#helluvabossalessio

Fandom: HelluvaBoss

Pairing: Crimson/Alessio

Rating: T

Crimson pushed open the large ornate door to his bedroom giving an irritated sigh as he entered the dark room. Running a crime syndicate wasn’t all it was chocked up to be, his work had gone long into the evening leaving Crim longing for a good night’s rest, trudging to his closet the imp shrugged off his suit jacket which he promptly hung up when a subtle clicking noise caught his attention. Crim turned to stare into the darkness across the room behind him, squinting suspiciously before kneeling to pull a small pistol from his ankle holster. Cautiously Crimson proceeded into the blackness only to feel a hand wrap around his throat from behind followed by another wrapping around the wrist of the hand he had holding his pistol, violently twisting it till Crim was forced to drop the gun. Crimson gave a strangled yelp fading into a hiss as he clawed at the hand around his throat with his free one before being forced to his knees by a harsh kick to the backs of them. As both his arms were easily yanked behind his back by two powerful hands from the blackness emerged a stocky hellhound with a bulldog face and upon looking behind him, Crim could see another hellhound this one with a wolfish face.

“Get the fuck off me!” Crimson demanded struggling against the hounds grasp around his wrists.

“Nah-uh, you’re coming with us,” The stocky bulldog stated, prompting the wolfish hound to shift to holding Crim’s arms with one hand while wrapping some kind of fabric around crimson’s mouth and nose. Crimson could smell something sweet on the fabric as he struggled harder to get loose only to feel his mind getting foggy.

Suddenly the wolfish hound released a harsh yelp, both hands disappearing from Crim allowing him to move freely unfortunately whatever he’d been exposed too made him sluggish. Crawling off to the side a bit the imp could make out the familiar form of Alessio silhouetted in the light filtering in from the hallway. Alessio had heard crimson’s conversation from the hallway thus he’d entered the room to investigate where he discovered Crim being held by a hound prompting him to attack, using his thick tail to shove the hell hound off Crimson.

“Crim!” Alessio exclaimed seeing crimson leaning against the wall by the hallway door barely conscious however that momentary distraction cost the shark greatly. The bulldog hound managed to come up behind Ale, surprising the shark with a pistol whip across the back of his head sending him to the ground.

“Grab the fucking imp and let’s get out of here,” The wolfish hound demanded of the bulldog.

“Right,” The bulldog agreed walking over to Crim, punching him once across the face promptly knocking him out before snatching him up.

“C-Crim…” Alessio trailed off as his vision faded to black watching the two hounds make off with his boss.

 …

 Crim started getting his vision back what he could only assume was hours later giving a soft groan in response to his aching head. Looking around briefly it appeared he was in a dark room with cement walls, a basement perhaps or…a warehouse? Either way it wasn’t an ideal situation. Moments later a door creaked open opposite of where Crimson was allowing a sliver of light to illuminate the small square room along with the chair Crim was currently tied too. Casually wiggling a little Crimson determined his hands were tied behind the chair and his legs were tied to the chair legs, his tail was tied to itself in a loop. The two hounds from before entered the room leaving the door open behind them.

“Well, look who’s finally awake,” The wolfish hound growled.

“Unfortunately, now I gotta stare at your stupid mug,” Crimson retorted.

“You might think your funny now but just wait till we sell you off to the highest bidder,” The bulldog hound shot back.

“Yeah, you’re one of the most wanted in all of Greed. The money we’re about to make off you is gonna be a fortune,” The wolfish hound added with a smirking grin.

“Whatever, I’ll have yer pelts on my floor before the end of the evening,” Crimson growled back.

“Ha! As if!” The wolfish hound barked, delivering a hard punch to crimson’s face making the imp groan in pain.

“You’d do well to just shut your face,” The bulldog hound advised.

“Never been great at that,” Crimson chuckled, spiting out a bit of blood to the floor.

“Oh, you’ll learn,” The wolfish hound chimed in delivering another punch this time to crimson’s side making the imp double over with a sharp inhale.

