Helluva Friend

by Conato

Rating: mature
Tags: Fetish, Profanity, Random, Violence, Crossover, Sex, Main 6, Gore, My Little Pony: Friendship is Magic, Death, Alternate Universe, Narcotics, Porn
Length: 4086

What do you get when you mix a hell hound and colorful ponies? One hell of a friend

One day, in a drunken rage, Loona opens a portal to a place she thought her "boss" wouldn't dream of following her too. What she finds may be even more than even she was expecting. Will she decide to stay? Will her old team come looking for her? Is there way to many questions to ask than can be placed in a description? The answer to one of these is a clear yes.

Warning: violence, drugs, alcohol, language and possibly even sex.
It's a helluva_boss crossover. Were you expecting flowers and cotton candy?

Published 2023-04-08 18:10:00 UTC
Last updated 2023-05-10 15:22:17 UTC

Chapter 1

That's it. Loona had put up with that red prick for too long. After all these years he was still holding the fact he adopted her over her head. And today he had pushed one too many times.

"Then quit. I'll just hire a new hellhound." He huffed.

"Fine! I will. And I'll do you a favor and move out so your new hellhound has a place to stay." She snapped before storming out, leaving him to stand dumbfounded.

She had left the office and took a beer from some random shlump off the street on her way to pack up. She managed to hold herself together long enough to get to her room before breaking down and spending the next hour crying over the fight. She knew… or at least thought he loved her like a daughter. But after he chanced off her fifth male friend. She couldn't take it anymore. She wanted to start dating. For love of Lucifer! She's practically an adult. And he knew it was a matter of time this'd happen or she'd flip and attack him for denying her a mate.

Noticing the grimoire out of the corner of her eye. Narrowing her eyes she made up her mind. It might not be the smartest idea. But she wanted and needed to go to a place where her dad would likely wouldn't dream of going. Somewhere friendly… somewhere colorful… somewhere that even she would probably gag at.

The portal opened and for a moment she considered taking the book as a final middle finger to her so-called dad. But the thought of him not having a clue of where she was going. She tossed it onto her bed and grabbed her bag with some food and rum before making her way into the portal.

It didn't take her long to realize that she got what she wanted. But there was a downside. Standing just on the other side of the portal was what looked like a horse. "Well." She thought. "I doubt he'd expect me to go to a place like this."

Smiling, she knelt down and looked into the eyes of the small winged pony. "Don't be afraid. I-" was all she got out before it screamed and galloped off.

Sighing, she got back up and looked around after noting the direction the little one went. "Ok… so I'm in some strange world… in a strange forest…" sniffing the air she gagged and turned to face the source. "And it has feral wood hounds." Cracking her neck she set her bag on a stump. Well… she did need to let off some steam somehow.

Scootaloo fled from the strange wolf lady and made it out of the forest before crashing into Fluttershy, who lived just outside the forest.

"Oh my." Fluttershy gasped. "Are you ok?"

"Forest. Portal. Wolf. Talking." Scootaloo rambled in a panic before quickly looking around. "Have to warn Twilight." With that she started off before immediately running into said pony. "Twilight! Portal! Wolf! Talking! Forest! Help!"

"Calm down Scootaloo." Twilight sighed. "Breath deep." She interrupted. As Scootaloo took a few deep breaths Twilight smiled and sat. "Now… What happened."

"I was on my way back from visiting Zecora. Then this weird glowing hole in space opened up and a two legged wolf stepped out. Seconds later I smelled Timberwolves. So I ran here." Scootaloo explained.

"Oh dear."

"We should help her." Twilight announced.

"But what if she's working with them?" Scootaloo asked.

"Scootaloo. I think your fear is making you imagine things." Twilight laughed. "Come on. The sooner we find her. The sooner we can get to know how she got here and why she's here."

With a sigh, Scootaloo led them over to the spot where she saw the large wolf thing. Blinking, they looked around. "I have a bad feeling about this." Scootaloo whimpered.

Twilight sniffed the air and looked back down the path leading to town. "And it's about to get worse. They're surrounding us."

