"What do you mean let her go?" Stoick asked his son.

Hiccup had asked his father many times for this request. It had been almost a year since the incident with the medallion and Merida had worked in the stalls. She became very close with Hiccup and Astrid. Hiccup loved having her around as did Astrid, but both could see her getting restless. She was less responsive as usual. The sense of confinement was driving her insane and even though Hiccup wanted her to stay. He knew she wouldn't be happy.

"I think she has gone through her punishment long enough." Hiccup stated.

"It hasn't been even a year yet Hiccup! You're willing to risk your life and your people's life for some prisoner girl to be happy. Reminder that she's the one that hit you in the first place!"

"She's changed. We've gotten to know each other she trusts me."

"Hiccup she's a thief."

"She only does it to survive if we give her basic needs then she won't steal I will give you my word." Hiccup said sternly.

"Fine she's allowed to walk the grounds."

"Thank you."

"Only if Astrid supervises."

"Why Astrid?" Hiccup asked.

"Because she won't get clouded judgement from a pair of pretty blue eyes." He replied.

"I don't know what your talking about but I'm feeling uncomfortable so I'm going to just ya thanks again." Hiccup stumbled with words as he walked back to Merida's cell.

Merida was lying there looking at the ceiling. Bored out of her mind. Hiccup stepped in her cell and sat on a little stool.

"Guess who got you the privilege of walking around the grounds." Hiccup said.

"Really?!" Merida perked up immediately.

"Yep except there is a catch" Hiccup said.

"What is that?" Merida asked.

"You have to be chaperoned by Astrid at all times."

"Great I get to have a babysitter. Still better than being stuck in this place. Can we go now!?" She asked excitedly.

"Noooo Astrid isn't back from her flight. When she comes back then you can."

"Ugggggh why can't you just chaperone me."

Hiccup didn't want to tell her what his father had told him. Instead he just shrugged and said "because Astrid's dragon is a tracking type so if you run away she can find you."

"Oh come on Toothless could find me if I ran off. Not saying that I will. I won't just please I can't take this cell anymore Hiccup."

Hiccup huffed. His head was screaming at him to wait for Astrid but what could go wrong?

"Fine but we have to be sneaky about it." He said "and please just don't do anything that will make me regret this."

"I won't thank you thank you thank you!" She said hugging him, realizing what she was doing she apologized and released him.

"Uh so lets go." She said blushing as she walked out the cell.

They both walked out, but due to precautions Merida had to wear a shackle on her wrist to show she was indeed a prisoner. They walked into the dragon stalls as they would usually for her work.

Instead they slipped out the back door near the forests. With Toothless of course.

Once they were in the forest Merida stretched her arms out with glee. Her eyes were as bright as the sky. She did a cartwheel on the grass just to show how happy she was she began running around.

"Hey don't go to far." Hiccup smiled.

"Don't be such a nag," she said "this is my first time out in years!"

"You've only been locked up here 8 months." Hiccup replied.

"It feels like 8 years." She said still running around.

She got outside of Hiccup's view. Which worried him.

"She's not going to run away." He reassured Toothless.

Toothless rolled his eyes and went back to clawing at a tree.

'Merida and Hiccup's time together had been nice considering the circumstances. He was hoping to get her a job here when she had served out her sentence. But he realized after today she wanted to be free and go on far journeys. Who was he to deny that?

Merida had realized she was out of Hiccup's view. She looked around and saw a pathway that she could go down. She could run now and be free of this place and free of cleaning dragon crap.

"Merida!" She heard him call out.

Her heart lurched at the thought of him following and finding her not their. His trust would be broken. She would have been the cause of that and he had been so nice to her. She couldn't do it.

"I'm right here!" She called back.

His body and mind relaxed with relief. "Good I thought you had run off." He said as she came into view.

"What?! And miss cleaning dragon poop? Why would I run away from that?" She said sarcastically.

"Hiccup!" Astrid called down. She was above them flying on Stormfly."you have a lot of explaining to do."

"I'd be happy to tell you Astrid but I'm afraid Merida has to get back to her punishment and I have....uh chiefly stuff to do." Hiccup replied. Hiccup took a hold of Merida's arm and pulled her towards Toothless.

"What are you doing!?" Merida asked as he pulled her up on Toothless.

"You don't want her to get us caught do you?" He said devilishly. "Hope you're not afraid of heights."

Toothless took off into the air spring through. Stormfly right on their heels.

"Hiccup! Does your dad know about this?"

"That is an excellent question." Hiccup yelled back and flew down. Merida screaming her head off as the dragon was going down towards the stalls.

Hiccup pulled him up so he landed safely. Merida was stuck to Hiccup like glue.

"Sorry he likes to be dramatic." Hiccup said prying her fingers off of him.

"Bloody hell! That was terrifying!" Merida finally said.

"Well I will see you later."

"You're leaving me here alone?"

"Nope Astrid is right there which means its time for me to run away." Hiccup left quickly as Astrid came down with Stormily.

"Coward!" Astrid playfully yelled. She looked at Merida "You I will get to later for now pick up a shovel."

"I made him-"

"I don't want to hear it go to work. If Stoick asks me about it I don't want to lie. So better I know as little as possible." Astrid said.

Astrid didn't say anything after that until Merida was almost done.

"Why didn't you?" She asked.

