Thanks to YesthenLucky9 and harrypanther for the reviews!

I'm going to kinda skim over this section. The actual Hiccup training Toothless is kind of hard to write. The important stuff is there though.

Enjoy!

"Hiccup?"

"In here, Astrid."

Astrid walked in, almost stepping on something. "What is that?"

Hiccup didn't even look up from his workbench. "It's a dragon saddle."

Astrid sighed. "You're actually serious about this?"

"Astrid, Toothless helped me out of the water. He knows he needs me to be able to fly. And I'm going to help him."

They walked into the cove, where Toothless waiting.

Hiccup smiled and held out the saddle. The playful look on the dragons face was not what he expected.

Finally, Toothless stopped running and allowed Hiccup to put the saddle on.

Astrid stepped forward. "What's your plan?"

Hiccup grinned. "I tied a rope to the tail fin. I can pull it to open the fin."

"Be careful."

He smiled at that. "When am I not careful? Okay...don't answer that."

Although she was worried, Astrid did chuckle when Hiccup and Toothless were dumped in the river due to poor timing.

That night, Hiccup worked on the saddle. "Ok. I'm attaching hooks to the saddle, that way I don't fall off."

Astrid smirked. "Good idea. Can't have you losing a limb now, can we?"

Next attempt, Hiccup tied the rope to his foot, so he could use both hands to steer Toothless. Predictably, this ended up in them crashing in a field, and Hiccup unexpectedly found Toothless rolling around in the grass. He picked up some, wondering if it could be used on other dragons.

He was still holding that piece of grass in the arena, where Gobber had just let lose the Gronckle for round two. And, as usual, it came straight for him. Hiccup cowered in fear and stretched out his hand, holding the grass out to the dragon.

The Gronckle, eyes wide, stopped and sniffed the grass, losing all thought of the boy in front of him. Hiccup left the grass on the Arena floor, and quietly shifted away from the dragon.

As they headed back from Training, Hiccup was unexpected surrounded by the other teens. Hiccup, due to his years of being bullied, decided to leave and, giving a conspiratorial wink to Astrid, made up some excuse about leaving his axe in the Arena, and headed for the cove.

Next attempt, Hiccup started to work on a gear system that would allow him to open the tail fin without endangering the flight. The next day, he got Toothless another barrel of fish while he worked on getting the various pieces in place.

After many attempts, and many successes at Dragon Training due to what he was learning from Toothless, Hiccup finally felt ready to take Astrid on a test flight.

"Ok, Astrid. Just hold on. You ready, Bud?"

"Hiccup, are you sure about this?"

"It's just a test flight. It's not like we're taking on the Berserkers or anything."

Astrid sighed. "Fine."

"Okay there, Bud. We're going to take this nice and slow."

He glanced down at the sheet of paper depicting various gears. "Here we go, position three."

Astrid looked over his shoulder. "Four."

"What? Oh, sorry, yeah. Position four. Thanks."

As they flew, Astrid was amazed. "You're actually doing it, Hiccup! You're flying on a dragon!"

"It's cool, right? Ok, Toothless, let's go up!"

The higher they got, the harder it was for Astrid to hold on, and eventually she fell off Toothless, falling to the ground.

"Astrid!" Hiccup turned Toothless around and tried to speed up to catch her.

"C'mon, Bud, Come on!"

He managed to grab her before she hit the ground, and pulled up hard to not crash.

Hiccup's cheat sheet flew away in the air, and he groaned as he saw a lot of sea stacks in front of him.

"Astrid, hold on. This might get tricky."

Utilizing what he had memorized about the various gears, Hiccup, Astrid, and Toothless managed to get out of the maze of seas stacks, and landed on a deserted island.

Hiccup glanced at Astrid. "You OK?"

She nodded. "Yeah. Thanks for catching me. You did good."

Hiccup smiled. "I wasn't about to lose you. You're more important to me than a flight on a dragon."

Astrid grinned. "I think that's the most romantic thing you've ever said to me."

"Also I need you to keep the bullies away."

"Annnd moment's past. Nice work."

Hiccup smirked. "So, what's next."

"It's down to you and me for Dragon Training."

"I think I'll let you win."

"Aw. Thanks. Don't go using any of your fancy dragon tricks."

"I promise."

Hiccup, don't make promises you can't keep. No wonder Astrid gets mad at you...

Thanks for Reading!