A Hellhound of a Good Time: An Erotic “Helluva Boss” Fanfic
Given how I have quite the crush of sorts on the character of Loona from “Helluva Boss”, this sort of thing was inevitable lol.
When a man named Tristan comes face to face with a certain surly anthro hellhound, what does he do? Why, fuck her, of course!
Be sure to comment and make what you thought of it known (creepy ones welcome lol).
The character of Loona is owned by Vivziepop.
Tristan slowly made his way downstairs after a sudden noise had woken him. All he knew was that he heard his refrigerator door opening and what sounded like various containers and bottles being thrown about. But yeah, sure, just get out of bed in just your boxers and investigate the creepy situation. Just who could be raiding his fridge this late at night? It was just the young man here, and only he and close family had keys to his house. What, did his brother suddenly decide to stop by and was out of food or drink? But as he crept into the kitchen doorway to see the culprit, he saw that it was definitely not his brother. Her eyes were closed as she gulped down the expensive vodka he had stowed at the back of the fridge. The first thing he noticed was that she wasn’t even human. She looked more like a black and white anthropomorphic wolf or dog. Unlike your average wolf or dog, she wore clothing, in this case being an all-black crop top with pentagram-shaped strings, torn black shorts, long fingerless black gloves, and black stockings that ended above bare paws. A black spiked choker adorned her neck. Long silver hair cascaded from the top of her head. An equally long and bushy black tail wagged lazily behind her. And despite her distinctly nonhuman appearance… she was fucking hot. But she also did somehow break into his home and raid his fridge for booze in the middle of the night, so he had to see about setting things straight.
“Excuse me,” said Tristan rather roughly. “I was saving that!” The canine opened her eyes, revealing startling red sclera and white irises, and looked at the human with what seemed to be a bored expression.
“Tough shit, man,” she said in a rather hot-sounding voice. “Are you Tristan Porter?”
“Yeah?” he said, turning on the light. He was starting to get a little bit afraid as he looked at the pile of trashed tupperware, various food, and broken beer bottles on the other side of the room, to which the canine girl added the now empty vodka bottle. How did she know his name?
“Good. Because I’ve got to kill you.”
“Kill me!?” asked Tristan. Yep, definitely afraid now.
“Remember that guy you snitched on for that vehicular manslaughter with a semi?”
“Yeah, he got the death penalty.” said Tristan. He questioned just why he was conversing with someone who wanted him dead. Was he going crazy?
“Well, he ended up in Hell and called the organization I work for to put a hit on you. I don’t normally do these kinds of jobs, but I was the only one available. I planned on just smothering you with a pillow until you suffocated, but it looks like things are going to have to get messy.” With that, she grabbed a nearby chef’s knife and walked toward Tristan, who backed up in a panic, sweat dripping from his head and heart beating rapidly. He couldn’t die, not now! And how the hell would he know that that guy would send an assassin from… well, Hell? When he felt the wall at his back, he resorted to pitiful begging.
“Please, there has to be some kind of explanation for this! I’ve got so much to live for! Let me go, I’ll do anything!”
The canine woman stopped just as she raised the knife. She wore a perplexed expression that quickly turned into something Tristan couldn’t describe. It looked almost like amusement or something.
“Anything?” she asked, setting down the knife. Tristan was starting to regret saying that as she bored into him with those red and white eyes of hers.
“Yeah?” he said again. Upon closer inspection, her face seemed to be a bit… amorous. Tristan wasn’t sure if he should be scared or turned on.
“The name’s Loona. Yours?”
“Tristan.”
“Cute. Now that we know each other, bedroom. Now.”
***
“I’ve been feeling really fucking horny the past few days with no actual dick available to satisfy it. I’m going to fuck you till I’m satisfied. Got that?”
“Yeah.” said Tristan, still feeling rather conflicted about whether to dive right in or run for the hills.
“Good. Now strip down and let me see what I’m dealing with,” Not wanting to potentially anger the one who was sent to kill him, he quickly removed his boxers… and the sight of Little Tristan made Loona stifle attempts at laughter. “Oh, sweet merciful Lucifer, I’ve seen bigger cocks on women where I come from!”
“Well it’s not exactly at full size yet!” said Tristan indignantly, blushing hotly as embarrassment spread throughout his body.
