Day 1- Gabe Cheats


A week with no jollys? Easy as pie.

Not as awesome as pie, but Dean's been in harder situations.

Or maybe not.

A half hour after their celebratory beers and halfway into an episode of Angel, Dean stomped into the main room and started yelling, "Gabriel, you son of a bitch!"

"What?" Gabe knowingly smirked from the same position Dean left him, a handheld videogame the only addition and the center of the angel's attention.

"Don't play smart. You spiked our beers!" Dean pointed down to his waist where the evidence of this was indeed quite evident. The coarse fabric of his jeans hugged him tight enough to show the erection pushing painfully hard against the seams.

Seriously, it literally came out of nowhere. Charisma was hot but it was her prego episode and no thank you to that. It wasn't a far leap before concluding Gabe's part in his surprise boner.

He hoped to god that he would never use 'Gabe' and 'surprise boner' in the same sentence ever again.

Gabe took his time leering over his Nintendo, making it clear that he enjoyed Dean's little display, pissing the hunter off more.

Well, it wasn't a little display. Dean's display was quite big.

Gabe chuckled and shrugged, "It's a small dose. I spiked mine too. See-" Gabe suddenly stood and thrust his hips forward, showing everyone in the room how his dick pushed against his jeans as well. "All's fair."

"So it's not just me?!" Sam stood up quickly but sat down just as fast when he realized he was sporting a pair of sweatpants that were much more show than tell. He curled the book on the table over his lap as his face turned a bright shade of beet red.

His cheeks almost turned purple when he looked up and saw the very erect Gabe sending him his very own wink. "Sporting a winner there, aren't you Sammy?"

How could someone blush that much and still sustain a hard on?

Oh, right. Viagra.

"Gross," Dean complained. "And that's cheating."

"Is not."

"Cas!" Dean called over his shoulder and waited until the guy quietly shuffled into the room.

Dean was glaring at him to hurry up on the outside, but on the inside he was trying to hold in a laugh. Cas had his trench coat wrapped tightly around his entire body like some weird human burrito. His hands held the fabric close to his side, one arm hidden to make sure it wouldn't move, the other bending awkwardly to hide his groin. He was trying so hard to look like he wasn't doing anything strange, as if he always stood like that.

Well…he kinda did.

Dean coughed, "We need a ruling. Gabe cheated."

"We never set any rules," Cas said, shifting awkwardly in place as he readjusted his outerwear.

"Exactly!" Gabe had no issue with raising both hands in the air, giving them all another glimpse of his pitched tent.

"That is true Dean," Sam reluctantly agreed but he was distracted as he said it. Gabe wouldn't stop wiggling his hips.

"I hate all of you," Dean groaned and pulled at the band of his jeans again. If he could burn the image long enough of seeing both big and little Sam standing tall in sweatpants, he would go fish out a pair for himself.

"Dean?" Cas' pained gasp had him nearly flipping a chair over he spun so fast.

"What Cas?"

"What is happening?" Dean gulped as Cas shifted again, his wrist pressing down on the area Dean guessed to be rather sensitive. Cas grunted at his own touch and shifted again. "It is not going away."

"It's not going to," Dean said with pity and suppressed hilarity before angrily spinning towards the angel in the room. "Gabe drugged us."

Cas whined aloud again and Sam sighed, "Guys this isn't fair to Cas. He's a thousands of years old virgin. Take it off him."

"Would if I could," Gabe smiled mischievously before flopping back down in the chair next to Sam and flipping his game back on.

"And you can," Sam reminded him.

"Dean?" Cas called again.

Dean groaned, "What do you want me to do?"

"It hurts."

"No it doesn't, you big baby. Just stop twitching so much," Dean urged him even though he found himself hypocritically twitching in his spot, grinding his chair across the ground. Cas' little dance was making him hotter than Mexico under the summer sun. Stupid Gabriel and his stupid drugs making him turned on by stupid human burritos. "Try and take your mind off it."

"How?"

"I don't know," Dean snapped the same time his chair did, tossing him straight to the floor as thanks for his frustrated convulsing. He grunted at the pain of smacking his ass on wood mixed with the sudden strange arousal that the shift of his own wood suddenly sent pulsing through him.

