Before I begin, I wanna ask that no one says anything about my other stories. I'll get to them, just be patient.

I have been watching Helluva Boss for a bit and I'm really loving Blitzo and co's adventure and I'm laughing my ass off, especially on the episode with the Agents and seeing what happened to those little angel… whatstheirfaces. I also love Pokemon… despite the fact that I pretty much dropped the series after Sun & Moon. And yes, I'm gonna be crossing over a child-friendly show with an adult show-this ain't the first time I've done this.

My username might say a little too much about what I write and how much I like writing fanfics with Ash and stuff. I just feel like Ash should become older and have some romance in his life… Yeah, I know there's Serena, but I love doing some crossover romance, so sue me. I'm not gonna run through, saying the backstory of Ash and all, and am gonna skip over that.

Ash had just gotten back home from his most recent journey and had decided to take a break from traveling for a while. After the whole ordeal that happened with Zygard and the fact that he immediately started a journey after going through Unova, he wanted to spend time home and tell his mother about his adventures.

I just wanna note that in this version of the story, Serena doesn't kiss Ash… I have nothing against Amourshipping, but there are so many fanfics of it.

Ash had awoken from bed after a good long rest. The sun was shining brightly through his window as he sighed, feeling refreshed. He got up and walked to his window seeing the bright blue sky, clouds passing by, even some Pidgeys were flying past without a care. He had no thoughts that today would go bad… and it won't… I said and it won't.

He looked back to his bed and found his buddy Pikachu still snoozing which put a smile on his face. After he had finished putting his clothes on, he heard a noise from downstairs. He looked at his door and saw some light from under it.

"Jeez, did I leave the TV on?" The boy says as he walked to the door while Pikachu woke up with a yawn and tiredly watched him exit the door.

Ash walked down the stairs while his yellow friend followed behind. As he had just reached down the stairs, he found that the light was not the TV, but what appeared to be from a gap in the ground before disappearing right as Pikachu got on his shoulder. That was what he saw first, then he stopped as he caught the sight of something else in the room.

That something was a birdlike creature that was standing on two legs, covered in black feathers with a feather-like tail about as tall as he was. The first thought that came to mind was that a Pokemon had appeared in his house. Except, last he remembered, he never saw a Pokemon dressed in a jacket or a beanie or even boots for that matter.

The Pokemon-looking being looked around the living room, not knowing of the other two's presence before sighing. "Stupid book. Where did I end up?" A feminine voice with an accent came from it as it took out a book and flipped through pages.

Ash and Pikachu looked righteously confused and had thoughts going through their heads. They didn't let go of the idea that what they were looking at was a Pokemon but it, or rather, she didn't look like how they would've expected a Pokemon to be, much less it was able to talk.

The boy started to approach the being who was grumbling while still flipping through the pages of the book. She turned to face his direction, taking a glance at his face while still flipping the pages before squeaking, almost dropping the book and hugging it tightly.

They both stared at each other completely wide-eyed, not moving a muscle. It was then that he finally got a look at her face. She had a white face with a matching-color beak, eyes consisting of red sclera, and bright white pupils that lacked irises. She also had hair matching the color of her feathers that partially covered her face.

Once again, the boy was wondering if he was actually seeing a Pokemon in human clothing, but he couldn't confirm it to be sure. Then a thought hit him. She did technically break into his house… however it seemed as though she didn't mean to… and then he realized that they were still staring at each other.

'S-Should I say something?' He thought to himself. He then stood up straight before looking to the side for a second. "Uh… hi?" He says while holding a hand up.

She just continued to stare at him for another couple of seconds before hesitantly holding her hand(Erm talons?) up as well. "H-Hi…" She says in a very nervous tone.

They stood and stared once more. Neither one of them spoke up, possibly waiting for the other to say something. The female 'Pokemon' then looked around again before she went back to flipping through pages, faster this time. She was taking slight glances back at him before back to the book and was starting to look a little distressed as she did so.

Ash started to feel a little bad for her and decided to finally say something. "Hey, are-"

"NO, NO, NO! This is not what-uh-y-you uh…" She interrupted while still flipping through pages. "T-this is uh-uh…" She says as she reached the end and started flipping to the other side. "This is a dream-Yeah, yeah. This is a-a-a weird dream. And you… y-you should go back to sleep."

"Woah, woah-" He started to say, but got talked over.

"I'll be out of your hair soon enough-Where is it?!" She says almost freaking out.

"Calm down! Stop!" He yelled as she stopped and stared at him once more. Seeing he finally got her attention, he stood up straight again and cleared his throat. "Okay, now, let me try again. Who are you and what are you doing here?"

"Uh…" The girl says before taking another moment to think about what she was to say next. "Well, I… I would say that you probably wouldn't believe me if I told you where I was from, but I have a feeling after already seeing me, you'll think otherwise."

