Later that night, Hiccup and Toothless met the other riders at Wild Beach, just five minutes before the challenge would begin. After dismounting Toothless, the black dragon changed form into human and walked with Hiccup toward Astro.
"Alright." said Astro, getting everyone's attention, "Before we start the challenge, I'm gonna need to volunteers to watch the dragons while they wait for us at Dead Man's Cove. I've had a talk with Jack and Draymore, and they're willing to cover that for us, so we won't worry about your dragons getting hurt."
Snotlout was shocked when he saw Hiccup. Hiccup was wearing a leather vest and gloves to prevent herself from using her powers. She had also brought her shield with her, along with a lit torch. Snotlout pretended not to notice as Hiccup glanced at him.
It was time for the riders to depart from their dragons, so each rider was given a minute to say their goodbyes. After hugging Draymore, Hiccup backed away a step and said casually, "Good luck with not being stomped on."
Draymore froze at the statement. "What?"
"I'm just kidding. You'll be fine."
Draymore nudged Hiccup's shoulder with his fist.
Hiccup turned to Jack, "If I arrive at the cave to find him dead, I'm holding you responsible."
Jack raised his hands sarcastically.
The teens waved to their dragons as they began their journey through Dragon Island, leaving Draymore and Jack with the dragons.
Jack was the first to speak when the others were gone. "So where's this cave at?"
"Follow me." said Draymore. Draymore mounted onto Stormfly's back and lead the other dragons to Dead Man's Cove. Jack flew above them.
"This is new: a dragon riding another dragon."
Draymore looked up at Jack confused.
"Well, you're two thirds dragon." explained Jack, "I thought it would make sense."
"Very funny."
"Okay, how about a new topic? How often does Hiccup purr?"
"Hiccup purrs?" asked Stormfly.
Draymore glared at Jack, "We're not supposed to be talking about that."
Jack shrugged and flew ahead of Stormfly, "I'm just curious. Does she purr when she's sleeping? Or does it only happen when she's having a specific dream?"
Draymore sighed, "It only happens when she has a good dream. But that hasn't happened in a long time. She keeps having the same nightmare, but she's never explained what happens."
Jack suddenly seemed concerned, "Did you ever see something that looked like black sand flying over her head when this happened?"
Draymore thought back. "No. Never. At least not that I know of. I never really look at her when she sleeps. It's creepy for a boy to do something like that."
Jack seemed more worried, "Draymore, next time you wake up before her, look at her. If you see any black sand flying above her, call me."
"Why?"
"Pitch might be attacking her in her sleep."
"Who's Pitch?"
"He's the King of Fear. He turns dreams into Nightmares just by looking at the sleeping people. He plays with their fears and forces them to stop believing in us Guardians. When too many people stop believing in us, we lose our powers, and eventually... we might lose our lives. But that's not the worst part. Once someone stops believing, it's difficult to help them believe again. And until they do, Pitch has all control over their lives. He could make Hiccup one of his Nightmares."
Draymore spotted Hiccup near one of the lagoons below. He began to worry for her.
