Ok, so, here's a collab between me and my gorgeous friend Maddy (castielstrenchcoat on tumblr). We hope you enjoy!


Chapter 1

Pallet Town. 1999. Dean Winchester has finally decided to venture out into the wide world of Pokémon, with the help of Professor Gabriel Oak's apprentice, Sam Winchester, his nerdy younger brother.

It's the night before he has to leave, and he and Sam are in their respective beds, facing each other in the darkness.

"I'm gonna miss you, Sammy," Dean whispered across the room, breaking the silence.

Sam sniffs. "I'll miss you too, Dean," he says, letting a single tear dribble down his face and onto the pillow below.

"I'll come back to visit you all the time!" Dean reassures, slipping out of bed to tip-toe to his brothers side. "You can always count on me, Sammy." Dean knelt down in front of Sam's bed, slowly leaning forward to press a soft, lingering kiss to his lips. As Dean moved back, Sam leaned forward, not willing to break the spell surrounding them, causing Dean to chuckle under his breath. He silently pushed Sam backwards, so he was lying on his back on the centre of the bed, and crawled on top of him, straddling his hips, kissing him all the while.

After a lot of lazy kisses were shared, Dean started flowing his passion for Sam into the kiss, feeling his brothers dick harden through his thin pyjama pants.

Dean let out a bark of harsh laughter. "Metapod used Harden, eh Sammy?" Sam cocked an eyebrow.

"Shut up, Jerk," he said, craning his neck up to resume the kiss.

"Now," Dean spoke against Sam's lips, "how about I give you something to remember me by?"

Sam groaned. "Oh, God yes." Dean grinned, gently thrusting his hips down, making Sam let out a soft whine. "Please, Dean, no teasing." Dean groaned at the weak, submissive tone, finally pushing down hard, causing unbelievable friction. They both let out loud moans, reveling in the pleasure rushing through their veins. Dean quickly pulled down Sam's pants, letting Sam pull off his own.

Frantically, they rubbed against each other, the slide of their cocks making them cry out, using the pre-come from the weeping heads of their dicks as lube. Dean brought three fingers up too Sam's mouth.

"Suck," he said in a hoarse voice. Sam immediately obeyed, bringing the fingers into his mouth, and swirling his tongue around them, moaning like a back-alley whore. Once Dean considered his fingers wet enough, he removed them from Sam's mouth, bringing them down between his legs. He rubbed his pointer finger at Sam's entrance insistently. Sam whined and jerked, the pressure constantly building as he thrust his hips down, desperate for penetration. Dean smirked, finally obliging.

He quickly shoved his finger in to the knuckle, forcing his lips onto Sam's to muffle his cry. After a couple of seconds of stillness to let Sam adjust, Dean slowly began to move his finger. Thrusting in and out, barely grazing Sam's prostate, making him whimper and slowly melt under Dean's ministrations. Dean gently inserted finger after finger, scissoring and stretching, until Sam was ready for the girth of his dick. He pulled his fingers out, spitting on his hand and smearing the saliva on his dick.

Dean leant down and guided his penis with his hand, gently rubbing as Sam's entrance. With one smooth thrust, Dean was in Sam to the hilt, covering Sam's mouth with his own to muffle their groans of pleasure.

"Fuck, Sammy, how are you still this tight?" Dean whispered against Sam's plump, kiss-swollen lips. Sam whined, a pitiful sound in the back of his throat, and bucked his hips, needing Dean to move. Dean slowly pulled out, until he was only half way in, before thrusting back in full force. Sam moaned, and wrapped his legs around Dean's waist for a better angle.

Dean swore, moving his hips faster and enclosing Sam's cock in his fist, stroking in time to his thrusts. They continued like this, Dean slamming against Sam's prostate, until the pressure grew too much to bear. Dean leaned down to Sam's ear.

"C'mon, Sammy. Just let go," he whispered. Sam let out an extremely high pitched note, his back arching grandly as he came across both their chests. The constricting muscles around Dean's cock were too much to bear, and he followed shortly after.

"Ca-Sam," he groaned, barely catching himself from the slip up as he came deep inside of Sam. Thankfully, Sam was still caught up in the aftershocks of the intense orgasm to notice.

They caught their breath, Dean pulling out and laying beside Sam as they curled around each other.

"I'll miss you, Sammy." Dean said. He looked down at his brother, already peacefully asleep, and let a single tear fall into Sam's hair, letting sleep claim him quickly.


