Chapter Text
2015
"Sorry I'm late, darlings," she smiled, wickedly.
The woman stood at the entrance to the abandoned warehouse was a woman like no other, even if you didn't know about what blood coursed through her veins. Vibrant pink hair cascaded in subtle curls over her shoulders and down her back, contrasting against her large, dark brown eyes that twinkled in the moon light spilling through a gap in the ceiling. She had a petite but curvy figure of 5'5 and wore a pair of slim fitting black jeans beneath knee-high biker boots threaded with dark laces. Under a black leather jacket, she wore a deep fuchsia vest top with lighter lace patterns just above the hem; from her earlobes hung short black earrings that matched the black glass beads on her bracelet. Her skin tone was a mix between tanned and pale, and if you looked closely enough you could see faint freckles spotting her quaint nose. The woman possessed a cherub shaped face that resembled a doll in proportion to her features.
But she was no doll.
She was a fierce hunter of Team Free Will.
She was Crowley's daughter; the Princess of Hell.
She was a demon/human/witch hybrid.
She was Jay.
And she was pissed.
With a smirk that carried no humour, she flicked her wrist and the two rings of burning holy fire that surrounded Gabriel and Castiel, dissipated into nothing.
The three demons, that were guarding the angels, leapt up and growled at the intruder.
"What're you looking at, demon dick?" she snapped at the foremost demon that was brandishing a shining knife- the knife she knew belonged to Sam Winchester.
The demon cocked his head and frowned warily. "You're...you're the Princess..."
"Give the man a cookie," she congratulated sarcastically, clapping her hands together for a moment before lunging forwards and throwing the miserable creature across the barren warehouse and into an iron wall.
Sharing a look that said well, now we're fucked, the two demons turned back to Jay as though they were confused as to what their next move should be. But before they could decide, Castiel and Gabriel were behind them with an angel blade piercing their meat suits' flesh. With a scream and a blazing orange light that stuttered from their eyes and mouths, they died.
Retracting their blades, the angels turned back to Jay. "Jay!" Gabriel greeted. "Took your time!"
With a genuine smile, the Princess focused her gaze on the archangel. His mousey brown hair was slightly ruffled but his hazel eyes remained bright and- though she convinced herself it was just a figment of her dire hope- seemed to sparkle a little when they locked on hers. "Sorry, sweetheart, you know traffic is a nightmare."
The archangel chuckled and threw a glance at Castiel, checking his well-being, before announcing, "So, looks like we're gonna have to save Bad Boys' asses again."
Castiel frowned momentarily, missing the reference to the action film, but cleared his expression with a deep exhale as he turned towards the back of the warehouse to point at a far door. "They're through there."
It took less than ten minutes to rescue Sam and Dean, and get out of the crumbling building, stabbing the first demon as they went.
After packing up all their belongings from the motel into the glossy '67 Chevy Impala, the five hunters decided unanimously that they deserved a well-earned drink.
Heading towards the bar, a block over, Jay noted that the roadhouse they entered was called Mackenzie's.
She patted the brothers on the back as she stepped through the door and told them, "Beers are on me, honeys."
Jay sidled up to the counter, leaving the rest of Team Free Will- Sam, Dean, Cas and Gabe- to find a booth, and quirked her full red lips into a smile.
"Well, hello there, darling," she greeted the bartender- a man of about 20 with a stature of muscle, handsomeness and a hint of arrogance.
"Well hello, and what can I do for you, Miss?" he shot back, a flirtatious smirk plastered on his face, which was chiseled like a model and bristling with purposely trimmed stubble.
"A round of five beers," she ordered sweetly, "if you don't mind."
The bartender finished drying the glass he held and returned her smile with a similar one of his own, flashing perfect white teeth that didn't look right on a bartender that probably earned five bucks a week. "Coming right up," he promised. "I'll bring them to your table."
