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Helluva Hookup - A fling with Death

Summary:

Loona went to a bar for some easy casual sex. She meets Death who just want´s to enjoy a drink after a long and slightly disappointing day.

Chapter 1: A fling with Death - part 1

Chapter Text

So I’ve watched The Last Wish recently…and just like so many I absolutely enjoyed the crap out of it.

I’ve also watched every episode of Helluva Boss and I really enjoyed that as well.

So here is the inevitable crossover featuring the hot ass canines from those two masterpieces.

Content Warning: There will be smut and bad language in this story.

Big thanks to Krai´kotak from our Discord for helping me with this!

 

Hope you enjoy!


Helluva Hookup – A fling with Death

“Can I get you anything else, girly?”  the bar-man asked the pretty and also rather lightly dressed young hellhound sitting by the counter. One leg crossed over the other, she was staring at the screen of her phone, almost angrily swiping through the lame-ass profiles on her lame-ass dating app.

“…nah” she waved it off, not even attempting to take her face off her screen, “I’m good, thanks.”

“Alright then” he answered, “Just call if you need anything.”

“Yeah, yeah…”

She truly looked a little lost in her current state. A mixture of frustration, anger, loneliness, possibly even regret shaped the expression on her face, an explosive and potentially really dangerous cocktail of emotions.

Now, finally being alone with her thoughts, she slowly but surely began to realise that it probably wasn’t just all the fault of her dad or her co-workers that her life felt so messed up at the moment. It was a great mix of different factors.

“Why don’t you come over to one of our hellhound-party’s sometime? My girlfriend throws a ton them and they get really crazy someti-“

“GIRLFRIEND?!”

Just that one word made her entire body shudder from the base of her tail all the way up to the tips of her ears. Thinking about the large handsome bouncer her dad’s rival-company employed almost got her shivering with excitement, but of course there had to be another bitch stealing him from her. Life just seemed so unfair sometimes.

“How hard can it be to find a fucking dog who’s willing to dick me down?”

Her right hand clenched around the almost empty glass of whiskey as her left one held onto her phone. She closed her eyes for a moment as the taste of alcohol ran down her throat when she emptied the glass.

In her lustful imagination, she was being lifted up and pressed against a wall, her tail wrapped around one of his legs while he gently sunk his teeth into her shoulder, slamming his hard length into her over and over again. She was fantasising about getting mercilessly pounded by a large and strong canine, this desire was plaguing her for quite some time already.

She opened her eyes again, taking a look around the bar, wondering if anyone had seen her daydreaming. Nobody seemed to be bothered, nobody even seemed to have noticed her being here.

She took a look down her body, still feeling quite comfortable and content with her looks. The dark blue top she wore was the favorite one in her wardrobe. She liked the star shaped cluster of strings that went up and around her neck, the airiness around her shoulders as it only really covered a small portion of her upper arms and also showed a lot of her well-defined torso. Her spiked leather necklace, the tight black shorts with the half-moon emblem, sleeve-gloves and stockings rounded off the rebellious teenage look. She didn’t really care if her dad thought it was too slutty or too arousing, maybe that was just exactly what she wanted to be.

A gust of wind crossed her fur when someone walked past behind her suddenly, they slightly stroked the tip of her tail but not on purpose as it seemed.

Taking a short look, she noticed it was someone wearing what looked like a black riding cloak with a build-in hood covering his head. He trotted towards one of the free barstools, it appeared the only one left was the one right next to her.

He slowly removed his hood from his head now, revealing his long wolfish snout, his white ears and his blood red, almost glowing eyes.

Something on his belt rattled when he took a seat next to her, it turned out to be two really sharp sickle-shaped blades. Being quite familiar with various different kinds of weaponry, the newly arrived guest certainly caught her attention for a moment. He looked mysterious, dangerous, maybe even somewhat scary to her, so he surely was more interesting than anyone else hanging around here.

When he rested his strong arms on the counter before him, Loona noticed that she still kept staring at him. There was something about him that got her excited, even though he very clearly wasn’t a hellhound and also quite a lot older than her, probably.

