1 - 20 of 467 Works in Alessio (Helluva Boss)
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For Whom The Sinsmas Bells Toll by Impudent_Piece_Of_Crockery
Fandoms: Helluva Boss (Web Series)
03 Dec 2025
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Being part of the Mafia isn't easy, but one imp from a VERY different lifestyle will find himself navigating the politics of family conflict to maintain one of his only friendships and climb up the ladder. . . Maybe.
A prequel exploring the last days of Crimson's time as a soldier for the Malidlfrend crime family in the Owl's Hell That Ends Well series.
Check out the series Tv Tropes Page!
https://tvtropes.org/pmwiki/pmwiki.php/Fanfic/OwlsHellThatEndsWellSeries
- Part 2 of Owl's Hell That Ends Well
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grotesque antics from Hell by Sandos for TalosLives, Omega47, SoulfulAzrael
Fandoms: Helluva Boss, Hazbin Hotel (Cartoon)
28 Nov 2025
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Since Talos, through his work, pulled me into the culture of his home country, Ireland. I decited to make some mash-up stories to show him and my fellow-readers my favorite short stories in the genre of intelligent, albeit grotesque, humor, from my native corner of Europe. The original text in English has never been published and it seems like a shame not to introduce it to you. However, Generation Z as a whole is not familiar with it either. The procedure is as follows: I select characters, either from the HB series or from Talos's (and sometimes from others) works, and based on the characteristics of the characters from those stories, I write a version that can be perceived as additional information that would fill in the blanks in the characters' pasts.
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The faceless deity by Bubble_Dreamer
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series), Hazbin Hotel (Web Series)
17 Nov 2025
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Ever since you became the ruler of sinners, fate threw new challenges under your feet. Being challenged was nothing uncommon for you, nothing sort of unwanted. But despite your resilience, would you be able to lift yourself back each and every time?
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- Part 13 of Hellish Afterlife
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Alessio succumbs to his urges, and Crimson discovers some new ones, as he shoots his shot with the famed mob boss...
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A back and forth narrative of Moxxie's childhood, teenhood, and young adulthood; focusing mainly on his first traumas and realization of them thereof.
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Crimson and Alessio share a moment as summer fades into fall
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The story of an imp and a shark and their journey through life together.
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The Great Deer Detective by Scungilli
Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)
08 Nov 2025
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Charlie reaches out to private investigator, Alastor, to help find her father who was kidnapped. Alastor teams up with his old pal Husk to find the toymaker he may or may not have grown fond of.
AKA: A noir detective RadioApple fic featuring a rescue mission and a whole lot of pining.
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“Equality and Balance cannot ever exist, the world is too far gone now; if you let yourself be trampled over then you’ll never be able to exist. Do what you want, break the rules, and seek justice because now it seems that everyone is a hypocrite; even the higher-ups. So reap what you sow because life is already unfair, unkind and cruel. You can either sit down and wallow in guilt for not trying hard enough or you could find your reason to living.”
Forgotten Wars is a show set in an Alternate Universe which messes with the Canon Universe timeline, but it's not the actual canon universe.
It's a four-series story which focuses on two fallen angel siblings called "Acheros" and "Athena", who had both been exiled from Heaven whilst losing their family. Now, Athena must face this world alone and find what happened to her little brother who went missing, breaking the laws of Hell and making some new enemies. Meanwhile, Acheros is no longer the same little boy, and is trying to achieve a mysterious goal which could result in the end of the Universe! Will they reunite and find happiness? Or will they both succumb to their grief and be forgotten?
Come Reader, join us on this adventure on a tale, buried beneath rubble.Series
- Part 1 of Forgotten Wars (AU) (HELLAVERSE)
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🥀Helluva boss Rewrite ❤️🩹
Alternate universe where Blitzø was forced to be a slave for the Goetia family as a punishment for stealing.
Years later Stolas misses his friend Blitzø and wants to help Blitzø with his company as a way to make amends.
