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Monopoly and Gift Bags

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It was chilly out, but not enough to dwindle the fire of pure nerves in Dean’s stomach. Today was Cas' birthday, so it was definitely the most special day in all of creation. But there was one problem.


Dean didn't have a physical gift to give.


Dean walked up to the front door of Cas’ house, swallowing thickly.


Just a night, right?


He could hold himself together and not fall completely and utterly into a storm of adoration for his best friend. Dean raised his fist, tapping it on the door lightly before he waited for a response.


It was only a few moments until the door swung open.


“Dean! I almost thought you were going to skip.” Anna said, opening the door farther to make way for the Winchester.


A small, courteous smile quirked on Dean’s lips, followed by a slight nod. He stepped into Cas’ house, and god he instantly regretted it.


Cas stood with a group of his friends, mingling and talking shyly just as he always does, those full lips pull up just slight at the corner whenever he talks. He had this wonderful insistent look on his face, passionate while he discussed something with the group.


Dean fucked.


And of course, Castiel noticed his staring, his blue eyes slowly turning to meet his own.


Cas smiled and ignored whatever his friends were saying, his hand swirling the wine within his glass. Their eyes stay locked for what seemed like an eternity, that is until Cas murmured something to the group and started sauntering over.


As soon as Cas was in front of him, Dean could get a good look at his outfit. It was slim fitting dress pants, a dress shirt that hugs his lean frame, and his tie, a deep blue that matched his eyes. Cas’ hair was tousled like he just rolled out of bed.


Damn Dean loved it.


Dean cleared his throat and sheepishly smiled at Cas, rubbing the back of his neck. “Happy birthday, Cas.”


Cas raised an eyebrow and smiled back, looking down at the floor. “Hello, Dean. Thank you.” He looked around the room a bit, sighing tiredly.


“They’re all as talkative as Gabriel. I don’t even know half of them” Cas admitted with a laugh. Dean chuckled at that, Cas was still as introverted as he was in High School, he just got better at staying calm and collected.


“So how’s college treating you?”


“Good. Although studying to be an Environmental Science teacher is hard, but I love the subject. Is the garage going well?” Cas’ eyes became soft and concerned.


Last year he had a bit of a mishap, an engine fell off the shelf near a few fuel tanks, and everything went up in flames. His crew barely made it out alive. After a giant lawsuit for the damage and endangerment of citizens, Dean didn’t have much of a punishment at least, just to pay for the damage and keep all equipment in special safety cases.


“’s good,” Dean said awkwardly.


“Yo! Let’s get this party actually started!” Gabriel hollered, holding up a monopoly board with a mischievous grin.


They all gathered around the table, earning an eye roll from Anna and Charlie. “Try not to break the board! Dean gets a little fussy!” She called.


“I do not!” Dean complained with a stubborn pout.


Gabriel snickered, flopping the board onto the table and placing all the money down. “I call banker. Jus’ sayin’.” Gabe grinned, a cheeky look on his face.


Cas snorted and rolled his eyes. “I call Gabriel on my team, then.”


A look passed between the two brothers that only meant mischief, and Dean squinted at it. “You two aren’t planning something...are you?” He asked suspiciously.


“I don’t know what you're talking about.” Cas retorted with a smug look.


“Uh huh…” Dean hummed.


Ten minutes into the game, Castiel chucked a green hotel at Dean with a scowl.


“Hey!” Dean yelped, glaring and crossing his arms. “Sam. Sue him.” He pouted.


Sam burst out laughing, rolling the dice and moving his player. “Oh calm down ya big baby.” He teased.


“I’m not a baby!” Dean fired back.


“Are too,” Sam said smugly.


“Am not,” Dean said.


“Yep.” Sam grinned.


“No-” Dean started again, but Cas cut him off.


“Oh for god’s sake!” Cas groaned.


Out of the corner of Dean’s eye, he saw Gabriel stuff some money into the bottom of his pile, immediately turning and pointing at him. “Hey! He’s cheating!” Dean yelped stubbornly.


