AILESS Whumptober 2026
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Other Things by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
01 Oct 2026
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Summary
When Hiccup is kidnapped from his own bed in the middle of the night and dragged to the Grimborn brothers, his survival instincts go haywire.
Vignettes of Hiccup's time in captivity, when he fights, when he flies, when he freezes - and when he fawns.
Written for ailess whumptober 2026 day 1: fight/flight/freeze/fawn
Series
- Part 1 of AILESS Whumptober 2026
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Going Overboard by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
02 Oct 2026
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Summary
Set in early RTTE. When Ryker captures Hiccup, Snotlout, and Astrid, he takes it upon himself to make an example of Hiccup and rid the Dragon Hunters of him right then and there.
Written for ailess whumptober day 2: pulled underwater
Series
- Part 2 of AILESS Whumptober 2026
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I Wouldn't Leave You Either by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
03 Oct 2026
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Tag to Dire Straits. Hiccup may have narrowly escaped drowning, but the water isn't ready to let him go. It follows him into his dreams, twists them into nightmares, reminds him intimately of what it is to drown. But Toothless refused to leave Hiccup alone at the bottom of the ocean, and he isn't about to leave him now, either.
Written for ailess whumptober day 3: struggling to breathe
Series
- Part 3 of AILESS Whumptober 2026
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A Quiet Chase by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
04 Oct 2026
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Summary
Hiccup and Astrid's date takes a horrifying turn when they are ambushed by a pack of Scream Stingers, dragons that use pain to paralyze their prey - and that hunt by following the sound of the screams. When Hiccup gets stung, it's up to Astrid to keep him quiet and get them both through the hostile woods, across the island, and back to their dragons before their hunters find them.
Written for ailess whumptober day 4: "Shhh, shhh, you're okay"
Series
- Part 4 of AILESS Whumptober 2026
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Where the Real Road Lies by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
05 Oct 2026
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Summary
Five times Hiccup's prosthetic leg makes his life more difficult, and one time it saves his life.
Written for ailess whumptober day 5: life-altering injury
Series
- Part 5 of AILESS Whumptober 2026
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Summary
Dragons protect their own - so this is what Valka vows to do when she discovers a young dragon trapper on the back of a poor, enslaved Night Fury. But the line between protection and vengeance is easily blurred, and dire mistakes are made when fury is given free reign. By the time she realizes the the truth, she's broken more than just his body, and it might be too late to fix what she shattered, too late to salvage what she threw away - if indeed she cares to salvage it at all.
Written for ailess whumptober day 6: misunderstanding leads to whump | BTHB: misunderstanding
Series
- Part 6 of AILESS Whumptober 2026
- Part 5 of Bad Things Happen Bingo
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The Hungry Dark by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
07 Oct 2026
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Summary
Hiccup wakes bound and gagged, crammed into a tiny space beneath the floor of Viggo's study - completely alone, drenched in darkness, unable to move or speak, barely able to breathe.
But as always, Viggo's plan is multi-faceted, and everything is about to get much worse.
Written for ailess whumptober day 7: trapped in a small space | BTHB: claustrophobia
Series
- Part 7 of AILESS Whumptober 2026
- Part 6 of Bad Things Happen Bingo
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Whatever Promises I Made by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
08 Oct 2026
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Summary
When Hiccup is captured and tortured by Ryker and Dagur, Heather wants nothing more than to break her cover and get him out. Hiccup, being Hiccup, is more concerned with Heather's safety in all of this than his own - and orders her to stand down long enough to mount an escape on his own. But Heather's seen the bruises, the blood, the burning hunger in her brother's eyes... and she fears that if she waits like he wants, Hiccup might not come out of this the same - if he makes it out at all.
Written for ailess whumptober day 8: "Me? What about you?"
Series
- Part 8 of AILESS Whumptober 2026
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All May Be Lost and Our Hearts May Be Worn by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
09 Oct 2026
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Summary
Johann loses his patience with Hiccup, who refuses to break under torture - so he decides a slow, painful execution might loosen his tongue. But Hiccup cares about others more than he fears death, and he's more than willing to die to save his dragons, his friends, and his home.
