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Where Flesh and Metal Meet by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
31 May 2026
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"The first thing that registered was the sound – the horrible metallic crunching of a trap snapping shut around flesh and bone. Then the pain hit, and it was so acute, so intense, and it brought with it so much agonizing pressure, all stemming from his right ankle – An animal scream tore from his throat, building with the crescendo of throbbing, piercing, gnawing, biting pressure, but when his voice gave out and petered out into a whimper, the pain continued to build, to bite, to claw at his flesh... He'd stepped into a hunter's trap. With his good leg. His only good leg."
AU of "The Dragon Eye of the Beholder, Part 1" where Hiccup steps into the hunter's trap with his right leg instead of his left. Now he finds himself at the mercy of Dagur, crippled by excruciating pain, as unable to help his friends as they are to help him. And as his friends race against time to save Hiccup's life - and his leg - Hiccup finds himself torn between the trauma of his past, the pain of the present, and the fear of the future.
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Never Break by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
20 May 2026
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Hiccup hasn't talked. They have broken his body but not his spirit — not entirely. Not enough to loosen his tongue. The information that Viggo wants, about the Dragon Eye lenses, about the riders, about Berk… Hiccup cannot give in. He will not. His friends will find him soon, he knows it. He just has to hold out until then.
Nothing Viggo does to him will make him talk.
Or so he thinks.
Prompt: Caving to Interrogation
Series
- Part 15 of Hiccup Horrendous Haddock the Hurt
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The Sandsnatcher by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
26 Apr 2026
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AU of Sandbusted: Hiccup can't believe he's about to willingly let a dragon eat him to save Snotlout. Well, partially eat him, he supposes. But either way, if he survives this, Snotlout had better not complain about Hiccup ever again.
In which the dragon lurking beneath the sand is far older, more primal, and hungrier than the Sandbuster. A dragon with one weakness that Hiccup can exploit in only one way: Play dead and let the monster swallow him whole.
Written for Writing Angstily's Whump Wheel Challenge: Sand + Skin
Series
- Part 21 of Hiccup Horrendous Haddock the Hurt
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Unhallowed Knife, Grim and Greedy by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
19 Apr 2026
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Ransom exchanges have a host of unspoken rules, a particular etiquette - an equal trade, a loved one for riches. But Dagur has never been one for rules. When he sees something he wants, he takes it, damn the consequences.
And what he wants is Hiccup.
Written for Write Angstily's Whump Wheel Challenge: knife + greedily
Series
- Part 20 of Hiccup Horrendous Haddock the Hurt
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The Brothers Grimborn by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
18 Apr 2026
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Midnight Scrum AU. Rescue doesn't arrive in time, and a triumphant Ryker drags a battered, bruised, broken Hiccup to his waiting brother.
Hiccup expects torture. He expects death. He expects anything but fire and fury at Ryker's treatment of Hiccup. And he honestly isn't sure what terrifies him more - the humiliation and pain Ryker heaped upon him... or the strange softness in Viggo's eyes as he strives to fix what his brother broke.
Written for Write Angstily's Whump Wheel Challege: stomach + mistreated
Series
- Part 19 of Hiccup Horrendous Haddock the Hurt
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Stay Awake by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
06 Apr 2026
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Hiccup cannot understand why Viggo, who almost certainly has a healer on board his ship, has taken it upon himself to treat Hiccup's wounds, why, despite his cold threats and the biting frost in his eyes, sometimes looks at Hiccup with something very much like fondness. Possessive yet protective. Dark, unwavering, unyielding, but still somehow… soft.
Ryker attacks Hiccup in a burst of anger, and Viggo takes it upon himself to put Hiccup back together again.
Written for Writing Angstily's weekly Whump Wheel Challenge: Nose + Brutal
Series
- Part 18 of Hiccup Horrendous Haddock the Hurt
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Surrender by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
30 Mar 2026
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The Edge has been under siege for two weeks. The good news? The Hunters want only one thing. If they get it, they will leave the Edge in peace. The bad news? They want Hiccup.
Prompt: Surrender
Series
- Part 4 of Hiccup Horrendous Haddock the Hurt
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Of Metal and Ink (And Stolen Futures Ripped from Grasping Hands) by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
29 Mar 2026
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The last time that Hiccup narrowly escaped Viggo's clutches, Viggo made a promise.
And now that Hiccup and Toothless have been shot out of the sky by Hunters, helpless at the hands of their greatest enemies, Viggo follows through on his horrifying, future-shattering, life-altering vow, and rips Hiccup's freedom, birthright, and future from his hands with one touch of ink and metal.
Written for WritingAngstily's weekly wheel Discord challenge: hands + horrifying
Series
- Part 17 of Hiccup Horrendous Haddock the Hurt
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Defiant Ones by Emachinescat for mushroomwizzard157
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
24 Mar 2026
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Hiccup's father has warned him about Savage, a man as brutal and ruthless as his name. Never antagonize him.
