Hiccup Horrendous Haddock the Hurt
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Listing Series
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All That Matters by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
28 Oct 2025
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Summary
Hiccup goes missing on his morning flight, and the ransom note Stoick finds in Toothless's saddle bag, written in Hiccup's own hand, reveals that he has been taken by a man who makes even Alvin the Treacherous look like a Valkyrie. The price for Hiccup's life is steep, but Stoick will pay any cost to get his son back from the monster who has stolen him.
Prompt: Ransom
Series
- Part 1 of Hiccup Horrendous Haddock the Hurt
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What the Boss Don't Know, the Boss Won't Mind by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
28 Oct 2025
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Summary
Ryker and his men decide to have some fun with Hiccup while Viggo is away on business, despite his orders to leave their prisoner alone. So when their fun spirals out of control and Hiccup nearly dies as a result, Viggo is far from pleased.
Prompt: Upside Down
Series
- Part 2 of Hiccup Horrendous Haddock the Hurt
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The Cracks Fear Made by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
29 Oct 2025
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Summary
It has been four days since Hiccup was struck by lightning. Gothi has treated his surface wounds — strangely beautiful, branching burn marks, like a winter tree reaching for Valhalla. But the healer does not know if Hiccup will wake, does not know if he will be the same if he does wake. And so Stoick does the only thing he can do: He waits, watches, and prays that his son will come back to him.
Prompt: Coma
Series
- Part 3 of Hiccup Horrendous Haddock the Hurt
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Surrender by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
31 Mar 2026
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Summary
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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Brave Face by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
31 Oct 2025
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Summary
We Are Family AU: Hiccup wants to be strong, to hold out no matter what Alvin puts him through. But he's also fifteen years old, chained in a cage about to be tortured. Kidnapped, far from his home in the heart of hostile territory, wrists a mess of pain and bruises. Dragons, he's used to. But cruel men willing to do anything to break him, wanting only to take what he refuses to give? These are uncharted waters, leaving Hiccup floundering far out of his depth.
Prompt: Wrists + Chains
Series
- Part 5 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
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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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Target Practice by Emachinescat for rachelteazer
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
19 Nov 2025
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Summary
"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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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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Summary
"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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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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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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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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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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Summary
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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To Hurt, to Heal by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
16 Dec 2025
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Summary
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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Never Break by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
20 May 2026
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Summary
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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Defiant Ones by Emachinescat for mushroomwizzard157
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
24 Mar 2026
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Summary
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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What Others Choose to Sell by Emachinescat for mushroomwizzard157
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
11 Jul 2026
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Summary
"I am a businessman, Astrid," Viggo said. He stood, sauntered over to Hiccup, and placed a heavy hand on his prisoner's shoulder; Astrid bristled, fists clenching, fingernails biting into her palms, at the way Hiccup flinched at the contact.
"This is the nature of my work: I make deals, I trade, I sell, I buy. But," he added, his fingers tightening possessively on Hiccup's shoulder, "I only buy what others choose to sell." The corners of his mouth turned up into a predatory smile that sent shivers crawling down Astrid's spine and shot bolts of dread into her heart.
"Oh, didn't you know?" Viggo asked, his face a furnace of hunger and triumph. He leaned forward, drinking in Astrid's despair and Hiccup's terror and resignation. "He signed the deal himself."
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In which Hiccup exchanges his freedom to save Toothless, and Viggo finally gets what he wants.
Written for Bad Things Happen Bingo: Prisoner Exchange
Series
- Part 1 of Bad Things Happen Bingo
- Part 17 of Hiccup Horrendous Haddock the Hurt
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Hiccup's Reason by Emachinescat for Astrid_Goes_For_A_Spin
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
15 Jul 2026
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Summary
When a bad pain flare hits both Hiccup and Toothless at the same time, dragon and rider take care of one another - and Hiccup learns a valuable lesson from his dragon along the way.
Tumblr Prompt: Chronic pain w/Hiccup and Toothless caring for one another
Bad Things Happen Bingo: Phantom Pain
Series
- Part 2 of Bad Things Happen Bingo
- Part 18 of Hiccup Horrendous Haddock the Hurt
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High Tide by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
26 Jul 2026
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Summary
Hiccup wakes chained in the bottom of an oubliette, far beneath the earth's surface, entombed in walls of stone. Completely helpless, completely alone, easily the most desperate predicament he's ever been in.
And then it gets worse.
A Triple Cross AU in two parts.
Series
- Part 4 of Bad Things Happen Bingo
- Part 19 of Hiccup Horrendous Haddock the Hurt