A/n: A short one, pooh stick's idea.
The air was, in Hiccup's opinion, the safest place to be. Many other Vikings didn't share the sentiment - they wouldn't admit it, but many had a fear of heights. They feared falling, and more importantly the result of them making contact with the ground.
Hiccup knew that the fear of heights was based off a lack of trust. No matter how comfortable the people of Berk may say they were in the air, only those who trusted their dragons with their lives would ever be truly at home. It was a shame, he thought, that there were so few who could trust their dragons like he did. Even after losing his leg from falling, Hiccup didn't fear flying - he knew that Toothless would always catch him. And if he didn't, he'd give it his best shot.
"Read, bud?" Hiccup checked, patting Toothless's neck. The night fury rolled his eyes, but Hiccup could tell that he was apprehensive of attempting their newest stunt. "It'll be fine!" he insisted.
'Yeah, like the wings were fine the first time...' Toothless muttered sarcastically.
Hiccup scoffed. "That was fine. Sure, we crash landed, but no harm done, right?"
Toothless didn't respond, and Hiccup took that as a signal to go. In keeping with his plan, he dived off Toothless's back. He didn't open his wings just yet, letting himself go into free-fall for a while, relaxing as the wind pushed his hair back. After a minute of uncontrolled drop, he pulled out the wings.
Toothless sped in front of him, moving from left to right as Hiccup tried to catch up. The plan was to try landing on a moving target; it would make jumping onto the backs of other dragons much easier, and it looked cool. The two started to slow down as they reached the tree layer, and Hiccup reached out for Toothless's wing.
Instead of grabbing it and pulling himself on, Hiccup managed to unbalance Toothless so that he lost control and span onto his back. Suddenly, the two were falling through the air, dangerously close to the highest branches now.
'I told you this was a bad idea!' Toothless yelled as they continued to plummet. They were hitting branches now, so neither could correct themselves.
"I think it's going - ow!" Hiccup slammed into a branch, knocking the air from his lungs. Toothless rolled his eyes and wrapped his wings around the Viking as they fell, protecting him from the majority of the tree-based assault.
They hit the ground with a snap, landing on the branches they'd knocked down during their fall. Toothless instantly unfolded his wings to check Hiccup's well being.
"Woo!" Hiccup shouted, jumping out of the protective cocoon clumsily. "That was awesome!"
Toothless snorted as he stood up, shaking some of the bits of tree from his scales. He hit Hiccup lightly with his tail.
"Fine. But we nearly had it!" Hiccup insisted. "If we just -" he let out a sudden yelp as he tripped over, landing in a tangle of limbs. "Little help?"
Toothless laughed; for all his grace in the air, Hiccup was ridiculously clumsy on land. He nudged his friend into a standing position and sniffed him down carefully.
"I'm okay," Hiccup said. "Now, let's try again, see if we can - oof!" he tripped for the second time, prosthetic getting caught on a root. "Okay... maybe we should just call it quits." he decided, letting Toothless nudge him onto his back to carry him home.