“Am not!” Gabriel denied.


“Are fucking too!” Dean snapped and stood up.


“Dean! Shut the hell up and just play. Stop being a baby about everything.” Castiel said, hiding a smirk.


Dean gawked and slowly sat down, squinting at Cas suspiciously. He pouted and looked away, crossing his arms again. Fucking Gabe and his fucking tricks. God, he was like an annoying in-law.


“Gabe is turning this into a fucking monopoly,” Dean muttered grumpily.


“We are playing monopoly, Dean,” Castiel said in amusement, handing the dice to the pouting Winchester.


At the end of the game, Gabe and Cas won. Which pissed Dean off even more than it should because Gabriel fucking cheated to win. Dean would’ve won if he hadn’t stolen all the money little by little!


“Oh come on, Dean. Don’t be such a pussy.” Gabriel snickered, tossing his money around, smirking proudly. “You just suck at monopoly because you're too busy staring at Cas.”


Dean choked on his spit, turning a deep red.


“No! I don’t stare at him!” Dean said defensively.


Castiel smiled to himself from his spot next to Sam, the two of them cleaning the game up and organizing all the thrown around money.


“You kinda do, Dean. You like...eye fuck him.” Sam said blatantly.


“I don’t! I’m straight! I like pussies and women… Tits!” Dean rambled, glaring at Sam and Gabriel stubbornly.


“The word tits isn't a sentence, Dean. Sorry to break it to you.” Sam corrected smugly.


“Hey. If it helps, Cas is a twink.” Gabriel snickered, bursting into laughter.


“Like hell I am! I’m not a twink!” Castiel squeaked, tossing a pillow at Gabriel and cutting off his hysterical amusement.


Oh yeah, Cas was so a twink. He had a slim body, a round ass that did all sorts of things to Dean’s fantasies at night. Cas had legs that went on for miles, and they’d look great wrapped around his waist. And he could go on forever about those blue eyes. They were timid and stubborn, just all the perfect things that made Dean’s heart beat in his chest.


“Dean. Put your wood away.” Sam said with a chuckle.


Dean suddenly snapped out of it, realizing that he was staring at Cas, a boner poking a huge bulge in his jeans. Cas smiled shyly and turned red, looking away.




“Fuck, um. I’m sorry.” Dean muttered, sheepishly rubbing the back of his neck.


Thankfully, Charlie chose that moment to burst in, holding bags and grinning. “I come bearing gifts!” She chirped cheekily, setting the gift bags on the table and starting to carry boxes in. Dean busied himself with helping, adding to the pyramid that was already forming on the table. Anna started carrying out a cake, turning the lights off with a smile.


Everyone started singing Happy Birthday to Cas, and Dean couldn’t stop grinning at the huge smile on his best friend’s face.

Chapter Text

Castiel smiled as Dean drove to his house. “So you have a gift for me there?” He asked softly.


“Y-Yeah,” Dean replied.


He just wanted to get alone time with Cas. His best friend.


And maybe his major crush.


“Dean. You passed your house.” Castiel informed in amusement.


The Impala skidded to a stop, turning in a circle and driving up to Dean’s house. Dean parked in the driveway, taking a deep breath.


“So…” He said awkwardly.


Cas blinked owlishly, tilting his head. “So? Are you going to take me inside? Or are we staying in the car.” He asked in confusion. Dean snapped out of his weird boyish nerves.


“Yeah! Right! Of course.”


Dean stepped out of the car and walked around the other side, opening Cas’ door with a sheepish grin.


Cas chuckled and climbed out of the car, ducking his head. “Thank you.” He murmured.


“Anytime.” Dean smiled and wiped his hands on his jeans, taking in a breath. “Well then! Off to my humble abode.” His bow legs started sauntering towards his front door, making Cas smile fondly. Cas walked behind him, following him into the house. Dean set his keys down in a bowl, shucking his leather jacket off.


