Mistakes

Chapter 1

Dean had been gone for three months and he was having the time of his life (sort of) running around with Crowley basically babysitting him (that part he didn't like at all.) He liked the drinking and the one night stands and the hookers and the strippers and most of all, he loved the killing.

Dean was starting to get bored of the one night stands though... He took a sip of his beer as an idea came to mind.

He could get Cas to have a one night stand with him.

Not only that but then he could piss off his brother by thinking he had a lead on him.

Dean suddenly got up making Crowley look up at him "Where do you think you're going? You better not be intending to have sex on my bed again." He said in annoyance.

Dean rolled his eyes as he made sure he had what he needed "Relax dude, that's not my plan. Now, poof me to Cas's motel" Crowley frowned at him but didn't say anything as he sent him away.

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When Dean appeared in front of the shitty motel room, he looked around in attempt to figure out if this was the right place.

Dean spotted Cas's beat up car and nodded. Yup, this was the place.

Dean collected himself and made sure he looked like he was supposed to and not like a demon. He hesitated at the door before knocking on it lightly.

Castiel sighed as he hauled himself out of bed. He didn't feel great without his grace. He felt much worse than when he had no grace at all. The angel shuffled over to the door and peeked out of the peep hole, his eyes widening when he saw Dean.

Cas quickly opened the door and looked up at the slight taller male "Dean...?" He asked in disbelief. Dean didn't answer him though as he stepped into his room and shut the door, locking it behind him. The next thing Castiel knew, he was being pressed up against the wall, lips planted firmly on his own. At first he thought Dean was attacking him until it registered that Dean was kissing him.

Why though?

Dean huffed and pulled away slightly "Dammit Cas, please kiss me back" He murmured "It's no fun if you just stand there. I might as well be kissing a dead person."

Cas cocked his head and furrowed his eyebrows in confusion "When have you kissed a dead person?"

Dean groaned but instead of answering, he instead went back to kissing Cas. The male hesitated before kissing Dean back, slowly starting to enjoy himself, sliding his eyes closed so he could focus just on the pleasure and standing there wouldn't feel so awkward.

Dean smirked at the fact he was able to get the boy to kiss him. He began to roughen the kiss, reaching up and sliding Cas's trench coat off his shoulders "I want you, Cas" he whispered, breaking the kiss.

Castiel opened his eyes, looking even more confused "you want me to do what?"

Dean groaned softly "Cas, I want to fuck you" he said blatantly. Cas blushed lightly and opened and closed his mouth, not entirely sure what he should say.

"Then... Let's?" He muttered "I want you to have sex with me too, Dean" he murmured.

Dean snorted at his response but took it. Castiel silently leaned down and picked up his coat that Dean had thrown on the floor before neatly hanging it over a chair. Dean shook his head as he led Cas over to the motel bed and sat down, pulling Cas onto his lap. "You shouldn't be hot but somehow you are" he muttered with a soft laugh. Castiel's ears turned red as Dean leaned in and kissed him hard on the lips, a small moan escaping his lips.

Castiel pulled him closer as the kiss became a bit more heated. Dean pulled away to lightly tug at Cas's clothes.

The Angel sat up and nudged Dean off before tugging off his clothes, wanting them to start already. Dean snorted at his eagerness and started undressing himself, haphazardly tossing his clothes to the side while Castiel carefully folded his clothes and stacked them. He slowly turned to Dean who immediately grabbed and kissed him hard on the lips, slowly grinding himself against Cas making him groan softly, never feeling something like this.

Cas felt Dean smirk against hid lips. The demon pulled away and and slid his fingers into Cas's mouth as he leaned down and licked up his cock.

Cas moaned against his fingers as he instinctively started sucking on Dean's fingers.

Dean smirked as he waited. soon, he brought his fingers out and slid one to the angel's ass. He didn't even ask for permission as he pushed a finger into Cas and started stretching him out.

Cas quietly moaned Dean's name and buried his face in Dean's shoulder, taking in a deep breath of his scent.

Dean snickered as he started adding in fingers, scissoring him all the way open.

Castiel buried his fingers deep in his hair as he moved along with him, enjoying the amazing feeling. Dean suddenly pulled out his fingers and lined himself up with Cas's hole.

The Angel squirmed in anticipation as the tip pushed itself into Cas making him arch his back and press against Dean's warm chest.

Before he knew it, Dean was fully inside him and was starting to thrust his hips, barely giving him a chance to adjust.

Cas cried out in pain and pleasure. The male had had sex before but this was so much different. It felt so good. He loved having Dean inside him and maybe...

Maybe this meant something to Dean.

Dean started thrusting harder, seeking out his sweet spot. Yes Dean was mostly doing this for himself but he wasn't such a dick he wouldn't even let his partner cum. Besides, it feels better when they do.

Cas jolted when Dean hit his prostate. He groaned as it sent wave after wave of white hot pleasure through him every time Dean hit the spot. Castiel started tightening around Dean as he realised he wasn't going to last long if he kept this up.

Dean smirked down at Cas as he thrusted deep inside him, nailing his prostate head on. Castiel snapped his head back, arching his whole torso.

Dean let out a soft moan as he thrusted harder and faster into him.

Castiel cried out Dean's name as he came over Dean's chest, the demon boy cumming moments after.

Cas collapsed back onto the bed, listening to the sound of the two of them huffing and panting.

Dean pulled out almost as soon as he got the energy to do so. The male watched over Cas as he got settled in, murmuring a small 'I love you' to Dean before slipping into a dreamless sleep.

Dean watched Cas for a few moments before getting up and quickly getting dressed. He walked over to the door, sent Cas one last glance before stepping outside where Crowley was waiting for him. "Perv." Dean mumbled to him as he walked over. Crowley rolled his eyes as he snapped them away.