Y/n is always looking out for his younger brother Hiccup always trying to keep him out of trouble and making sure he doesn't get hurt. However, one fateful night everything changes when Hiccup finally takes down his first ever dragon and helps his b...
As Stoick returned to the island and questioned about the fates of his two sons, the pair were actually just off the coast of Berk flying both Toothless and Shadow. Hiccup had wanted to test his flying abilities and feel the freedom of flying in the sky without some rope restricting him to the ground. Y/n was on edge and was surprised at Hiccup's request to join him in soaring through the air. Y/n had argued in the beginning but had remembered that he cannot babysit his brother forever and needs to let him 'spread his wings.'
The two pairs were gliding high over Berk outside of the visual range of anyone below, Hiccup was leading as Y/n was giving him enough room whilst also staying within a close proximity should anything happen.
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(Imagine Y/n and Shadow following behind)
Hiccup: "Okay there, bud, we're gonna take this nice and slow. Here we go. Here we go... position three, no, four."
Hiccup had opened up Toothless' tail which would allow him to go into a wide left hand turn with Y/n following his every move. During the turn Hiccup had kept checking his safety harness to make sure that everything was working properly since the previous accident last night. After coming out of the turn Hiccup had adjusted the tail once more quickly followed by another to just make sure that everything was in working order for what had planned next.
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Hiccup: "Alright, it's go time. It's go time."
With this said Hiccup took Toothless into a steep dive towards the ocean and the sea stacks that were located just off Berk's coast.
Hiccup: "Come on, buddy, come on, buddy!"
Y/n: "Come on Shadow, show me what you can do!"
Y/n and Shadow quickly began their descent and started to chase after Hiccup and Toothless. The two was ahead heading towards the sea stacks as Hiccup wanted to now test his turning only to adjust it too late. With his slow reactions Hiccup had caused Toothless to make contact with several sea stacks before flying away from them.
Hiccup: "Sorry!"
Hiccup (cont.): "That was my fault."
Meanwhile, Y/n and Shadow slightly cringed as the events were unfolding in front of them followed by Toothless' pained cries, as they had successfully manoeuvred themselves without any problems. Hiccup had looked back, slightly jealous that his brother were so in sync with each other, whilst he and Toothless struggled at but did not let it distract him from the job at hand. That moment was quickly forgotten as Toothless made himself known by whipping Hiccup with his ear to show his frustration in him.
