He felt the familiar pang of guilt in his stomach and turned to get his gear. Toothless followed behind him curiously and continued to nudge Hiccup and tug at his clothes.

"Toothless, I said don't do that. You want to go for a fly, don't you? Don't make me have to...discipline you or something." the dragon grinned and Hiccup sighed. He knew that Toothless knew he could get away with anything. He picked up his riding saddle and put it on Toothless. The dragon wiggled his tail and rolled over, wallowing in the dirt and kicking up dust in the process. Little grunting noises of appreciation made their way out of his mouth and Hiccup had no choice but to laugh. He pulled the reigns out from underneath his friend and tugged.

Toothless took his que and knelt low on the ground. His body wiggled with anticipation and as soon as he felt the familiar weight of his flying partner on his back, he took off, straight up into the sky. He flew through the clouds, and licked at the dew that formed on his nose. Hiccup leaned forward and patted his head in approval. Toothless hooked a left and flew towards the mountains, where their day's adventure were supposed to begin. Hiccup scanned the horizon and watched below as some adolescent dragons tried to keep pace with the two. They failed, and one by one fell back, a dejected tone to their grunts and howls.

Toothless neared the edge of the mountain peaks and let out playful coos. His tongue lolled out of his mouth and he did somersaults, much to Hiccup's dissatisfaction.

"Toothless, what are you doing? Are you just trying to make me vomit, because if you keep it up, your wish will be my command." Hiccup held his stomach with one hand and led Toothless to where he wanted him to go with the other. The two came up on a small beach, and Toothless squished the sand between his toes. Hiccup dismounted and took a look around; marine creatures scurried about on the sand, birds and dragons alike flew overhead, and the soft smell of brine wafted on the breeze.

"You overgrown kitten, get over here. I have an idea, but you've got to bear with me." Toothless's ears perked up and he scrunched his sand-covered nose. He picked up the crab he was playing with and trotted over to where Hiccup was, dropping it at his feet. "Thank you, for that. It's what I've always wanted. A crab. Now get over here and stop fooling around for just two minutes. Listen, I want to try something that we haven't exactly tried before. I want to try going for a swim."

Toothless looked at Hiccup with a confused look. He eyed the water nervously and shifted, and walked towards the water. He stepped in up to his knees and let his tail float on top. He dipped his head in and snapped at the few fish that swam by. He pulled his head out when Hiccup got on his back. He sat low and close to Toothless, and it baffled the dragon. Hiccup spoke into his ear softly.

"Okay buddy. I want you to walk until the water gets deep, and then we're going to dive in. If you get too scared you can always come back to shore. Now are you sure you want to try this out?" He rubbed behind his dragon's ears and breathed deep. He wasn't sure how the swimming would pan out, but he had faith in his companion. He felt Toothless walk forward and braced himself closer to the dragon. He shifted his foot and pulled his tail fin in, just as Toothless went for the dive.

The two practically flew through the water, and Hiccup strained to open his eyes, he kept them closed and hugged tight around Toothless's neck. The dragon went deeper and deeper, twisting and turning until coming to a complete stop. Hiccup lifted his head and opened his eyes, and what he saw next surprised him: a small dragon stared bewilderingly at them, looked almost identical to Toothless. It held up its paw, and the webbing between its toes glistened in the water. Toothless looked at his own paw and back at the new dragon's, before Hiccup motioned for him to swim back to the surface. Toothless followed the request and swam back up and to shore, turning around to stare back into the waters. He paced at the edge, and Hiccup dismounted him.

"Hey, you saw that too, then. Kinda funny, huh? He looked just like...you." Toothless's ears perked and he looked almost unhappy that his new encounter was cut so short. Toothless looked up and over Hiccup's shoulder, and when Hiccup turned to see what had the dragon so distracted, the small look-alike had its head poked ever so slightly above water, his long, forked tongue gently flowing in the water. Hiccup took a step towards the water's edge and the small creature hissed at him and disappeared.

Toothless ran towards the water and looked around nearly frantic. He hopped around, and flew out and kept looking between the ocean in front of him and his friend behind. Hiccup eyed Toothless apologetically and rubbed the back of his neck. He could tell already that whatever he had planned for the day just wasn't going to work out.