He glared at Gabe and Sam and dared them to say anything with his bitchiest bitch face. They didn't, but Gabe whispered something to Sam and it was apparently the funniest fucking thing in the entire goddamn world.

"Dean," Cas whined again.

Dean growled and threw up his hands, "I don't know! Think about something gross. Or random. Like bees. You like bees right?"

Cas barely blinked before he complained, "It's not working."

"Well Cassie," Gabe winked. "You can always take care of it. Relieve the pressure."

"Is that an insinuation?"

The douchebag gave him a round of applause, "Very good Cassie!"

"You could do that," Sam nodded. "But you would lose the bet."

"I don't care," Cas growled and pulled the trench coat tighter around his side as he stomped his feet. "It is quite uncomfortable."

"Then have at it," Sam stifled a chuckle as he gestured towards the hall leading to Cas' room.

"Only a few hours." Gabe shook his head, "Humans."

"You know what Cas?" Dean glared at Gabe and shook his head, finally getting up from the ground. "No. You'll be fine. You're not losing so soon."

"But Dean-"

"Come. Sit." Cas longingly looked towards his bedroom door but dejectedly walked to the chair next to Dean all the same, still wrapping his blanket of a trench coat tightly around his sides. "There you go."

Dean smiled in a small victory for Team Human but soon questioned his alliances. Cas would not stop twitching! Dean was afraid his chair was going to break too pretty soon. Then came more complaining out loud and it was just really sad.

The worst part of it was that Dean had to hear every wanton little whine that pipsqueak made. Every single raspy breath he took was tugging at Dean's drug induced erection, teasing him and asking him to come out and play. He ground his toes into his shoes and turned his knuckles white gripping his chair but nothing was blocking Cas out.

Then Sam cut in with the most pitiful puppy dog look of all, "Cas, buddy. If you really need to-"

"No," Dean cut him off but after two more minutes of silent torture he just caved, "Fine. Whatever. Go ahead, Cas."

Gabe chuckled the same time Cas thanked him with desperate relief.

Cas turned towards the hall and Dean suddenly found the ability to breath normally again but, of course, Cas had to just go and turn right back around, looking just as confused and adorable as ever. Wait…no, not adorable. The flip of his hair, the sheen of sweat on his forehead, the frustration in his brows, all mixed with the way he bit his lip in complete erotic confusion and desperation…not adorable. It was mouthwatering and immoral. Oh, hell yes it was immoral. It was downright dirty.

Shit. His new chair was starting to creak.

What Cas said next just made it so much worse. "How do I… I understand the practice but how… what do I…"

"I thought you said you knew how!" Sammy practically laughed and it must have been funny from his point of view. Dean was too preoccupied trying to think about the deer.

The dead, dead deer.

"Watching and doing just aren't the same thing," Gabe sympathized. "Oh you're gonna have so much fun little bro!"

Sam kicked his chair, "Creepy."

"I feel proud," Gabe shrugged. "Little Cassie's growing up."

"Dean?" Cas called his name again and dammit, dead Bambi was not distracting enough.

"Jesus Christ, Cas." Dean huffed and flailed his arms. "Just…do it." As Cas started to unravel his coat, Dean jumped and added, "Not here! Go to your room and do it."

"Do what?"

"Dean, you gotta help him out," Sam shook his head and gestured from behind the safety of his table. "Look at him."

"Yeah Dean, look at him." Gabe chuckled again and winked in Cas' direction. "I think he needs a helping hand."

"You're just trying to make me lose," Dean accused.

"He's the one jerking off, not you. Unless you think you can't handle yourself?"

Dean's foot tapped and his mouth moved but all he could do in the end was frown, "Fine. Come on, Cas. Let's go."

"Thank you."

"Thank me…actually never thank me."

Dean led the way to Cas' room, the entire time bitching in his head about stupid angels, stupid Gabriel, and stupid Sam for suggesting Dean help him. Why was it always Dean's job? Then again, the thought of Sam helping Cas with this sort of thing caused bile to rise to his throat.

Nope. He could do this. No problemo muchacho.