“My late wife couldn’t…get me ta shut up…what makes you think you can?” Crimson shot back, trying to catch his breath.

“I think you’ll find us far more persuasive than your late wife,” The bulldog hound growled lowly inches away from crimson’s face, one hand yanking crimson’s head backwards by his hair followed by raking his claws across one of the imp’s thighs causing him to scream out in pain.

“You mother fuckers!” Crim screamed out right before the wolfish hound slashed his claws across Crim’s chest.

 …meanwhile…

 Ale regained consciousness with only one thing on his mind, finding Crimson. Staggering to his feet the shark immediately left the mansion in pursuit of the hounds that had made off with his boss. Ale was always good at tracking that’s one of the many reasons Crim made him the right hand. Morning was just starting to break over the Greed horizon when he arrived at an abandoned business building on the cusp of the city. Clambering out of the vehicle he'd taken Ale armed himself with a revolver before heading into the building, surprised that not only was the door wide open but there was no one in sight. Opting for caution Ale slowly made his way through the abandoned business when he heard the familiar cackling of the two hounds coming from what the shark assumed used to be a main office. Hiding around the corner Alessio listened in on the conversation being had between the two hell hounds.

 "Glad we finally got that ass to shut the fuck up," The bulldog hound snarked.

 "Yeah, I was getting tired of his mouth," The wolfish one agreed.

 "We'll let him stew in the basement for a while then go back," The bulldog continued.

 "Doesn't matter he'll be sold off in less then 48 hours," The wolf snickered.

 "True," The bulldog agreed. 

 Ale snarled although now he had his answer there was no need to be gentle with these two. Taking one final glance Ale determined where the hounds were sitting and flung himself around the corner, firing four shots in total. Two hit the wolfish hound while two more hit the bulldog before either knew what happened, with the hounds taken care of Ale proceeded to the basement where a massive safe took up the one wall. The safe door was slightly ajar allowing Ale easy access however upon slipping inside the dim yellow light from outside illuminated what lay within forcing Alessio to take a moment to compose himself. Crim was still tied to the chair except he was slumped forwards now, black blood soaking his clothes or what was left of them before dripping onto the floor where it pooled around the chair. Claw marks had torn his clothes leaving glaring deep gashes in his flesh. 

 "Crim!" Ale exclaimed once his brain managed to refocus. Running over to his boss Ale knelt in front of the imp, quickly untying the ropes holding him allowing Crimson's body to fall against his own. Gently Alessio lifted Crim, holding him against his chest. 

 "Ugh...took Ya long enough...Ya fucking gal lute," Crimson weakly groused out barely coming back to consciousness. 

 "Sorry sir, I'll get you home," Ale stated trying desperately to hide the concern in his voice although he didn't need to as Crimson passed out again almost instantly. 

 ...Later that evening...

 If he was being honest Crimson was getting tired of opening his eyes to darkness however at least things were familiar this time. Vaguely the imp could make out the familiar shapes of his own bedroom as well as the familiar feeling of his bed underneath him. Shifting Crim made a move to sit up only to be met by sharp throbbing agony in his chest area and sides eliciting an unintentional yelp from the imp.

 "Crim? Please lay back down!" Ale's voice came from a lit corner of the room where an armchair was. The shark hurried to Crimson's side where he gently eased him back into a laying position. Crimson got a glance of his torso revealing bloody bandages wrapped around most of it and what little skin was visible had deep purple bruising.

 “Quit your fussing Ale, I’m not some fragile dame,” Crimson growled with a wince.

 “Forgive me sir, that is not what I meant to imply. You were injured badly by those two hounds I simply didn’t want you to reopen the wounds,” Alessio explained, placing another pillow behind Crimson to help him slightly sit up.

 “Well next time think a little more carefully before opening your mouth,” Crimson retorted irritably.

 “Of course, can I get you anything?” Alessio wondered with a small head nod.

 “Black coffee and my black book, I’ve got some calls to make,” Crimson stated simply.

 “Right away,” Alessio confirmed, heading out of the room to do as asked.