After a few tense moments Luna stepped out of the trees and looked at them. "I thought you were running away." She huffed.

"Is that…" Twilight gasped at the sight of the Timberwolve's head stuck on the hellhound hand.

Scootaloo hid behind Twilight as Luna followed their eyes to the head. Sighing, she ripped it off and tossed it into the forest. "Plenty more where that one came from."

"Why did?... how did?" Twilight stammered.

"Those things aren't really much of a problem. Give them a week and they'll be back." Loona replied, kneeling down to look them in the eyes. "Now. What the fuck are you two doing here?"

"Please watch your language." Twilight scolded. "We came to find you and get you out of this dangerous place. It's a death trap if you don't know your way around."

"And what about her? Doesn't her parents know she's here?" Loona asked. She paused and blinked in shock as they looked away quietly. "Where are they?" She growled.

"Doing important research all over the world." Scootaloo sighed.

Loona sighed and knelt to look her in the eyes. "Then how about I look after you till you're big enough to be on your own?"

Twilight thought for a moment. "Well… as princess… I do have the power to appoint you as her guardian. But you'd need to stop by the castle to pick up some books to learn about our customs."

"Fine. But I have a few rules." Loona sighed before pointing at Scootaloo. "No hiding things from each other. No matter what." She paused till Scootaloo nodded. "Two, I'm in charge of the house. That means money, who does what chores and bedtime."

"That sounds reasonable." Twilight agreed, as Scootaloo nodded.

"Good. Then let's go. Sooner we get there, the sooner I can figure out a way to get food and money." Loona announced before starting for town.

"What about the Timberwolves?" Scootaloo asked in concern.

Loona smirked back at them. "I got this." She announced before running off.

Author's Note

I don't know why. But I had the urge to start this story. Don't know what will happen. But, now that it's here. A part of me is going to enjoy this. Yes, I am open for shipping suggestions. And who should introduce themselves to her next.

Chapter 2

Several minutes passed before Twilight and Scootaloo saw Loona come out with an odd looking dagger in her hand. "Will one of you grab my bag?!" She called.

Smiling Scootaloo made her way over as Twilight carefully used her magic to carry the bag over to the now shocked wolf. "What's in it?"

"None of your business." Loona snapped as she snatched her bag and turned to follow Scootaloo. "Let's just go with stuff that would make you sick. Deal?"

Twilight nodded and moved up next to her. "You looked shocked or… scared when I brought over your bag.

"I wasn't expecting you'd be able to use magic." Loona shrugged. "Just something I'd need to keep in mind."

"Is there something wrong with magic?"

Loona laughed. "Fuck no. Just gave me a few things to think about."

"Like what?"

Loona glanced at Scootaloo's wings. "Just a few things I'm starting to notice."

It wasn't hard for Twilight to notice what she was looking at. "We can talk about it later." She informed softly.

The rest of the trip back to town was spent in silence. To Loona's surprise, the ponies that saw her walking with Twilight seemed to just smile after a moment of shock at seeing her. She watched Scootaloo speed off down the street before following Twilight into a large crystal castle.

"Scootaloo can't fly." Twilight explained. "Nopony knows why. And other than risk messin with dark magic. I don't really know what to do."

Loona rubbed her chin. It was an interesting subject. Perhaps… learning their magic might explain how she got there. "Maybe I can take a look. I have a bit of experience with magic back home. Maybe I can take a look at some of the Dark magic books and-"

"No. Dark magic corrupts whoever uses it." Twilight interrupted.

Loona rolled her eyes. "Yeah. I doubt that'll be a problem."

"What are you talking about? Of course it's a problem." Twilight snapped.

"Have you ever wondered WHY it's called dark magic? Or why it corrupts the user?" Loona asked, moving to a shelf of books on spells.

"Because it's evil?"

Loona sighed and pulled out a book and flipped through it. "Right. So by your logic. A dagger is evil because it kills. Even if the one using it has good intentions. They become evil for using it."

"That's not what I-"

"Oh look. A spell to make others do as you command. Not evil… I bet someone who can use it can come up with evil uses." Loona pointed out.

