While above the ocean a boundless sky. Vast. Clear. Crisp. And from it, two specks rockets across the horizon. The image of unbridled freedom. Tucked into his riding position, Hiccup appears to be part of Toothless. They dip, roll and dive, over a sea teeming with Thunderdrums, pulling off daring maneuvers with honed refinement, making them seem effortless. Flying beside Toothless was Optimus as Emily was making sure not to fall off as her hair was blown back by the fast breeze of their flight.

"Yeah!" Hiccup cheered in delight

They jackknife, heading skyward, rolling and tumbling through the ethereal cloud-scapes and joining high-flying Timberjacks as they soar in formation. Hiccup is bound head-to-toe in a snug, aerodynamic flight suit with an asymmetrical, functional design of leather and articulated plates. It has an air of Viking bike leather. Emily was wearing something similar but to her style as she stands on Optimus' back while enjoying the view and the Timberjacks flying above them.

"What do you think, guys? Wanna give this another shot?" Hiccup asked as he looked between Toothless and the pair flying beside them.

Toothless grumbles in protest as he knew what Hiccup meant. Emily and Optimus looked at Hiccup with a raised eyebrow.

"Hiccup, you're seriously asking for a death wish." Emily said as she gave him a deadpan look. How many times he tried to do this stunt was beyond her but she couldn't help but find it amusing.

"Guys, come on! It'll be fine." Hiccup reassured them before moving the pedals and locked it.

With a click of a lever, he locks the pedals in the flared tail position. Hiccup then unhooks himself from the saddle.

"Ready?" Hiccup asked while Emily just rolled her eyes with a smile while Optimus warbled while watching Hiccup carefully with Toothless snorting unenthusiastically.

Suddenly, Hiccup slides off of Toothless, peeling away from him like a skydiver from a plane, yelling as he plummets. Toothless dives after him. They spiral through the air, face-to-face. Toothless is having fun, despite himself.

Both Emily and Optimus watched them from above while Optimus warbled and looked at Emily from the corner of his eyes. Emily could tell that Optimus was worried about Hiccup and Toothless.

"Don't worry, sweetspark. We just gotta make sure they don't hurt themselves in the process." Emily said with a reassuring tone but she couldn't help but agree with Optimus.

When Hiccup sees the ocean, he slips his forearms through a pair of tucked leather flaps, and yanks, unfurling sheets of leather as he extends his arms. They catch the wind, snapping like wings, and sending him gliding! Toothless unfolds his wings, too, catching up with Hiccup as Emily and Optimus were flying behind them. The freedom is palpable. Hiccup and Toothless are, for the moment, the same. Feeling the same rush of adrenaline. Independently together. They plunge past cloud formations, splitting apart then crossing paths again.

"This is amazing!" Hiccup exclaimed back towards his friends.

But it looks like karma decided to take effect as a cloud layer washes past, exposing a towering rock formation, dead ahead. This made both Emily and Optimus gasp in shock as Toothless roared worriedly.

"Hiccup, look out!" Emily exclaimed worriedly.

"No longer amazing! Toothless!" Hiccup exclaimed in fear and nervousness.

Hiccup tries to steer himself away, to no avail. Toothless pours on the speed, trying to catch Hiccup as he hurtles toward collision. His locked tail makes maneuvering difficult. He's unable to pull up at a steep enough angle.

"Oh, no! AHH!" Hiccup screamed in fear of the collision.

At the last second, Toothless blasts the jagged rocks just ahead of Hiccup, then wraps Hiccup in his wings as they fly through it. The obliterated peak rains down around them. Toothless emerges through the cloud of debris and hurtles into the trees of a neighboring peak. They tumble down the uneven terrain, coming to rest on a small plateau.

Both Emily and Optimus arrive after and quickly check on both of their friends while Hiccup emerges from the cocoon of Toothless' wings. He switches his prosthetic riding foot to his walking foot and stows his leather wings.

"Oh Primus, are you two okay?!" Emily asked worriedly while checking the two over as Toothless got up painfully from the impact.

"Ems, we're fine." Hiccup reassured her as he continued to fold up his leather wings back.

"That really came out of nowhere." Hiccup said as Emily snorted.

"You tell me. You almost crashed into it." Emily said.

They both perked up and turned around and winced as the sea stack cracked and fell apart from the blast of the plasma blast Toothless used on it. Toothless grumbles to ask if anyone would notice.

"We gotta work on your solo flying there, bud. That locked-up tail makes for some pretty sloppy rescue maneuvers, eh?" Hiccup said as Emily rolled her eyes.

"Toothless won't take that comment lightly, Hiccup." Emily said as she started to tie her hair in a french braid.