Dean woke up hazily, barely registering the curled up form of his little brother against his side. He rubbed his eyes and looked at the clock on the table, which was shaped like his favourite Pokémon, a Blastoise. "Son of a bitch" he growled as he hopped out of bed, hurriedly grabbing clothes out of his drawer and pulling them on. He heard stirring behind him.

"Dean?" Sam yawned, his hair tousled and his eyes bleary.

"Sammy, we're late to meet Professor Gabriel!"

Quick as a flash, Sam hopped out of his bed and pulled on the nearest pair of jeans he could find. Barely glancing in the mirror before pulling a comb through his hair and opening the door. "There won't be any starter Pokémon left for you, we have to go now!"

Dean picked up his backpack and ran out of the door, stopping only to grab a cookie from beside the fridge, freshly made by his mother, Ellen. He skids to a halt in front of the Pokémon Lab, Sam just behind him.

"Good luck" Sam says bracingly, pushing Dean forward and through the door. Dean slowly walks through the auditorium, the place silent apart from his footsteps. It seems like hours before he reaches Prof. Gabriel's door. He takes a deep breath and knocks on it. The door opened almost immediately and Dean was stood, almost nose to nose, with Castiel Novak, Gabriel's nephew. He held his breath. He had always had some sort of fixation with the boy, no matter how cold and distant he was. Looking into Castiel's deep, sea blue eyes he cleared his throat.

"Oh uh, hey Castiel. Is your uncle Gabe in?"

"You're late." Castiel said simply, turning around and walking over to a table in the corner of the room, perching himself on it. Dean walked in, an awkward silence hung in the air. He must admit though, Castiel's ass looked fantastic in those jeans. As Castiel opened his mouth to say something, Professor Gabriel walked in to the room, with a lollipop in one hand and a Pokéball in the other.

"Oh, Dean, you've finally decided to join us," he said sarcastically.

"Sorry Gabriel, I woke up late, my mom didn't bother to wake me up this morning."

"No harm done, however, most of the Pokémon we had up for grabs today have already been taken. Luckily, we do have one more." Gabriel held up the Pokéball in his hand, surveying it for a moment before throwing it to Dean, which he caught with one hand.

"Woah, thanks Gabriel, really!" Dean smiled and looked at the Pokéball. His own Pokémon! He could hardly believe it!

Just then, there was a knock at the door. Gabriel walked over to answer it.

"Why hello there, young Samuel. How the devil are you?" he said teasingly, a smile playing at the edge of his lips.

"Oh! H-hey Gabe," Sam stuttered, turning a light shade of red. "Is my brother here?"

Gabriel moved out of the way of the door and Sam walked in.

Dean smiled in greeting to Sam, stood up and took a deep breath. "Come on out, little buddy" he said, throwing the Pokéball to the floor. The Pokéball opened and in a flash of brilliant light, out came a Squirtle! Sam sighed, it was the cutest Pokémon of the bunch in his opinion. Gabriel glanced at Sam out of the corner of his eye, a smirk forming on his face. Dean huffed, the Pokémon just looked girly in his opinion. The smirk on Gabriel's face grew.

"Don't you worry, Dean," he said. "It'll evolve into something more manly for your liking soon enough." He winked, leaving Dean looking disgusted at the Pokémon he had just received. Castiel stood up and yawned, a glint in his eye. "Hey Dean, how about a battle? I'll show you how much of a pipsqueak your little Pokémon is.

"Yes, Dean, let Cassy here show you his skills." Gabriel said, a wide smile evident on his face.

Castiel rolled his eyes. "Shut up Gabe, no ones called me Cassy since I was about five years old."

"Well obviously, they still do, Cassy." Gabriel replied, putting emphasis on the last word.

Dean looked over at Castiel.

"Challenge accepted."

Castiel pulled a Pokéball from his belt and threw it to the ground dramatically.

"Charmander, go!"

Another dazzling flash of light and a Charmander appeared, the flame on its tail dancing in the dim light of the room. It's loud chirrup echoed through the room, sending a shiver of thrill down Dean's spine as he watched Castiel. Great. He had to get turned on now. By Castiel Novak, too.

Dean looked towards his new Squirtle.

"We have to work together now buddy... so uh... attack!" Squirtle waddled forward, towards Charmander.

"Charmander, use scratch!" Castiel commanded.

"Squirtle, dodge it!" Dean shouted in return.

