So apparently Dean was a chauffeur hired by an obscenely rich family that owned a chain of car showrooms. The head of the family - honorable mister Robert Singer - had two children from his first marriage. His second wife, Pamela, was much younger than him, but their marriage was a result of true love. Obviously.
Driving the heir of the Singer's fortune to the local airport was Dean's first job. Of course he could do that. Piece of cake. There wad no reason to hurry, because the plane would wait for as long as they needed. Private jets tend to do that.
The hunter was toying with the car keys, standing almost at attention next to a black Rolls-Royce Phantom. Every curse he muttered under his breath echoed in the huge underground garrage. The fact that he didn't take a stroll through the chamber to appreciate the collection of vintage sport cars and limousines spoke volumes about the state of his mind. He felt that his fingers were getting colder and stiffer every second, almost to the point where merely holding the keys was difficult. So far there were no squealing teenagers groping him or trying to make him make out with a guy, but the idea of him being a chauffeur was more than disturbing. He'd watched too much porn not to know where it could lead.
Oh, yes. Young master was named James Singer, but for some reasons he preferred to go by a nickname. Friends called him Cas.
Dean's head jerked up and the car keys landed on the floor with a dry clank when he heard footsteps. Winchester swallowed loudly, having noticed the familiar dark-haired man approaching him at a brisk pace. He managed to almost-keel over and almost-retreat a couple of times before Cas finally stopped, inches from Dean's chest. The expression of his face was inscrutable when he was steadily examining the hunter. Winchester wasn't sure what it meant, though he could have sworn that he spotted this ever so familiar affection in the angel's unearthly blue eyes.
After a moment that felt like a lifetime Cas's lips budged in a barely noticeable smile and his head tilted in that inimitable, birdlike gesture.
"Hello, Dean," he rasped, taking that ridiculous cap off his friend's head.
Dean's sigh of relief must been audible everywhere within a radius of three miles.
"Cas, man, do you know what's going on here?"
"In fact I do know, Dean," the Seraph answered, "I suggest you drive us to somewhere nice so that we can talk."
It was a simple task. Dean could do that. Almost.
"Somewhere nice? How do I know where's to go? I've been here for like an hour."
Castiel seemed to be amused by his own thoughts.
"I presume that in this world everywhere is nice."
Dean scratched the back of his head and shrugged, guessing that he would never get angelic sense of humor.
-xXx-xXx-xXx-
"Dean, please. I do understand your irateness, but you have to try to understand my situation. The fact that Gabriel does not wish to confine me does not mean that I have any way of influencing his decisions regarding you. Besides, he managed to convince me that it will be for the best."
Dean snorted angrily, walking back and forth along a small lay-by over a cliff on which he'd parked the Rolls-Royce. Cas had been right - the world created by Gabriel was nauseatingly idyllic. Soft, warm breeze carried the scent of the ocean that shimmered and hummed at the foot of reddish rocks. Palm trees and cedars soughed softly. There was no cloud on the azure sky, but the sun wasn't torrid. A part of Dean's mind wondered why there was no table with a selection of colorful treats and drinks served in coconuts with those ridiculous little paper umbrellas anywheget in sight.
Nonetheless, he was mainly pissed.
"Best? For what? Giving me nightmares?"
Cas responded to his friend's glare with a sigh.
"This reality is not devised to torment you. My brother intends to teach you a lesson."
"Oh, 'cause that sounds so much better," gnarled Dean.
"I admit the difference may be too subtle to discern from a certain point of view. Still, following Gabriel's guidelines will prove beneficial to you."
"Damn it..." Dean's voice became deeper and throaty, "By the way why is he suddenly dead set on mind-fucking me, huh? I'd get it if you wanted to nail me to the wall, but him? What is it, some kind of a blood feud? Brotherly solidarity? He doesn't even like you."
"It is personal, yes, but not in the way you think," there was less leniency and and more exasperation in Cas's voice every second.
Dean came to an abrupt halt. He turned slowly to squint at the angel.
"Wait, Cas. How do I know it's not you doing this? Gabe was dead... How come he just went back?"
"Why would I do this?" Castiel challenged.
"Dunno, maybe 'cause I was an asshole? I get that you're pissed and you probably wanna smite me, I mean I'd smite me, but man..."