But Blitzø doesn't know If he can forgive Stolas for what he did.
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The control Crimson has over the sinners and ex mobsters in his operation has always depended on the support of Don Bianca's grandson, Alessio. When Crim scapegoats Alessio in a desperate move, he destroys the only protection he has, and has to face the worst of Hells mobsters alone.
31,000 words, finished.
TW Rape, childhood trauma, murder, guns, explosions, its the mob! While there's a relatively happy ending in store for Crim and Alessio, its a bumpy ride. -
Frozen Heart by InkBlotSpotShot
Fandoms: Helluva Boss (Web Series), Hazbin Hotel (Cartoon)
02 Nov 2025
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Can a man of the world thaw the heart of a man who's world he does not know?
A frigid royal becomes infatuated with a working class incubus. Lord Andrealphus, (aka the Mighty Marquis) and Jesse, (A bouncer at OZZIE'S) fall into a working relationship that threatens to spiral into something more. Yet, as the vast differences in their lives conflict and conjoin with one another, unintended consequences lurk right around the corner.
Magic, combat, and homosexual romance await. ✨️
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In the mindscape of Moxxie Knolastname, the imp assassin dreams of being in an action hero in his own story. Terrorists have seized control of his wife's work during a Christmas party. And Moxxie is the only one who can stop them and save Millie and her co-workers. One imp. 13 Terrorists. What the hell can go wrong?
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A sequel to Sadistic Tendencies.
(please read the prequel's tags)Series
- Part 3 of Sadistic Tendencies
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A late night storm causes Crimson to reminisce about his past with Alessio, and how it has influenced their future.
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After Fizzarolli gets kidnapped by Striker for Crimson, Ozzie gets a phone message telling him exactly what to do to get him back. Which is to go alone to a warehouse garage. Ozzie gets there, and things take a turn for the worse after he gets lassoed by Striker.
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When Crimson retreated to his office to escape the phallic rainbow paraphernalia strewn throughout his house, he spied his lieutenant, Alessio, hard at work in the yard. His body coated in sweat, arms rippled with muscle as he moved the makeshift pavilion into place to prepare for the wedding. Crimson stared, intently, to ensure he got it done before his son got home. It was only a coincidence he held his cock while he watched.
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It's easy to crash and burn. It's harder to pick yourself up and get better. And it's a lot harder when you're someone like Chaz.
But - somehow - he's still kicking. And it's going to take a lot of patience and kindness before he can figure his shit out - not to mention find a way out of his latest mess.
Lucky for him, Collin shows up.And things sure do happen!
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Helluva Boss: The Great Pirate War AU - The Sinister Siren by HelluvaScribe
Fandoms: Helluva Boss (Web Series)
23 Sep 2025
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Inspired by the Great Pirate War AU Merch drop on August 18, 2025. Fueled by my rage of not seeing my favorite underrated villain Rolando part of the merch drop YET AGAIN! Another missed opportunity. I could’ve called it “Legend of the Golden Grimoire” or “Helluva Captain” or “Blitz’s Buccaneers” or just “The Great Pirate War,” but Rolando deserves to be in the title, so there.
Created August 18 – August 31 2025
Warning: “Helluva Boss The Great Pirate War AU” contains violence, drinking and sexual references, no modern swearing and Rolando. Viewer discretion is advised.
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- Part 1 of HELLAVERSE GREAT PIRATE WAR AU
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A group of mobsters walk into a hospital to go after a Hellhound...
The punchline has something to do with the fact that they're unaware of the other half of I.M.P, as well as Millie's entire family, are already there.As Loona tries to heal from her injuries, a looming threat is drawing closer with the intent in finishing what they started back in the Greed Ring. Blitzo is out for blood, Millie is devastated while Moxxie continues to keep fighting for the family he truly thinks are still lost...
The third and final part to my Hearth series, LET'S GO ~
EDIT: Indefinite Hiatus due to taking a break from the fandom.
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- Part 3 of The Hearth Series