“Rico!” the bar-keeper greeted him casually, walking over towards him, “How’s business?”

Not even asking what he wanted, the imp grabbed a bottle and poured the wolf a drink, putting it in front of him with great confidence in having made a good choice.

The new guest wordlessly began drinking from the glass in a quite impressive pace, emptying it in one go before putting it back down onto the counter before him.

“As if that business is ever going to change” he then replied to the bar-keepers question, “People reach the end of their life-line, I’m the guy who shows up.”

Nodding silently, the bar-keeper swiftly grabbed his glass and gave him an immediate refill. The imp seemed a little intimidated by the wolf’s deep and raspy voice as well, it appeared this level of respect didn’t just come from anywhere.

The wolf didn’t down his drink in one go this time, he just pulled his glass a little closer and nodded contentedly.

“You look somewhat dissatisfied if I’m allowed to say” the bar-keeper mentioned carefully, “Something not going your way?”

He took his time answering that question once again, but he wasn’t too arrogant to do it.

“I guess I’ve gotten a little too excited about it this time. I was proven wrong about someone and there was no legitimate reason to kill him in the end.”

“Well…” the imp behind the bar told him, “Guess we all have days like these sometimes.”

The wolf just nodded, staring back down at his glass again.

The barman now just put the bottle down next to him so he could fill his glass back up himself if needed, then he left him alone to his thoughts for a moment, serving another customer further down the counter.

Loona kept watching him from time to time. Even though her own drink was empty and she already wanted to call the imp for a refill, the wolf’s presence somewhat stopped her from doing that right now, even thought that might have been a good way to gain his attention as well.

The next time she looked over, the quiet but high-pitched screech from a blade brushing against something got her attention. He now had one of his two sickle blades lying on the counter in front of him, inspecting it with strong but prudent paws. The wooden handle seemed to be somewhat damaged, it was cut off in a weird crooked angle, almost as if it had been cut by a sword or something of that nature. Then he put it away again, not being able to do much about the damage at the moment.

“First time you lost a fight?” she asked him quite plainly, trying to kickstart a conversation, not wanting to insult but maybe tease him a little bit about it.

The mostly white furred wolf slowly turned his head towards her, eyeing her from top to bottom. Then he chuckled dryly.

“I don’t lose fights.”

She was taken aback, looking back down at her empty glass for a moment. 

“Ah” she said, acting as if that had answered any further questions. It hadn’t, obviously, but her seat neighbour either had no intention of engaging in a conversation or he was trying to tease her as well. The latter seemed kinda unlikely to her.

“Can I have a re-fill, please?” she then asked the bar-keeper, not feeling like extending that conversation any further either if it was going like that. But it seemed like he still was rather busy and she wasn’t even sure if he heard her.

The wolf looked at her from time to time while she was waiting for her refill, it appeared her cocky and somewhat standoffish attitude amused him a bit. He’s met a lot of different people in his time, carrying a lot of different attitudes, fears, desires and fates.

It seemed like she wasn’t looking back at him anymore on purpose now, he deducted it either was her pride being hurt by him shutting her down like that or she was ashamed about starting a conversation in the first place. It might have been a combination of the two.

But what she did next he hadn’t expected. As the barkeeper had left him the entire bottle of whiskey earlier and it was still standing next to his glass on the counter, she now just shamelessly grabbed it and topped off her glass herself. It appeared she had expected him to be a gentleman and maybe offer it to her, the expression on her face was not entirely insightful. Be he fine with this or not, she really didn’t mind helping herself to his whiskey.

“Don’t take it personal, mi perra” he now sighed with a quiet chuckle, “Maybe I’m truly just a bit…dissatisfied.”

She now slowly turned her head towards him again, trying to look behind his façade.

“Did you just fucking call me a bitch in spanish?” she then asked dryly, putting the bottle back down onto the counter between them, “Did you just call me ´your bitch´?”

