Day 8 - Dean's Dilemma


"WHAT DO YOU MEAN YOU WON'T GET HERE TILL TOMORROW?!"

"Are you drunk, boy?" Bobby yelled at Dean through the phone. "I mean tomorrow! The day after today. As in when the sun rises above that big, fat head of yours."

"Yeah, okay fine," Dean just barely restrained himself from slamming the phone onto the floor and following up with the edge of his boot. "Whatever Bobby."

"See you then." Bobby hung up.

Dean mimed smashing the phone down while swearing on the top of his lungs but it didn't really help. It also didn't really help that the phone slipped from his fingers and went crashing into the wooden table. The stupid battery popped out and went sliding under a cabinet. Why could they never have nice things?

"I think you're the reason Mr. Anger Management," Gabe strolled into the room eating a strudel, slapping him upside the head and leaving a trail of sticky lemon goo in his hair. "What'd papa bear say?"

"You got shit in my hair, asshole."

"Did he really say that? Who did he spend the night with?" Even Gabriel stumbled under Dean's death glare. Or at least mumbled over his breakfast. "Oh, quit your whining. Gives you an excuse to take another shower." He sniffed the air and cringed. "And you need one."

"And what you need is an attitude adjustment."

"Attitude adjustment? What are you, my mom?"

"Gabe." Sam warned as he stumbled into the room –a bottle of Advil and a glass of water in hand. "Dean. Shut up. Just…shut the hell up." He slumped into his chair and dug out a couple of pills while holding the glass to his forehead.

"What's the matter Sammy?" Dean teased. "We're just talking." He raised his voice just enough to watch Sam's face twitch in pain. "Would you prefer it if we started shouting?"

Serves him right for bailing on that fucking weird ass thing the night before.

"No." Sam gulped and pushed his hands over his eyes. "No yelling. No talking. No…anything."

"What about singing?" Gabe teased. "If you give me a little Boyz II Men, I promise I'll make love to you." Gabe elbowed him in the side, making him moan in pain. "Like you want me to."

Sam cradled his head in his arms and whined, "Why don't you just heal me or something?"

"And give drunk Sammy another crack at the whip? I don't think so."

Sam groaned and was only just able to lift his eyes to Dean. "What'd Bobby say?"

"He'll be here tomorrow," Dean growled. "Something about a ghost in a schoolhouse. Some hunter fucked it up and now there's more than one. I don't know. I don't care."

"Another day to slip up," Gabe raised his brows. "Think you can make it?"

"What I think is that this bullshit is over with. We said a week. It's been a week."

"Nuh-uh-uh," Gabriel wiggled his finger back and forth. What Dean wouldn't give to snap it off. "We said till trucker daddy gets back."

Sam groaned with his forehead resting on the edge of the table. "He is right, Dean."

"He is right, Dean," Dean mocked in a high-pitched whine. "This is bull. Where's Cas? He can call."

"Yeah," Gabe hummed and stood to exit. "Where is that dancing diva? You better go find him before the little guy wears himself out."

Well, Dean didn't trust that statement more than he could throw it -or Gabe. Then again, it'd been a while since he tried to throw the tiny angel. He could give it another go. There was enough room in the basement for a throw down. Cheating would be an issue. The issue being Gabe had no issue with it. Not that Dean couldn't take him even with the cheating, but he was going with The Beat Down as plan B. Plan A, The Beat Off, was still on the table… half passed out.

Dean waited till Gabriel was out of the room to yell at Sam. "You need to suck it up and suck him off."

Sam's glazed eyes just barely lifted from his arm. "I've thrown up twice this morning. That doesn't exactly scream come and get me."

"Then actually scream it."

"No way man. I tried. It didn't work. I am done. I'm going to bed and lying down." He sloppily pushed up from the table and added, "And sleeping. It's not worth it."

"Sam-"

"Go away, Dean."

"Sam, stop. Sam!" Dean chased him all the way to his bedroom but the big baby slammed the door in his face. "Son of a bitch."

A few hours of clock glaring later and it was time for plan B.

