A/Ns: Welcome to the main event!

Chapter References: Before being thrown into Gabriel's pocket dimensions of hell, the boys were at Bobby's. While waiting to head out, Dean hollered to Sam that he was taking so long because he was packing like a girl, which Castiel then had to ask about, not understanidng the differences between the genders and their packing habits. See Chapter 115.

Chapter Warnings: We've got some rapid fire gaming to do, but first! Sam gets to have a conversation with Castiel (well… a one-sided one, at least), becasue he's patient, unlike his brother.

-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-

The Road So Far (This Time Around)

Season 2: Chapter 89

-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-

Sam approached the bound angel a lot more cautiously than his brother had, careful not to cross the line onto that final stone where Castiel sat. She watched him, head turned practically ninety degrees, blue eyes full of warning and frustration.

"Are you okay?" he asked, crouching down just as Dean had so he was at the angel's eye level, but keeping a good foot back so he wouldn't trigger the end of the game.

She nodded slowly, eyes neither blinking nor moving away from his own. She tried to speak again, the words still muffled by the tape that Sam didn't dare reach out for. It sounded different than what she had tried to say to Dean, but it was still a warning. Sam could hazard a guess.

"We know," he said softly, nodding at her doubtful expression. "About the Trickster. We know."

When both eyebrows rose in surprise, Sam sighed.

"Dean's known the whole time."

Those same brows dove sharply in the opposite direction, and the younger Winchester found himself nodding again.

"I know. I know. He's bad at this. We're… working on it." Sam sighed again, mentally shelving his own frustration with his brother's inability to communicate in anything even remotely resembling a timely manner. Instead, he focused on Castiel. "Are you really okay?"

Her nod was firmer this time, eyes softer (yet no less fierce, a talent Cas seemed particularly skilled at). Sam was still learning how to read the far more stoic angel, but he was fairly certain she was trying to tell him to worry about himself. And his brother, of course.

"I'll watch out for him," Sam said firmly, just as firm as her own, non-verbal response had been. He rose to his feet. "Stay safe, Cas. We're coming for you, okay?"

With that promise, Sam crossed the finish line, placing his hand on the angel's shoulder as he came to stand in front of her. Those blue eyes looked conflicted – no doubt a protest about them prioritizing her when they should be escaping themselves – but they were quickly overtaken by the blinding light of the next transition.

-o-o-o-

"Oh, don't look at me like that," Gabe said the minute Castiel rematerialized in his living room. He hadn't even lowered his hand from snapping her back into existence. Sheesh. "I told you you'd get to see them. I didn't promise anything more."

Her glare spoke whole lectures, all at once. It was pretty impressive, actually. Gabe snickered.

"Dean's face was pretty good, wasn't it? You think he'll ever learn to look before he leaps?" The archangel threw himself into the Lazy Boy once more, rocking back and forth with the obnoxious squeak of old springs. "And Sam! Clearly the brains of the operation. We knew that, of course, but sometimes it's just nice to be right."

Castiel's glare continued. In fact, that lecture was quickly deteriorating into a scolding. Gabe might even get it up to a full rant, with a couple more well-placed pokes and prods.

Grinning, the trickster dug the TV remote out from under his butt and flipped the device on. He gave a sharp whistle and Jack, curled up next to the TV stand in his little donut bed, popped up. He swiped the game controller off the edge of the coffee table and trotted over with it, short tail wagging.

"Who's a good boy?" Gabriel cooed as he took the controller from him, exchanging it for chin scritches. "You are. Aren't you?"

With a chirpy little bark, Jack returned to his bed, circling several times before settling back into a curl. Gabe pressed a couple buttons, then settled in to watch the loading screen pop into existence.

Time for the next game!

-o-o-o-

It was dark. Sam blinked at the pitch black that confronted him. He tried to turn, to look around, but found that he couldn't. He was able to turn his head, lean side to side, but he couldn't turn his body. Or seemingly move forward or backwards at all.

The wave of panic wasn't unexpected. Sam tried to keep his thoughts on top of it, rather than get pulled down into the fear of not being able to move. This was just part of whatever trick the Trickster – archangel – was playing now. He was fine. Once he figured out what he was supposed to do, he'd be able to move again.

With that line of reasoning helping keep the panic at bay as much as possible (which wasn't to say all that much at all, just enough to keep thinking through it), Sam started testing what he could move. Neck, fingers, arms all fine, although only so much as up and down. He couldn't cross his arms in front of him or reach behind at all. Just up and down in line with his sides. A pattern was forming, as far as Sam could tell. He could only move side to side, along a line.

"What the friggin' hell is this supposed to be?!"