"... O… kay?" The boy says, looking a bit puzzled.

"I'm gonna get the point. I'm from Hell."

Hearing that, Ash and Pikachu took a second to process what she just said. "... HUH/PI?!" They both practically shout.

"Okay, I know what you're thinking and before you do anything, I'm not gonna do anything to you… I don't know if I can do anything to you actually." She says with her hands up before looking back to the book. "I'll be gone in a second." She goes back to flipping pages.

"Uh… okay… b-but when you mean Hell, do you mean like actual Hell or-?"

"What do you think?"

"... Okay, so, you're not a Pokemon?"

"A what?" She says while looking at him.

"N-nothing never mind." He says as she went back to what she was doing.

She then stopped again and looked back at him. "... You're not going to… attack me or anything? Shoot me?" She asked.

That was a good question to him. Why didn't he attack her? She just admitted to being a demon in his house from HELL, where evil people go to. However, she wasn't doing anything to him and had yet to really do something to attack him or anything.

"Well, you're not attacking me right now so…" He says.

"Oh… right. It's just, not really the type of reaction people would have from learning there's a demon in their house."

"I mean, I've seen crazier."

"Pikachu." Pikachu says.

"Yeah, I guess." She says before she took notice of the yellow mouse on the boy's shoulder. "Is that a… Poke… Poke…" She says trying to remember what she heard.

"Pokemon." He asked as she nodded. "Yeah, he is… you don't have Pokemon in Hell?"

"I've never heard of that kind of creature before."

"... Really?"

"Well, I didn't go to Hell, I was born in it, so I wouldn't necessarily know what happens on Planet Earth."

"Planet Earth?"

She almost went back to the book before she realized what she was asked and once again looked back at him. "You know the planet we're on?"

"We just call this the Pokemon World."

"Pikachu." Pikachu also speaks up.

The bird girl once again had a moment to think. 'Is the information we had in the books outdated or something?'

"Um… okay, how about we get to know each other's names." Ash says, hoping to make things less awkward. "Nice to meet you, my name is Ash Ketchum." He says while holding his hand out.

He got the feeling that she had a thing for staring as she did it once again before hesitantly reaching out and shaking his hand. "Um… sure, whatever. Octavia." She says before looking at the mouse on his shoulder. "Does… that thing say anything else?"

"His name is Pikachu first of all. Second of all, not most Pokemon tend to do that."

"That's a little weird."

"Well, I can see how it could be weird."

"Right."

"So…" The boy thought for a second. "What are you doing here?"

"I just… I wasn't planning on coming here but… well…" She looked back to the book. "Oh, shit… what the fuck was I thinking?" She says as she turned away from him and lets out a frustrated groan. "So uh… a bit of a long story, but… the short version is that I used my dad's book without knowing what I was doing."

"Oh, I see."

"Yeah uh… I'm just gonna be going in a second."

"Already?"

Octavia once again looked at him, puzzled. "Did… did you want me to stay here?"

"I didn't say you couldn't. If you wanna leave, I'm not gonna stop you." He tells her as Pikachu spoke his name in agreement.

"Well… I guess… Now that I think about it, I don't really know where I am and all."

"Okay then. Make yourself at home. Want some cereal?"

"Umm… sure?"

"My mom is out at the moment, and I'm a little lazy this morning. You can just sit at the table if you want." The boy says while making his way to the kitchen.

"A-alright then." She says while going to the table.

While Octavia sat down, she began to wonder why she was being treated in such a way. She expected to be attacked or even shot if possible, but being treated like a normal house guest was not the first thing to come to mind, especially since she was a demon of all things. Did he just not believe that she was a demon or something? She pushed those thoughts aside and started going through the book she had once more.

Ash was in the kitchen with Pikachu and began to think to himself. He wanted to talk to Pikachu, but he didn't want her to hear make things awkward with her being in the room next to him. He wondered if what she had said was true about her being a demon and all. Being in a world of Pokemon, it would be hard to know what could be a 'demon' or not, but she seemed to be fine.

Still, he knew he was acting stupid, especially during such a situation, but even so, it was in his blood to be kind to someone he doesn't know no matter what. His partner understood him without needing any words to exchange.

Regardless he still got food ready. He chose cereal because as he said, he was a little lazy and didn't think that breakfast would need to be something that he'd need to cook on the stove or anything. When he was done he took the three bowls to the table. Placed Pikachu's food down first, hers then his.

"Bonappetit." He says as she stopped and placed the book down. "So, what's with the book?" He asked, wanting to start a conversation.

"This? It's how I got here to Ear… I mean… Po… Pokemon World? Is that right?" Octavia asked as he gave her a nod after taking a bite of his breakfast. "Yeah, well, it's how I got here. I basically used a spell and… yeah I'm here."

"Makes sense."

