Hello all! This is my very first fanfic so I'll just start off by saying to NOT go easy on me. I'd like to keep writing stories and to do that I need to know where I screw up. So I'm counting on you guys okay? So this little monstrosity just popped into my head today and I just had to make a story out of this before I went insane. SO of course the idea that popped into my mind after re-watching Supernatural again for the 100th time was this, "I want to put Team Free Will into a different universe, and watch them just wreck all the shit".

But what universe to choose? So after much deliberation I decided to roll the dice and lo and behold, Highschool DxD was choosen. So lets see where this takes us. Now I'm going to mess with some powers a bit because I love watching these guys just straight up own people. So be ready for some "slightly" more powerful men in flannel, beige, and suits. Ye have been warned! So sit back, drink some scotch and prepare for the ride ya Idjits!

I own nothing but my own insane ideas! (How's that for a Disclaimer?)

Issei had absolutely no idea what was going on. Yuma-chan had pulled him into some random park at the end of their date. A date that, at least in Issei's mind, went very well. He was of course a complete gentleman… He only looked at her Oppai 10 times in the last hour! He was definitely being a model male citizen. So when Yuma-chan suddenly asked him to die, he was sure he had misheard her. "Ano, Yuma-chan, could you repeat what you said? I think I misheard you." Issei asked while cleaning out his ear so he could better her the busty women in front of him. "Ah, sorry Issei-kun. I must have not said it loud enough." Yuma said while smiling gently at him. He eagerly leaned forward and watched his date open her mouth and say," Would you kindly, die for me?" "huh?", was all he was able to get out before three things happened simultianiously. The first was that Yuma shredded her clothes into a skimpy outfit that quite literally had him drooling and almost knocked him uncouncious… or maybe that was the black wings that had spread from her back. Wait, wings!? The event that immedietly followed her transformation was what snapped him out of his funk and turned his attention away from the impossibility of wings. Yuma's hands erupted in light and suddenly she was GRASPING light that seemed to be shaped into spears. Unfourtunatly for him, the light spears were screaming towards his chest faster than he could even blink.

Light.

Peace.

Serenity.

The flap of wings and rather strange smell of alcohol, gunpowder, and blood was all he knew for a brief instant. When he snapped out of the daze he was in he found himself several feet from where he was just standing about to be skewered. Yuma was laying several feet from where she had been standing as well. Issei focused on her face first, after all how could he not? Her eyes were burned out of her skull, and a burning imprint of her wings spread across the ground.

He heard a rough and gravelly voice tell him that everything was going to be alright, before the events of the night caught up to him and he passed out.

-Line break-

"He's fine Cas. Kid's just had a rough day." A gruff male voice called out to the being that was gently shaking the boy to wake him up. "Oh let feathers worry about his new boy toy Squirrel. Unless of course your jealous?" A man and a black suit said in a snarky British acsent in response to "Squirrel". "Shut your pie hole Crowley. At least he's doing something. What where you doing when the kid was about to get skewered huh?" The man asked angrily. "Calm down Dean, you know that dick won't lift a finger unless he gets something out of it." a rather calm voice coming from a giant of a man stated as he tried to calm Dean down. "Sam, why is his nose bleeding? It started after that thing changed his clothes. Do you think he might have suffered brain damage?" The one known as Cass stated as he worriedly checked on the comatose boy laying in front of him. "Don't worry Cass I'm sure he's fine. He probably just needs a little rest after today." Sam told Cass reasureingly. "But what kind of monster was that. I've never seen anything like it. What about you Crowley? You know anything about this?" Sam asked pointing a shotgun at the dead creature at the other end of the park. Crowley crossed his armed and looked up thoughtfully before answering Sam, completely ignoring the glare that Dean was still sending his way. "Considering the fact that I've never really bothered coming to Japan except for various parts of some Kitsune. I've got no bloody idea Moose."

"Hey guys?" Dean asked as he stared at something that was sitting innocently on the ground where the kid had been standing before Cass had saved his bacon "What the hell is that and why is it glowing?" The other three shared a glance before staring at the piece of paper that was…glowing? 'What the hell' was what crossed the four men's mind as they wearily stared at the glowing sigil coming from the paper, waiting and ready for anything.

They were not however ready for a very buxom redhead to appear out of the circle and a bright flash of red light. The two parties stared at each other for several moments before Dean perfectly expressed what everyone in that clearing was thinking… "What the actual fuck is going on and who the hell are you!?".

Annnnd scene! Well that's the first chapter done. For reference, I'm using the appearance of everyone from season 12. Hope you all are just as excited as I am for this. Hope to see you all in the next installment of "Team Free Will Dxd". Leave a review and a like and I'll see you guys later. Peace out!