For as long as Hiccup could remember, on more than one occasion where he found Toothless wanting to have him sleep with him. At first, this puzzled him, as the dragon was usually very solitary. But then he simply took it as the Night Fury wanting some company to possibly amuse him.

Toothless would often sit up in Hiccup's house at night and nudge and breathe great gusts of air through his nostrils until his rider was awake.

"Go to sleep, Toothless," the boy would say, and roll over until he was facing away from his friend. Then Toothless would plod on over to the other side, taking large, heavy steps that shook the foundation of the structure before lapping at Hiccup's face with a slimy tongue. By this point, Hiccup would sit up and glare at the dragon. Toothless sat down on his rump like a bunny and stared back. This would go on for an undetermined amount of time before Hiccup blinked. Then he would give in to oblige and accept the dragon's invitation for a much more comfortable bed that night, wrapped tightly in those wide spanning leathery wings against Toothless' plump body. He usually tried to escape his clutches after Toothless did and was able to tell when the dragon began to swell and deflate in a constant rhythm. He would slowly and carefully try and slide out from his arms.

It didn't work.

Ever.

Hiccup would promptly be yanked back and pulled into an even tighter bear hug.

"This is going to be a long night."

Over the weeks, Hiccup learned to resist such temptations.

Toothless tried every tactic in the book this night. He plopped his massive head down at the foot of Hiccup's bed and would whimper and pined for his companion, terrorizing Hiccup with his oh-so-innocent, wide puppy dog eyes that were absolutely irresistible with those beady, cute, narrow cat-like pupils that darted around expressively and spread his lips apart into a gaping, toothless smile.

"No," Hiccup said firmly before turning over in his sheets and readjusting his pillow.

Toothless began to pout and jumped to his perch on the wooden beams of the house and prepared for his attack. He leaped and tackled the human, crashing through the wall and out into Berk with Hiccup's head inside his mouth.

Hiccup recalled how Toothless enjoyed many positions in getting comfortable. If it was a particular hot or muggy day, the fire breathing beast preferred to laze around under the shade of the trees on his back while Hiccup slept on his belly. If it was sleeping, he curled up and usually had Hiccup under his wings.

This time was completely uncalled for.

Astrid expected to find the two in their home, but instead came upon the discovery of the destroyed walls. And so she traveled by foot all the way to their usual hiding spot and found Toothless hanging upside down by a tree branch. Where there was Toothless there had to be Hiccup. But Hiccup was nowhere to be seen.

"Astrid," a muffled voice squeaked as she approached the sleeping dragon. Hiccup's head popped out of Toothless' wings, similar to the pouch of a kangaroo. "Help me!"

"How?"

"Do something! Anything! I can feel the blood rushing to my head!" he cried.

"Oh, I don't know."

"What do you mean, you don't know? Get me down!"

"Alright, alright," Astrid said. She poked Toothless' head and waved. The dragon acknowledged her and went back to snoozing. She poked him harder and he scrunched up his nose in minor annoyance. Hiccup thrashed and flailed and finally they both collapsed into the snow.

"Ow..."

"At least there was snow," Astrid said.

Hiccup, crushed beneath the dragon's weight was unable to reply.

Toothless picked himself up and dusted himself off as if nothing happened, licking his paw.

Hiccup gave chase. "By Thor's hammer just you wait until I get my hands on you, you oversized salamander with wings!"

Toothless ran away, tongue sticking out.