"Ok I get it." Twilight huffed. "Magic can be used for evil purposes. But dark magic is different from other spells. It literally corrupts the user's soul."

Loona closed the book and smirked. "What if that wasn't a problem?"

"I… don't follow."

Loona put the book back and was about to say something before getting slammed into the wall by a dark coated mare. "Fear not Twilight Sparkle. I'll take care of this monster."

"Wait luna!"

"Stay out of this." Both females called before Loona kicked the princess in the gut, forcing her to back off and summon a sword.

"Speak not to our sister's student, monster." Luna spat.

Pulling out her dagger, Luna took a defensive stance. "I am sooo going to enjoy kicking your ass bitch."

Twilight could only sit and watch in shock and confusion as Luna fired spells at Loona as the wolf blocked them with her dagger before charging in with a kick that the mare dodged by jumping to the side.

Luna aimed her spell at Loona's hand knocking the dagger from it before preparing another.

Not wanting to risk getting hit by whatever it was, Loona quickly moved closer and grabbed her horn and started twisting it. "Say it bitch."

Luna's eyes shot open as her spell broke and a jolt of pain shot through her body. "I will never-"

"Enough!" Twilight shouted. "What's wrong with you two?"

"My apologies Twilight. I sensed this evil creature appearing and followed it's energy to here." Luna sighed.

"I might be a hellhound. But at least I didn't label someone I never met." Loona huffed.

"A what?"

"I was born in hell. Basically I'm a demon dog." Luna explained.

"As I said, Twilight. She is an evil creature." Luna added.

"If you call keeping a group of Timberwolves from eating two ponies evil. Then I'll take it." Loona spat.

Blinking in shock. Luna looked over at Twilight who nodded in agreement. "I'm sorry princess. But she has a point. We can't judge her based on where she's from. She hasn't given us any reason to doubt her. In fact, she offered her assistance with understanding and dealing with dark magic."

"She has?" Luna asked.

"I did?" Loona asked.

Twilight nodded. "She will need to be paid for it of course. And no doubt she'll have a special diet. So… I see no problem with her offer."

Luna thought for a moment. "Very well. On one condition. A spell is casted so that you and I are notified the moment she succumbs to the dark magic."

"Deal." Twilight replied before turning to Loona sighed and shrugged. "Whatever. Deal."

As Loona let Luna go, the three sat as the two princesses performed the spell. Moments later Loona turned and smiled at Luna. "Next time you want to get your tail kicked. Let's do it in a place we can let loose."

Luna huffed and smirked. "I shall keep that in mind. And I shall remember that little trick of yours." Getting up she turned to Twilight. "Be sure to inform us on the book she is studying. And what you find out."

"Yes princess. I was thinking of starting her off on one that involves pegasus magic." Twilight replied.

Luna thought for a moment before nodding and leaving. Once she was outside, Luna paused and smirked back at the door before flying off. "Maybe… just maybe."

Twilight levitated over a few books. "These are books on magic and how each tribe uses them." She explained before bringing over a box. Taking a deep breath, she opened it with her hooves and turned it to Loona. "And this is the… other book."

Loona noticed Twilight wouldn't use her magic or even touch it with her own hooves. As she reached for it she saw Twilight preparing a spell, just to be safe.

Taking the book, she opened it and quickly felt what she was talking about. But either because of what she was or where she's from. The corrupting powers only felt like a tickle. "This stuff is weak." She huffed before scanning the spells.

Twilight sighed and turned away. "Let me know if you need anything. I'll see about setting up the rest of what we talked about."

Loona nodded and turned to a page that talked about pegasus wings. Smiling, she scanned the page before turning to another that talked about making things out of magic. "Sure thing… you'll be the first to know."

Author's Note

... I wonder how often I should have them meet up. Or how many people got confused because of "text to speech" lol. Oh the fun that can be had. What to do next...

Chapter 3

Scootaloo Twilight Loona

Twilight examined Loona's dagger as she was reading the book. She had given Loona the benefit of a doubt for saving her and Scootaloo. But she had a few questions she needed answers to. And the dagger was one of them.