"Gabriel! Get your annoying ass over here!" Dean screamed until the angel popped back in front of him. "Me. You. Basement. Now."

"Why, Dean," Gabriel stumbled back with a hand dramatically flung over his heart. "You're so forward! What about your Cassie muffin?"

"My what muffin?"

"I'm sorry Deanarino but I'm not interested in being tossed over the hood of a car while my poor baby bro waits down the hall. At least not by you, little Winchester."

Dean kinda felt like joining his brother in the throwing up department. "You're disgusting."

"You're the one that came crawling to me wanting to play chicken cock."

"Chicken cock?"

"A little circle jerk?" Gabe went ahead and mimed that, which was super annoying and not necessary. Kinda like a regular mime. "Hot hands? Frenzy fuck? The final round-can't take it anymore-overtime-push to the finish-whoever reaches checkers first loses? You just can't take it can you? You can't wait just one more day. You have to settle it now by watching me get my rocks off or do it yourself. No way man. You're the one that's disgusting."

"What?!" There was that baby vomit creeping up his throat, threatening projectile. "No! I meant fight!" Dean punched his hand –now the one miming. "We should go fight, fist to fist, man on man. Not man on man."

"That's a lot of testosterone you got pent up there." Gabe skipped forward, wiggling those detachable eyebrows. "I think I'll put the lid on and let you simmer before I beat your gargantuan ass. But hey, check in on Cassie. I'm sure he's up for a round. Or maybe a roll around."

"What does that-" Gabriel popped away before Dean could finish asking, "-mean."

Dean hadn't seen Cas since the night before –except in his dreams- and it was probably better that way. The things he had Cas doing in his late night fantasies would bring a blush to anyone's face. Hopefully Cas'. A full body blush that rendered him a shy, pleading mess.

How did he get here? How did he get it this bad for an ex-angel with the sexual know-how of a potato chip? This stupid contest was so…stupid. It was wrecking him. Another day? How the fuckity fuck was he supposed to last another day?! This was supposed to be it. He was supposed to be jacking it by now. Headphones on, pants off -Sunday afternoon spent right.

Instead, he was locking himself in his room for the millionth time with the intention of finding the unsexiest thing in the world and staring at it for twelve plus hours. Picturing Gabriel naked worked pretty damn well. Picturing him full clothed worked pretty damn well too. Sam had weird taste.

Not that Dean could judge. His pie-murdering, spastic dancer was wandering around the bunker's halls somewhere. Probably doing something weird like corn shucking or poetry reading or the hokey pokey or- NOT.

Not at fucking all.

Dean froze in the doorjamb to his room. Both his door and his mouth hanging wide open.

Cas was not wandering the halls doing something weird. He was in Dean's bed. Doing something beyond weird. It was- was- was-

"Hello, Dean."

Fucking awesome.

Cas had all parts out, turning himself around. He was on his knees, in the nude, spread out like a bacon themed dinner buffet. The appetizer was that cocky smile lopping up the side of his panting face. Followed by a course of shining skin pulled over taut muscles, stretching as his body rocked. Rocking was the main dish because he wasn't just rocking to the beat of imaginary tunes like his seizure from the night before. No. He was rocking back and forth, thrusting himself into the palm of his hand –each buck revealing a few inches of shiny purple dildo splitting him open.

Cas might have snorted or laughed or moaned, it was hard to tell when he was panting so hard, his body making the springs on the bed screech. Or maybe that screech came from Dean.

"C-Ca-C-C-" Oh no, that was just stuttering. "What're- what- wha- what?"

"Dean, I've been doing a lot of research on penetrative sex between two males."

"Holy fuck."

"I was an angel, so that is the idea." Cas paused to twist his hand to get a better angle. "And I believe I understand, but I would like to try it with a partner. With you."

"Cas I-" Goddammit. "You can't just-" Goddamn. "You-" Dammit. "I can't- I really can't-"

"Can't or won't?"

"Did you just use that fucking line?" The face-palm was immediate. "Fucking hell."