The scream – pure annoyed outrage Sam was way far too familiar with – caught the younger Winchester by surprise. It was coming from some distance away, but most definitely in front of him. Sam squinted, trying to locate his brother in the darkness. There was a far-off light source, but it was too distant to identify as anything other than a rectangle of light. There was nothing else but the black.

"Dean?"

There was a moment of silence.

"Sam!"

Sam let out a breath he didn't realize he'd been holding. "Yeah. You okay?"

"Oh, I am so far from okay-"

"I can't move," Sam interrupted what was mounting into a surefire rant. "Can you?"

"No!"

Ignoring the anger behind that barked response – like it was somehow Sam's fault – the younger hunter tried again. "Can you move side to side?"

Another stretch of silence followed. Sam could almost make out whatever curses his brother was grumbling, loudly. But not loudly enough. He was at least fifty feet away, Sam estimated.

"Yes. What the fuck game is this, Sam?"

Before Sam could answer (that not only did he not know, but why did Dean think he had all the answers to these places?), there was a loud, low, electronic beep. It droned out once, twice, then a third time.

"What the-" Sam tried to look around for the source of the sound.

A ball of white, like a perfectly round balloon filled with light, flew out of the darkness, straight at him. With a yelp, Sam threw himself to the side and out of the line of the projectile, whatever it was.

A second beep blared out from the darkness, and a giant, red '1' – like one of the numbers on the face of a digital clock – appeared in the sky to Sam's left.

"What just happened!" Dean yelled from the other side of the darkness.

Sam climbed back to his feet, rubbing at his elbow which had taken the brunt of his fall. The gears in his head started clicking, in tune with the next three beeps. A countdown.

"Dean, hit the ball!"

"Hit the wha- holy shit!"

There was a beat of silence, then the low-tone sound rang once again, and a second, giant red '1' appeared in the sky, this time on the right. Sam pinched the bridge of his nose.

"I know what game we're in," he called out, tone giving it away well before Sam actually gave name to it.

"This better not be Pong!" came Dean's absolutely furious, outraged response as the countdown began again. "Are we in friggin' Pong?! I'm gonna kill him!"

-o-o-o-

"I don't know how to drive oxen!"

Branches creaked around them in the building wind, leaves rustling. The air smelled like wheat, sun-soaked dirt, and an approaching storm.

"I don't even know what oxen are!"

Sam shook off a shiver as a push of wind swept his bangs off his forehead. His grip on the hunting rifle tightened, for all the good it would do him. This was tornado country, and he didn't like the look of those gathering clouds. "I don't think they're what you should be worried about, Dean. Pretty sure most people die from dysentery in this game."

His brother cast him a side-eye that lasted a little too long, reins in hand as the oxen trotted along, pulling their wagon behind them. "I don't want to know what that is, do I?"

"No, you do not."

-o-o-o-

"Run!" Dean screamed, just about at the top of his lungs, as he streaked down the blood-spattered hallway faster than he ever had in his entire life.

"I am running!" Sam yelled right back and backwards, given he was ahead of Dean.

"Run faster!" Dean tried to close the widening gap between him and his stupidly long-legged brother.

"Is it even following us?" Sam didn't turn around to ask; he kept his eyes and flashlight – the device having been in his hand when they landed in this awful, awful game – trained on the ground and walls in front of them as they came up fast. Outside of that ten-foot circle of light, they could see nothing. The hallways they'd found themselves trapped in were the darkest black Sam had ever encountered.

Dean made the mistake of checking over his shoulder, following it up with his own flashlight. Whatever he saw caused him to whip back around and start gaining ground on that gap. "Nope! Nope, nope, nope!"

"There!" Sam yelled as he rounded a corner just seconds ahead of Dean. "There's an elevator!"

"Oh, thank fuck!"

The taller of the two Winchesters slammed into the open space at the end of this nightmare labyrinth. He twisted around just as Dean hit the wall beside him and scrambled forward for the 'close' button by the time his brother righted himself. With the button hit repeatedly, Sam pressed himself back against the rear wall next to his brother. Two beams of light and two pairs of horrified eyes were locked on the darkness beyond the elevator doors.

"Come on, come on, come on!" Dean glared at the panel of buttons beside the still open doors.

"I thought you said it was chasing us," Sam whispered harshly, somehow afraid to raise his voice. If it had lost them in the dark, he certainly didn't want to attract it back.

"Yeah," Dean panted, eyeing the 'close' button just scant feet away, taunting them. He weighed whether it was worth moving closer to the open doors so he could hit the damn button again. "But like, slowly. Dude's fucked up."

"What kind of game is this?" Sam hissed. "Who plays games like this?"

"Normal people, man." Dean swallowed heavily before making a sharp lunge for the buttons. It was at that same moment that the doors started to slide shut.

And the thing chasing them staggered into the light, arm raised and already swinging.