As she took care of some paperwork she did a few scans on the dagger. "Does it have dark magic in it?" "Is it magical at all?" "Can I tell anything about where it's from?" Were just a few questions bounced around in her head.

As she finished the paperwork for "temporary" housing, the scanning spell also finished. Blinking, she looked over at the dagger before groaning. "It's just a regular dagger?" Twilight gasped. "Then… does that mean?..."

Just then her ear twitched as she heard laughing coming from the other room. Twilight quickly rushed into the room and saw Loona still looking at the same book. "What's so funny?"

"The dark magic in this book is pathetic." Loona laughed. "All I'd need to do is change a few words and that'll destroy the dark magic."

Twilight blinked in shock. "Wait… seriously? That's it?"

Loona nodded and took a scroll and quill before writing down the altered spell. "See? Just don't read it out loud or try and cast it until you know what to change." She paused for a moment before laughing. "Seriously. I can't believe none of you figured it out already."

Twilight looked over the spell. After a few moments she turned her gaze on Loona. "I'll have Spike send this to the princess so she can look it over too."

Loona nodded and sighed before looking back at the book. "You think if I'm able to alter one of these spells…"

"You can use magic?"

"Magic is more common for my kin." Loona admitted as she looked through the book. "Anyway. There's one spell I noticed that I'd like to try."

Twilight took a deep breath as she fought to control her fears. "Luna did put an alert spell on you to let us know if you used dark magic. But… I'd like to test how skilled you are with our magic first. If you don't mind."

Loona rolled her eyes and grabbed another nearby book. Before quickly flipping through it. She turned it to show Twilight. "How about this one?"

Twilight looked it over. "That's rather advanced. Maybe we should start with-" She replied before cutting herself off as she watched Loona turn and wave her hand to the pony head that sat on the table as it turned to crystal and started to glow. "But… how?... you… you just combined two spells into one."

Loona facepalmed. Taking a scroll, she drew two lines and a dot on both sides of the paper. "Simple. The same way you can draw a line from one dot to the other without crossing more than one line."

Twilight looked at the paper. "I don't get it."

"You layer it." She explained, folding the paper along the lines making it look like there was only one line. "If each line is a spell. Then knowing how to put them together will allow you to put them together."

Twilight thought for a moment. "I see…" Blinking, she pulled out the spell Loona wrote and opened the forbidden book to the page the spell was on. "Wait… if that's the case. Then is it possible that there's hidden dark magic in these spells too? Dark magic that was hidden under the…"

"That's exactly why you need to understand the spell and what to change." Loona groaned as she started to get annoyed. "Changing one word changes the meaning."

Twilight thought for a moment and nodded. "I see." She sighed before writing a letter and rolling the two up and leaving a note to Spike. "Come on. I have the paperwork to allow you to look after Scootaloo until we get things taken care of… oh and I'd like to see the spell you want to cast before you use it."

Loona nodded and followed her out. "Sounds good to me."

Once outside, they were stopped by five mares and three fillies. "See!" Scootaloo cheared. "I told you guys she was real!"

Loona and Twilight looked at each other before sharing a sigh. If she was going to stay here and not draw too much suspicion. She'd need to play nice with these ponies. What might help is if they had something to help her unwind.

"I was just going to show Loona where the mayor is before bringing her to Scootaloo's home." Twilight explained. Seeing the unsure looks on her friends, Twilight rolled her eyes. "I get it. You don't think I should be so trusting. But I'm the princess of friendship, right? And we're trying to spread the message of friendship."

Her friends looked at each other and sighed before turning to her with a smile. "You have a point, dear." Rarity sighed.

"Sorry if it seemed like we don't trust your judgment, Twi." Applejack added sheepishly. "It's just… there's a lot of questions we have about her."

"I don't think hearing about where I'm from would be a good idea… especially around certain ponies." Loona mentioned glancing towards the CMC.

"Then how about telling us in private?" Rainbow suggested. Loona shrugged and nodded. "Great. Tomorrow while the kids are at school then?" Loona nodded again.

With a smile the girls nodded and left the two to their tasks.

