So I apologize for the wait, I just started school today (ugh) but I managed to get this done. Enjoy and excuse any mistakes. ^-^
You'd taken (D/n) to the dragon stables and chosen a (d/t) to fly. You'd chosen this dragon regularly, so it was normal and easy to fly (him/her). (D/n) flew beside you, keeping an eye out for Hiccup as you soared over the islands.
A squawking noise coming from (D/n) tells you he's near. You nod at her and she swoops down to a small island below you. You follow her through the clouds and land in the clearing where Hiccup sits, on a cliff looking over the sea.
Toothless looks in your direction and smiles, jumping up after (D/n). They play, reminding you of two cats. Hiccup turns and smiles at you.
"Hey." You say, walking to him.
"Morning milady." He says happily. You sit down beside him and pull your knees up to your chest. "What are you doing here?"
You sigh and look down at the thick grass beneath you. "Well," you say as you pluck a piece of grass out of the ground. "Stoick was asking me, again, where you were."
"He was?" Hiccup mumbles.
"So I told him that I wasn't sure but I'd come find you." You look up and smile at him. "So here I am."
"Yeah." Hiccup sighs and scratches the back of his head.
"Hiccup I told you that I'd be here for you. You don't have to run off on your own all the time." He looks down and you take his hands. "Look, I understand how-"
Hiccup shakes his head. "No." he grumbles. He buries his face in his hands and sighs. "No, you don't understand!" Hiccup suddenly shouts. He stands up and begins pacing. You sigh and turn your body to face him. "I'm the 'pride of Berk' and only son of Stoick the Vast. I have no way out of this. I can't do this! I'm not like my Dad I'm like-" He stops. "I don't know who I'm like." He whispers.
"Well Hiccup, maybe you're like your mom." You say, smiling at him.
"I-I never knew my mom." He whispers, his green eyes staring down at you. You see tears threatening to spill and you stand up.
"So how am I supposed to know what I'm here for?" He whispers as you wrap your arms around his waist and lay your head on his chest.
"You can figure this out, Hiccup." You whisper back. "I'll be here."
Hiccup pulls away and takes your hands and smiles at you. "And I'll be here for you." You smile back and he sighs. "Would you... Tell Dad that you didn't find me?"
"You want me to lie to your Dad?" You laugh quietly.
Hiccup scratches the back of his head and shrugs. "That would be ideal."
You shake your head and roll your eyes. "Alright. You owe me though." He nods and grins that adorable goofy smile. "I'll see you at dinner." You wave and walk back to your dragons. Hiccup waves as you shoot off into the air.