“Then make it full size!” commanded Loona, narrowing her eyes as she poked at Tristan’s chest.
“I try to at least once a week,” said Tristan. “But I just can’t seem to get hard.”
“Fucking hell, I’ve got to do everything my-fucking-self, don’t I?” Loona shoved the human onto the bed and raised a hindpaw, stepping rather roughly onto his flaccid penis.
“Ouch.” complained Tristan, embarrassment quickly turning to pain.
“Oh, suck it up, you little bitch,” she scoffed as she began to rub her paw up and down his cock, which to the surprise of them both, slowly began to harden. “Christ on a stick, you’re actually getting hard from this? You’re a fucking freak!” Tristan could only blush and groan as Loona mocked him, but the embarrassment and pain she brought him had since turned into pleasure. The feeling of her soft paw pads and the fur between them brought him to full mast in no time. Apparently he was into paws. Go figure.
“Alright, now that you’re nice and hard, let’s get to the fun part…” said Loona in a tone of voice that again simultaneously scared and aroused Tristan.
Kneeling down, she inspected the human’s penis, which had naturally grown upon hardening. He was actually a bit of an impressive length… for a human. She took a tentative lick at the tip, earning a gasp from Tristan as he tensed and gripped the bedsheets tightly. He was truthfully a bit scared of having an anthropomorphic hellhound’s teeth so close to his member… okay, a lot scared. Loona must’ve sensed or smelled his fear, because she gripped his penis tightly in one hand and leaned in close to Tristan’s face.
“If you even think of moving, I’ll bite your fucking dick off,” she hissed. “Got it?”
“Got it,” squeaked Tristan as Loona smiled devilishly. She rapidly turned her head to the side and opened her jaws with a snarl, teeth even closer than an inch to his dick. “I didn’t move!” shouted Tristan, fearing that this hellhound had gone back on her word.
“Oh, quit your fucking whining! It was just a little joke,” sighed Loona. “Man up for Lucifer’s sake. I’m going to take you balls deep in my mouth now.”
“What!?” asked Tristan, his heart beating faster than ever before. Should he have mentioned he’d never done anything with another woman before?
“What I just say?” asked Loona back, fire in her eyes.
“Man up?”
“Good to see you listen.” said Loona before she took his cock into her maw and thrust her head downwards. Indeed, Tristan’s balls nuzzled against her chin as the entire cock was thrust into her mouth. Sweet Lucifer, it felt so fucking good to finally have a dick inside her after so long. If Loona was being honest, he was bigger than he looked. He wasn’t the biggest one she’d had, but a modest specimen nonetheless. She savored the feeling for a few more seconds, closing her eyes as she moaned and lapped at Tristan’s balls with her canine tongue. Once she was finished with her savoring session, she slowly drew her head up with a wet slurp, popping off the cock with a small gasp for air. Upon looking at Tristan, she found that he was practically catatonic from the sheer pleasure of it.
“Hey, snap out of it,” she growled as she flicked his forehead, bringing him back to reality. Tristan couldn’t believe how good that felt. And this was just the foreplay? “Just warn me when you’re about to cum. I don’t want any getting on my clothes or fur.” And with that, Loona again took Tristan’s cock into her mouth and began to bob her head up and down, causing the human to moan and pant in absolute ecstasy. If a simple blowjob managed to make him feel this way, how the hell was the main event going to go? He wondered if he’d even be able to last long… something that was very quickly becoming evident as he already felt his orgasm approaching. The hellhound’s hot, wet mouth was proving to be too much for his feeble human body. A life so far devoid of any intimacy between another woman had taken its toll on him, and he decided to make his warning known as the pressure in his loins only increased. Spurts of salty precum landed on Loona’s tongue, the hellhound loving the taste and texture as they flowed down her throat.
“Loona, I’m gonna cum!” he grunted before Loona quickly removed her mouth from his dick.
“Already!? I don’t fucking think so!” she snarled as he wrapped her fingers around his throbbing dick and squeezed hard. Tristan groaned in a combination of pleasure and pain as his penis throbbed and throbbed, wanting to expel its cum but couldn’t. The pressure slowly died down as Tristan panted heavily, feeling as though he’d just ran a hundred yard dash all-out.