“You can take that trench coat off.” He suggested, glancing Cas over.


Cas nodded, shyly sliding it off his shoulders and setting it over a chair. “So… How was tonight?” He tried to start a casual conversation.


“Good. It was good.” Dean mumbled, rubbing the back of his neck. He walked closer, standing next to Cas. He was gonna do it. Now or never, right?


“Are you busy the rest of tonight? Or can I stay and-” Castiel asked, getting cut off by Dean’s lips. Dean kept his eyes closed, his heart beating in his throat relentlessly, his body tense. And then he realized something.


Cas was kissing him back.


Dean cupped Cas’ face, their lips melding together in one smooth movement, both of them moaning in unison. Dean deepened the kiss, curling his tongue into Cas’ mouth. Cas wrapped his lips around his tongue, and it sent a coil of heat through Dean’s stomach.


Dean lifted Cas up, holding onto his ass as they walked to his room. “Gonna fuck you, yeah?” Dean murmured into the kiss. Cas nodded, pulling back to catch his breath.


“I’ve been waiting since first grade for you to kiss me, of course, it’s a yes.” The blue-eyed boy said with a shy laugh.


Dean groaned, his cock perking up a bit. “Christ on a tortilla. Okay.” He breathed out.


Cas burst out laughing, burying his face in Dean’s neck to hide his face. “Dean! You ruined the moment!” He whined.


Dean chuckled, laying Cas back on the bed. “I can bring it back, lemme just get your clothes off.” He said with a huff, unbuttoning Cas’ dress shirt and sliding the tie from around Cas’ neck. Dean slowly pushed the shirt up and off Cas’ shoulders, staring at the lean and smoothe torso before him. Cas still wasn’t very built. He didn’t even fill out his shirt, but he would with age. Dean thought Cas made one hell of a twink.


Dean slowly slid off Cas’ dress pants off his body, glancing up to look at his flushed face. “You’re beautiful. You know that?” Dean asked, leaning down and pressing a gentle kiss to Cas’ hairless legs. Cas turned a deep red, shaking his head. “I’m not-“


“Lemme stop you right there,” Dean said pointedly. “You’re absolutely angelic. You’re perfect. And don’t let yourself think otherwise. Screw insecurities, because I think you’re perfect. And you are. You’re gorgeous.” Dean stated, spreading Cas’ legs apart and kissing up the soft skin with a hum.


Cas gasped, closing his legs before Dean got too far up. “Take your clothes off too, it’s not fair.” He murmured.


Dean grinned and nodded, standing to throw his shirts off, dropping his belt to the floor. Cas could only swallow at the sound, watching Dean’s skilled fingers pop open the button on his jeans. Dean let his jeans fall to the ground, stepping out of them. He finally tossed his briefs off and crawled back onto the bed, running his hands up Cas’ thighs and carefully prying them apart.


“Allow me,” Dean whispered, leaning in and sealing his lips around Cas’ hole.


Castiel gasped, his thighs clamping around Dean’s face as his hands gripped onto the sheets shakily. Sparks flew in his vision when he felt a tongue slide out, flicking around his hole deliciously.


Castiel moaned high in his throat, his chest hitching up in stuttering breaths. “Breathe...calm down.” Dean coaxed, his hands smoothing over Cas’ legs and pulling them apart again. Cas nodded, sucking in a slow breath and letting out a tiny cry. Dean chose that moment to slide his tongue past his rim, licking against the rings of muscle to coax them open. Castiel whimpered, his hips jerking and his hands clutching, he couldn’t think of anything except for Dean. Dean Dean Dean.


Dean used one hand to hold Cas’ hips down, the other pinning his leg out to the bed so he had full access. “There you go...that’s what I like to hear.” He murmured, sliding his tongue deeper and deeper until Cas was arching in pleasure, his slim hands flying out to fist into Dean’s hair. “O-Oh, fuck!” The blue-eyed man moaned in surprise, his breathing labored and nervous.