"I believe you are going in the wrong direction." Cas paused and felt the need to explain, "Holy would imply heaven, meaning me or another angel. Though Gabriel is the only other angelic being here and I don't believe you or he-"

"I said fist to fist! Not fisting!"

"-would be interested. Hell would imply Lucifer. As he is stuck in a cage that would not be possible. Besides, I do not believe intercourse with the devil would be-"

"Yeah, yeah, I get it-"

"Unless you meant Crowley. In which case I must also disagree with your choice of-"

"No, Cas. I get it. I just meant-" Another face-palm felt right. It didn't help jog him back to reality. Cas was still there MASTURBATING ON HIS BED looking all fuckable and begging and goddammit all to hell. But not to Lucifer or Crowley or ah- son of a bitch. "I meant nothing- I just. I just can't. I mean- I can't."

"I know you may feel you are taking advantage of me because I am new to this but let me assure you that I am very interested and ready. I believe I am old enough to make the decision. I have done all I can do on my own." He started up his rocking once again as if to prove his point. "And I want to do more. With you. I want you."

"Cas-" Dean squeaked again. "I can't-"

"Of course." Cas slowed down to a full stop and held himself in place. It was a horrible sight to see. Like getting to the actual bacon plate and seeing only crumbs left behind. Tiny, delicious burnt pieces just waiting to be licked up. Cas spoke over Dean's lusting whimper, "After you win this contest with Gabriel. I can wait. I have been waiting."

Dean's hand slipped across the door, another unidentifiable noise slipping between his lips. Cas moved but he wasn't stopping with his rock. He slid off his knees and collapsed onto his back, spreading his legs and taking his hands away, showing Dean every bit of that dessert.

The purple dildo's flat, black end was slipping without Cas supporting it- his tight hole pushing it slowly out of his body. His pucker was red from having been abused, a deep blush rushing out to his quivering legs. That thick dick was standing straight above the scene –as if it were nothing but an innocent bystander to the mouthwatering display.

All laid out right there. For the taking. For Dean's taking.

The only thing that stopped him from rushing right over and ripping the fabric of his jeans with his bare hands –and a little extra help from his frustratingly hard as steel dick- was Cas moving his fingers under his legs and blindly grabbing the end of the dildo again, slowly pushing it back in. His eyes twitched, his forehead crinkled, and his mouth pulled open as he gasped in pleasure.

"Can you shut the door?" Cas panted.

Shit. Right. Door.

Dean looked behind himself, glad no one else was watching this, and quickly shut it behind him.

Cas made another noise that could have been a laugh, "I believe you once told me the point was to get outside the door and shut it."

"Ugh-" Dean looked at the door behind him wondering why the hell he thought it was a good idea to lock himself in this room anyway.

"It's fine," Cas said. "You can stay."

"I can't-"

"Your mouth is open too."

Dean quickly clamped his mouth shut again.

It fell right back open as Cas shifted again, slowly pulling the dildo out of his body. Inch by inch he saw it now. A slick little thing, smooth along all edges –shining in the dim light overhead. It was wider at the base and slimmed to a rounded head. That head slipped out with the tiniest of pops. It wobbled there, just barley grazing the access point, tracing circles around Cas' entrance. After a bit more teasing –where every pass made his hips quake- he finally slipped it back in, his body jerking up into the air.

"Come here," Cas gasped.

Dean could actually feel his legs giving out -shaking like he was the one taking it in the ass. His knees pulled too sharply and he had to grip the wall to keep himself from falling on the fallen angel. He moved, slowly but surely toward his own bed.

What the hell was going on? This was Cas. Bumbling, innocent, potato chip Cas! Since when was he the one giving the orders? Since when was he the one tempting Dean like a wanton whore? Since when was Dean one to listen to such obvious attempts at seduction?

Gabe put him up to this. There was no way Cas already had a purple playmate waiting in his bedside table. Unless he did... NO. It was dick face Gabriel. It was part of the game. But Dean could play too.

He was pretty sure.

Maybe.