Written for ailess whumptober day 9: in the nick of time | BTHB: defiant to the end
Series
- Part 9 of AILESS Whumptober 2026
- Part 7 of Bad Things Happen Bingo
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Don't Flinch by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
10 Oct 2026
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Summary
Viggo challenges a captive Hiccup to a contest of endurance: If Hiccup wins, Viggo will release him, unharmed, to his people. If Hiccup loses, he stays Viggo's prisoner and will be ransomed back to his father at a hefty price. The only rule? Don't flinch.
Written for ailess whumptober day 10: flinching
Series
- Part 10 of AILESS Whumptober 2026
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The Comforts of a Gilded Cage by Emachinescat for MoonlightStorms
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
11 Oct 2026
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Summary
The Brothers Grimborn Part 2: Viggo moves a captive Hiccup to his new base and showers him with luxuries beyond Hiccup's wildest dreams. But a gilded cage is still a cage, and no amount of riches or comfort is enough to detract from the abhorrent way Viggo plans to use Hiccup against his own people. Or the way Viggo looks at Hiccup, touches him... wants him. And Viggo Grimborn is a man accustomed to getting what he wants.
Written for ailess whumptober day 11: gilded cage | BTHB: gilded cage
Series
- Part 2 of The Brothers Grimborn
- Part 8 of Bad Things Happen Bingo
- Part 11 of AILESS Whumptober 2026
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Where You Belong by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
12 Oct 2026
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Summary
The Brothers Grimborn Part 3: Viggo forces Hiccup to dine with him under threat of the unspeakable, where Hiccup
learns in no uncertain terms what could happen to him if he continues to spurn Viggo's gifts and hospitality and doesn't learn to be content in his gilded cage. What could happen to him when Viggo's patience eventually runs out.Written for ailess whumptober day 12: "This is where you belong."
Series
- Part 3 of The Brothers Grimborn
- Part 12 of AILESS Whumptober 2026
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Maybe One Day by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
13 Oct 2026
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Summary
Branded Part 3: When Eret, Son of Eret suggests that he and his crew of dragon trappers travel a bit south of their usual territory, he has had no idea how lucky they'll be. He's never even seen a Night Fury before, let alone trapped one. Until today.
But all is not as it seems, because atop the unholy offspring of lightning and death itself rides a young man with Drago Bludvist's mark branded on his chest. Thinking the boy is a deserter, Eret drags both him and his dragon to Drago, only to discover that Hiccup Horrendous Haddock III is braver, kinder, better than Eret has thought any man could be. And as Hiccup's screams reverberate through Drago's flagship, Eret realizes the enormity of his mistake - and vows to do whatever it takes to fix it.
Written for ailess whumptober day 13: surprised at being offered aid, "you're hurt because of me"
Series
- Part 3 of Branded
- Part 13 of AILESS Whumptober 2026
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Any Way the Wind Blows by Emachinescat for mushroomwizzard157
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
14 Oct 2026
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Summary
Midnight Scrum AU: Hiccup's already awful day gets so much worse when Savage rips his prosthetic leg right off his body - and tosses it overboard, into the sea. Of course, then Hiccup gets kidnapped again, this time by a masked bounty hunter whose cruelty knows no bounds. Hiccup's day of bounty hunter hell would be bad enough with his leg, but without it...
Hiccup will be lucky to make it out alive, let alone with the rest of his body intact.
Written for ailess whumptober day 14: "Look at you. Pathetic."
Series
- Part 14 of AILESS Whumptober 2026
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Those Who Sing in the Dead of Night by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
15 Oct 2026
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Summary
The Brothers Grimborn Part 4: After months as Viggo's prisoner in a gilded cage, the first of Viggo's negotiated "ransom visitations" has arrived. Hiccup's captor has exchanged one hour with Hiccup for three Dragon Eye lenses - and Hiccup is at long last reunited with his father. But their allotted time together is too brief, and Hiccup's caged bird's heart might not be able to take being separated once more.