Dean pulled back, kissing his way up Cas’ body and pressing a single kiss to his mouth. “Shhh, it’s okay. It’s okay. Just gonna stretch you.” Dean said soothingly, grabbing the lube out of his bedside table and slicking his fingers up.


He pressed one digit inside of Cas’ hole, working it gently and sliding in a second. Once he could fit three, he pulled them out, coating his cock in lube. Dean spread Cas’ legs, slotting his hips between them and resting his elbows next to Cas’ face. “You okay?” He asked.


“Y-Yes. Do it. I’m ready.” Castiel whispered with round eyes.


And at that, Dean pressed inside, keeping a close eye on Cas’ face. Castiel seemed fine until Dean had about four inches inside him, then he started gasping, trembling and grabbing at Dean’s biceps. “’s okay. You’re okay.” Dean said softly, leaning their foreheads together.


“B-Big. So big. Oh god.” Cas choked out, his thighs trembling around Dean’s hips as Dean bottomed out, his full nine inches stretching him fully. Cas panted raggedly, burying his face in Dean's shoulder.


After a minute or so, Cas nodded. “You may move.” He breathed out.


Dean took a deep breath, wrapping his hands around the back of Cas’ head to keep him still before he started pulling out, stopping the tip of his cock at the rim of Cas’ hole. He took a breath and pressed back in, heat roiling in his gut at Cas’ reaction. Castiel let his head fall back into Dean’s grasp, a dazed look spreading over his face. The thrust punched a moan from his throat, his hands clinging onto Dean’s shoulders and running along his back, touching everywhere he could possibly reach.


Dean started at a slow pace, his hips rising up and falling back down steadily. He wrapped his elbows underneath Cas’ knees, lifting his legs up, planting his own hands by Cas’ head. On the next thrust, Castiel practically snapped in half at the change in angle, his eyes blown wide and his mouth hanging open in a beautiful cry. “D-Dean!” He gasped out.


Dean smirked, carefully holding Cas still. “It’s okay, baby. I got you. Just breathe, hold onto me.” He assured, guiding Cas’ hands to his hair. Castiel immediately latched on, burying his hands in his hair and grasping for dear life.


Dean started thrusting again, humping Cas in slow motions, with no fancy tricks. The boy would whimper and moan and cry out in joy, his hands running through Dean’s hair and holding onto Dean’s neck for support. “Yeah? That your sweet spot?” Dean asked lowly, giving Cas a sharp snap of the hips to his prostate. Castiel wailed, nodding hazily and trembling in Dean's arms. “Y-Yes. Yes. Right there. More.” Cas rambled, making Dean's ego shoot through the roof.


“Mhm? You like that? I can give it to you, how hard do you want it?” Dean teased, grinding his hips.


Cas’ eyelids fluttered with each movement, his cheeks flushed in pleasure. “H-How hard can you give it?” He asked in a tiny voice.


Dean raised an eyebrow, bending Cas in half so his knees were up to his chest, his thick cock pressing right up against Cas’ prostate. “Oh angel, you really shouldn’t have said that.” Dean purred, rolling his neck around on his shoulders.


Cas frowned and looked up. “W-Wha-?” He started, cutting himself off with a shrill moan, his hands smacking down onto the sheets. Dean’s hips worked like a piston, smacking against Cas’ round ass mercilessly.


Each thrust forced an ‘unh’ from Cas’ lips, his tiny body jostling on the sheets as Dean’s cock pummeled his prostate.


“Oh fuck yes. Look at you. Fucking drunk off my dick. I can give it to you. I’ll give it all to you.” Dean said breathlessly, pounding into Cas faster and faster until the headboard clacked against the wall like a machine. Castiel was choking on his breath, his chest flushing red and his back arching. His blue eyes rolled back into his skull, a scream of ecstasy falling from his lips as ropes of cum shot from his cock, coating his chest like a work of art.


