Title: Too Late
From a request by Canadachild9 on Tumblr
They were the closest friends, both considered outcasts on the island of Berk; Hiccup for the trail of misfortune of everything he touched at least in the eyes of the vikings around them, and Jack for his pranks, tricks and constant fooling around instead of taking on the seriousness their occupation demanded. They were never apart, nearly attached to the hip with Hiccup involving Jack in his inventions and plans to take down a dragon, then Jacks dragging Hiccup into his jokes and plotting of fun. While they were trouble, it was always a relief at least to Stoick that Hiccup wasn't alone.
At the days from childhood became years, the emotions between them strengthened, to the point neither could put words to the feeling when Jack would climb into Hiccups loft room, would lay besides them, eyes locked, knees brushing and slowly, a hand tangling their fingers together in awkward, but wonderful confusion they couldn't explain. They both felt it, but neither had the words, had the guts. And neither of them believed the other felt the same way.
Toothless was a shocking addition to their duo, and Jack felt ease(After Toothless threatened to drop him at first from the top of a tree) on the dragons back, arms wrapped around Hiccups waist as they soared the clouds. He pressed close to the other young viking as they hid with Toothless in the dragon nest, they figured out the raids, they found the truth and real danger, he felt the darkening storm coming between the war of viking and dragon, how it was either going to end with peace … or the end of vikings or dragons, even both. Jack had been the first to give his help to Hiccup to save Toothless, to prove dragons were not the monsters they thought, to take down the Red Death that Hiccup and him had seen in the dragons nest.
They were winning, they were winning! He could see it as both dragon and boy raised to the sky with the Dragon Queen behind them, plan in the green eyes Jack knew every shade they held, they were going to win, they were going to succeed!
Yet success, they found out, did not always mean everyone made it out alive. He couldn't hear the cries, the sobs of regret and sorrow from those around him over his own screaming, scrambling to the remains of the two he had considered friends, considered family after his own had drowned under the cracked ice of the lake.
Jack didn't know what hurt worse, to never see that smile again, those freckles, the crinkle of green eyes in happiness when they spoke, to feel their fingers tangle together, to hear that sarcasm or that the words he had tried to figure out for so long came too late.
"I love you, I love you, please! HICCUP! PLEASE DON'T LEAVE ME, I LOVE YOU!"