"Do what?"

"Leave, I saw you when I was flying I could see you thinking about taking the path but you didn't. I want to know why."

"I don't know." Merida replied.

"That's not a reason."

"I knew how much it would betray him alright. I know how much it would kill him to find me not there under his trust. I know how much he has given me and I'm thankful so that's why I didn't leave." Merida stated.

"I think it's cause you actually started to care for him." Astrid smiled.

"I do not! At least not in the way your implying." Merida said.

"Oh yes you do. If it had been me to let you out. You would've been half way up the coast."

"That's not true." Merida said.

"Fine but the reason you stayed was because of Hiccup."

"So?"

"Because that's good. You gave me and Hiccup more reason to trust you and listen I'm not suppose to know this but Hiccup has been asking very often for you to be released. And Hiccup doesn't like confronting his father but he's willing to keep doing it for you" Astrid said.

"He's trying to let me go?"

"Yes you idiot because he cares for you gods know why! Now if you say that you don't like him like that then fine I understand, but make sure he does. He deserve to know." Astrid said.

Merida and Astrid didn't talk anymore. She went to her cell and sat alone with her thoughts."

......

"Dad she had a chance to leave but she didn't!"

"You shouldn't have given her that chance!" Stoick yelled. "This is exactly why I didn't want her out in the first place."

"Dad she only wants to leave and travel out there I know what that's like to want to leave a place you can't get out of."

"This girl sure has done a number on you son. How about this, I'll make you a deal. Tonight you go to her cell and offer her freedom."

"Thank you dad you won't regret it."

"But! She can never come back here. Ever." He said.

"Ever?" Hiccup asked.

"That's the deal son she can either have her freedom now and never come back or she can stay for the rest of her sentence which is another winter, and then can be released and be free to choose to stay or come back anytime she pleases." He said.

"That's another 6 months." Hiccup said sadly.

"I know son, I'm doing this to protect you. So you know what you're getting in to." He replied.

"Well better start tonight wish me luck."

"Good luck son, I hope she makes the right decision."

"Which is what?" Hiccup asked to himself.

There was no way Merida would give up her freedom to stay here for 6 more months cleaning after dragons. For what? For him?! The man who got her captured in the first place. She wouldn't, and he wouldn't blame her. He would love to have adventures and not know where he was going next but he was committed here.

He walked into her cell. She was surprised to see him so late. She yawned and stretched out her arms.

"What are you doing here so late Hiccup my shifts not till dawn." Merida asked.

"Well my dad has offered you a deal."

"Really and what is that?" She asked.

"Well you could stay here and serve out your sentence until winter comes and come and go as you please...... Or you could leave now but never come back to Berk ever."

Merida let the information consume her mind. Forever? She could never come back. Never see Hiccup or Astrid again? The only friends she has come to known. The closest thing to family she has known since running away after her mother insisted on an arranged marriage.

"I....I ...."

"I'll understand if you go now. I just want you to be happy."

"Why?"

"Because I know you're not a bad person......and I care about you and I know you're not happy here as you could be out there."

"Do you want me to go?" She asked.

"I do if it will make you happy. Although Astrid is going to be pissed because I think she's grown more fond of you then I have."

"No she hasn't. She likes to make my punishment more difficult."

"That's how she shows she cares. When she gives you a hard time." He replied.

"That's what's making this so hard. I don't want to clean up after dragons and be stuck in this dungeon for another 6 months but you two have become friends to me. And I don't make friends a lot. And especially you, I- I never had someone trust in me so much. Especially when I hit them with a medallion." She joked trying to break the tension in her decision making.

Suddenly she realized how close he was. He was kneeling down next to her cot as she was lying down keeping her head propped up with her arm.

"Hiccup, Astrid told me you were trying I get me set free because you...cared for me in a certain way is that true?"

Hiccup was taken back by the question. He might as well tell her if she leaves he'll never see her again to face the humility but if she stays because of his answer.......

"Yes I do happen to care for you in that way. I like that your adventurous, and sarcastic, and you talk to yourself sometimes when you work. I like that you tell me stories about things I don't know about." Hiccup said. "Again that's why I understand if you have to leave because I want you to be happy." He said.

"Hiccup you need to stop making everyone else happy and do what makes you happy," she said,

"I can't, not in this situation." He replied.

"Well I guess I have to do all the work then." She smiled. She caressed his face with her hand and took him by the chin. She planted her lips on him. On an instinct he brought his hand to hold her hair back from her face and entangle it in his fingers. It felt like hours but was only minutes when their foreheads rested against one another.

"I'll stay,"'she replied.

"Really?"

"6 months won't kill me. Especially if you keep making these nightly visits." She smiled.

"I think I can arranged that." He said.

She did serve out the rest of her sentence to Stoick's surprise. Hiccup and her decided to journey the rest of the world after she was released. They even asked Astrid to come which she did and teased them playfully everyday about their relationship. They met many new travelers, some who even joined their journey and Merida never stole anything.........except for the people that deserved to be taken from which wasn't very often. That was how the Chief To Be and the Princess of Thieves became free.

Authors note: sorry it took so long. I literally could've written a whole book on this subject but I won't because I'm too busy working on drabbles and Journey to Corona and a separate project that is in the works. So maybe someday but not soon. I hoped you all liked it! Please comment vote and share!