Dean screamed as the doors stuttered closed on the blade of a giant knife – more like a friggin' sword – and, thank fuck, they stayed closed around it. That did not stop Dean from continuing to scream like a little girl until that rusty, blood-splattered blade was tugged free from between the doors and the elevator started a shuddering, chuggy trip upwards.

"Dude." Dean stood on shaky legs, hand pressed over his pounding chest.

Sam wasn't doing much better. He was pressed to the wall like he thought he could melt into it if that thing came back. "I know."

"It had a triangle for a head, Sam!"

"I know." Sam closed his eyes, trying to see anything other than that. "Though, uh, it was, um… technically more of a pyramid."

Dean turned his head slowly to stare at his brother with an expression one could almost call it a bitchface, though Sam would never deign to say such things aloud.

-o-o-o-

"I feel ridiculous. I look ridiculous!" Dean yelled into the sky in his polo shirt and plaid, knee-length shorts. He glanced over at Sam, whose long hair was elegantly tucked behind a lime green paddy cap. It matched the color of his shorts. "You? You fit right in."

"Oh, shut up," Sam snipped back as he raised his arms back in an elegant arc before swinging the club down and through. The whack of a golf ball sent flying into the air was surprisingly pleasant. He raised a hand to block the sun from his eyes ('Making the purpose of the stupid hat, what, exactly?' Dean grumbled under his breath) and watched the little white ball plop down and bounce onto the green, coming to a stop a dozen feet from the flag.

Dean stared at, both impressed and disgusted.

"Right. In."

Dean sliced his ball directly into the nearest pond. Whether that was on purpose (as an act of a rebellion, according to Dean) or not (even remotely, according to Sam) was a matter of some debate.

-o-o-o-

"This is copyright infringement! You hear me!"

This game found Dean shaking his fist at the sky he continued to yell at. Sam ignored his brother in favor of directing the twelve-foot stone statue of a horse to F6. He, himself, stood in the position of the King's Rook. His brother had chosen to be the King. Sam wasn't entirely sure Dean knew how a game of Chess was won.

"You're going to hear from Rowling's lawyers!"

-o-o-o-

Sam kicked his ass at Chess. Literally. The final move from his Queen quite literally kicked Dean off the board. Which hurt like a bitch.

But that was okay, because he repaid his nerd brother the favor when it came to Risk. Dean knew how to command soldiers, as much as it irked him (stupid divine destiny and all that crap). Plus, he always had taken a little too much joy in conquering Australia.

-o-o-o-

When Sam slammed into him three games later, pushing him off the main path to stumble back to his home base, he shouted out a very, very unapologetic, "Sorry!"

-o-o-o-

"You have to throw it."

"Why do I have to do it?"

"Because it's your battle." Sam pinched the bridge of his nose when his brother continued to stare obstinately at him. "You're the one with the Pokéball."

"Pokéball," Dean grumbled, glaring down at the red and white sphere in his hand. "What a stupid name."

"Dean."

"Yeah, yeah, alright." He tossed the thing up once, caught it, then pitched it into the field in front of them.

Their apparent opponent (a friggin' child who was fourteen at most, if they were lucky) stood on the far end of the circle of grass. In the center was a really big, orange, gecko… lizard… thing that had come out of the kid's pokéball.

Its tail was on fire, so that was neat.

According to Sam, that was a Pokémon, summoned by the snot-nosed brat across the way from them, and Dean was going to have to fight it. Well, not Dean himself, but his Pokémon. Whatever the hell that was gonna be.

The red and white ball bounced twice on the grass before rolling to stop a few feet from the cute lizard. Nothing happened. The orange reptile blinked at the unopened pokéball, making a cute noise of confusion, but keeping its distance.

"No, Dean, you have to-" Sam cut himself off, planting his face into his hand. Through the meat of his palm he mumbled, "You have to call out the Pokémon you chose."

Dean pulled his head back, making a face that would not be out of place on a toddler. "I have to what? Why?"

"Have you seriously never heard any of this before?" Sam blew out an exasperated breath and his bangs lifted off his forehead from the strength of it. "You have to say the name of the Pokémon, then 'I choose you.'"

The older hunter just stared at him, face perfectly portraying exactly what he thought of that.

"Dean."

"That's stupid. This is all stupid! You're in pigtails, Sam!" And he wasn't even going to mention the short-shorts and red suspenders, or the weird, multi-colored egg his brother was just… carrying around for no apparent reason. Dean spun back to face the field, where Charmander and his inactive pokéball both sat. "You're stupid! Your game is stupid, your orange lizard is stupid! You hear that! You're all stupid!"

Sam buried his face in his hand once more.

"Dean."

"Well, which one am I supposed to pick, man?" The older Winchester crossed his arms over his chest defensively. "I don't know any… po-kay-whatever-they're-called."