“Pathetic,” growled Loona, releasing her grip on his penis. “Figures the one human I decide to fuck is a one-pump chump. But no matter,” said Loona with a lustful, fang-baring grin as she began taking her top off, revealing a pair of white-furred breasts, around C-cup size, with black nipples poking out from the centers. She did the same with her shorts, then black panties. Tristan stared at her human-like pussy, which was already quite wet, if only from anticipation of the sex that would ensue. “Because I’m gonna take my sweet-ass time…”
Tristan still couldn’t believe what was happening as she crawled onto the bed and knelt over him, their sexes lined up and mere inches apart. Given her penchant for mocking him, what would she say if he mentioned he was still a virgin? More ridicule? Still, it was certainly better than having one’s dick chewed off.
“I should probably mention I’ve never actually been with a woman before. Like, at all.” he said. Loona gave him a devious smirk as she loomed over him with her hand-paws on his chest, her red and white eyes softening just a little bit.
“Then it’s a good thing you won’t die a virgin.” said Loona in a voice that Tristan could’ve sworn was one of sincerity. Before he could thank her for the comment, Loona dropped her hips roughly, impaling herself on Tristan’s cock. It took almost all of Tristan’s willpower not to immediately cum, gritting his teeth and gripping the sheets tightly in an effort to focus. Loona ground her hips in circles as she moaned quietly before beginning to slowly bounce on his hips. Tristan looked up at the hellhound, looking at how her breasts bounced each time the raised and lowered herself. Looking at how her eyes were closed to focus entirely on the blissful pleasure she was no doubt feeling. Looking at how she actually was smiling, at least a little bit. Tristan figured such an expression was unimaginable for such a surly creature. Maybe underneath that tough exterior was really a big softy? Still, he wouldn’t bet on it, seeing as though she was someone who was literally from Hell. Loona actually was feeling some slight regret about having to eventually kill this guy, but she decided to focus on the sex for now. The hit could wait…
After a while, Loona felt her long awaited orgasm coming.
“Hey, I’m close,” she moaned. “Brace yourself if you don’t want your hips and shoulders broken.”
“What?” asked Tristan before Loona roughly grabbed onto his shoulders and pounded onto his hips hard and fast, almost painfully so… Alright, in actuality, it was quite painful. Tristan’s cock rammed against Loona’s cervix as she rode him hard, causing her to scream out loud in pleasure.
“Fuck yes! That’s the stuff!” she cried, her claws drawing a few drops of blood where they punctured the skin on Tristan’s shoulders. He grit his teeth and bore the pain. It’d be worth it to cum inside this awesome woman… however nonhuman she was.
“Loona, you’re so-” he started.
“So what? Beautiful? Amazing? Cut the lovey-dovey shit and cum! Come on, I know you fucking want to! Cum inside my hellhound cunt! Fill me up!” Without being forced to hold back, Tristen fired load after load of semen into Loona’s pussy. The thick, white fluid splashed against her vaginal walls and cervix, which contracted hard as Loona herself came with an orgasmic scream, squirting a flood of her femcum and soaking Tristan’s hips and sheets.
Once they came down from their sexual highs, Loona raised herself up from Tristan’s spent cock, causing a small flood of cum to leak out of her pussy, making a hot, sticky mess of Tristan’s hips and bed. The two of them looked at each other, exchanging lustful expressions.
“That was quite the fucking,” said Loona. “So thank you for that.”
“You’re welcome, Loona.” said Tristan as he reached up to scratch behind the hellhound’s ears.
“Touch me and the hand’s coming off,” growled Loona as Tristan quickly pulled his hand back with a fearful expression. “Anyway, I’ve got good news and I’ve got bad news.”
“I’m sorry, what?” asked Tristan, confusion and fear spreading throughout his mind and body.
“The good news is,” said Loona as she began to put her clothes back on. “I’m not gonna kill you now. The bad news is… I’ve got syphilis. Like, super syphilis from Hell. That should ensure the hit goes through. See you later, one-pump chump.” And with that, a flaming portal appearing in the floor behind her. She walked backwards into it with a flick of her middle finger at Tristan. He was now all alone, faced with the revelation of having just contracted a supernatural S.T.I. from a sexy hellhound hitwoman that would eventually kill him.
“FUCK YOU TOO, YOU FUCKING BITCH!!!” he shouted at the floor as he flipped it off.