Hiccup then removes his helmet, revealing a 20 year old Hiccup framed by wild hair, complete with a Viking braid. He walks to the edge of the cliff, taking in the new land that he, Emily and their scaly friends discovered.

"Oh. Looks like we found another one, guys." Hiccup said as he missed the annoyed look Toothless sent him before he somehow threw a small pebble at the back of Hiccup's head.

Wincing, Hiccup turned to see Toothless with a scowl on his face but it seemed that he's pouting while turning towards the other way while Emily snickered.

"Oh, what? Do you want an apology?" Hiccup asked teasingly as Toothless answered with a grunt as a yes.

"Is that why you're pouting, big baby boo?" Hiccup asked and Toothless gave a deadpan look while imitating his question and caused Emily to hide her face on her arm on Optimus' side to stop herself from laughing.

"Well... try this on! Ya feeling it yet? Huh? Picking up on all of my heartfelt remorse?" Hiccup challenged and he didn't see how Emily was snickering with suppressed giggles and how Optimus was looking quite amused as Toothless stood up on his hind legs.

The Night Fury walked towards the edge of the cliff and waited for his rider to notice.

"Hiccup better notice what's happening before Toothless puts the drop on him." Emily giggled as Optimus nodded in agreement to that.

"Oh, come on, Emily. He wouldn't hurt a one legged- AHH!" Hiccup started but yelped loudly and clinged against Toothless when he looked down and saw his situation.

Toothless lets out chortles like laughter while Emily just burst out laughing as she leaned against Optimus for support whilst laughing and won't fall over as the Predabot Prime let out what sounded like a chuckle like warble.

"You're right! You're right! You win! You win!" Hiccup said and Toothless soon fell backwards and caused Hiccup to laugh.

Emily shook her head at their childish antics. Their bond is strong and hoped that it would be strong enough for their next adventure.

"Whoa, whoa, whoa! Aha-ha-ha!" Hiccup laughed as they both started to playfully fight.

"He's down! And it's ugly! Dragons and Vikings, enemies again, locked in combat to the bitter-URFF!" Hiccup said dramatically before getting pinned down by Toothless' head.

Toothless then starts to lick Hiccup like a dog as Emily wrinkles her nose in both disgust and amusement and to Hiccup's dismay, he's gonna smell like fish and dragon breath again not that Revna minds the smell anyways.

"Gaaaaagh! You KNOW that doesn't wash out." Hiccup groaned in disgust yet fondness as he tried to remove the saliva off him.

Toothless chortles a laugh and Hiccup splashes some spit on Toothless' face with a smirk.

"You know that you might wanna take a bath twice after this, right." Emily said as she finished braiding her hair and checking her staff.

"At least Revna doesn't mind the smell, Emily." Hiccup said with a chuckle as he thought of his very special fiancee.

He still remembers the day he was 16 when he met her at Outcast Island when he and Toothless tried to find more Night Furies. Turns out Revna can turn into a full Night Fury and she likes to blend in with other humans as well but the dead giveaway would be the Night Fury ears and wings and tail that still stayed out in the open.

Hiccup looks around at the new island that they discovered before kneeling down and pulling out his map. He started to unfold it to reveal it's size. He sharpened his charcoal pen before checking the coordinates of the island they were on.

"So what should we name it?" Hiccup asked.

Emily was about to answer but was interrupted by Toothless who started to chew on his itchy armpit.

"'Itchy Armpit' it is." Hiccup said with a snicker as he wrote it down while snorting out a laugh.

"Miko would tease you for that, Hiccup." Emily commented before she went to his side and sat down beside him and looked over the map.

"Whaddya reckon, guys? Think we might find a few Timberjacks in those woods? The odd Whispering Death or two in the rocks?" Hiccup suggested questioningly as Emily added a bit more detail to the map as she shrugged.

"Dunno. And Whispering Deaths aren't Toothless' favorite. Especially Optimus. You know how the two feel about the Boulder Class dragons." Emily reminded him.

She still clearly remembered their first encounter, specifically, Toothless' arch rival and the Whispering Death invasion and their first face to face battles with the Screaming Death. To say the least, those experiences were really scary but they managed to get out unscathed. Hiccup shrugged as he looked over the horizon.

"Who knows... maybe we'll finally track down another Night Fury." Hiccup said hopefully as he and Toothless looked at each other.

For the past 5 years, they've been trying to find at least a sign that a Night Fury is still alive somewhere. And so far, they were nowhere near closer to finding one.

"Wouldn't that be something? So, whaddya say? Just keep going?" Hiccup said dejectedly with a sigh before turning to Toothless who let out a warble.