A few minutes went by as the three were still eating, not saying a word to each other. Ash did try to start some conversation, but Octavia shot him down with short and simple answers in an instant which clearly got him nowhere.

She seemed to notice the awkward tension and had reached into her pocket to take her phone and earbuds out, discovering that she had forgotten them back at her home. She sighed, knowing she had no way to ignore things like she always could've. She just continued eating before looking back at Pikachu.

Being of where she came from, anyone would probably mistake him for a cherub, though something about him seemed completely different from that of an angel. Sure, he wasn't human and didn't look like any normal animal, but if he was from heaven, he'd have wings and a halo above his head. At least from what she heard. Then she thought of something to talk about.

"Hey uh… if you don't mind me asking, could you tell me more about these Pokemon?" She asked the boy as his eyes lit up.

"If I don't mind? I would be glad to." Ash then says with a look of excitement in his eyes.

Guess she found something he liked. Something about asking him such seemed to spark a bit of innocence in his eyes. Ash then rushed to finish his food, almost choking before Pikachu quickly rushed over and jumped into his chest allowing him to swallow properly.

He caught his breath before thanking and placing Pikachu on the table and leaving to go upstairs. She took another bite as he rushed back down with his hat and some red and white ball and some red gaming device or something. He sat back down and placed his hat on his head.

'Does he really need that?' The bird girl thought to herself.

"Now sit back and let me tell you… Now normally the professor in my town would explain something like this, but I'm down to explain if I can." He tells her.

"Pika." The yellow Pokemon says with a smile of his own.

Knowing she'll probably be in for a long talk. "Now, allow me to explain about Pokemon-" About an hour of explaining to her. "And that's what Pokemon are." Ash finished as he held up his Pokeball and Pokedex.

"Pika, Pikachu!" Pikachu cheered.

Octavia stared at him, blinking before finding words. "So… if I'm hearing right… you guys put these super-powered animals in these tiny balls… and force them to fight each other?"

Hearing that, the other two had dumbstruck looks on their faces. "... Uh…" Ash says trying to find his words. "Well… that's a bit of a harsh way to put it."

"Am I wrong? It sounds like that's exactly what you do here."

"No-no-no, that's not… uh… y-you see, Pokemon actually like fighting. It's like a sport for them."

"Fighting to the death is a sport? Sounds no different from places in my home."

"No, it's not for to the death. It's just… until one is unable to battle."

"Like, until they need to go to the hospital?"

"What? No! Not even close to that. It's just like friendly competition and all." The boy then goes through his Pokedex. "Look, see? This Pokemon is known as Machamp." He showed her. "They're a Fighting Type Pokemon and a couple of wild Machamps fight with each other."

She stared at the image of the four-armed Pokemon and thought for a second. "... So… like wrestling or something?" He stared for a second before sighing. "Hey, I'm trying to understand, okay?" She then says annoyed.

"It's fine, I don't blame you. Just… I uh… well…" He groaned before scratching his head, thinking. "Ya know what, it's better that I show you rather than tell you. Give me a second." He then goes to the TV and through the shelf of DVDs, mumbling to himself.

Octavia watched him do this, wondering what he was about to show her though didn't seem to care much. She looked back to Pikachu, who noticed and hopped towards her. They stared at each other without making a sound. She just stared, not knowing what she should do at this moment.

She reached her hand out hesitantly as he leaned back a bit, concerned about her talon-like fingers at first. She then slowly put her hand on his head, being careful of her claws as she started rubbing. Pikachu seemed to like this as he cooed and rubbed back against her to which she did find cute. It felt a little weird since they were both technically animals, but she didn't think too much about it. The corners of her lips seemed to curl up a bit before-

"Found it!" Ash called as she stopped and shook her head, returning to her frown. "Hey, I got it ready if you want." She got up and walked over to the couch, sitting on it as he loaded a DVD. "Alright, I'm gonna show you an example of a proper Pokemon battle."

He stood up and walked over to the couch with the remote and sat next to her. He wasn't right next to her, but she still scooted away from him which he showed a bit of annoyance towards, to which he shrugged and turned on the tv.

After watching the battle end, the boy paused the video and looked towards the bird girl. "So, what do you think?" He asked.

She looked back at him. "... I… am surprised that no one died?" She says with her lower eyelids up, not knowing how to respond.

"... Okay, but what do you think?"

"... I guess I can see why it's fun?" She still didn't have any idea of what to say. "... Since I guess you could get bored in a world where everyone has superpowers or something."

Ash looks at her again, thinking his next words. "Okay, that's… something."

"Is that… all they do?"

"Well no, that's not all that Pokemon do. People treat them like they're a part of their family and some even help people out of situations."

"Okay, I think I understand… for the most part."

"Sorry, it took so long."

"It's fine. Honestly, listening to you talk is the most entertainment I've had in a while honestly."