He made it to the bed and stood, watching over Cas as he had the first time he watched him masturbate. Cas wasn't messing around now. This wasn't a gasping, needy haste where he wrapped his hands around himself and frantically struggled to the finish. This was deliberate. Slow. Cas was even staring up at him, their dark eyes locking as he licked his lips.

Dean cleared his throat but his voice still caught, "You're very- um- good. At that. For a noob."

Cas' mouth curved into a smirk as he twisted the dildo around, his body curving against the mattress. "I've been practicing."

Dean was pretty sure he could come up with something witty to say to that but all that came out of his mouth was, "Y-yeah."

"Touch me."

Dean's fingers twitched and his hands swung at his sides. He was suddenly very aware of the fact that he didn't know what to do with them. He forced them into his pockets. Great, now he had a double case of awkward pocket surrounding inconvenient bulge number three. "I can't."

"So you keep saying."

"Dude, this isn't-"

"I've been waiting for you to touch me again," Cas continued as he continued to fuck himself open. "I've been thinking about it constantly. I need you to put your hands on me. I need you to wrap your fingers around my genitalia and perform the necessary actions to make me orgasm. I need it. I need you. Dean."

That was the closest to dirty Cas' talk had ever been. Dean coughed and pushed his hands further inside his pockets. Man, they were itching to perform necessary actions. "Since when have you had such a mouth on you?"

"Since I met you. I can use my mouth on you too, if you like." Cas stopped on the spot and tilted his head to the side. "Is that right? I think that was in the documentaries. Is that what I'm supposed to say? I can't think-" He swallowed audibly and resumed rocking. "Can't think straight."

"Join the club." With this new image to keep him company on his loneliest nights, Dean wouldn't be thinking a straight thought for the rest of his life.

"Deeeeean, please." Cas whined and reached for Dean's hand. Most of him landed on jeans but Dean could still feel the pull of those slippery fingers. "I don't need to think of someone I like touching me, you're right here. Please."

"Dammit, Cas." Dean wanted to scream be careful what you wish for. His wishing sure as hell got him into one giant pickle. One very long, thick, giant pickle.

Since when had Dean not taken the pickle? …wait, no. He didn't want to take the pickle. He wanted to give it but….uh….he wanted to play with Cas' pickle? Oh screw the pickle. But with his hands not…up his…for the love of god. He wanted the fucking pickle.

Dean's hands ripped from his pockets so fast he tripped and slammed his shins into the side of the bed. He wrapped his hand roughly around Cas' shaft and started those actions with a squeeze. Dean pulled his hand up and twisted it around, easily sliding around the head of Cas' cock with the ease of previously applied lube. That explained the smell of strawberries. Cas' dick was rub'n'sniff. Not that he was sniffing...ah fuck.

Dean's voice came out gruff, "You like that?"

"Mmmmhmm," Cas moaned and his body shook again, his hands clawing at the bedspread as the dildo slipped all the way from his body.

Now that Dean was closer it became quite clear that there was a power button located along the bottom edge. It had settings that shifted from a zero to three marked lines. It rested at the zero and that just wasn't going to work out. "Then you'll love this."

Dean didn't waste time in jumping onto the bed fully and seating himself between Cas' greedy open legs. He switched hands on Cas' prick and dove for the vibrator, slamming it back into Cas' compliant body.

The reaction was instant as Cas' dick jumped against Dean's palm and his legs twitched against his side. But that was just the beginning.

Dean smirked, enjoying this view, before clicking the dial to the first setting. The hum was quiet but Cas was not. The vibrator tingled Dean's fingers as he shoved it in and out, his other hand just as occupied by slipping up and around that shiny strawberry flavored head.

Cas cried out, his body unable to sit still as Dean thrust into him again and again. All the ex-angel could do was reach up higher, trying to lift himself for better presentation.

Dean dropped his hand from Cas' dick in order to kick the vibrator up to level number two.

"Shit," Cas actually swore.

