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In the prologue, Hiccup is the scrawny, (somewhat) attractive kid. This takes place a couple months after Toothless and Hiccup save Berk and the Dragons from the Red Death. Most of the chapters after this will take place in HTTYD 2, a few of them will be flashbacks to HTTYD 1. okay? okay.

This takes places in HTTYD 2

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“Okay, so maybe I did get my directions mixed up a little, but you can't exactly blame me. The clouds are extremely thick today.” You said while folding your arms, giving your Stormcutter a pouty face as he swooped down towards the sea, the tips of his big wings gliding across the salty water. “I'm more than sure we're heading the right way though, I can feel it.” You hummed while laying back, looking at your nails before staring up at the deep blue sky in complete boredom, starting to grow bored with flying. Your stomach began grumbling fiercely at you, and you realized that you were extremely famished. “What do you say boy, how about we fly for a few more hours and then find some land? I'm getting pretty tired.”

(Dragon Name) growled at you, turning over so you hung off his back, your finger tips grazing across the sleek water. You tightened your legs around his saddle, giggling at the upside down view of the world. For a few minutes you flew like this, enjoying the silliness your partner only offered to you before (DName) returned to the proper position, his movements causing the blood to rush through your head. “Hey look bud! I think I see land!” You exclaimed, pulling out your looking glass before putting it to your eye, squinting to get a better image.

“Yep! That's definitely land, a big fat hunk of rock.” (DName) let out a roar in an excitement, pulling his wings tighter before rocketing towards the land. “Whoa! Buddy, slow down, I think I see something.” You murmured sharply, twisting your head to look down at the slowing Stormcutter. “A village. Could it be-?” You grabbed on tighter to his saddle. “Try to stay in the clouds, we don't know if this village is hostile or not. But I think I know which one it is...”

You deadpanned at (DName) when he swooped down towards the island, despite the fact you just told him not to. “Okay then, don't listen to your owner, that's cool too.” You could practically feel the smirk he was emitting as you neared the harbor, your stomach doing backflips when you saw a very familiar mast. “Well (DName)... It looks like we're home.” You murmured, a smile growing on your face when you saw bodies moving on the island.

“Let's make this a very calm entrance, okay? Don't do anything stup-ID!” You screeched when (DName) rocketed forward, your hands gripping at the saddle as he barrel rolled towards the center of the village. “(DName)! Don't you dare!”

Crash!

You shot forward off the Stormcutter, tumbling over yourself until you slammed into the side of a building, a throbbing pain beginning to form in your head. You groaned and sat up, holding onto your bleeding forehead with a glare aimed towards your partner. He gave you a sheepish grin and crawled towards you. “Nice going buddy! Now the whole town knows were here, I didn't want a lot of attention! You useless good-for-nothing reptile.” You snorted while folding your arms, ignoring your partner when he nudged your shoulder.

(DName) put his head in your lap and purred, nuzzling your stomach before licking your cheek. You giggled before scratching his chin. “That's an interesting dragon you have there...” A mellowed voice spoke up, breaking your concentration.

“Oh... him? Nah. He's pretty useless if you ask me. He just gives me these owl looks all day.” You murmured before looking up, a faint blush rising to your cheeks. Brown hair, jade eyes, prominent cheek bones, man this guy was absolutely gorgeous.

“I've never seen anything like him before.” The man said again, shaking his head with a grunt. “I'm sorry. Perhaps I should introduce myself. My name is Hiccup.”

Your face went blank, your mouth opening in shock as you took his hand. “Hiccup Horrendous Haddock III?”

“You've heard of me?”

“H-Heard of you?!” You exclaimed when he pulled you up, your arms looping around his neck as you pulled him into a tight hug. “It's me! (Name)! We used to be best friends.”