This just made him chuckle even more. He shook his head slightly, obviously not having meant it like that but knowing full well that no matter how he would try to save it now, this wouldn’t turn out in his favour.

“…is that what you would want me to call you?”

There was a moment of awkward silence as the imp running the bar now finally came over to fill up her glass like she had asked him to, only to find out that the problem had solved itself already. He soon noticed that they were good on drinks and left them to their conversation again.

“…so if you don’t lose fights” Loona asked, using her moral high-ground now, “…what could make you so ´dissatisfied´ then?”

“I don’t take pride or gratification in talking about my…profession. I’m sure you wouldn’t even want to know what-“

“I killed a lot of fucking people myself already. Spare me the bullshit, okay? I was just trying to make some friendly fucking conversation. Just tell me you’re not interested.”

It now was his turn to be taken aback. He raised his head a little bit, looking somewhat surprised indeed. He kept on watching her as she slowly turned her attention back to her glass, picked it up and took another small sip.

He wasn’t quite sure if he’d ever met someone with that kind of attitude before. She didn’t fear him for his appearance, she apparently hadn’t tried to start a conversation because of malicious intent either. Neither did she seem suicidal or even aware she was literally talking to death himself right now.

Usually, the only ones who were casually chatting with him were the bar-keepers, most of whom just knew him by his made-up name anyway. He occasionally enjoyed talking about anything else but his victim’s forfeit lives, but this bratty barely adult hellhound being interested in him surely felt somewhat different.

“…so please, I’m curious” he asked after a minute of silence, “What about my appearance made you feel like…starting a friendly conversation?”

She now looked at him once again, checking him out from top to bottom. Then she tilted her head a little bit, apparently not entirely sure if he was actually serious about that question.

“Do you honestly fucking believe I would go to a bar dressed like this if I was only here for a friendly fucking conversation? Are you like…a fifty years old virgin or something?”

This just made him chuckle even more, he wasn’t really able to help himself. The cockiness of that girl just had something joyous about it, it truly made him forget about everything else for a moment.

He now took another look at her as well, unashamed about closely inspecting every feature of her body. He could tell she really was trying to look appealing to the male gaze, and he also had to admit that it kinda worked out for her as well. The long voluminous hair complemented her slender but well-defined frame, her strong juicy thighs underlined her probably quite impressive physical abilities.

“So it’s flesh you’re craving?” he asked her in amusement, taking another content sip of his drink.

It appeared she yet again hadn’t expected what he just said to her, though she still was torn between feeling busted or straight up understood. She hadn’t been telling him that for no reason after all, so she couldn’t really blame him for making that assumption either.

“Well, I guess you at least don’t beat around the bush” she commented that dryly. He just shrugged his shoulders with a little chuckle.

She now turned the screen of her phone back on again, continuously swiping through the at best average profiles of her boring dating app, apparently signalling him that he had to try a little bit harder than that after all.

The wolf, not being all that bothered about her teasing, now took in a slightly more relaxed pose on his barstool, one foot resting against the counter, one hand holding onto his drink and the other one resting in his lap, waiting for anything else interesting to happen.

“Now I’m a tiny bit curious after all” he started the conversation again, “If killing people is just like daily business to you, how do you get up on earth?”

This made her think about it for a moment. She wasn’t really supposed to talk about the book, and she wasn’t all that interested in actually explaining it either. This was none of his business anyway.

“Well…how do you?” she asked back instead of answering.

“…Señorita Loona” he now sighed, straightening his pose a little bit, “I’m death himself. I get to whereever I need to be whenever I want to be. I was just coming back from a timeline many years before those were even invented.”

He pointed at her phone right now, she looked at it even though that was by far not the bit that confused her the most.

“How do you know my name?”

“I also know how old you are and the age you’ll be at the time of your death.”

She now slowly took her face out of her phone again.

“Yeesh…” she commented with a stale chuckle, “You surely know how to turn someone off.”

Yet again, he could just chuckle about what she said. She still didn’t really fear him, but at least she seemed to be somewhat respecting him now.