"Shit," Dean joined in. He placed a hand against Cas' thigh and forced him to remain open and watched the purple end completely disappear as he held it all the way inside. Cas squirmed but Dean kept him firmly in place as he twisted it around, searching for just the right angle. As soon as he found it Cas knocked him over with a scream.

Literally. Cas punched him so hard in the shoulder he went rolling off the bed.

"Sorry," Cas was apologizing profusely as he reached for Dean, grabbing the only thing he could reach which just so happened to be his hair. "Sorry –sorry- You said to stop doing that. I- I didn't mean to push you. I just- Dean-"

"Fine," Dean huffed just to shut him up before slamming his mouth against those pouting lips. Cas wriggled underneath him, his hands climbing under Dean's shirt and slipping against the sides of his ribs. Stubble scratching, tongues twisting, and fingers flicking. With a hasty retreat Dean slipped out of the tshirt and dropped his boots on the floor as well.

He joined Cas back on the bed but only for a moment. The vibrator had slipped out completely, humming in place beneath Cas' ass. Well that just wasn't right.

Dean slipped off the bed and grabbed the tube of KY standing on his nightstand. He dripped a large amount into his hands and re-slicked the hot metal end of this torture device. Cas watched with wide eyes, his body rocking towards him, waiting to be filled again.

Dean took pleasure in slowly lowering the tip down, watching as Cas was forced to wait as he deliberately pushed it inside. Only when it was seated all the way did he rip it back and thrust it up at the magic angle he found before.

Cas screamed.

Dean gasped and quickly flicked the setting all the way up to three.

Crouching there, he watched closely as Cas convulsed, his body tensing and retracting more times than a fish orgasming out of water. Then he found himself face to face with that cock again, wondering just how much he could fit in his mouth.

Would it just be the one lick? How many licks did it take to get to the center of Cas' orgasm pop?

Shit, he'd been hanging with Gabriel for too long.

Dean popped open his mouth as far as he could jam it and gave it a try, nearly choking as Cas bucked up too hard, nailing the back of his throat and scraping along his teeth on the way. More apologies came from above but Dean ignored those and slowed the thrusting of the vibrator so he could concentrate on playing with his tongue. Cas didn't seem to mind. Dean slowed the vibrator altogether, holding it tightly up against the certain spot that had Cas swearing under his breath.

The sound of vulgarities mixed with Dean's name. Perfect.

One artificially flavored lick and Cas' body was coiling tight. Two licks and Dean felt the pain of being crushed between two powerful legs. Three licks and Dean's hair was being pulling from his scalp. Four and he felt a wet heat crash over his tongue as Cas peaked and cascaded cum down the back of his throat.

One more than he thought.

Dean leaned back and swallowed the salty aftertaste down, smirking at his handiwork as the vibrator started to slip back out of Cas' body on its own.

Game played and won.

Cas looked smashed, his hooded eyes glowing as he looked up at him. That full blush, those open legs just begging for more attention, that red pucker wishing for something more than some slick piece of metal. Late night fantasies be damned.

This was exactly what douche angel wanted. If ever a douche there was, Gabriel caused the most yeast infections.

That thought alone should have killed Dean's happy bone, but it didn't. Cas was just so fucking- fucking- fuck-fuck-fuck-EDIBLE. Edible, okay? He was fucking fuck-edible.

Gabe sure was gonna grill his hide till extra crispy, but hell. The burnt pieces were worth it. Right?

"Ah fuck. Fuck it," Dean growled. "What's the worst he can do?"

Dean scrambled to get out of the rest of his clothes, fairly certain he heard the rip of his boxers on the way down and that he missed the sock gap. He jumped back onto the bed and shifted his sedated companion. Cas didn't complain about that either.

Dean gripped the base of that purple imposter and chucked it to the ground, the vibrations now sounding against the wood of the floor. He didn't hesitate. He couldn't slow himself if he tried. With one sharp sweep he impaled Cas, pushing his entire cock deep inside the slicked up body. He screamed into Cas' shoulder, the heat of him coiling around every inch as he pressed deeper. He didn't waste time thinking this could be it, that he could just pull out now and not do a thing more. He would play the second round. Boss battle, bring it on.