She thanked him and turned around to try and find the booth where the boys were sitting in. It took her a minute before she spotted Gabriel waving his hand at her through the small crowd surrounding the small static TV in the corner. Jostling her way through the shuffling bodies, she inwardly cursed human men and resisted the urge to snap a neck or two when a cheer rocked the whole party backwards and some beer got spilt on her jacket.
"Urgh," Jay huffed as she slumped down into the seat that Sam offered. "Humans."
"Well don't look at me," Gabriel gasped in mock offense.
The small group chuckled quietly at that, before the discussion of the case Dean had found in Georgia arose.
Unfolding a newspaper, Dean laid the article out and began to explain it. "So, three couples have gone missing at this couples' retreat thing. One of the couples showed up a week after they went missing. It looks like they were stabbed to death, but the thing is that when the cops went to identify the weapon, it was some kind of blade they've never seen before. Left burn marks and all sorts of messed up looking crap."
"OK..." Gabriel interrupted. "So some psycho is getting it on with a knife and lighter, that doesn't sound like us."
Sam rolled his eyes. "Dude, we've gone further for less."
With a sigh and a barely concealed grumble, Jay input, "Well, people are dying right, and isn't it kinda our job to stop any evil things doing that?"
"Yeah, I know." Gabriel scratched the back of his neck. "Was only wondering, is all. So, we setting off tonight then?"
"God no, I'm shattered," Jay interjected, cracking her neck and trying to stifle a yawn. "We can set off tomorrow morning."
"Right," Dean agreed. "So, for tonight let's have a beer or two, hustle some pool and pick up some girls."
The party laughed hushedly again... but it didn't escape Jay's keen eye, the muscle that jumped in Castiel's jaw and his lips became a thin line. She frowned and tilted her head a little, discreetly, at the tightness that settled in the angel's ocean blue irises.
But she put the thought out of her mind when the bartender came over to their table, placing a metal tray laiden with five beer bottles on the dark wood.
"There you go, ma'am," he smiled, whisking Jay's bottle into the air. "Allow me," he grinned crookedly, wielding a bottle opener that he aimed towards Jay's drink.
"Oh, that's no problem-" she tried to tell him but he was already struggling with the cap. "Yeah, OK then..." she grimaced and winced a bit as he visibly grunted under the effort of...just...pulling...a cap off- wait a minute.
She sent a sharp look in Gabriel's direction and saw him trying to hide a smirk.
"Gabe!" she hissed and he shot a what?! look. She narrowed her eyes a little, gesturing her head slightly at the bartender who was actually breaking a sweat trying to open the bottle.
The archangel sighed dramatically and subtly clicked his fingers under the table, the minute he did so almost caused the bartender to fall over as the cap sprung effortlessly off the bottle. This consequently caused the rest of the table to try and suppress their laughter.
Clearing his throat, the bartender handed Jay the drink and shuffled self-consciously away, leaving the table to their own devices after that.
"Gabe," Jay moaned, the corners of her lips quirking upwards uncontrollably and ruining the message she had been trying to deliver.
"What?" he grinned back, shrugging his shoulders. "The guy was arrogant. It's called just desserts, I am the trickster after all."
She couldn't help but smile at that. "Trickster or no trickster," Jay spoke to Gabriel. "You still can't mess with people just for the fun of it."
"Oh, can't I?" he retorted and Jay felt her hair pulling itself upwards and dancing around her head.
This resulted in another course of laughter around the table as everyone reached for their drinks and knocked the caps off on the edge of the table or twisted them off by hand.
Jay quirked her eyebrows, challenging. "Oh it's on, sweetheart," she warned, her voice teasing. Flicking her wrist, Gabriel coughed suddenly and then a cluck bubbled out of between his lips.
His eyes went wide and he opened his mouth again, only for another cluck to come out.
Dean burst into laughter and managed to gasp out, "Oh my God, never turn that off!"
Gabriel scowled and let out another, more frustrated, chicken bacaw before Jay reluctantly snapped her fingers and gave him his voice back.