"Well, uh…" Sam struggled to recall some of the names he'd heard in passing when the game had been such a craze. "There's Pikachu. And, um… bull… bull… asaur? I think he's a water Pokémon, which is probably good against a Charmander-"

"Castiel, I choose you!"

Light flashed on the field as the ball sprung open. When the glow dissipated, Castiel sat on the field, still bound to her chair. Her back was to them, the angel facing her soon-to-be opponent. She blinked down at the small, orange dragon with its big eyes.

Dean was grinning, clearly proud of himself, by the time Sam lowered his hand from his face for the third time.

"Dean."

"Well, it worked, didn't it? She's all I could think of!" Dean snapped back defensively, grin shrinking. When Sam's eyes climbed into his hairline, that smile turned right upside-down. He shoved a warning finger his brother's way. "Not like that!"

Their opponent cried something out in the background of their bickering, and Charmander charged. Dean spun back to the field as the little thing let out a battle cry – something between a squawk and a roar that was way too cute to be remotely frightening – whipping his body around to lash his tail out against Castiel. Fire streaked around him as he spun out of the attack, sliding to a halt on all fours to face his enemy once more.

The angel stared down at the small creature, face stern but otherwise nonplussed. The very bottom corner of her tan coat was on fire, lazily burning against Castiel's leg. She didn't seem to care much, though her stare darkened as she continued to smolder.

Charmander actually looked repentant, taking a step back and letting out something of a meep of confusion.

Dean was back to grinning winningly. Beside the older Winchester, Sam groaned.

"Dean."

-o-o-o-

"Are you kidding me right now?!"

"Well," Sam reasoned as he dodged something that was round, blue, and really fast. It shot by on his left and kept spinning forward. "We did, technically, want a racing game."

"This is not a racing game!" Dean bit back, despite the fact that they were, very much, racing. He struck his palm against the steering wheel of his very pink go-kart. "This is not my Baby!"

Sam snickered from the next cart over, swerving dangerously for a moment on the translucent, rainbow road they were speeding across. The ridiculously large, polka-dotted mushroom cap he was wearing slid dangerously to the side, almost coming off his head. "I think it suits you."

Dean put all his weight down on the pink pedal beneath his high-heeled foot just so he could pull in front of his brother's stupid, blue car and drop a banana peel.

-o-o-o-

"We can't keep doing this," were the first words out of Sam's mouth as they came into existence in the next twisted game Gabriel had lined up for them. Sam didn't know how long they'd been at it, but it had to have been at least two days. He suspected longer. The younger Winchester was exhausted, even if his body didn't ask for food or water. He didn't know how much longer he – either of them, given Dean's own exhaustion and increasing frustration – could keep this up. "We could die here. For real, I mean."

He held out the colorful pieces of paper to the man behind the teller, who looked suspiciously like Milburn Pennybags. "St. James Place, please."

"I know," Dean said beside him, pulling his wallet out of his back pocket with a grumpy look on his face. The folded piece of leather had a silver shoe stamped into the surface, the style of which matched the thimbles printed across Sam's tie. Dean shoved a handful the same colorful paper at the teller, a lot less politely than Sam had. "Electric Company. And St. James? Really? Rude."

"You're the one who insists on wasting money on the Utilities." Sam took a small slip of cardstock in receipt of his purchase, turning to Dean. "We can't wait for him to put the Impala in a game. If he puts it in at all."

"It's not wasting; Utilities matter. And she is not an it, mister. But, yeah… I know." Dean collected his own card, turning away from the monocled teller. "What do you want me to do? We didn't come up with a Plan B, Sammy, and I'm out of ideas over here."

"Well… is there anything else we can use against an angel?"

The man from the future scoffed. "Yeah, sure. Uriel's angel blade."

For a moment, Sam lit up in surprise at another option even existing. It didn't last, however, when he realized where that weapon must be. They were right back at square one. "I didn't know that was in the trunk."

"It's not. It's at Bobby's." At the look of surprise on Sam's face, Dean gave a one shouldered shrug, leaving the extravagant lobby of the bank through the old-timey, wheelhouse door, glass set into tarnished brass. "I figured he needed it more. Didn't think an angel would make a move against us anytime soon. But if they found where Cas was hiding out…"

Sam's gaze slid away from his brother's as they walked into the hustle and bustle of a city mid-day. He hadn't thought of that – that Cas had likely become a target of her own family years earlier in this timeline. And she'd been defenseless in that healing trance. Bobby too, though not so much on the defenseless part. Certainly outmatched, regardless. They could have lost them both, and it hadn't even been on Sam's radar.

Sometimes, he supposed, Dean had good reason for keeping things to himself. Knowing was a burden. Of course, keeping all that weight to himself never ended up well for them in the long run. Plus, Sam really didn't like not knowing. But he got it. At least, sometimes.

