It's known as 'the point of no return'.
The little family walked, behind a crowd of chattering, excited passengers, along the brightly lit gantry towards the gleaming blue Eagle Air 747, both Sam and Bobby keeping a close eye on Dean who had grown increasingly quiet and agitated as boarding time approached, then finally arrived.
They were about halfway along when Dean's stride faltered and he stumbled to a halt; "Sam … I-I don' think I can …"
He leaned against the side of the gantry; grey-faced, trembling and looking for all the world like he was about to pass out.
Dropping his holdall, Bobby stepped over to support Dean as he subsided weakly into the wall.
Already at his brother's side, Sam dropped to his haunches so his face was level with Dean's.
"Hey Dean;" he gripped Dean firmly but gently by the shoulders, feeling his brother's whole body thrum as his heart raced, "look at me bro, c'mon, look at me; what's wrong?"
Dean looked up at Sam, a sheen of sweat glistening across his bloodless face. He shook his head; "S'mmy; I don' think I-I can go through with this."
Sam nodded slowly, giving Dean a moment to compose himself. He crouched in silence kneading soothing circles into his brother's heaving shoulders with his thumbs.
Eventually he spoke; "Dean, a couple of weeks ago, you asked me not to make it easy for you to talk yourself out of this, so I'm not going to."
Dean looked up at the two concerned faces hovering over him, ignoring the fascinated gawks of curious passers by.
"Dean, you're my badass big brother, you are the bravest, most reckless, most stubborn person I know and you're not gonna have your fantastic vacation taken away by that piss-ant pile of nuts and bolts out there," Sam coaxed, tilting his head towards the plane, it's gaping entrance hatch now only fifty yards away.
Dean nodded mutely, fighting to prevent his racing heart driving his gulping breaths into a full blown panic attack.
"Look dude;" Sam continued, "when you get off that plane the other end, there's balcony waiting for you …"
"... An' a sunset?" Dean asked, barely above a whisper.
"You betcha; a sunset, right over the ocean," Sam nodded, rubbing his hands up and down Dean's arms.
"You taken your meds son?" Bobby asked, picking up Dean's discarded carry-on bag.
Dean scraped a shaking hand over his clammy face; "yeah, m-maximum dose of everything," he replied, swallowing back an increasingly rising nausea.
"Plus one for luck," added Sam glancing at Bobby as he rubbed circles of reassurance over Dean's hunched shoulders.
Dean hadn't told them about the sly nips of whisky he'd put away during his frequent visits to the mens room, and he didn't need to. Sam could smell the alcohol on his breath and chose not to say anything on the basis that desperate times call for desperate measures.
Taking several stuttering deep breaths, Dean worked hard to fortify himself, and hauled himself up into something approaching a standing position, reaching out to Bobby for his carry-on bag.
"C'mon, l-lets do this," he grunted hesitantly.
Sam smiled; "that's more like it; c'mon, that sunset's waiting dude."
"It had friggin' b-better be otherwise I'll kick it's ass," Dean replied with a defiance he really didn't feel.
Once again, the three began their slow trek toward the aircraft's waiting door.
A young stewardess with a fuscia pink lipstick smile took their boarding passes; the smile dramatically fading as she saw the sickly complexion of the young man standing in front of her, holding out a shaking hand for his boarding pass to be returned.
"Are you okay sir?" She asked with genuine concern. Dean nodded without once meeting her eyes and managed to croak out a thanks; "he's just an uneasy flier," Sam replied politely over his brother's shoulder.
The fuscia smile appeared again, even more sunny than before; it was accompanied by a reassuring verging on patronising pat on the arm with fuscia pink nail varnish; "oh Sir, you'll be absolutely fine. Captain Crabtree is the most experienced pilot on the fleet, no need to worry, he'll get you to Oahu just fine."
Dean nodded again, plastering a watery fake smile across his face.
"If there's anything you need, sir, just ask any of the crew; we're here to help."
Sam thanked her warmly on Dean's behalf, deciding that the necessity of getting Dean seated, strapped in and comfortable outweighed the social niceties of chatting with the prettier members of the cabin crew.
Having chosen seats as far away from the window as possible Sam and Bobby sat themselves either side of Dean, forming a protective cocoon around him, as he settled stiffly into his seat, wide eyes scanning the filling aircraft cabin with the look of a man about to attend his own execution.
As the electronic voice of the Captain drifted through the cabin announcing that the aircraft doors were being closed, Dean took a long shaky breath, and burrowed back into his seat, assuming his customary in-flight position; eyes squinched closed as he gripped the arm-rests with a white-knuckled ferocity, an empty sick bag cradled in the crook of his arm like a comfort blanket.
He opened his eyes momentarily, just long enough to briefly glance at Sam; "it will be worth it, won' it?"
Sam grinned, placing his hand over the top of Dean's clammy fist. "It'll be all kinds of awesome bro', totally awesome."
Dean felt Bobby's calloused palm enfold his other hand. "Doin' good there kid: now try an' get some sleep."
It was as the plane was banking out of it's climb that Dean felt the first crashing wave of nausea roll across him. The hollow pit of fear that had been gnawing it's way through his stomach since the Winchesters had bedded down at Bobby's place last night, had been his constant companion all night and all morning; lurching between a tickle of unease in the pit of his belly, a creeping, lurking nausea and a burning ice-cold fear.
But this was the first time he knew for sure that he was going to be seeing that half slice of toast and honey Bobby had forced down his neck this morning.
He tried to fight it off as long as possible, gulping great, goldfish-like lungfuls of air as he desperately tried to quell the rising queasiness. This was so not fair; he had taken all his meds and done exactly what he was told (okay, apart from the whisky) like a good little traveller.
Sam knew perfectly well what was happening so was ready to be there like a flash, strong arms supporting Dean when he suddenly lurched forward, retching violently into the paper bag.
Dean could feel a strong hand rubbing his convulsing back and a duo of calm but concerned voices coaxing and soothing him through his misery as he continued to heave, grimacing as the whisky burned it's way back up his throat.
"I thought he'd taken all his travel sickness stuff?" Bobby gasped, looking across Dean's hunched back in dismay at Sam.
"I think it's the nerves, the Dramamine can't touch that," Sam responded sadly, "I just hope he's got enough of the sleeping tablets in his system to make it easier for him soon."
Bobby sat back in his seat with a sigh, and his heart ached for the poor suffering figure beside him.