Cas' room was a lot like Dean's only bare. There wasn't a mess to be had as Cas had no real personal objects just yet. Even as Cas walked into the room Dean could see the trench coat open just the slightest bit to reveal one of his borrowed t-shirts and borrowed…oh, holy Jesus. Cas was wearing his pants and they were barely containing that erection, pushing so tight across the zipper that Dean swore he saw the color of Cas' boxers. His boxers. Oh, fuck. Cas' dick was pressing up against his navy blue boxer briefs. Fuck, fuck, fuck.

Dean cleared his throat and lifted his gaze to find a head-tilting Cas quizzically staring at him with that pained aroused expression. Triple fuck again.

"You've really never…?"

Cas shook his head and explained, "I understand the mechanics from observing but I've never tried. As an angel, I found I had other interests. Besides, I cannot recall my memories with perfect clarity anymore. Only recent events."

Dean nodded awkwardly, hoping to skip over that uncomfortable conversation and dip into an extremely uncomfortable situation instead. "Alright go lay on the bed, take your pants off, and uh- go to town."

"To what town? We are stuck here, remember? Gabriel-"

"No, not- okay look. This isn't a thing, a normal thing. People don't do things like this- like- ugh- like- like this, unless they are very…close. Or drunk."

"I thought we were close?" Dean huffed but Cas cut him off before he could try to explain again, "Dean it is very bothersome. Can you please just show me? Please."

Fuck, Cas' voice cracked with that plea and goddammit, there was no refusing that tone.

"I'm not going to show you anything. I'm going to tell you. Walk you through it. I'll be right here if you need me. Okay?" Cas nodded urgently and Dean gestured towards the bed. "So, take off your clothes and lay down."

Cas finally unraveled the outer layer of his outfit, dropping his coat and gently hanging it up in his closet. Dean was about to tell him it didn't matter but then he jumped for his shirt and the jerk of Dean's interested dick reminded him that this was not supposed to be a strip tease. "Oh, whoa. Hold on there. Go by the bed and strip. And uh- Wait till I turn around."

It was a painfully long time before Cas was done -probably folding his socks. When he finally finished he called out from the bed, "What now?"

"Just, get comfortable." God knows Dean never would. He leaned against Cas' dresser and stared into his closet, closing his eyes as he heard the bed squeak and the naked Cas adjust behind him.

"Okay."

"You got lube or lotion or-"

"I have this lotion. Sam said to use it after showers because-"

"Yeah, yeah, yeah, okay, that's fine. Just- um- put some on your hand." The pump of the bottle made Dean jump as he imagined Cas squeezing it out into his cupped hand, readying it to slick up his thick, hard, throb- "You wanna- um-" Dean grabbed the air with his fist as he tried to mentally prepare himself for the words to escape his mouth. "You wanna grab yourself."

"Grab myself where?"

"Where? Where do you- Where it hurts Cas. Just wrap your-" Dean sucked in the rest of that sentence at the whine that came out of Cas' mouth, penetrating the silent air with the cry of a virgin. "Oh fuck."

"Bad?" Cas actually sounded concerned.

"N-no." Dean swallowed and pushed on. He could do this. "Wrap your hand around yourself and uh- spread the lotion around."

Lucifer was back and he was playing tricks on Dean because goddamn it all to hell that could not be the sound of lotion sliding all over Cas' dick and he was not making those godforsaken sounds. The bed was squeaking as his body shifted and Dean had to bite his lip in order to prevent telling him to stop moving.

"O-okay," Cas squeaked when the bed stopped shaking.

"Hold yourself tight." Dean just couldn't stop doing the hand gestures to match, hoping Cas was staring at him so he would see.

Oh hell, was Cas looking at him? With his cock in his hand? Really? Oh fucking fuck.

Dean started to jerk his hand and pictured Cas doing the same. He would be so nervous staring down at himself. Had Cas ever really looked before? He probably had. He would be so curious about the stiffening in his pants and he would love to inspect every inch of himself for hours, poking and prodding and fingering. Such a great being reduced to a quivering mess as he innocently strokes, desperate for orders that he only asked for from Dean.

He would jerk at the cold of the lotion, arch his back and hiss, but sink down when it heated up on his skin. He would fumble when his other hand brushes the inside of his thighs and slides against his balls and probably think he did something wrong, look around to see if anyone saw, and then do it again.

He would lurch at the rush and grip a little tighter, pulling that loud moan out of his mouth. He would twist his hand just the slightest, drag his thumb over the curious, throbbing vein, and watch as he started to fall apart.

