A/n- So... Been awhile. I'm sorry but this awful thing called life reared its ugly head, I've barley written anything lately which was killing me inside. But I'm back now so YAY.

Also this fic has changed a bit, as you may have noticed the '5' has been removed from the tittle. I kept having crazy ideas and my friends have even put in requests. Which is something you guys can do to. If you have a Movie,Show, or song you Want me to Supernaturalize drop me a review. If I know the show/movie/song I'll do my best to write it.

Don't request Wincest, I won't do it. Most other pairings are fair game though. The fics will all be different lengths anywhere from a paragraph to 10 pages, so if you want a longer one let me know (I usually just take one scene from a show/movie and a verse from a song to base the fic on)

But I have plenty of fics (counting the original 5) planned, so please be patient, I'll get to your requests as soon as I can.

Now I know I promised Princess Bride but I recently read a Destiel PB fic that blew me away and I just won't even ATTEMPT to top that.

So what I have today is a request from my Sassy shipping friend who wanted something cutesy for his birthday gift and decided on this:

How To Train Your Dragon.

Rating: PG-13(Barely)

Pairing(s)/Characters: Sam/Cas, Dean, Ruby, Gabriel.

Warnings: Language and Slash.

Summery: "Lost your brother, lost your tribe, lost your best friend. In a course of an hour you've lost just about everything." "Wow... Uh thanks for that. Really I feel so much better."

Disclaimer:Don't own.

Enjoy!

-How to Train your Demon-

"I can't believe this!" Dean exclaimed as he stormed into the had thrown Sam in moments ago. "All this time, everything in the ring... Was a damned trick?"

"Dean I'm sorr-"

"You're sorry Sammy? SORRY? Well, Sorry doesn't cut it."

"Listen-" Sam began to plead.

"You lied to me."

"And I'm SORRY. Listen do whatever you want with me. Just don't hurt Ruby." Sam begged.

"The Demon? All the shit your in and you're asking me to spare a DEMON?"

"She didn't do anything."

"Oh so all the people she just nearly killed, that was my imagination?"

"She was protecting me!" Sam exclaimed, desperate to make his brother see reason.

"They have killed hundreds of us!" Dean shouted.

"And we've killed thousands of them!" Sam yelled back. Dean gave him a shocked look at his outburst as Sam took a breath to calm down. "They aren't bad-" Dean gave a snort of disbelief "Listen to me! If they don't kill they get killed themselves. There... There's something on their Island that-"

"Island? You've seen it!"

"No. No no no no. Dean No." Sam said remembering what he had seen when Ruby had flown him there with Castiel. The sheer size of Lucifer's true form was... "No Dean you can't handle this."

Dean as usual though wasn't listening "Where is it."

"I don't know." Sam said, Dean glared "I really don't. Only a demon can-" he quickly stopped talking but the damage was done. "Dean no. This isn't like anything you ever faced. You can't do this" Dean was already on his way out the door. "Damn it Dean for once would you just listen to me?"

"So you can lie to me some more?" Dean snapped, he looked at his brother in disgust "You throw your lot in with them. You're," he looked physically pained by the words he was about to say "You're not my brother."

Sam watched with wide eyes as the door was shut in his face.

...

Sam watched as Ruby, in her true form, was being hooked up as his brother prepared to go find the island.

Sam remembered one of his first conversations with the Demon. How she had told him that her true for was more for her peace of mind than a state tactic, like hunters had beloved for ages. How her human form was fragile, weak, how she would never change into it in the presence of a human unless she was close to death or felt completely safe with that human. Sam had asked which reason she was human for him and she had just given him a smile.

To see her now, in the form of a black dragon like creature, her Ruby eyes searching wildly for Sam... He knew now that she was terrified. And he hated that it was because of him.

He hated that he could do nothing but watch as the boat sailed away.

"You really screwed up." Came a gravely voice, that even now made his heart skip a beat when he thought of the boy who it came from.

To think everything had been going so well just hours ago. His brother was proud, the tribe loved him, he had the best friend he could ask for in the form of Ruby, and Castiel had accepted him and his secret, had promised to help, had kissed him. And now that was all gone.

Cas seemed to be thinking the same thing "Lost your brother, lost your tribe, lost your best friend. In a course of an hour you've lost just about everything."

"Wow... Uh thanks for that. Really I feel so much better." Sam said sarcastically, glaring at the older boy "I didn't feel bad enough before but that pep talk really helped."

"That wasn't my pep talk." Castiel informed him, "This is: You still have me, and I'm not going anywhere." he assured with a gentle smile.

Sam hoped his eyes could convey how much that meant to him. He sighed as he tore his eyes away from the other boy. "I should have just killed her when I found her in the woods."

"You're right." Cas said "It would have saved you a lot of trouble." Really, Sam adored the guy but he shouldn't be allowed to give pep talks "The rest of us would have. So why didn't you?"

Sam shrugged "I just... Couldn't."

"No, there has to be more to it than that." Castiel said staring at him in that intense way he had.

"What does it matter?" Sam asked, annoyed.

"Because I need to hear you say it"

"Way what? What do you wanna hear? That I was weak? A coward? Do you wanna hear how when push came to shove I couldn't shove and I wouldn't kill a demon! Is that what you want to hear Cas?" Sam yelled at him.

For his part Castiel remained silent and calm until Sam was done and then he spoke softly. "You said wouldn't that time."

Sam groaned in frustration"Yeah okay fine! I wouldn't kill yet! I'm the first hunter who refuses to kill demons."

"Also the first to talk to one. First to fly one. First to be allies- no friends with one. That has to count for something."

Sam stared at the blue eyes he'd been obsessing over for since he was 12, almost 6 years now. Maybe he wasn't so bad a pep talks after all. He sighed "When I found her, she was in human form, bleeding and terrified. She was just a scared girl who begged me with her eyes... When I looked at her... I saw me."

Castiel nodded, understanding "I bet she's pretty scared right now." he said calmly and Sam looked down in guilt and shame. "What are you going to do about it?" Sam looked up to see a mischievous look in Castiel's eyes he had to have gotten from his cousin Gabriel.

Sam shrugged "Probably something stupid."

"Good start. But you've already done that." Castiel pointed out.

Sam nodded in agreement when suddenly an idea hit him "And then something crazy." he said before he took off running.

Cas smiled "That's more like it." he said before running after Sam.

-The End-

A/n- I hoped you enjoyed it.

Lot more where that came from. Fics that are planned and you should be seeing soon: Scott Pilgram vs The World, Psych, How I met your Mother, Star Trek, Reality Tv, Sherlock And a shit ton more.

Leave a comment or a request in a review :D