"Dean. Enough!" suddenly the Seraph's voice was powerful, deep and sonorous, reverberating clearly over the hum of waves and the sough of wind. Winchester instinctively took a step back. From Cas's stance - jaw set, fist clenched, shoulders squared - and a slight tremor of his muscles Dean could tell how angry the angel was and how hard he fought to keep his power in check.
"I said that I forgave you. I don't see why you refuse to believe me," he heaved a deep sigh to come down a bit, "This is Gabriel's plan. He explained his motivation to me and I agree with most of it. It is not only about me. It's about Sam, about Gabriel. It is about you calling him a coward and encouraging him to act."
His words seeped slowly to the hunter's consciousness.
"Woah," Dean breathed, "Are you telling me that your eternal, infinitesimally powerful big bro has a small dick syndrome? That he's so touchy that he'll create a whole new world just to get back at me for calling him names? Geezus, I made this toffee-nosed twat do the right thing for once and the first thing he has on his mind after coming back from counting worms is messing with me?"
"This is exactly what I am trying to explain. Gabriel doesn't want to punish you. He wants to return the favor. Try to get something out of it."
They stood immobile for a while, inches from each other, until Castiel capitulated and ended the stare down.
"Please," he added more cordially, "You will come to no harm. I don't like his methods either, but there is no help for it. Archangels are extremely willful."
"Dude, I've already..." Dean was interrupted by a rustle and a rush of air. He didn't even have to look around to know what it meant. He gestured widely in helpless annoyance.
-xXx-xXx-xXx-
Although he was not sure if other people in Gabriel's fantasy word had a sense of time (or even if they existed when he wasn't looking) Dean spent an hour or so driving aimlessly before returning to the mansion to make the cover-up story of driving Cas to an airport more plausible. The Royce wasn't Impala, but taking slightly banked turns while he was speeding on the road thoughtfully provided by Gabriel let him let off some steam and wrap his head around this new situation. He guessed that if Camp Gabe wouldn't require dying multiple times, being tied to a ball-whacking machine or talking about genital herpes, he could actually survive it. At least he wanted to believe so.
Having parked the limousine Dean walked back to the mansion along a wide, curved marble walkway flanked by lemon trees, cypresses and lavender. He was so lost in thought that he noticed nothing until he bumped into a warm and oddly familiar mass. The only thing that shocked him was that the mass smelled of suntan oil and Axe.
"Sammy?"
"I told you not to call me like that," the man opposed coldly. He looked exactly like Dean's brother, save for the fact that he was tanned, had his whole body shaved clean (which stood out, because he was wearing nothing but surf shorts and flip-flops) and his hair bound in a tight, sleek ponytail. Plus, he spoke with a recognizable Hispanic accent, "My name is Samuél."
Sam-Samuél walked away, followed by Dean's dumbfounded stare. Winchester snapped out of it upon hearing a clink of teeth against a hard candy behind his back. He swung around with his fists ready, but he hit thin air. Gabriel reappeared a second later slightly further from the hunter.
"What did you do to him?" Dean bellowed, ready to charge again.
"Relax before you develop a seizure, mister rabies" Gabriel smiled over his lolly, "I wouldn't haul your bro's ass here. I like Samsquatch too much. This one here is a dummy. Dummy-Sammy. Heh."
"Don't push your luck."
"Or what, you big walking talking wiener?" the archangel crossed his arms.
Dean exhaled angrily through gritting teeth.
"All right, Jigsaw," He tried to unruffle a bit; he was still in high dungeon, yet he understood that scuffling would do him no good, "What is this... Dunno, place? World?"
A sleazy grin spread on Gabriel's face.
"It is a so-called alternate universe. One of many, actually. This one is about rich people. You know. Subtle dominance. Or not so subtle. The-Bold-and-the-Beautiful kind of thing," he reveled in Dean's ill-concealed panic, "Fear not, Dean-o. This is one of the least twisted ideas I stumbled upon. I saved the best for later. I'll take it slow, cause it'd be pity if I gave you apoplexy right at the start. Baby steps."
"And why exactly am I here?" Winchester fought the sudden dryness in his throat, "What's the deal?"
"The deal is," Gabriel purred with fake suaveness as he was approaching Dean "that I let you go back to your world when you stop being a sophomoric, bipolar, emotionally constipated, insecure, narcissistic, masochistic, uncommunicative, self-loathing, self-defeating, self-centered, screwed up coochie."