It would be so new, so overwhelming. He would cry and pant and moan as he tries to beg for orders. He would start to rock as he climbs higher and builds until his body can't take it. His hips would shake-

Dean had to shake his head to clear that image from his mind. His cock decided to repay him with an extra harsh and painful jolt. Worst timing for a cock tease Cas fantasy ever.

"And-" Dean squeaked before dropping his voice back to normal. "And move your hand up and down. Like uh- like I'm doing."

The provocative noises that filled the room had Dean whining behind clamped lips. The lotion suctioned against Cas' hand and the smacks of each popping pass were only the tip of the inappropriate erection iceberg.

Cas was going slow but the bed was still shifting as his body swayed with his arm, rocking back and forth as his hips started to pick up the instinct. Every whack of the bed against the wall pulled at Dean's will just a little bit more and added a new layer to the agonizing anticipation thrumming from his center. On top of that, Cas was muttering again. It was obviously that he was trying to be silent but Dean could still hear the tiny whimpers and moans that sounded behind him.

Dean moaned in his own time, glaring down at his fully erect dick, hating Gabriel more than ever since it would not go down. It seemed to only be getting worse –tighter, firmer- as the noises continued and his jeans were near suffocating. His cock was going to burst in its cage. Stupid Viagra.

His cock was just screaming to be touched and he was not going to lose this stupid bet so he tried to relive just the tiniest bit of pressure by slipping a hand in his pocket and over his boxers, pressing down just the slightest. A jolt of energy flushed his system and oh god yeah, that's what-

"Dean-" Cas gasped behind him.

Dean literally jumped, his hips thrust up into his hand, and he had to grip the dresser to keep himself upright on his buckling knees. That was his name. The most indecent pronunciation of his name, but his name all the same. And it sounded perfect coming from those distraught lips.

"C-C-Cas?" Dean gasped and ripped his hand straight out of his pocket like his dick was on fire – and it was-, afraid he would come from just that simple touch. It was enough to set his system into overload just hearing Cas moan his fucking name, let alone to say his back. God, he was so screwed.

"Dean I- unngh-"

"Are you hurt?"

"No. No. It feels- it feels-"

The room was getting hotter. Dean pulled at the collar of his shirt. It couldn't physically be this muggy. Gabe must have screwed with the thermostat.

Dean tried to pull in a breath from the thick air, but his voice came out in a pant, "Feels good Cas?"

"Yeah. Mhmm." Cas mulled over the groan and Dean suddenly found himself dizzy and dug his fists into the wood of the dresser with both hands. "Yeah De-Dean. Feels- feels- mmm- yeah-"

"Oh god. Okay. Move your hand faster and hold yourself tighter. Move over everything. Head and uh- god just- over everything."

Cas was breathing so loud and the bed wouldn't stop squeaking and Dean's hands were digging into the side of the dresser so hard, taking all of his weight, he was sure he would break it somehow.

Dean couldn't take it anymore. There was a buzz traveling everywhere, making him antsy like he couldn't believe. Every pulse of blood that pumped more drugs straight to his hyperaware cock made his body convulse. His hands started to slip on the wood and he tried to readjust himself without moving too much. The friction was nonexistent and the pressure was too constricting. And to know there was nothing he could do about it? That it was only day one? Day fucking one?!

Why was it so fucking hot?!

He closed his eyes tight but that only brought new images to tag onto the sounds he was hearing. Of turning around, straddling Cas, unzipping his jeans, and showing him what else Team Human could do. Maybe it would be good for him. To shut him up. To have something in his mouth. Screw the contest. He would be able to handle it. Cas would swallow him down with those big pink lips of his and Dean would talk him through it. Cas would lick him to the brink but he wouldn't come because he could control himself and oh god. Fuck his fucking jeans for hurting so damn much.

Dean was tempted to peek over his shoulder but remembered the golden rule of telling and not watching and focused on the dark of the closet. There was another of Dean's shirts hanging up in there, brushing up against the trench coat. Cas had been wearing his shirt and it had been touching

him all day. Why did his clothes get to touch him and why were his jeans so fucking tight?!

Screw it.