Dean groaned and pulled out, quickly flipping Cas over on his hands and knees. He slid right back into him, relishing in the surprised sound Cas made. Dean flattened his chest to Cas’ back, one hand reaching out to pull Cas’ head back by his hair. Castiel was a complete mess, his body pliant and limp, swinging forward and yanked back onto Dean’s cock. Dean panted into his ear, his hips humping forward with a vigor that Cas didn’t even know humans could possess.


It was like Dean wasn’t even tired.


“You look so pretty like this. All hazy and taking my cock like it keeps you breathing. Does that feel good?” He asked in a growl, pinning Cas‘ chest to the bed. Castiel nodded, moaning and grabbing onto the pillow in front of him. Dean struck his prostate again, making him sob in pleasure, his lips parting and his eyes became hooded.


Dean chuckled, snapping his hips and sitting up to watch his cock slide in and out of Cas’ body. Castiel came with a wail when he felt a hand smack his ass, his whole body lurching forward and tensing up as he came all over the sheets. But Dean didn’t stop. He only pulled out and rolled onto his back, sliding Cas back down onto his cock. Castiel gasped at how deep he felt, his hands scrambling to press onto Dean's chest. Cas started riding Dean in abandon, his head lolling back with a mewl.


“Jesus Christ, Cas. You’re so hot.” Dean growled, his hands grabbing onto Cas’ sharp hips. He lifted him up, pounding his hips upwards and watching Cas’ teeth rattle a bit at the force. Castiel let out a guttural moan, his eyes rolling back when Dean aimed right for his prostate again.


“Dean!” Cas cried out.


“Yeah, baby? Say my name.” Dean growled, snapping his hips so his cock jabbed into Cas with a merciless pace. Cas choked on a cry, his oversensitive prostate sending overwhelming pleasure through every nerve in his body. He couldn’t think of anyone, or anything, except for Dean. The way his hands manhandled him, the way his dirty words fueled a fire in his throat, the way his cock filled him to a completion he couldn’t even imagine.


And at that, Cas was cumming.


The blue-eyed man arched and squirmed, coating Dean’s chest in his cum with the most embarrassingly girly wail he’s ever let loose. But Dean fucking chuckled. Oh fuck him, the man was going to kill him.


“That’s it, baby boy, gonna make you forget your own name.”


Dean flipped them over, pinning Cas to the bed and hitching his legs over his elbows, watching the man’s beautiful features morph into a blissful surprise. He started fucking Cas in an abandon, railing him into the mattress hard enough for the neighbors to hear.


Castiel scrambled for the sheets, his red chest tensing up with a delirious moan of pleasure. Dean felt a coil in his stomach, curling tighter and tighter with every thrust, but he wasn’t done yet.


“One more time, come on, baby.” Dean coaxed, grinding the head of his dick into Cas’ prostate in ways that made fireworks shoot through the smaller man's entire body. Castiel cried out, arching, grabbing at Dean’s shoulders. He shook his head. “I-I c-can’t! Too much!-“ He whimpered in a glorious haze.


Dean grinned. “I think you can. I think you’re going to right now.”


“N-No. Gonna hold back.” Castiel choked out.


“Are you sure about that?” Dean rumbled lowly into Cas’ ear, thrusting his hips forward hard enough to send Cas reeling.


“Oh fuck, I’m cumming!” The blue-eyed man moaned, clenching around Dean’s thick length, milking it for all it was worth before his eyes rolled back, screaming Dean's name in such ecstasy that Dean’s heart skipped a beat. Dean groaned long and low, his hands grabbing handfuls of Cas’ ass while his hips rolled and rocked. He filled Cas with his cum, panting right into his ear.


“Jesus fucking Christ...” He breathed out.


“I know,” Cas whispered back hoarsely.


The two burst into soft laughter, wrapping their arms around each other. Dean pulled the covers up over their bodies, stroking Cas’ hair. He planted a soft kiss to his forehead, the sound of gentle snoring coming from Cas. Dean tucked his head into the crook of his neck, reaching back to click the lamp off.


“Happy Birthday, Angel.”