"Good," the younger Winchester agreed, clearing his throat when his words came out quieter than he'd intended. They stopped at the curb, waiting for the traffic to clear so they could cross the street. "That was a good plan, but with Cas awake now, we, uh, we should probably keep it on us."

Especially if they were going to keep running into angels Dean hadn't told him about.

"Gee, thanks, Sherlock. Where were you twenty-four hours ago?"

"You mean before getting killed a couple dozen times by a trickster you forgot to tell me about?" The side-eye Sam cast him was Ultimate, and Dean flinched because… fair. "Pretty sure I was being accused of packing like a girl, Dean."

Surprise flashed across the older Winchester's face for a moment before that memory came flashing back. He managed not to laugh, but just barely. Instead, Dean cleared his throat loudly, glancing away and making the wise choice of not commenting on that one because touché.

"There's nothing that'll make a dent against an archangel. At least, not that we're gonna find in a friggin' video game. We're pretty much weaponless unless he gives us the Impala." Dean ran a frustrated hand through his hair. "I mean, we could blast him with the banishing sigil, but I don't think that'll kick us out of this place. Just him… away from us."

Which was tempting, both Winchesters could admit, but ultimately unproductive. If this is what an archangel did for fun, they didn't want to see what he could think up to if they made him angry.

With a tired sigh, Sam reached up and adjusted his way, way too expensive thumble-stamped tie over his equally too-expensive dress shirt, which felt like the softest silk against his skin. He didn't even want to think about how much it cost. The last car passed in front of them and Sam stepped into the street to cross, drawing up short once he noticed his brother hadn't followed.

The man from the future was still standing on the curb, gaze almost a decade away. Back in a library with an exhausted, bloody-eyed Cas suffering an Attack Dog spell.

"Dean?"

"There is something else that might work," the older hunter said, coming back to the present and stupid capitalist boardgame they were trapped in. There was an idea forming behind those green eyes. A risky one, but they'd faced worse odds. Dean stepped into the street with renewed confidence, briefcase swinging at his side (which he absolutely did not need; it made him look like a total douche and was completely useless as an accessory. It didn't even have anything in it). "We just need a game with cops."

Sam frowned, jogging after his brother as they crossed Wall St and headed for a lower-leveled, green building with orange trim. The sign above the main doors identified it as a Hospital. A very old-school one, apparently. That Sam now owned, given it was on St. James Place.

"What can we get from the police that would work against an angel?"

Dean grinned. "Handcuffs."

-o-o-o-

Dean was a frog. A frog that looked very much like Dean Winchester, in open boots ill-fitted on slim feet, his green jacket open and flapping in the breeze, and an abundance of bracelets wrapped around a thin, green wrist.

"I am so done with this shit."

Sam's big, bulgy eyes were no less puppy-dog effective in frog form. Which was deeply disturbing. "Not like I'm enjoying myself over here. I think I'm sitting in my own slime."

Dean's eye slid his way in a very disorienting roll. "Ew."

"So… we just cross the road?" Sam tried to look either direction down the pavement they were sitting on the edge of, but his vision was distorted and entirely unhelpful. Except for flies. When those passed by, he seemed to actually have some degree of focus. Everything else was a wet, warped blur.

"Uh… I guess?" Dean was looking around with bulbous eyes of his own, rolling in his sockets as he tried to glance back and forth. "Can you see anything?"

"Not a thing."

"Great. Well, here goes nothing."

Dean took a mighty hop, launching into the middle of the road right as a speeding truck went by. Sam flinched as it slammed into his brother mid-leap with a blaring horn, not even stopping.

-o-o-o-

"Oh, come on!" The older Winchester yelled up at the metal ceiling. "Is one stupid pair of handcuffs too much to ask!"

Sam adjusted the cap on his head, staring nervously at the panel of blinking lights, buttons, knobs, and gauges in front of him. He turned to his brother and hissed, "I have no idea how to use any of this."

"And you think I do? Just push one and hope it does something." Dean hissed back, pulling at the navy blue neckerchief around his neck. The striped shirt beneath was a particularly garish detail of the game. Sailors stopped wearing that shit before submarines even existed, damnit. He pointed at the radar screen in front of him, which looked conveniently more like a grid than any radar he'd ever seen, but at this point who cared. "Aim here."

"Like I know how to aim," Sam grumbled. Nervously, he raised a hand and, after only a second of hesitation, pressed a button that looked like it might fire a torpedo. There was a soft thud and a minor shudder throughout the control room. They waited in silence as the seconds ticked by.

There was the distant sound of an explosion, muffled by water and metal, but the crew around them broke into cheering. Someone shouted in the distance that the enemy battleship had been sunk. Sam let out a breath of relief, and Dean slumped in his chair.