He jumped for his button with one hand and popped it, unzipping in one swift move and relieving the pressure. Oh god that felt good. No, wait. No. Now there was practically nothing touching him and his cock was bouncing in the air and, fuck the world, he wanted it to be touching something. It was just a thin layer of boxer barely grazing him and Cas had been wearing his boxers. Cas' dick was almost popping out of his boxers. The soft pink head which was beating in Cas hand right now. Oh god, couldn't he hurry up? Didn't virgins blow their load quicker than this?

"Cas-" Dean breathed his name pleadingly.

"D-Dean," Cas groaned and the bed started to shift more, the squeaking coming faster.

Dean could just jump over there and make the bed break if he wanted. He could jump on Cas and show him what real torture was. He could make him so hard that he would do more than just beg for it. He would have him reeling harder than any drug. He would give him a show like he'd never known and have him screaming.

"Dean-" Cas was already begging for it.

"Cas." Dean cock jumped again and he pushed his palm over it, just to keep it in place. There was a flash of heat that spread through him and he fell into the dresser again, crying out as the rush of pleasure overtook him and his judgment. "Fuck."

"Dean. Oh, Dean." Cas was really desperate out now, the bed was pumping against the wall like Cas' cock was pumping into his hand. "It's not- I can't-"

The poor kid was practically crying and that just buckled Dean's knees more. He wanted to face him, watch him, to see what he could do and how wrecked he could make him. Instead, he turned to the wall and pressed his body against it, giving his cock just a bit more pressure as he brokenly instructed, "Yes you can. Just relax. Think of something that turns you on."

"On?" The squeaking slowed. "I'm not a machine. I don't have a button that functions as-"

"No," Dean knocked his head against the sheetrock. "Picture someone that makes you feel all hot and bothered. Like a celebrity or whatever. Picture someone you like doing to you what you're doing now. Imagine it's them touching you."

"Someone I like?"

"Yeah," Dean gulped. "Anyone. Just-"

"Deannn-"

"It's okay. I'm here. You just relax your stomach and-"

"D-D-Deaaaannnn."

Dean started to thump his head against the wall as his hips started to jerk with the shallow intakes of his breath.

I – thump – will not – thump – hump – thump – the wall – thump

I – thump – will not – thump – hump – thump – the wall – thump-

"Oh-oh-oh- I- - I- Oh- oh my- Dean- Dean- Dean! I need you- I need- I need-"

Cas needed him.

Screw it. Again.

Dean tilted his bruised head just the slightest bit and finally saw Cas. He was jerking his hand with lightning speed, his other so wound up in the sheets that the bed was falling apart beneath him. He was arching off the mattress and squeezing his taught legs tighter as he bucked into his fist, every thrust causing the bed to shake. His skin was shaded pink and his body was beyond tense with anticipation. His face was twisted in a frustrated grimace so hard he didn't even see Dean looking at him.

"Oh fuck. Fuck, Cas." Dean pressed harder into the wall just enough to gasp and relieve some of the new excitement that flared through him.

Shit. He was humping the wall.

"Cas, fuck."

"Dean-" He looked completely wrecked, so destroyed.

"You want to come?" Dean licked his lips as he watched Cas nod, his hand pulling tighter on the sheets below him. "Cas? What do you need?" An evil smirk crawled up his face as he listened to another strangled growl come from behind Cas' lips. The teasing gave him a sick thrill, a sense of undeserved revenge. Well, it was Cas' fault for looking so delectable. "Do you want to come?"

"Yes, Dean. Please- oh, Dean. Dean, please."

Screw it. Screw him. No wait, don't screw him. Just- ah fuck.

Who even cares? He pushed away from the wall, replacing the pressure with his resting palm, and stepped to Cas, his shins pressing the side of the bed so he could get a better view.

"Lay back on the bed-"

Cas jumped at his voice suddenly so close and pleaded in the pause, "But Dean-"

"Lay back on the bed." Cas struggled to let himself go and push back onto the tangled covers below. In his messy movements, his cock bounced against his stomach and splashed a drip of precum on his abdomen –just a tiny sample, a tiny taste.

Dean licked his lips as he watched Cas quickly grab himself again,

It was just as he imagined.

No, it was better.

