ℐ𝓃𝓉ℴ 𝒯𝒽ℯ 𝒪𝓅ℯ𝓃 𝒜𝒾𝓇 (Hiccup x Winged reader)

𝚃𝚎𝚜𝚝 𝙳𝚛𝚒𝚟𝚎, 𝙵𝚒𝚛𝚜𝚝 𝚏𝚕𝚒𝚐𝚑𝚝

*Authors note!- Heya! I'm back and ready to update! Sorry for the long wait! But I was pretty tired don't worry I'm taking care of myself and being the best of myself that I can be but I had lost a lot of motivation and needed a break... But I'm back and ready to feed you Hooligans! Enjoy this Chapter!*

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The boats pulled into the pier, holes on the side and a burned flag was seen within the mist. Gobber stood there, and sighed. He was hoped they had had at least gotten close. But he was a sarcastic meat-bag that had hope for the Chief. He could see them...the destroyed longships from the expedition heading back. He walked closer, as the remainder of the sailors came back. He eyes searched for the Chief.

And there he was...

"Well, I trust you found the nest at least?" Gobber asked trying to raise the Chief's spirits as he walked with him back to the Village. Stoick didn't move to look at him, his eyes glued to the floor, as he walked. "Not even close." He replied.

" Ah. Excellent." Gobber replied.

Then finally as they were on the steps Stoick looked at him, Gobber couldn't help but get that look in his eye, the look of his best friend. Which undoubtedly made Stoick feel a little better. Then Stoick shifted the conversation to something that Gobber was lowkey, okay highkey, proud of. "I hope you had a little more success than me."

"Well, if by success, you mean that your parenting troubles are over with, then... yes." With that being said, people started coming up to the Chief saying things like,

"Congratulations, Stoick! Everyone is so relieved."

"Out with the old and in with the new, right?!"

"No one will miss that old nuisance!"

"The village is throwing a party to celebrate!"

Stoick looked at Gobber and the question came out fast, no hesitation... "He's gone?"

"Yeah... most afternoons. But who can blame him? I mean the life of a celebrity's very rough. He can barely walk through the village without being swarmed by his new fans." Gobber replied.

"Hiccup?"

Gobber chuckled and said, "Who would've thought, eh? He has this way with the beasts."

Oh how right he was!

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    You know Hiccup, actually tried to prepare himself for this. Yeah. When (Y/n) told him the amazing bit dreaded words. He was gonna fly with her and Toothless. He had to prepare himself mentally and physically. (Y/n)'s wing had healed pretty nicely although it did worry him on how she was going to be able to keep up from what he witnessed with Toothless, he was actually pretty fast.

    But here he was, over the ocean flying as (Y/n) flew next to him, her wings extended as she adjusted a lot of his posture. Even though Hiccup seriously wondered where her dragon was and why wasn't she riding it. "Look straight." She commented, "Lean lower." Then pushed his forward, "But-" He started about to comment on the list he made for the steps to fly Toothless. "I'll let you go but remember, no wind resistance, hurts you and your dragon." She said, "And if you want my advice lose the sheet!" She added, before she flew off a bit farther down near the water. Hiccup looked over and watched in awe as (Y/n)'s dragon formed from the shadows. Slowly and surely watching her get into her formation. Wings tucked and leaned forward no saddle, but held on to the dragon's scruff. The way (Y/n) rode the dragon made him understand, she truly had done this much longer than than him.

No shit Sif- Of course she had been.

    He cleared his throat and focused back on Toothless. "Okay there, bud, we're gonna take this nice and slow." He started as they started flying, it started smoothly which made Hiccup a lot more calm, "Here we go. Here we go..." He shifted himself to fix the tailfin into a different position "Position three, no, four. Alright, it's go time. It's go time. Come on, buddy, come on, buddy!"

    The look of happiness on his face when he successfully changed the positions made (Y/n) smile as she flew back up to be nearby and watch over just in case anything happened. "Yes, it worked!" He cheered. As the two flew. (Y/n) looked at him, smiling as she lowered her helmet. Hiccup blushed, losing his focus as he watched her fly, her (h/c/l) billowing in the breeze as she flew ahead once again. He couldn't help but smile like a complete idiot.

May the Gods have Mercy, he must stay focused!

    And just in time, Hiccup accidentally flew Toothless into one of the sea stacks.

"Sorry!" He said,

The the pai hit another sea stack

"That was my fault."

    He caught himself back on, when Toothless gave him a nice bonk in the face, from his ear. "Yeah, yeah, I'm on it. Position four, uh, three." He started then shifted positions, it was perfect, as he started flying upwards (Y/n) following after him, hearing him cheer in support. "Yeah! Go baby! Yes! Oh, this is amazing! The wind in my..." It was the worst of timing.

The wind with all its power pulled the his cheat sheet out of his hand

" ... CHEAT SHEET! STOP!!" (Y/n)'s eyes widened in shock as she saw the situation unfold.

    It was all bad timing, bad timing indeed. Hiccup's diagram flew higher out of reach, away from him. (Y/n) could only watch as he tried to catch it, but unhooking the safety cord, made the protectiveness in her unsheathed and she leaped off her dragon, reaching out to help Hiccup.

" NOOOOOO!!! Oh, gosh! Oh, gods! Oh, no!"

The three of them were now falling, as Hiccup tried to have Toothless position himself to try and remount Toothless. Getting smacked with Toothless' tail in the process.

"Alright! You gotta kind angle yourself! Okay, no, no, no... come back down towards me! Come back down-- YOW!"

(Y/n) moved a bit closer helping him remout Toothless, and reattaching the safety cord, it was (Y/n) quickly returned to her dragon, the cheat sheet smacked into Hiccup's face. He tried to memorize the sheet...Fuck it! He tossed the sheet, as he started to take control his own way. (Y/n) cheered for him as she and her dragon phased through the sea stacks like a shadow. Hiccup watched in astonishment, as he swerved and dodged the stacks, as (Y/n) laughed and cheered, feeling more and more free as they both flew.

"YEEAHHH!" Hiccup whooped with joy, and Toothless feeling the happiness and excitement shot a blast of fire, feeling so happy, and flies through it.

Forgetting that Hiccup was on his back, "Ah, come on.."