"The next came better have friggin handcuffs in it, or I swear to god-"

-o-o-o-

"Oh god." Sam didn't entirely know how his brain was processing enough to get the words out, but they bared repeating now that he had. "Oh god, I'm traumatized."

Dean was standing beside him, equally dazed, a little shocked, definitely a little too curious, but holding his prize.

"I'm never going to see again. No amount of soap will ever fix this."

While his brother lamented the irrecoverable loss of his (questionable) innocence, Dean lifted the handcuffs up, dangling from one finger. He stared at the pink fur that lined both the inner and outer rings. "I didn't even know they made games for Fifty Shades of Grey."

Sam turned his way. The ruddy-red blush high on his cheeks (and ears) (and neck) had yet to subside, and Dean found that just fantastic. (No comment on his own coloring, of course.)

"Fifty shades of what?"

"Don't ask. It's a future thing you don't wanna know about." Dean tucked the pink monstrosities into his jean's pocket (happy to be fully dressed, once more) before anyone in this new game might notice them. "Let's just figure out where we are and find somewhere safe to carve these guys up."

He didn't bother wondering how they were going to draw sigils in that fluff. That was a future Winchester problem. Sam gave a one-shouldered, 'here goes nothing' shrug, and opened the door in front of them.

-o-o-o-

"Just get out of the pool, Sam!" The older Winchester stood at the edge of the backyard swimming pool, watching his brother swim laps back and forth on route. Occasionally, the beanstalk of a man would stop and try to pull himself out of the swimming pool, which couldn't even be six feet deep. But he fell back in every time he tried. Dean, tapping his foot against the edge of the pool impatiently, repeated himself, this time with more expletives.

What Sam heard through the splashes of water around him was, "Whippna choba dog."

"You think I haven't tried?" he yelled back, stopping mid stroke to turn and grab the ledge of the pool. For the fourth time, he braced his wrists, locked his elbows, and tried to pull himself up. A second later he was back to doing laps.

What Dean heard was a bitterly growled, "Boobasnot."

"Speak English, damnit!" Dean yelled, now pacing the poolside, but it came out as, "Garnar frash. Uhh shamoo ralla poo."

Sam gave it a fifth attempt with no better luck. "Mik mak maka!" He splashed back into the pool with a flail of arms that suggested frustration.

This would all be pretty damn hilarious – annoying as hell, sure, but still hilarious – if Sam wasn't actually starting to look tired and was, apparently, no longer able to climb out of a swimming pool without a ladder.

"Ooh shanga day!" Sam whined as he started yet another lap.

-o-o-o-

"Are you friggin' serious, right now?!" Dean yelled from the driver's seat of a modified '67 Chevy Impala. The car swerved at incredibly dangerous speeds as he found himself, quite suddenly, behind the wheel and on a racetrack, mid-race. He'd be pissed about the alterations – and he was, let there be no mistake about that – if having the inside of his Baby rearranged to resemble a professional racing car wasn't at least sort of cool and maybe a childhood dream come true. "Now we get a game with Baby?!"

"Just stay focused," came Sam's voice from within Dean's helmet. His kid brother must be part of the pit crew. "You still have the handcuffs, right?"

A flare of panic resulted in a very-near miss with the car next to him, but Dean corrected pretty smoothly and started patting himself down with one hand and driving with the other. Luckily, they were on a fairly straight stretch of track. There was an audible sigh of relief in the car and through the headset as he found them tucked inside the racing jacket he was wearing.

"Yeah, I got 'em," he reassured his brother, who echoed his sigh of relief.

Dean could practically picture him: a pair of racing overalls (not quite long enough for his stupid beanstalk legs, of course) that matched Dean's own suit, clipboard in hand, big ole' headset over his ears, mic in front of his mouth which he would be unnecessarily pressing closer as if that would magically make Dean listen to him.

Total nerd.

But back to the part where they now had Baby – meaning they now had holy oil – which Dean was driving around a course at truly impressive, thrill-inducing speeds. Really, he'd be enjoying the hell out of this if it wasn't for the timing.

"Do you have any idea what I went through to get those cuffs!"

"Yes, Dean," came Sam's pained, pointed response. "I do, and I will never, ever be the same."

The older Winchester rolled his eyes. His brother was such a prude.

"But now we have cuffs and holy oil." Sam was ever the voice of reason. It annoyed him as much as it calmed him down. "That's a good thing. So stay focused."

Dean took a deep breath, fingers flexing around the wheel of his Baby before he did as his smart brother instructed and kept his focus. Driving a race car was no easy thing, not at the speeds he was currently rounding the track. A crash could be deadly. At the very least, it would totally suck.