“Still up for some friendly conversation?” he asked with an amused smirk.

She took another slow sip from her drink, then she slowly turned towards him again.

“…does that mean you’re gonna come for me someday?” she asked with a slight chuckle.

“When your time has come, I’ll come for you.”

“So are you like…eternal or something?”

“I’ve seen a lot more than you could ever imagine.”

This was just what she needed.

“Well…everything apart from a vagina I guess.”

He just remained smiling a little about that statement of hers, she looked at him like someone would look at an innocent little school boy.

She truly wasn’t taking him as serious as she probably should right now, it was a feeling he indeed had rarely experienced before.

“…so when you’re like an eternal spirit or something…” she continued asking, now with newborn interest as it appeared, “When did your body stop ageing? I can’t really tell because of the tent you’re wearing, but you don’t look so much like a grandpa to me.”

The wolf didn’t really feel the need to answer that question either, he just kept on smiling in slight amusement about her attempt of bringing him out of his calm.

“…is that why you’ve been so defensive?” she continued with a dirty grin nevertheless, “You can’t get it up anymore?”

She just raised an eyebrow at him right now, it slowly but surely started getting on his nerves a little bit.

“This body served me well for a long time already. It’s a prison of flesh and bones, but I’m keeping it well, strong and healthy.”

“So have you ever listened to its needs and cravings? Like the touch of another body, the experience of love and passion?”

This barely legal hellhound slowly but surely pushed him into a corner he was struggling to get out of with her questions. Having shown her his cards, telling her who he really is, he had lost every little bit of authority to her as it seemed.

She obviously still was somewhat interested in him on a physical, maybe even emotional level, her continuous teasing didn’t leave much doubt about it.

To his great embarrassment, he couldn’t quite deny he was somewhat interested as well. The fact that she wasn’t scared of him, the fact that she was literally still laughing in the face of death, even after she found out who he was; it actually got him a little excited to get to know her better.

His drink now being empty again, and not having a reason to take another sip in order to pause the conversation, he found himself in a bit of a tight spot right now. He had a hard time staying classy and centered about this in the meanwhile.

“What sort of answer are you looking for exactly?”

“Is it really that fucking hard to understand?” she asked back, “I don’t think I could ask any clearer.”

“De nuevo, perra” he now lowly growled, “I’m literally who they call death.”

“The barkeeper called you a different name earlier.”

“That name exists so innocent people are not scared of me and I can enjoy a drink from time to time. As I was saying: As the spirit who brings people on the edge of their lifelines to hell, I’m not supposed to-“

“Supposed to?” she stopped him right there again, “What the fuck does that mean now?”

“I can’t…I…I mean…I’m not supposed to…“

“But…what the hell are you afraid of?” she asked while shaking her head in pure disbelief, “Would you get punished that badly for getting your fucking dick wet from time to time? Huh, Rico?”

He now for the first time felt the need to actually shake his head in this conversation. It was not as much as that he couldn’t answer her question, he found himself not wanting to do that. Her intentions really were clear at this point, and it also was clear that she still was totally on top of this conversation.

“Why are you having so much fun with this topic?” he now asked her instead, “What’s in it for you? Are you trying to bribe me, is it that? You know you won’t live any longer just because-”

“Come on dude” she now sighed deeply, shaking her head in great disbelief, “It’s not like I insulted you in any way, is it? I was just trying to tease you a little bit. Don’t be so salty now.”

She now slowly took another sip from her second glass, then she opened the app on her phone yet once again. There were no interesting matches for her, she knew that, but this conversation was just so frustrating in the meanwhile.

But it was not just her. Even though he hated to admit it, this actually was getting to him a little bit in the meanwhile. She still wasn’t taking him seriously, and she misinterpreted his words yet once again. He might as well could have asked her if she wanted to die right here and right now, and she probably still would just shrug her shoulders about it.

Not knowing where else to look right now, and not owning a phone to look into either, his gaze now first went back to his whiskey glass and then even a bit lower than that. He obviously wasn’t oblivious to his body’s needs and functions, but he also never really thought about giving up authority just for the sensation of physical pleasure.