Cas' cock was thick –Cas' hand could barely contain that girth-, a deep shade of pleading pink, and throbbing with need against the inside of his palm. Dean had to wonder how long Cas would last if he wrapped his lips around his head. Could he even fit Cas in his mouth? It would just take one lick. One lick and Cas would be shooting off inside him, coating his tongue and crying his name. Dean could do it. He could handle himself. He could do it and refuse his body's need to come the same time as Cas.

Before Dean had a chance to test that theory, Cas was tugging his fingers over his glossy member and doing just what Dean said, covering every single inch.

"Good," Dean cooed. "Now twist your wrist as you go up."

"D-Dean-"

"You're doing good, Cas." Dean wanted to reach out and pet him, run his nails down his inner thigh, and pull him close so he had something to rut against other than the palm of his hand –but he didn't. He just watched as Cas stared up at him with an open, panting mouth and hooded, dark eyes. "Just relax and go just a bit faster. Don't try to push yourself."

"Dean- please-"

"Relax and- Fuck." Cas moaned too loud that time. There was no way they couldn't hear him out there. There was no way to escape it in the room. "Fucking just come Cas," Dean was pretty sure his lip was bleeding he was biting so hard. He could barely catch a shallow breath as the words escaped him, "Oh fuck. Such a fucking mess. Perfect. Fuck. Cas just, mmm, let me see you. Let me see you come. Let me hear you come for the first time. Uh fuck, first time."

Cas' eyes met his again and that was it for Cas. His body contorted with the intense vibrations and hot streams of cum shot over him and the bed, most landing on his chest and some on his face. Dean whimpered at the sight and pressed even harder on his begging cock, willing it to keep in line as he forced himself to remember what was at stake. He was not going to let Gabe win and he was not going to lose. Right?

He spun around quick and tried to catch his breath as he heard Cas do the same.

"Oh no," Cas mumbled tiredly behind him.

"What? What's wrong?"" Dean started to panic and doubled checked himself. There was a thin line of cum sprayed across his boxers…did he cum too? The fully standing, near bursting erection said otherwise.

"Your shirt I-"

"What?"

"I um-"

Dean spun around – he already watched the guy whack off, wasn't much else to see- and sighed when he saw Cas fiddling with the shirt he had worn that day, picking it up and showing another stream of cum crossing over the design.

"Oh." That was fine except Cas was trying to clean it up by pulling his fingers through the mess and gathering it in his hand. Then he went to touch his face where some was dripping and- "Oh god. Fuck. Okay. Um-"

"You don't look well Dean."

"I um- that's fine just um- put that down and – um- I'm going to go take a shower."

"Dean?"

"Just um- sleep." Dean started haphazardly buttoning the jeans that did not want to be buttoned and tripped back towards the door. His hands kept slipping in the cum that rubbed past the fabric of his boxers and into the small gap that showed skin. He could feel Cas on him, rubbing over his flesh and soaking into his skin. He needed to get out of there. "You're tired right? Just sleep till the drugs wear off."

"Thank you, Dean."

"Sure, whatever, and uh-" Dean stopped for a moment. This was Cas' first time after all and he was new to being human so Dean had a responsibility or something. "You know you can do that whenever you want. I mean in your room. In private. Um- find out what you like and-" Cas nodded and the cum on his face shone in the light. "Ah fuck Jesus- I'll see you later-"

Dean bolted to the nearest bathroom and locked himself in. He ran to the showerhead and turned it on the coldest setting, jumping straight in with all his clothes. He moved so the water sprayed directly against the cock bouncing against his chest and he cursed so many times, he wasn't sure he said one proper word. At least Cas' cum was off his dick. Oh fuck.

Dean' pulled himself from the shower and peeled off his wet clothes, changing into sweats since his body decided to calm. Thank god Gabe only gave them a small dose.

Gabe and Sam were waiting outside his room with great big school-girl smirks and he groaned because he was far too wound up to deal with them.

"Cassie out?" Gabe danced.

"And did you-" Sam gestured. "Are you still, what did you guys say, master of your domain?"

"Oh, I am master of my entire domain." Dean nodded and cross his arms. "My domain is my bitch."

"Why's your hair wet?" Sam went to touch him.

"Shut up," Dean growled and avoided him with a slap. "Bitch."

"Jerk."

Gabe wiggled his brows at them both. "And then there were three."