Hiccup loved flying. The way the cold, icy wind whistled past his ears and through his hair. The way the land; all the trees, sheep and buildings, shrunk to such an insignificant size as he soared way above them. The way the salty spray from the sea splashed up at his face, should he ever fly close enough.

Hiccup loved flying. But only on Toothless.

Flying on Toothless was exhilarating and relaxing and terrifying all at once. Flying on other dragons...wasn't. He had flown on other dragons lots of times, for a variety of reasons, but never had it felt the same as flying on Toothless - it had always felt...dull.

Hiccup didn't know why flying on toothless felt so special to him. Maybe it was because of all the time he had spent, at the beginning, trying to train Toothless. Hours upon days upon weeks of watching and waiting and patience were spent before he had been allowed to touch the dragon; a simple hand on his snout; and yet, it was still a massive declaration of trust. For Toothless to have gone from shying away from an innocently intentioned hand in fear, to allowing himself to be ridden, showed the large amount of trust he had for Hiccup.

Maybe that's why flying on Toothless was special.

Maybe it was because when he was flying on Toothless he was never fully in control. Hiccup made the decisions, hiccup controlled the tail, but if Toothless disagreed with him he would make it known by a slap from his ears. All the other dragons did as he said when flying, if they disliked his path or instructions they showed no objections or protests; he was the dragon trainer, the dragon conqueror -dragons obeyed him. Toothless was different. Toothless chose the path they took just as much as he did, Toothless gave instructions just as much as he did. They were co-pilots when flying, neither more dominant than the other.

Maybe that's why flying Toothless was special.

Maybe flying on Toothless was special to Hiccup because they weren't master and pet. They were friends. Whenever Hiccup was flying on Toothless, he was with his best friend, going out for an adventure.

Flying with Toothless was exhilarating and relaxing and terrifying to hiccup. Maybe that's why he found it so special.