"Right." Ash says before he starts to think again. "So, why are you here?"

"I already told you, I didn't know where I was going since I've never been here before."

"Right, but that's how you got here. I kinda wanna know why you're here in the first place."

"Oh, right. Well…" Octavia then begins to think herself. "It's a bit hard to explain… but I basically was just looking for a reason to get away from my house cause my parents were fighting."

"I see… wait you just leave Hell whenever your parents are arguing?"

"Did I ask for your opinion?" He was immediately taken aback by her sudden harshness. "Sorry." She calmed down.

"No, it's fine. Again can't blame ya."

"Why? What do you do when your parents fight?"

Hearing that Ash looked a little nervous. Pikachu saw and felt bad for him. "Um… I… just live with my mom."

"Oh, well, lucky you."

'Lucky me?'

"But yeah, my dad's Grimore is how I got here. I'll show you the spell if you want." She then starts going through the book she showed him. "If I can find the damn page. Here it is." She then shows him a page with a Pentagram on it. "See, all need to do-Wait…" She then looked at the page. "What the…?" She says as the boy and his Pokemon look puzzled. "Oh, fuck." She says before turning to just the other page which had a similar shape, but slightly different. "Ahh… SHIT!" She then yelled before groaning as she covered her face.

"What happened?"

"I ju-I-DH… I drew the wrong fucking shape." She says while gesturing to the other shape. "I was supposed to draw this-" She pointed to the Pentagram. "But I accidentally drew this one." She then pointed towards the more similar-looking shape. I'm too lazy to come up with an actual shape.

"So, you weren't planning to come to this planet?"

"No, apparently not… Wait…" She then thought to herself before groaning once more. "Ugh, I didn't even go to Earth, to begin with. I'm so fucking stupid!"

"O-okay uh… c-can we tone it down with the swearing please." Ash asked her as she glared at him. "... Okay, sorry."

"I just… I have no idea why I did this."

"Maybe it's because you were still tired or something?"

"... Ya know, now that I think about it, I guess losing sleep in the morning can do that."

"Was their arguing that bad?"

"I could go on about what a pain it is."

"Sounds rough."

"No kidding." The bird girl then looked at the time. "Shit, I should probably get back before they notice that I'm gone. Do you have some chalk I can use for the symbol?"

"I mean, I think chalk is a pretty old thing here."

"Okay, anything else? A pencil's not gonna cut it."

(Later)

"You sure this'll work?" Ash asked after handing her a marker.

"If this does, then the symbol should be gone by the time the portal closes." Octavia tells him before she starts to draw the symbol on his bedroom wall making sure it was the right one this time. She stops for a second before looking down. "Hey, Ash, right?" She says while looking at him. "Ya know, you're pretty cool. Would you mind if I… I don't know, come back here… just to hang or something?"

The boy thought for a second. "I mean, I don't see why not. You're free to come whenever you want. Just be careful not to show up when my mom is around."

"I'll try not to." She says before finishing the symbol. The symbol began to glow and then created a rift that showed a bedroom and the sounds of a woman screaming in anger along with crashing was heard. "Oh joy."

"Geez." Ash says while rubbing the back of his head.

"So… until we meet again, I guess?" Octavia says while looking at him.

"Yeah, till we see each other again." He says with a smile and thumbs up.

She didn't know how to respond to that and walked through the portal before giving a small wave. The moment he waved back, the portal closed and as she said, it was gone without a trace. The boy felt bad after what he was told about her and while it did seem like they would eventually become friends, he wished that he could've met on her better terms.

The boy looked at his partner, Pikachu. "What do you think of her, Pikachu?"

"Pi, Pika." The yellow Pokemon says with a smile.

"Yeah, she does seem pretty nice."

Octavia was of course back at home, currently putting in headphones to finally use her phone to ignore the drama at her home. She was annoyed but after her encounter with that human, her morning was made more tolerable… if not even the slightest. Something about his attitude towards her seemed to make her feel… better than she normally had.

His genuine smile when greeting her even knowing full-well that she was a demon, the spark of innocence and excitement in his eyes when asked to talk about Pokemon, it seemed to brighten up her morning until her home drama ultimately and inevitably put a damper on it. But she could deal with it for now and she did like what little time she had spent with him.

'Maybe I could at least go visit him once more.' She thought before she heard the sound of a pot shattering and sighed.

To be continued...

I could've gone with a few girls for Ash. Millie is a no-go, I love the M&Ms couple and I don't want to cuck Moxxie. Verosika was mostly considered, but not like one that people would really consider. Loona might be the most obvious choice for such, but I decided otherwise. I went with Octavia because… okay, because I've seen some crappy fanart, but that's beside the point.

I also think Octavia should get some more screen time as well and want to see more of her. Of course, I'm gonna continue this.