Written for ailess whumptober day 15: "Whatever happens, just remember that I love you"
Series
- Part 4 of The Brothers Grimborn
- Part 15 of AILESS Whumptober 2026
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Somebody Had to Do It by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
16 Oct 2026
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Summary
Four times their captors have dragged Hiccup out of the cell. Three times they've brought him back, each time with more blood and bruises decorating his battered, broken body. But they've never kept him this long before. Snotlout waits for his cousin's return, chains clanking with every pacing step, panic gnawing at the edges of his dwindling composure.
Then they return.
But this time, it's worse. There's so much blood - too much blood - and more than Hiccup's leg is broken: Something deep inside of Hiccup has shattered, and Snotlout - helpless, terrified, bad at feelings - has to find a way to not just bind Hiccup's wounds, but to salvage his broken pieces. Even though it's hard, even though he doesn't know how. Because Snotlout's all Hiccup's got right now, he's the only one who can... and Snotlout sure as Hel isn't going to let his cousin suffer alone.
Written for ailess whumptober day 16: a moment of softness
Series
- Part 16 of AILESS Whumptober 2026
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Hail the Dragon God by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
17 Oct 2026
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Summary
Not many Vikings remember that once, long ago, there was a dragon god. Of those who do remember, some say the Æsir killed him because they feared his power, others claim he abdicated his godhood and took on the mantle of mortality. Still others believe that he lost a part of himself and now wanders Midguard, either fully dragon or fully human, eternally searching for that which he lost. One tribe in particular worships the dragon god, has dedicated centuries to the search.
And now they've found him. Tall, slender, beautiful, one-legged, deceptively human but with a divine radiance that outshines the sun. He has no memory of his true self or his godly form... but this tribe is eager to remind him of the truth. It will only take a snowy trek up a tall mountain, an altar on the highest peak, and blood staining the snow like rose petals, and then their god will be freed from his mortal prison and return to his full power.
They are unmoved by his fear, unconvinced of his pleas that he is not what they believe. He might be scared now, they reason, but when he embraces his true form, he will honor those who gave him life by taking it away.
Written for ailess whumptober day 17: apotheosis/deification
Series
- Part 17 of AILESS Whumptober 2026
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How You Repay Me by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
18 Oct 2026
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Summary
Dagur tries to treat a captive Hiccup's arrow wound, but, as usual, Hiccup is determined to make things as difficult as possible. And yeah, Dagur might have been responsible for the wound in the first place, but good gods, would it kill Hiccup to show a little thanks?
Well, if Hiccup keeps this up, Dagur can think of some other ways Hiccup can repay him for his kindness...
Written for ailess whumptober day 18: "This is how you repay me?" | BTHB: harmful healing
Series
- Part 18 of AILESS Whumptober 2026
- Part 9 of Bad Things Happen Bingo
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My Name Looks Good on You by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
19 Oct 2026
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Summary
Zippleback Experience AU: Dagur stakes his claim on Hiccup by tattooing his name into Hiccup's arm, so Hiccup never forgets who he belongs to.
Written for ailess whumptober day 19: nonconsensual body modifications
Series
- Part 19 of AILESS Whumptober 2026
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I Carry You With Me by Emachinescat
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
20 Oct 2026
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Summary
In which Snotlout gets to be the hero, but it isn't all it's cracked up to be. It actually kind of... sucks. Because it's Hiccup he's rescuing, Hiccup who's drugged to all Hel, limp and vacant in his arms, Hiccup who's covered in blood and bruises and scars deeper than flesh and bone.
How can he enjoy being the hero when those images of Hiccup are seared into his mind forever? And how can either of them ever find normal again?
Written for ailess whumptober day 20: bridal carry/weakness
Series
- Part 20 of AILESS Whumptober 2026