Easier said than done.
A much whumpier Defiant One AU where Hiccup mouths off to the wrong person and ends up paying the price.
Series
- Part 16 of Hiccup Horrendous Haddock the Hurt
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Power Trip by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
09 Feb 2026
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A whumpier "Wings of War" tag: Hiccup has no idea that it is Spitelout who saved him from the Singetail. All he knows is that he's being dragged roughly through the forest, into an isolated cave, and that a gigantic hand is now clamped over his mouth, silencing his screams.
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To Hurt, to Heal by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
16 Dec 2025
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Sometimes healing cannot come without a lot of pain. Fishlegs learns this the hard way when Hiccup is shot with a barbed arrow and his friends are forced to hurt him even more if they want to save his life.
Prompt: Viking painkillers, Fishlegs healer moment
Series
- Part 14 of Hiccup Horrendous Haddock the Hurt
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A Gift for Viggo Grimborn by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
09 Dec 2025
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Hiccup goes from getting a gift to being the gift, and Ryker Grimborn gives his younger brother the best Snoggletog present ever.
Prompt: Weighted Net + Gag
Series
- Part 13 of Hiccup Horrendous Haddock the Hurt
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In the Shadows by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
01 Dec 2025
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Summary
Hiccup knows he shouldn't separate from his friends in the Northern Markets. He knows he should stay on guard, shouldn't let his mind wander. But he does anyway, and the price is far steeper than he ever could have imagined.
OR
Hiccup is mugged while visiting the Northern Markets.
Prompt: Mugged
Series
- Part 12 of Hiccup Horrendous Haddock the Hurt
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Not a Hero by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
30 Nov 2025
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Summary
The Zippleback Experience AU: After Hiccup is brutally tortured by Ryker, Dagur does something neither one of them expects.
OR
Dagur's shifting feelings towards Hiccup as he realizes that what he's wanted for so long - to see Hiccup suffer - doesn't at all feel like he thought it would. In fact, it might not be what he wants at all.
Prompt: Dagcup + Forced Caretaking
Series
- Part 11 of Hiccup Horrendous Haddock the Hurt
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How to Train Your American Dragon by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon), American Dragon: Jake Long
26 Nov 2025
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Summary
On an evening flight with Toothless, Hiccup encounters a new dragon, one unlike any he's ever seen before. But when he tries to train it, something incredible happens, and everything Hiccup knows about dragons is turned on its head.
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Hiccup is having a very weird day, and, let's be honest, Jake probably is too.
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Impulse Control by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
23 Nov 2025
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Summary
In a moment of panic and anger, a reformed Dagur lashes out and accidentally hurts Hiccup, shattering the trust and comradery he's worked so hard to maintain with his former enemy. AU of Sins of the Past.
Prompt: redeemed Dagur relapse, Dagcup
Series
- Part 10 of Hiccup Horrendous Haddock the Hurt
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A Downed Dragon by Emachinescat for rachelteazer
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
21 Nov 2025
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"You know," Ryker said, "there's a little saying I've always enjoyed." He bared his teeth in a violent grin. "A downed dragon," he murmured, wrenching Hiccup's face forward painfully, his breath tickling Hiccup's ear, "is a dead dragon."
Hiccup fights when Ryker tries to take his prosthetic - so Ryker, knowing it will hurt Hiccup far more to see his dragon grounded, takes Toothless's instead.
Series
- Part 9 of Hiccup Horrendous Haddock the Hurt
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Target Practice by Emachinescat for rachelteazer
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
19 Nov 2025
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"I have eleven throwing daggers on my person. One for every year you have plagued me. What say you? Shall we reminisce about old times as I practice my craft?"
Johann uses a captive Hiccup as target practice.
Prompt: Johann being evil, knife-throwing
Series
- Part 8 of Hiccup Horrendous Haddock the Hurt
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Down to Earth by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
07 Nov 2025
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Summary
The Eel Effect AU: Either the gods hate him, or he's their favorite punching bag. Because Hiccup can't think of a better explanation for the day he's had. But even curled on the ground, body broken and battered and bruised, Hiccup is more concerned about curing Toothless and getting the Eel Pox remedy back to Berk than his own injuries.
Prompt: Crash
Series
- Part 7 of Hiccup Horrendous Haddock the Hurt
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Defy by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
02 Nov 2025
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Summary
The moment Hiccup sees the vial, he knows with crystalline certainty that Viggo has no interest in playing games with him today. But if Viggo wants him to drink its contents, he's going to have work for it - because Hiccup isn't going down without a fight.
Prompt: Drugged
Series
- Part 6 of Hiccup Horrendous Haddock the Hurt