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Moonlight Night
The End wasn't The End - Found a new home after the great exodus of 2012

He was a pumpkin farmer. One Nightmare Night he was carving a pumpking with a magic knife for earth ponies he bought. The knife malfunctioned and something went horribly wrong.
LucianTheBlaze

Addicted to the shindig
@Crowley: Perhaps. Maybe he’s often associated with the legend, yet not connected to it at all. People think he’s THE Headless Horse from long ago, when in reality, he’s not.
Crowley
Wallet After Summer Sale -
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Birthday Cake - Celebrated MLP's 7th birthday
The End wasn't The End - Found a new home after the great exodus of 2012

Can't we all get along?
It shouldn’t involve Trixie, either way; the Headless Horse is supposed to be more of a widely known, centuries-old story before Trixie’s time, I’d think.
LucianTheBlaze

Addicted to the shindig
As for why he’s headless, I want it to be something hilarious and embarrassing. I’m thinking a magic trick gone wrong with Trixie (Maybe wheels were involved.), how about you guys?
LucianTheBlaze

Addicted to the shindig
@Crowley: Accepted. He was a blacksmith working with his father in Canterlot since he was young, and with his father’s help, he crafted his very first weapon; an axe.
Crowley
Wallet After Summer Sale -
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Birthday Cake - Celebrated MLP's 7th birthday
The End wasn't The End - Found a new home after the great exodus of 2012

Can't we all get along?
Better theory; the Headless Horse, pre-beheading, was a blacksmith. His cutie mark just so happened to be an axe/guillotine/etc due to that talent, and it’s only irony that he happened to become headless later on.
 
Just a suggestion.