Charmander missed Squirtle by an inch as he moved towards him, his sharp claws outstretched.

"Squirtle! You know bubble beam, right? Use it now!" Dean said imploringly, looking between Castiel and his Pokémon.

Squirtle stopped for a split second before releasing a large amount of bubbles from it's mouth, speedily sending them Charmander's way. Charmander stumbled for a second.

"Charmander! Try to get out of the stream!" Castiel bellowed. But it was too late. Charmander was down.

"What? I won?" Dean said, disbelievingly. "AWESOME! High-five, Squirtle!" Dean ran over to the half turtle, half squirrel creature and put a hand up, waiting for the Pokémon to raise its little hand up too. Squirtle seemed to consider Dean for a second before putting his tiny hand to Dean's, its lips curling up at the sides.

"You know what, little buddy? I'm sorry I doubted you. You full on swayzee'd that mother!" Dean stood up now, walking over to Castiel where he was sat with his Charmander. "Hey man, is Charmander alright?"

Castiel looked up, resentment and an emotion Dean couldn't quite register in his eyes. "Charmander'll be fine. Good work, I guess. But we're gonna train up and next time we battle each other, I'm going to win!"

Dean smiled before putting out his hand. "Deal."

Castiel took it and gave it a brief shake before turning his attention back to Charmander.

Dean walked over to his new Pokémon, bending down and picking up the Pokéball. "Come on, little guy, back in here for now!" Squirtle looked up at him.

"Squirtle!" he said cheerfully. Dean hoped this meant he wanted to go back into the ball. Dean pressed the button in the middle. "Squirtle, return!" A flash of red light and Squirtle was gone.


"Sammy? Where are you?" Dean looked around the laboratory, checking everywhere it seemed before giving up. Sam's probably just gone home, he thought to himself. As he was leaving out of the door, he heard a crash coming from Gabriel's office. Dean doubled back and walked over to the door, opening it tentatively. "Gabriel? Are you okay?" Dean entered Gabriel's office and saw that the computer that had been on the desk had crashed to the floor. Sam then appeared from the corner of the room, his hair ruffled and his lips looked red and swollen. "Sammy? What're you doing in here? I thought you'd left?"

"Oh um, I was just... I-" Sam was cut off by Gabriel coming out of the store cupboard.

"Sammy here was just helping me fish out this for you, Dean." Gabriel took something square and red out of his pocket before opening it up and handing it to Dean.

"Dean, this is a Pokédex. It should help you on your journey to being a Pokémon league Champion. It has all you need to know on it. If you ever need to find out what a Pokémon is, what special attacks it has, what different evolution states it has or what level it is, refer to this."

Gabriel handed it to Dean and he turned it around in his hands gingerly. He opened it up and a robotic voice came from within. "Hi! I am Ash, your Pokédex. I will be your personal aid through your long journey. If you need anything, don't hesitate to ask." Dean looked up.

"Woah! Thanks Gabriel, this will be a great help!" he put the Pokédex in his back pocket and put his arm around his younger brother.

"We'll see you later, okay?" Dean called as he got to the door. He saw Sam and Gabriel share a fleeting glance and he swore he saw Gabriel wink at Sam a split second before the door closed.

Dean decided to shower and change his clothes before starting his journey. He got home and proudly displayed his new Pokémon to his mom, before putting it back in it's Pokéball and taking a quick shower. He stepped into the shower and let the hot water go over his body. He thought about earlier, his first ever Pokémon battle. His battle with Castiel. The mere thought of the man caused ripples of arousal to zing down his spine. He glanced down at his already half-hard cock, and reached down to take a firm hold of it. Images of Castiel flowed through his mind, providing plenty of inspiration. Castiel's ass in those jeans. Castiel in the midst of battle. Castiel comforting his fallen Pokémon. Just about anything he did was making Dean horny, but he still came up with his own scenes: Castiel on his knees. Castiel naked and writhing beneath him. Castiel, Castiel, Castiel.

Dean groaned, speeding up the movements of his hand to keep up with the images flashing behind his eyelids as he sped toward climax. In the brief moments before his orgasm, he pictured what Castiel's face would look like in his position. Screwed up, unable to take the pleasure.

Dean climaxed violently, his knees shaking as he came over the shower stall wall. He fell to his knees, the trembling too great to hold himself up. He sighed happily and rested his head against the glass.

Much better.


TBC~