 Crimson had far worse in his day, this wasn’t anything too get excited over at least in his mind although Ale apparently saw it differently as he continued to fuss over the imp. Crim couldn’t understand it but as long as Ale didn’t annoy him too much it didn’t really make any difference although he was curious. Ale was gingerly changing the bandages on Crim’s torso as the imp sat on the edge of the bed, a few days had passed meaning the claw marks were already starting to heal although they were still deep.

 “You’ve been quite dutiful these last few days, if you’re lookin’ for a pay raise it ain’t gonna happen,” Crimson joked.

 “That’s not why,” Ale retorted in his usual stoic way.

 “Then why?” Crimson pushed out of curiosity.

 “Simple, it’s my job,” Ale continued.

 “Humph, shoulda guessed, you’re a workaholic,” Crimson smirked with a small chuckle.

Inspired by a post by Codie on X

Fandom: HelluvaBoss

Rating: M

Pairing: Criminale

Crimson hated when things interrupted his usual schedule a fact everyone knew well hence why many gave the mob boss his space however sometimes it wasn’t a person who interrupted his time. Crimson sat at his massive oak desk in the library casually doing his usual paperwork when he felt the tell-tale signs of his rut starting to creep their way up his spine. Crim irritably growled to himself because of course on the night he had a stack of papers to attend too this would happen luckily Alessio walked through the large double doors to the library just as Crimson was about to pick up the phone to summon him.

“Ale, I require something of you,” Crimson declared catching the shark off guard for a moment before he obediently approached the don’s desk.

“Go to my bedroom and strip down,” Crimson bluntly ordered once again eliciting a surprised look from Ale.

“Um…yes sir,” The answer came with a hint of a question.

“I’m in rut and you know what that means…now go get ready, I’ll be up in a moment,” Crimson elaborated having picked up on Alessio’s slightly confused tone.

“Ah, yes sir, I’ll go now,” Ale obediently stated heading back out the double doors he’d come through moments before.

Now to anyone else this interaction might have seemed strange however to the duo it wasn’t anything new, Crimson had started going into rut regularly after marrying his late wife unfortunately after her…disappearance, he’d not stopped having his regular ruts meaning he needed an outlet. Ale had been the only one Crimson trusted in the slightest, although he wasn’t pleased with having to fuck a guy it was the best option considering getting even a stripper was dangerous now a days. Crimson had dealt with the concept after all it was simply to satisfy an ich once every few months, making Ale no more then a sex doll to Crimson in those moments at least in his mind.

Ale did as he was told heading to the don’s private room where he made certain the door was shut before stripping down. Ale would always be there for anything Crimson needed, ANYTHING, he wasn’t ashamed nor hurt by the fact Crim used him to pleasure himself during his ruts as far as Alessio was concerned this was just another part of his job. A long time ago when he was still foolish, he’d hoped for more from Crim however after years of serving under the don he’d learned better than to hope for anything more then what was already here, speaking of learning Ale had also learnt that Crim didn’t care about his partner getting what they wanted during this time. Ale had brought a small bottle of lube with him into the bedroom and set to work prepping himself, bending over the bed while inserting a pair of lubed up fingers into himself with the hopes he had enough time to prepare before Crimson arrived.

Crimson opened the doors to his private bedroom a short time later revealing Ale just standing in the dimly lit room completely naked as he’d instructed. Pleased Crim closed the large doors behind himself then proceeded to remove his own clothing, draping them over a nearby armchair however this was where the routine changed. Crimson wondered over to his closet where he pulled out a length of rope causing Ale to eye him with both suspicion and curiosity. Crim walked over to stand right in front of the shark with the rope in hand, giving it a snap that made Ale narrow his eyes slightly and furrow his brow.

“Turn around,” Crimson instructed.