"Alright, I'm fine. I'm good. Totally calm, totally focused." The older Winchester took in and let out an even breath and worked on passing the car beside him on the next curve. "What's the plan?"

"After the next lap, come into the pit." Sam adjusted the microphone in front of his mouth, glancing between the clipboard in his hand (full of information he couldn't actually make sense of) and the Impala zipping its way around the far side of the track. "I'll grab your cuffs and get the holy oil out of the trunk."

"And I'll keep racing while you set the trap!"

Sam lobbed a generalized bitchface in the direction of his brother. "You could try to sound a little less excited about me doing all the work."

"Oh, but I am so very excited, Sammy. I was born for this."

Dean's grin was audible, his excitement evident. Fanboy vibes were practically dripping off him, and the only thing that kept Sam from rolling his eyes was the fact his brother was driving a hundred plus miles an hour around a track where a resulting crash could very easily cost him his life. The younger Winchester didn't dare take his eyes off the Impala for even a second.

"Get the crew ready. I'm coming in for a pit stop."

-o-o-o-

Watching the crew work in a flurry of perfectly timed motion around the vehicle was really impressive. Sam had only just shut the trunk, holy oil in hand, when a member of their pit crew hit the side of the car twice and Dean was speeding off with tires spinning and smoke trailing. He hadn't been stopped for more than ten seconds, if that, and six of them had been taken up tossing the fluffy cuffs to the closest, random pit crew.

"You got them, right?"

At his brother's voice in his ear, Sam dropped his eyes down to the light green thermos gripped tightly in his hand. It had been right where Dean said it would be, in the trunk (Sam considered themselves lucky the Impala still had a trunk in this game), next to the holy water and rosaries. Their best chance out of here.

"Yeah, I got them," he answered, gesturing to the pit crew guy who was still staring at the pink handcuffs in his hand, clearly confused as to why his driver had tossed them to him, or had them on his person to begin with. With a surprisingly complex expression for an NPC, he handed them off to Sam with both befuddlement and relief.

"Alright. We've got six more laps to halfway and we can switch drivers then. So get a'carving, Sammy."

This time Sam did roll his eyes. It was just like Dean to leave him with all the actual work while he played and somehow made it sound like he had the hard job. The younger Winchester left the pit but kept his headset on so he could keep track of his brother, who was busy humming Metallica's 'Fuel' as he drove. Sam made his way into the stadium tunnels, hoping to find a quiet place to set their trap. The wide hallway had an underground feel to it, with its twenty-foot cement walls and lack of windows. It didn't seem particularly utilized, either; it was limited to crew and staff only, and with the race in full swing there weren't many, if any, wandering the halls. It would work.

Sam set to work pouring out the circle of holy oil. He kept it as wide as he could without risking running out before it was complete. It wasn't as large as the one they'd drawn for Cas – the thermos didn't have as much holy oil as Pastor Jim had given them – but Sam wanted to increase their odds that Gabe showed up inside it, or close enough they could get him into it without the archangel noticing their plot.

Once he finished and was fairly satisfied – if not also fairly nervous – that they had as good a trap as they could, Sam looked around for a place to stash the thermos. He left it atop an electrical box attached to the wall a few feet down the hallway. The beat-up thing blended right in; an innocent something left behind by a passing employee. Then he pulled out Dean's fluffy cuffs and a knife he'd snagged from the Impala as well.

Time to give a pair of handcuffs a shave and a carve. But no, no, Dean had the hard job.

-o-o-o-

By the time Sam made it back to the track, their next driver was suited up and raring to go. There was a twitch in his leg and enough other crew hovering around him for Sam to realize the computer-simulation of a man was annoyed.

The Impala was nowhere near the pit lanes. Heading away from it, actually.

"Dean, it's been six laps," Sam said into the mic, voice tense. "Where the hell are you?"

"One more, Sammy."

His brother's tone was anything but in trouble, and Sam dropped his head, rubbing his forehead and the headache forming behind it. How. How was he technically four years younger than this man, who also had ten years in the future on him.

"Dean."

"Just one more lap! Come on, what's one more gonna hurt?"

Sam pinched a little harder. "Need I remind you, we are trapped in this game by a souped-up Trickster and this is our only chance to get out of it."

Despite the fact his older brother probably didn't mean for him to hear it, the grumbling came over the headset loud and clear. "Guy can't even have a little fun around here."

Sam dropped his hand to glare at the approaching Impala as it pulled off the track and into the pit lane. He grabbed the microphone at his cheek so he could pull it closer to his mouth and say, "I think you got plenty of fun in the last game. Don't you?"

He could see Dean's grimace as the car came to a quick halt. A deep whistle came over the headset, reverberating painfully through the speakers. Sam could see his brother's lips pursed through the windshield even as his crew started pulling him out of the car. "Low blow, Sammy. Low blow."