He wasn’t sure if his appearance was what females would call attractive or sexy, but he knew he was not in a bad shape for a member of his species. Nobody had defeated him in a fight yet, nobody had been fast enough to outrun him for long either. He had all the functions of a regular wolf’s body, he had no doubt he could give her just what she wanted.

If he was totally honest with himself, he now actually was somewhat interested in what it would feel like. What the big deal was about that. Why he was so strangely attracted to that female hellhound after all and why it annoyed him so much that he couldn’t get back on top of this conversation with her again.

He kept on thinking about it for a while, having a few more quiet sips of whiskey every now and again, but then he suddenly knew what he needed to ask her.

“So…how come you have such a hard time finding someone who’s willing to share a few hours with you?”

“What?” she asked, apparently a little taken by surprise.

“I figure your appearance is not the problem. You’re moving your body with elegance and confidence. You’re well aware of your looks. So what is the problem?”

She stalled in her actions for a moment, it seemed that he had hit quite a sore spot with that statement. She couldn’t deny she was kinda desperate.

“…so…you think I’m attractive?”

“I mean…” he said, “You seem youthful and healthy, like the kind of person I walk past as I search for prey. Time has not struck you yet and won’t do so in a long time. You seem like the kind of woman young men would show off for, maybe even die trying to impress you, forcing me to pay a visit earlier than expected. …so yeah, I guess other living ones may find you attractive.”

She tried combining all that into a simpler, more on point package, it really seemed like a bunch of hollow words after all.

“So you’re saying I’m pretty with extra steps?” she asked plainly.

He sighed. “Si. If that’s what you want to hear, you’re pretty.”

She nodded slowly, still not being able to answer his earlier question though.

“So…?” he asked again after a little while. “Cuál es el problema?”

He could tell that this really got to her as well now. Her fur and body language expressed emotions of anger and frustration, most likely also self-pity and in-denial.

“Fuck! I don’t know, okay?” she almost yelled at him in great annoyance suddenly, “I don’t know why! All the guys seem to be afraid of me, and the ones who aren’t already have a girlfriend! And if even death is such a fucking pussy, it really does feel fucking hopeless!”

“Excuse me?” he now asked with a little bit of a growl himself.

“Oh did you not here me?” she snapped back, “I’m sorry. I called you a fucking pussy!”

She looked him right in the eyes during that statement, she noticed that his eyes were glowing even redder now, just like hers usually did. The greyish fur on his face started moving a little, making him look even scarier.

“I think you misunderstood my kindness for weakness” he explained, “Just to be clear with you, perra, I would have no problem showing you the ropes. I’d be careful with that big mouth of yours.”

She now quite vigorously planted her phone face down onto the counter before her, not taking her gaze off of him. She accidentally nudged her half empty glass of whiskey and a little bit spilled out and onto her hand in the process, but she didn’t care about that.

“Are you gonna fucking do it already or what?” she then asked him in the same teasing and growly voice. It appeared she had finally gotten him where she wanted, and she just needed to put in that one last drop to make the barrel overflow.

She raised one of her eyebrows a little bit while waiting for his reaction, it seemed like it was finally about to happen.

“Hmm” he now growled with a dark little chuckle, picking up his own half-full glass and emptying the rest in one go. “Lista para bailar con la Muerte Perrita?”

“What?” she asked, raising both her eyebrows now as he put the empty glass back down onto the counter. He licked over his lips and then looked her straight in the eyes again.

“Yes” he dryly answered her earlier question, “Let’s see if you still think like that when I’m done with you.”


I’m working on part 2 already, hope I get it finished soon. Gonna be steamy.

Tell me what you think, I’d be really glad about your feedback!

In the meantime, why don’t you say hi on Discord and join our joyful conversations, memes, artwork, smut-posts and everything else you can think off?

My handle is Furrwolf#8163 and I’ll personally invite you to the server! I promise you’ll be in good company ;)

 

See you soon for more!

~furr