Ale did as told although it was a little hesitant, whipping his head around moments later when Crim suddenly yanked one of the shark’s arms behind his back swiftly followed by the second. Crimson proved his skill with rope as he tethered Ale’s wrists to one another, he also proved his stocky stature shouldn’t be taken lightly because the imp was incredibly strong, manhandling Ale to turn him around then shoving the shark backwards onto the bed. Ale grunted as his back hit the mattress, scooting up as much as possible before Crim started crawling up between his legs, shoving them apart aggressively. Ale tipped his head up to the side as a submissive gesture that apparently was welcomed because Crim latched onto the shark’s neck with a series of aggressive bites with undertones of growls. Crimson’s tongue lapped up the blood that ran from the marks he left, moving down to leave a mark on Ale’s chest all of which wasn’t for Ale’s benefit, these were possessive markings brought on by crimson’s rut instincts nothing more. Ale let out a pained groan as the imp sunk his fangs into Ale’s inner thigh right before grabbing onto the sharks’ hips with his talons, pressing his girthy cock right into Ale with no warning or prep fortunately the shark had done that earlier.

“Ugh…shit…” Ale cursed under his breath.

Crimson sunk balls deep in one thrust only to pull almost all the way back out then shove back in. The pace was brutal as usual but as usual Ale just laid there to take whatever Crimson dished out unfortunately with his wrists tied behind his back Alessio couldn’t touch himself like normal leaving both his dicks aching with want. Crim selfishly chased his own pleasure quickly reaching that point of no return, burying himself deep in Ale as he spilled into the shark with a grunting groan however, he didn’t withdraw. Ale braced for what he knew was coming and without fail Crim started up a second round instantly causing Alessio to groan, drawing his bottom lip up between his teeth. Hours passed with crimson spilling into Ale several more times till after about the tenth time when he was finally spent, withdrawing as he panted with sweat beading along his skin in the dim light while Ale panted heavily in turn, cocks flushed the same deep color as his cheeks as they ached for release. Alessio watched as Crimson raked his eyes over him, a small smirk building on his features at watching his own cum leak from Alessio’s ass while pre-cum drooled from the shark’s double dicks.

Ale closed his eyes to await Crimson to leave as he normally did which would allow Ale to take care of himself however tonight Crimson did something for the second time that surprised Ale. Alessio gave a sharp inhale as he felt a hand wrap around one of his cocks, immediately stroking swiftly causing his eyes to fly open to glance down. Crim was smirking as he stroked Ale’s left cock at first eliciting a confused furrow only to have it swiftly fade into a needy upwards furrow as he moaned through soft moans. Crimson grabbed Ale’s other cock with his other hand making sure to stroke in opposite intervals making Ale tip his head back with deep groans that turned into a full out cry when he came, arching his back as his body shook from the orgasm.

Fandom: HelluvaBoss

Pairing: Crimson/Alessio

Rating: M

Notes: Non-Con elements ahead! 

Crim had a tendency to get used to things, he liked consistency, which was why when things changed, he would often react poorly...unless it was his bodyguard Ale apparently. Crim called on Ale for almost everything and the shark would always be there like clockwork however on occasion even Ale could be tardy. Crim would scream and throw things at his bodyguard in frustration with his loyal guard taking all of it however apparently even the most loyal can have enough. Ale was only five minutes late in returning to the mansion from a pickup, the duffle now sitting on Crim's desk as he fumed with Alessio taking the abuse as normal unfortunately for Crim this was apparently the night he should have thought twice.

 "You stupid fucking fish! What do I even pay you for?" Crimson barked irritably. 

 "Enough!" Ale suddenly barked back, hands slamming on the desk. Crim wasn't surprised by much but in that moment, he was completely taken aback and even more so by what Ale did next. Alessio shoved the duffle off the desk to reach across, snatching Crim by the collar and yanking him forwards. 

 "What the fuck do you think your doing?" Crim demanded, snarling at Ale. 

 "What I should of a long time ago, shutting you up!" Ale growled back right before harshly pressing their lips together. 

 Crim immediately struggled against the unwanted gesture, but it was too difficult to get leverage from the awkward way he was bent over the desk. Ale managed to force his tongue into Crim's mouth and a hot coal sunk to Crim's lower abdomen as he felt heat rise in his cheeks. Questions raced through Crimson's mind, his heart racing in a slight panic as he struggled to get on the desk in hopes of getting a better angle to shove the shark off. Once in a better position Crim started trying to pry Ale's hand from his collar, claws raking across Alessio’s knuckles and wrist yet all it did was prompt the shark to flip him over, pinning the imp's arms behind his back. 