The Impala was screeching back out of the pit before Dean was done pulling off his helmet. He watched after her with a deep frown. He did not like strangers driving his Baby. But this was a video game. The real Baby was waiting for him on the outside. With a determined growl, Dean headed for his brother and the two hurried into the cover of the stadium's lower levels.

Sam pointed out the ring of holy oil as they came up to it in the hallway. Dean could just make out the shine of it on the linoleum. Sammy had done good, keeping the liquid spread as thin as possible so it wasn't noticeable but would still light. Hopefully, this way Gabriel wouldn't spot the trap before they could spring it.

The younger Winchester pulled a lighter out of his breast pocket and the de-fluffed cuffs, holding both out. Dean took the bracelets – eyeing the patches of pink that still remained with a side-eye his brother only returned (in the form of a far more successful Bitchface) – but held the lighter back out to his kid brother.

"Keep it. He might expect it less coming from you."

Not that he thought the archangel suspected anything. They'd likely already know if he had. But there was something about Sam that was always just… less aggressive. If Dean kept his attention, maybe he wouldn't pay much attention to what Sam was doing.

It had worked the first time, at least. Of course, Sam had been a car in that version, but details.

Sam raised his eyebrows in response but didn't question it. He tucked the lighter into his palm, keeping it loosely fisted at his side. "So… cuffs first, then fire?"

Dean let out a puff of air, tucking the carved cuffs into his racing jacket where he could grab them quickly. His hands settled on his hips as he stared down at their trap. Hopefully, with the last-minute inclusion of the Impala and the switch back to Plan A, they wouldn't need handcuffs at all.

"Let's stick with the fire. It's the safer bet. Cuffs'll keep him from using his powers, but he could still rabbit the old fashion way. Fire will keep him in place. Keep him trapped."

Plus, the circle would be easier to trick the Trickster into than the cuffs. Dean hadn't been looking forward to getting them on the archangel when they'd become the primary component of Plan B.

"Alright, this is gonna go down fast," Dean warned, rolling up the sleeves of his race suit. "I'll call him down, you light the oil soon as you're sure he's inside it. Got it?"

Sam nodded firmly, eyes also trained on their trap.

Dean let out a breath and physically shook the tension out of his shoulders. "Ready?"

Sam glanced at his older brother, then nodded with all the confidence he didn't entirely feel. He thumbed the lighter in his palm, reassuring himself that they were as prepared as possible for this dangerous plan. He flicked it open.

"Ready."

-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-

A/Ns: [*Author cackles maniacally*]

Games in Order of Appearance: Pong, Oregon Trail, Silent Hill, Golf Pro, Chess, Risk, Sorry, Pokemon, Mario Kart, Monopoly, Sims, Frogger, Battleship, Casa Erotica (the Game!), Grand Turismo. The previous chapters were inspired by a mix of Skyrim/Zelda, then Chutes and Ladders. Some were more inspired-by, others were downright copyright-destorying-but-what-is-fanfiction-for-right, yaaaaay!

Fun Fact 67: I am not much of a gamer, which means most of this chapter required assistance from my gaming friends! So a big THANK YOU to my partner for many meals spent describing various games and how to write certain genres accurately, to Forestpelt for helping me come up with all the games to throw the Winchesters into (you all can thank her for that Silent Hill excerpt), and Vaesse for Beta-ing this chapter!

Fun Fact 313: All the sims language I used is legit and translatable ;P

Fun Fact 314: I had a part planned in Sims where Cas showed up, presenting Dean with a heart, asking him out on a date but no clue as to why, or what Dean was saying (in a language the angel had never heard, and she'd heard them all). Buuuuut that didn't end up working out because Gabriel isn't onboard the Ship yet. (Key word there? *yet* ;D) If we weren't Jane-Austen-On-Steroids slow burning, here, we would have gotten so much game shippage [insert verbose-AF-sobbing here]

Comments: Alrighty, wonderful people! If I am being quite honest, I could use some cheering on. This is probably my favorite chapter I've written so far, and I hope it was cackling-worthy for you all as it first was for me. Unfortunately, I have lost that joy. I don't know if I've read through the chapter too many times or if I'm just having some holiday blues (maybe stress more so than blues? It has been a very rough year, which I think I'm only just catching up to mentally and emotionally), but I was so, so excited after I first wrote this, yet that excitement has since withered. Which is so disheartening.

So, on that note, I would really, really like to hear from you on this one. Pretty please, if this chapter made you laugh or grin like an idiot, share that with me. Whether you're a lurker or a first time reader, a regular commenter or a only-on-the-truly-delightful-chapters, please let this be your one comment for the year! I will always, always take the simple but much appreciated, "Like Button pushed!"

Thanks everyone!

Silence