Author's Note

This story may end up being one of those that's going to be a slow build up. But I may end up adding more drama from Helluva Boss. Or I might end up switching things up a bit. I don't know yet.

Chapter 4

One trip to town hall later, Twilight brought Loona over to Scootaloo's home. "We're all set." Twilight announced as they entered the house. "So… when you figure out how the dark magic works in the other spells. Let me know."

"I can probably do more than just fixing spells." Loona sighed.

"I believe you. But until Luna believes that you're not going to use dark magic against the subjects of Equestria. The only times you'll be permitted to use magic is under the supervision of the princesses or myself."

Loona sighed and sat on the couch. "So how am I going to prove that I'm not going to be taken over by dark magic?"

Twilight thought for a moment. "Well… that is a good question… if I knew more about where you come from. I might be able to come up with something to help."

Loona shrugged. "Hell."

"What?"

"I come from hell. I'm what you call a hellhound." Loona explained. "Not really the lowest level demon." She sighed, crossing her arms and looking away. "But we're still treated like pets at best."

Twilight sat and hung her head. "That sounds terrible."

Shrugging, she smirked. "It has its perks. Not many rules. Free drugs and cheap booze." Blinking, she turned to Twilight. "Speaking of which. What do you have to smoke or drink?"

"Hard cider is the most popular. And as for smoking… I can look into it." Twilight replied with a soft smile. "I'll tell the princesses about what you told me." Pulling out a scroll, she wrote down what Loona told her as well as her request.

"So… if I was to cast a spell for you. You'll lift the restriction?" Loona asked.

"Well… I can learn about how you cast spells and compare it to our known methods… even if I can't permit you to use dark magic. I should be able to let you use common spells…" Twilight muttered as her expression brightened with each thought. "I can see the range of magic you can cast."

Loona smiled and opened the dark magic book to a marked page. "I was hoping I could cast this spell… at least once."

Twilight looked it over. "Magic and body augmentation?... that's… I don't really know if that's dark magic or just forbidden…"

"Why would it be forbidden?"

"One, it's extremely complicated. Two, it's a runic spell. And three, it alters the body. It's up there with gender transformation in difficulty." Twilight gasped.

"Really?" Loona asked in shock. "This looks rather basic to me. All I need is some chalk and space to make the circle and the rest is easy."

Twilight tapped her chin in thought. "Who would you be doing it on?"

"Scootaloo. But I want it to be a surprise." Loona sighed.

Twilight blinked in shock before noticing how she said it and instantly calmed down. "Before I agree to this. I need to know why. Why do you want to cast this spell on her. And why you were so eager to agree to this arrangement."

Loona rubbed her arm nervously as she considered what to say. "You remember how I said my kind are treated like pets?"

"Yes."

"I… I was kept at a place you can consider an orphanage till someone adopted me." Loona admitted. Before Twilight was able to remark, she added. "It was more of a kennel than anything. I was kept there till I was adopted when I was close to becoming an adult."

Twilight gasped in shock. She didn't know what to say, but she quickly understood why Loona felt bad for Scootaloo. Thinking for a moment, she nodded. "I see… well. If her parents don't respond to the princess's summons… then I can fast track the adoption. If you would like to stay, that is."

Loona thought for a bit and smiled. "I don't see why not. I just have to find a job."

"For now. You can consider working with me on dark magic as your current job. We can see about a second job later if you want." Twilight explained before levitating a few items in the livingroom to make space. "Just make sure it's clean from dark magical influences."

"I'm a hellhound… from hell… even if some dark magic wasn't involved, I'm pretty sure this spell you put on me will see it as dark magic." Loona countered.

Twilight stopped and thought for a moment. "Good point… we should run a few tests before you can cast that spell." She agreed before turning and having some quills and scrolls appear. "If we're going to be ready before she gets out of school. We best get started."

Author's Note

Short chapter. But I hope I was able to pull off a nice set up for what is coming or might. Also I think I did the background for Loona well. If not, let me know. Anyway, I have a few ideas on what might happen with the mix of hell magic a Equestrian magic. This is going to be fun.