 "What the fuck!? What's gotten into you!? Hey, hey, hey! What...Gah!" Crim exclaimed as Ale swiftly yanked the imps pants down his thighs. 

 "I said, Shut. Up!" Ale growled tightening his grip on Crim's arms before bringing two fingers to his mouth where he lathed them with saliva. Crim flushed a deeper shade as confusion swiftly set in, he had no idea what Ale was doing nor why his body was reacting to it all. 

 "Now hold still, unless you wanna get hurt," Ale warned earning him a furrowed brow of confusion from Crim. 

 "For fuck’s sake! What are you going on, Ah! Fuck!" Crim exclaimed again as Ale's previously slicked fingers pressed between his cheeks straight into his asshole. The burn shot straight through the imp making him struggle worse against Ale's vice grip. 

 "I said hold still! Be grateful I'm even bothering as I coulda just shoved my dick up your ass instead," Ale snarled.

 "Fucking bastard!" Crim shot back, it was at this moment he could smell a strong scent coming off Ale, a strong musk. Could it be? Was Ale in rut? Crim had heard shark demons could become incredibly predatory during rut, till now he'd not seen Ale go through it though. 

 Crim clenched his teeth with a hiss as Ale roughly finger fucked him and what was worse the imp's traitorous dick was getting hard off it. Crim tried to wiggle free of Ale's grasp unfortunately with his pants around his midthighs and Ale's powerful grip around his arms the imp was effectively immobilized against the surface of the desk. Ale's fingers brushed a spot inside Crim that made his stomach tense and dick throb as he bit down on his lower lip to muffle a moan. Alessio caught the reaction though, smirking wide as he started assaulting the spot with his fingers. Crim cursed how good it felt and how his cock leaked precum beneath him, why did he enjoy this? Why did he nearly whimper in disappointment when Ale's fingers pulled out? 

 Crim could hear Ale undoing his pants, eliciting another wave of panic as he craned his neck to see over his shoulder, eyes growing wide at the sight of Ale's two hard cocks. Crim felt one slide between his cheeks pushing against his entrance till the head slipped inside him causing a shudder to run through his body followed by a burning pain as Ale pressed forward. 

 "Shit! Ugh!" Crim groaned out.

 Ale managed to seat himself fully inside Crim, growling in a low possessive manner as his head bowed to the imp's nape. The shark's claws dug into Crim's hip as his teeth sunk into his nape eliciting a string of strained curses from the imp beneath him. Licking over the fresh bite wound Ale pulled back then pressed back into Crim making do with the awkward position as Ale needed to lean over Crim on the desk, luckily though his height made it a little easier. Crim unintentionally found himself moaning after a bit, cock begging for release as Ale plowed his ass from behind and just as Crim was beginning to think he'd never be able to cum he was taken off guard by the feeling of Ale shoving into him and hot cum spilling into his ass while more spattered across his back.

 Ale panted against Crim's shoulders for a few moments then reached underneath him, wrapping his hand around the imp's cock. Crim groaned as Ale stroked him to finish, cum spilling onto the desk beneath him. Suddenly Ale's grip vanished from Crim's arms as he pulled back, flaccid cock slipping from Crim's ass leaving him panting as his senses slowly regained themselves. Snarling Crim pushed himself into a sitting position on the edge of the desk while rubbing his sore forearms and glaring daggers at Alessio. Ale averted his gaze as his rut subsided enough for him to fully comprehend what he’d just done, doing up his pants as he awaited the inevitable tongue lashing or perhaps worse punishment that awaited him. 

 "I, I'll leave you," Ale quietly stated, moving for the door when Crimson remained silent. 

 "Ale, be thankful you've been one of my favorites for a long time, because if you weren't your jaws would be on my wall by now," Crimson warned, narrowing his eyes at the shark who swallowed hard then nodded his understanding before leaving.