He folded his arms under Cas' body, barely noticing as Cas gripped his shoulders. He picked Cas' torso off the bed and hauled him up to a better angle. He pulled back quick and slammed inside again, biting on Cas' neck so he wouldn't scream aloud.

Cas' legs scrambled to lift up his center, his hands falling to Dean's hips and pulling him back inside again. "Dean-"

The gasp of his name made a moan louder than his screams pass through his teeth and vibrate down Cas' spine. There was no fucking way, but maybe he could just do a couple thrusts and then be done. Just one or two. It just felt so damn good.

With speed and power he rarely had a chance to use anymore, he pounded into the man under him, bucking wildly until his vision started to blur. The coil that had been twisting his insides for over a week finally started to unwind.

Just one or two more.

His center heated, his body tensed, and before Cas could do such a thing as say his name again he was screaming Cas' name into his shoulder.

He had to stop. No. He was so going to lose. This was it. No turning back. But- ah-ah-ah fuck it- fuck it so hard-

"I am the pickle giver!" Dean screamed towards the headboard. Blissful whining escaped his mouths as he released himself, his body finally relaxing into the pleasure that swept from head to toe.

Game over.

Not a moment later he felt Cas' hands running up and down his sides, his hands pulling at his head. He lifted it, only to feel warm lips replacing those hands, trailing to his mouth. The stubble was welcome this time, scratching against his chin and hand. He gripped Cas close as he pressed into him, moving his mouth at a pace that matched his former motions.

Cas pulled away to breathe, "I've wanted to do that since I was a woman."

"Cas, I can honestly say no one has ever said that to me before." Dean smirked and ran his hands over this new terrain, his fingers grazing the same path they made before, when they were tracing the feathers of a dark tattoo. Man, that tat was cool. Cas still squirmed under the touch too. That was so damn hot. Everything was so damn-

"You lost the contest."

Dean laughed. He actually forgot about that for a sec. "Sure did."

"Does that mean I seduced you?"

"Yeah," Dean chuckled. "You're the sexiest Potato Head of them all."

"Potato Head?"

"Head again, Cas? You sure are quick on the rebound."

Cas' head tilted to the side again, those confused eyes bouncing around Dean's face and landing on his lips. With a small smirk reminiscent of the one he greeted Dean with he said, "So we fornicate now?"

"We forni-fuck plenty."

Dean and Cas were only human and after a couple of rounds they both needed some water and food. Dean offered to go grab it for them since Cas could barely walk –thank you very much- but that was totally the wrong thing to do.

"Did I just hear what I think I just heard?!" Gabriel skipped into the kitchen with Sam trailing behind as Dean made sandwiches. "Did you just pop Cas' cherry? And pop two of your own?" His eyebrows danced as he eyed Dean's dick.

"Shut it, Gabriel!" Dean yelled over a mouth full of ham as he covered his junk with the bread.

"What exactly is a pickle giver? Is Cassie the Dill keeper?"

"Why are you wearing socks?" Sam asked, looking at his feet.

"I said shut it ass hat," Dean said to Gabe and added, "You too, Sammy."

"Dean Winchester is no longer master of his domain! The king is dead!" Gabe clapped his hands and glitter fell from the ceiling and landed on absolutely everything –including the cheese. "Long live me!"

"Does that make you the queen?" Dean teased Sam as he tossed the Kraft at Gabe.

"Sammy makes a fine queen," Gabe winked and stuffed the slice in his mouth.

"Nope," Sam sighed. "My head still hurts too much for this. Sleep for me."

"Me too," Dean said with a wink as he headed back to his bedroom, sandwiches and beer in hand.

"Not with Cassie in your bed. Better take out the batteries or the energizer bunny won't fuck like the rabbit you-" Gabe was just about to follow but Sam grabbed his shoulder.

"Gabriel, don't make Dean mad."

Gabe smirked at Sam and watched as Dean turned the corner, "Just wait until tomorrow."


TBC