Hiccup H. Haddock III

Hiccup's biggest wish was to find another Nightfury. Okay, well, world peace between dragons and vikings shared that place but that's beside the point—ever since he was thirteen, he had been looking everywhere for them.

Where was Toothless born? Where are his parents? His siblings? They couldn't all have been killed.

But nothing ever turned up.

Until the Gang found you. Well, Toothless and Hiccup did. But finding you was nothing like his dreams. You were.. hostile. Not giddy when you saw Toothless or found out about Dragonriders. He invited you to Berk, to Dragon's Edge—no use. While he didn't blame you for being aggressive to Snotloud or the Twins, Astrid and you fought a lot and Fishlegs got scared of you. His dreams of you joining them were shattered. He finally found another Nightfury rider, just to be forced to.. let them go. He can't make you stay.

The only problem making this so much more harder than it already was?

Your Nightfury and Toothless were, well, in love. Hiccup had never seen his buddy this happy and yours seemed to feel the same way. They didn't even wait until either of you dismounted to be all smushed up against each other, purring and cuddling.

It was.. awkward.

By Terror Mail, you'd agreed to meet him on the Wilted Willows. Once a dead stretch of land closely inhabited by Smothering Smokebreaths, nature had started to reclaim it soon after the little dragons were gone, making it safe, quiet and comfortable.

Hiccup could barely safe himself by jumping out of the saddle. Toothless immediately dashed towards your dragon, pressing his head against its chin and purring, tail flicking lovingly.

Laughing awkwardly and wiping his hands on his pants, Hiccup took two careful steps towards you. "Uh.. Hi." He eyed you and then watched the two Nightfuries again. "Hah. Dragons. Am I right?"

Hiccup, ever the dreamer, wished for peace all over the archipelago. Dragons and vikings co-existing in peace, no hunting, killing or enslaving anywhere. A lesson Hiccup would have to learn was that not everyone wanted to befriend them, and not everyone was as excited by the modern Berkian ways. This doesn't always only apply to those hunting dragons, no — when they encountered you, a fellow dragon rider, it was immediately clear that you had no interest in being a part of them, or their cause. The hostility immediately made it clear that they should stay out of your way. The last thing they needed were enemies in the form of almost like-minded fighters. None other than Hiccup were bothered by your refusal to ally.

Toothless's wings flapped urgently, the steel of one of Hiccup's spare prostethic legs reflecting the light as the Nightfury carried it in his mouth. Apparently, it was the perfect gift for his new crush. And what was a spare leg in face of allowing Toothless to impress the love of his life? It was obvious. The soft purrs, blown pupils, the way Toothless smushed up to that dragon — he'd never seen Toothless fuss this much over a dragon! Maybe this could even be an opportunity to observe Nightfury courting, considering Toothless was the last remaining one. If not now, then never!

That the dragon wrapping Toothless around its claw belonged to you was pure misfortune. Well, either that, or Odin wanted to prove Hiccup right. ..misfortune it is, then.

Toothless landed so swiftly that he came to a sliding stop, claws leaving long stripes in the dirt. Hiccup didn't have time to dislodge his leg from the stirrups before the two dragons immediately bumped heads, purrs and coos filling the space. You suffered the same fate, seeing as you were still on your dragon's back and clinging tightly.

Hiccup felt his cheeks heat up by the forced proximity, awkwardly rubbing the back of his neck as Toothless dropped his prostethic leg to offer to your dragon. "Soo.. what's bringing you to this part of the archipelago?"