But considering where I was? That chance was zero to none. "Start walking!" The demon whispers. The demand was more threatening than anything. He grips tighter and walks me out of the alley.

I try to stop only for the demon to growl. "Do not stop walking unless you are told otherwise!" He growls. I sigh.

"I will not!" I shout. "If you're gonna kill me, get it the hell over with!" I growl. I then smirk. "Anything is better than dealing with a pathetic, irritating, piece of shit like you."

The demon turns my head to him. "The fuck did you just say to me?" He demands. "You're the one at MY mercy. So how about you just-" he starts but stops suddenly. He screams in pain. And loosens. I didn't realize why until I turn to him, and see a dagger stuck in his shoulder.

"Nice one Mox!" A voice shouts causing me to look up. There are three other demons. The one who had spoken had a suit and a face that was half black and half white. The other two were shorter compared to the main one. The shorter one seemed prim and proper and the other was a female wearing a skintight black shirt.

"Hell yeah Moxxie!" The female shouts. Moxxie jumps down and so does the female. While Moxxie and the female land on their feet, the taller one lands flat in his face.

The demon behind me growls and grunts in pain. I look back and see he had yanked the dagger from his shoulder leaving a small geyser of blood to ooze down his shirt. There was a hole where the dagger had been.

"He's mine!" The demon yells running at the trio until the female shoots him in the stomach. The demon shouts in pain. The tall demon grabs him by his throat and says "I'm sorry, what was that? I couldn't hear ya over your screams of pain," the tall one mocks.

"You son of a-" the demon tries to say until the tall demon tightens his grip.

The tall one laughs. "If anyone is getting a reward, it'll be us!" He shouts in his face. I gulp nervously. Great I think to myself. These three want to kidnap me as well. I try to sneak away until the female jumps in front of me pointing an axe in my direction.

"And where do you think you're going?" She asks with a cruel smirk.

"Far away from here?" I challenge. "I have had enough bullshit for one day." The demon stifles a laugh and my blood runs cold.

"Yeah, good luck with that!" She says chuckling. "You're gonna run from three highly skilled assassins?" She inquires with a raised eyebrow.

The tall one walks up to me. "Ok guys," he says confidently. "Now we got a human AND a demon," he continues. "Where do you guys want to the head?" He asks lifting up the demons decapitated head. My response? I faint.

ZZZ

I open my eyes and I see the inside of a van. I remember what happened. I had been attacked and kidnapped. Now I'm kidnapped again. I decide to play the smart ass card. "Where in the hell are you assholes taking me?" I inquire innocently causing the tall demon to slam his fist into the metal separating us three times.

"Shut the hell up in there!" The demon demands. "We're taking you to Stolas!" says as if answering my question.

"Great," I say sarcastically. "Take me to some guy I've never heard of. REAL professional assassin's you are," I mock causing the van to screech to a halt.

The metal door opens. The tall demon looks at me with a pointed finger. I quickly take notice of the demon head hanging from the mirror in the front. It takes me all my strength not to vomit and act tough.

"Now you listen here you miserable little shit." He begins angrily. My glare intensifies. "I'm so NOT in the mood to deal with a whiny bitch like you. So i suggest you keep your DAMN MOUTH SHUT! OR I SWEAR TO SATAN YOU'LL LOSE ALL YOUR PATHETIC FINGERS! GOT IT?" He roars.

Still glaring, I say nothing. The demon nods his head before slamming the metal door. The demon makes an oddly uncomfortable noise.

"You ok Blitzo?" The female asks.

"That human has a glare that literally makes me feel like my insides were on fire." He makes the sound again and I realize he shuddered. "And I usually like kinky shit like that!" He adds

I stifle a laugh. I no longer care if I die now. At least I got one good scare out of that whiny excuse for a demon.

ZZZ

The van stops and I am grabbed forcefully out of the vehicle. I look up and see a castle where a four eyed owl demon waited.

"Hello my precious little Imp!" The owl says, in an oddly sexual manner. Wait are those two-

"Stolas, please don't talk to me in a horny manner when my employees are around," the demon says. Yep, those two have a weird relationship going on. A VERY sexy one. "Especially not in front of a victim," the demon adds.

The owl who I know now is Stolas chuckles seductively. "We'll talk later," the owl finishes. He then glares at me. "So this is the human causing you trouble?" He demands glare never leaving. I cough awkwardly and look away.

"Yep," the demon says grabbing me by my shorts and pushes me towards Stolas. For the first time in a few hours...I actually feel fear. "He's all yours to do what you want with," the demon says walking away whistling.

Stolas nods and then grabs me by my shirt dragging me away. As he does I hear Moxxie laughing.

"That kid is so dead!" He cackles. I resist the urge to clarify that I'm twenty two as the demon pulls me up to the castle door.

He opens the door, says, "Get in there human!" And shoves me in. I look back quickly to see Stolas slam the door.

Author's Note: I hope you guys like this so far! Thanks for reading!