It wasn't that Dean hated time travel, or even the feeling of actually time traveling, it was the fact that he hated being tossed from one decade to the next without so much as a "good morning, Deano."
On this particular occasion, Dean and Sam had been on opposite sides of town. Dean had just settled down on his bed, a cold beer in his hand and the smell of Irish spring drifting through his T-shirt. He gave a blissful sigh and turned on some Dr. Sexy MD, Pay Per View. Sam wouldn't be back for a few more hours, he might actually get some sleep. Even if it was fitful.
Without warning, or even that obnoxious buzzing in his ears, his stomach dropped into his toes, his heart leapt into his throat, and every organ seemed to be in some place that it shouldn't have been.
He pinched his eyes shut unable to look anywhere, though he didn't know exactly what he was expecting to see.
Then, just as abruptly as it all started, it stopped, and Dean dared to open his eyes.
He shouted a curse and jumped/ran to the sidewalk out of the way of a honking and very angry looking taxi driver. He watched the cabby yell not at him, but at the passenger in the back. Dean's eyebrow lifted and he ran his hand over his damp hair, as the cab pulled up practically onto the sidewalk.
The door burst open and a familiar head of long brown hair popped out. Dean dropped the beer, that he'd managed to hang onto, and he'd already started walking away before it hit the ground. His eyebrows furrowed together in a frown as Sam frantically attempted to clamber out of the cab, holding up his arm to ward off the drivers loud and aggressive swats.
"Sam?" Dean asked, steadying his brother as the cab sped off. Sam fixed the tie of his suit and ran his hand through his long hair. "Dude, what the hell?" A smile started to form on his lips as he looked at Sam's astonished and confused face, and he tried not to laugh.
Sam turned and gave him that look he had when Dean was being "Unprofessional." He sighed and dusted himself off looking around before finally asking the question they both knew the answer to. "What just happened?"
Dean gave a shrug and looked around for any sign of angel douchery or demon handiwork. Not even Castiel popped up when Dean called. People were bustling along the sidewalks, hardly even looking up at the boys, who were glancing around wondering where and when they'd been dropped this time.
"New York." Sam said out of the blue, looking up at the tall buildings.
Dean raised an eyebrow, "How do you-" He paused, when he too noticed what Sam was looking at. Two identical towers stretched into the sky. "Holy crap."
Sam shook his head and sighed through his nose, running his hand through his hair again. "What this time, what could have possibly-"
"Dean, Sam." A gruff voice, and the flutter of wings made the Winchesters turn around. "What are you doing here?"
Dean gave him a look, "Oh, I don't know, Cas, we decided to take a quick time jump to the 90's, thought it would be a fun vacation."
The angel cocked an eyebrow, tilting his head to the left a bit.
With an exasperated groan Dean threw his hands in the air, turning his face towards the sky for a few seconds.
Sam took a pensive half-step forward, "Look, we just want to know what we're doing here."
"I don't know," Castiel replied after a pause, looking into the street. His face suddenly scrunched, as though someone had twisted his ear, and his eyes darted to Sam. "Something's pulling me back, I can't stay here."
"Wait, Cas we need to know-"
Dean grabbed the angels shoulder, "When and where are we."
Cas seemed to be struggling, but quickly spat out, "1999, New York. Go to Boston." He said. "I'll come when I can-" He looked as though he would say more, but before he could get out the words, he disappeared.
Dean was holding empty air, and gently drew his thumb across his other fingers, taking in a deep breath through his nose. "Dammit!" He exclaimed, turning to face Sam, clenching and unclenching his fists.
"What the hell are we supposed to do?" Sam asked, looking around and feeling vulnerable in the middle of such a large city. He fidgeted with the lighter in his pocket and watched Dean roll a plan around in his head.
Finally the older Winchester pressed the heel of his palm against his forehead.
Sam pressed his lips together in a hard line and nodded thoughtfully. Dean finally seemed to be getting his head around the situation, and he said, "Alright, first of all, we need a ride to Boston."
"Dean it's 200 miles from New York to Boston, we hardly have that kind of cash." Dean opened his mouth but Sam cut him off, "Our credit cards don't work here."
"Shit," He cursed, crossing his arms over his chest and closing his eyes. Taking three long, deep breaths he said, "Fine, we get as far as we can then hitch hike the rest of the way."
Sam gave him another skeptical look, "What?" He demanded, giving Sam that 'I swear' look.
"I'm in a suit and you're wearing socks." Sam pointed towards the ground, and Dean's gaze followed. He was indeed wearing a mismatched pair of socks, one white and one black. With a scowl, he wiggled his toes and looked back up at Sam.
"Fine," He spat, "We'll get you some gigantor clothes."
"And you shoes."
"And my freakin' shoes." Dean replied shortly.