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Before anyone asks, I just based Shadowflight's saddle after the saddle Toothless wears in HTTYD 1 minus the added bits like the stirrup used to move the tail fin prosthetic around. Originally I wanted Jim to ride bareback, but figured it'd be a bit too dangerous and our practical Trollhunter would want to use a saddle to keep himself from falling off midflight.

Also,  while my updates are far and few, I won't be updating anything as much due to now having a job so I could have some money in the bank and so I won't be sitting idle at home most of the time. So please no dropping comments asking when I plan on updating if I'm working five to eight hours serving food and having barely any time to write

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"You know, I just realized something. We have never gotten to fly together." Jim comments one afternoon as he lays his pencil down and looks to the living room where his dragon is gnawing on a big plastic ball. Shadowflight looks up from his chewing to give him a puzzled look, now having his attention. "Like those past two times I got to ride on your back, but we never did any riding, unless you wanna count jumping high over things as flying. Toby told me he and Claire got to ride on your back, a terrifying but fun experience. Maybe one of these days when I don't have my duties to fulfill or homework to do, we can go on a little flight, just the two of us?"

Shadowflight perks up and gives an excited warble before getting up and walking to the backdoor leading to the yard and nudges the knob with his head. Jim gives a small chuckle before backing up his pencil again.

"No not right now, I have homework right now. Maybe...Saturday."

Shadowflight gives a small huff in annoyance before walking back into the living room and climbs onto one of the couches with a pout on his face. Jim gives a chuckle, knowing what the dragon was trying to pull and knowing too well not to fall for it.

"Saturday bud, Saturday."

Another huff of annoyance.

"Bud, you're not going to guilt trip me like you did a few days after returning from the Darklands by taking my lunch."

Shadowflight gives an annoyed warble, followed by another huff.

"Go guilt trip Draal, I need to finish this English assignment. I swear on Saturday, we'll do it when mom is gone and it's dark enough."

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"You are way too eager for this flight aren't you?" Jim asks as his dragon wiggles in delight as the tanner is trying to fit the saddle on his back. "Hold still, Snok looks ready to tie you down to get the saddle on.

"Very tempted at this point." The tall grey skinned troll mutters as she blows a strand of hair from her face. "Alright, it's done. Took some liberties on the drawings you showed me from that book, removed the extra bits like the ones connecting the stirrups to the tail fin and added an extra strap that goes under the arms to avoid having the whole thing flop around."

"Oh that's actually a good way to keep me from falling off. Kind of thought this was gonna be like a horse saddle in the second reference I showed you." Jim says as he watches.

"Useless looking thing, how could a single strap keep an entire saddle on a pack animal's back?" Snok mutters as she finishes adjusting and strapping the saddle down. "Alright, have him move around, see how he likes it and if it's comfortable. If he feels it's too tight I'll just loosen it a bit."

Shadowflight turns his head to try and examine the object on his back before pawing at the leather straps around his neck and under his arms. He seemed confused about it, wondering why Jim asked this troll to put this odd thing that smelled funny. He looks to Jim and lets out a confused croon, but makes no attempt to try and remove it.

"It's a saddle bud, it's supposed to keep me from falling off your back when we go flying this weekend." The teen explains as he walks over and puts a hand on the dragon's snout in comfort. "Don't worry, you won't have this on all the time. We'll only put it on for missions or just for flights if you feel comfortable with it. "

"Best have him get used to wearing it, break it in so he won't be trying to remove it." Snok suggests. "Try sitting in it, see if it works and feels comfortable."

"I was just going to ask if I should do that! Thanks for suggesting it though." Jim placed a foot in one of the stirrups and held on as he hoisted himself up, the way he had seen professional horse riders do in the instruction videos he'd been watching. There were two looped straps in the front that would allow him to use to hold on like reins (there was no way he was putting a bridle on Shadowflight, that'd look stupid) and grasps them tightly as his dragon starts to move around, attempting to get comfortable to the feel of the saddle with Jim's added weight.

"Huh, not bad." Snok says with a nod. "Never thought I'd live to make a saddle for a dragon, much less the Trollhunter's own dragon."

"Well if we actually end up finding more friendly dragons willing to get along with trolls, perhaps you can make more saddles for them." Jim suggested and the tanner shook her head.

"Dealing with one dragon is enough for me, I won't make another saddle unless this one needs to be fixed." Snok responds. "Now shoo, I have some armor to make."

"Thanks Snok!" Jim chuckles as Shadowflight walks out of the shop and into the busy streets of Trollmarket.

They had gotten some odd stares from the other trolls but they just looked away either chuckling in amusement or muttering and shaking their heads. Jim couldn't help but crack a grin, enjoying the fact that he was finally going to get to do something he could only dream of as a child. It was already night time and his mom had a shift at the hospital, so maybe it wouldn't hurt to have a quick ride tonight to test out the saddle. And on top of that he had no Trollhunter duties for the night, and he finished his homework as well.

"Hey, what do you say about taking this saddle for a test flight?" Jim asks and Shadowflight's ears perked up in excitement and gave an excited croon before turning towards the direction of the entrance with the teen hanging on for dear life.

Once the two managed to slip out and were in the woods located near the canals, Shadowflight began climbing onto one of the trees until he reached the top and looked to Jim before giving him a croon, as if asking him if he was ready.

"If you are asking if I'm scared, I am, but I'm sure it will go away if I don't look down." The teen assures his friend. "Man I probably should have brought a jacket, maybe we should run home to grab one so - AAAAAAAAAAAAAAAAAAHHHHH!!"

JIm clung onto the straps of the saddle for dear life as his dragon took off into the sky, praying his grip wouldn't loosen and send him plummeting to the ground. His eyes were squeezed shut and he could hear Shadowflight grunting and panting as he pumped his wings to climb higher. This was a bad idea, a very bad idea!

He then felt the dragon right himself and heard him croon softly, encouraging him to open his eyes. Jim slowly opens his eyes and gives a small gasp when he realizes they're above the clouds. Out of curiosity, he reaches over and stretches his hand to touch the clouds, nearly expecting them to feel solid, but feels nothing. Glancing down he could see glimpses of the town below, the blinking lights of the cars, houses and shops looking like little flecks of light. It looked just so...beautiful.

No wonder Hiccup loved flying his dragon every day over Berk, the view from a dragon's back is amazing. Jim thought with a smile as he pulled his hand back to grab onto the straps again. Oh this would be fun to do with Claire, just go on a flight over the town to show her what it looks like from the air. Maybe when we resolve all this .

This was at least more fun than the last time he was being tossed around in the sky. At least this time he was seated securely on his dragon and not dangling from the grasp of a stalking from his feet. Feeling a surge of adrenaline, Jim gave a whoop as he threw his arms up, letting the wind rip through his jacket and Shadowflight let out a roar of happiness before grabbing onto the straps of the saddle again as the dragon began to descend through the clouds down towards the lights of the town. Taking care not to be seen, they soon find their home and land safely on the roof of the house.

"That...that was something." Jim says as Shadowflight climbs down from the roof and drops down into the yard before he climbs off, yelping when he feels his legs give out under him. Shadowflight was quick to catch him and keep his friend from falling onto his face and into the dirt before balancing him upright. "Thanks bud, lets hope next time we go for another flight my legs won't be so weak again."

The NIght Light gives a happy croon before leading Jim back into the house, letting the human lean on him for support. At least now they knew the saddle worked, all thy needed now was just some practice.