She was crying from her laughter by the time Gabriel managed to bite out, rather bitterly, "Yeah, well, archangel/trickster still trumps demon." He sipped his drink and avoided Jay's smug eye contact.
"Everything trumps demon," she shot back, sipping her own drink. "But kickass demon/witch/human...that trumps all."
Sam and Dean grinned before returning to their beers, and the table split into several different conversations: Sam with Cas, Jay with Gabriel, and Dean with a woman from the next booth.
The night carried on like that until the hunters eventually returned to the motel- Dean and Sam sleeping in one room, Cas and Gabriel watching a documentary in the next (criticizing every fact that they knew was wrong), and Jay left alone to toss and turn in another.
With a heavy sigh, she grunted and rolled over again.
She detested being alone, especially in bed- not in a sexual way, more in a lonely way.
Jay was the daughter of the King of Hell, Crowley. Consequently, the blood that ran her veins was a beautifully powerful mixture of demon, human and witch.
5 years ago, when she was only fifteen years old, Crowley had come to her adoptive home in Lincoln, Nebraska to take her to Hell where she would 'become the rightful Princess'.
But Jay had refused.
Therefore it had taken little more than an exasperated sigh and an elaborate click of his fingers before both Jay's adoptive parents were lying dead on the floor.
However that had done nothing but fuel her hatred of her demon father and she had resolved to the hunting life, discovering her awe-inspiring powers along the way.
Two years ago, she met Sam and Dean at Bobby's house in Sioux Falls where she had followed a demon called Meg who was on a killing spree.
Though bursting in through the door to confront the demon had done little to soften the brothers or Bobby's nerves, she had saved Dean and Bobby's lives from the demon that was controlling Sam. She had offered a quick explanation before expelling the demon from Sam's body with just a command, 'Get out of him, you black eyed bitch.'
Then just as she was trying to leave, Bobby had stopped her and asked her, 'So, who are you, kid?'
Jay's reply had been no more than, 'Nobody. I'm not someone to keep around.'
But the brothers and their almost surrogate father had argued enough that she had reluctantly obliged and taken them up on the offer of free beer.
After passing every test that Bobby laid on her, they unanimously decided that she was safe to keep around and had taken her under their wing, effectively naming her one of their small patch-worked family.
And she had never looked back.
"Rise and shine, Candy Floss," Gabriel cooed early next morning, flinging the curtains that covered Jay's windows wide open to allow the blinding sunlight to burst through.
Jay hissed menacingly and with an animalistic edge that came from being part witch and part demon, and also from general hatred of early mornings.
With a primal growl, she snarled, "You better bring me a coffee, pronto."
Gabriel replied only with a fond chuckle before leaving the room in a ripple of light that came as a perk of being a trickster.
"And there better be gummy bears waiting for me!" she yelled into the now-empty room, but she could faintly hear the archangel's amused compliance.
It took Jay only thirty minutes to shower, brush her teeth and get dressed into the clothes she wore yesterday- favouring putting her leather jacket over her arm instead though because it was a hot morning.
She grabbed her wash bag and decided to put her makeup on in the car- and she would not be sitting bitch again.
As Jay left the room, she cursed under her breath when she remembered her adoptive mother's necklace which was still laid carefully on her bedside table. With a sharp click of her fingers, it flew across the room and into her outstretched palm.
"Morning sweethearts," Jay greeted her small family as she clambered gracelessly into the passenger seat. "Aw, you remembered, Gabe. Il mio angelo custode," she smiled gratefully and almost lovingly- though totally not!-at the archangel behind her when she spotted the packet of gummy bears and travel cup of coffee on the dashboard. Jay was fluent in Italian, thanks to her father (though she wouldn't willingly admit her tutor) and had got into the habit of calling Gabriel her guardian angel in said tongue- mainly because she loved nicknames but also because it sent a slight flush across his face that was positively endearing...
"Yeah, yeah, save the romance and get that off my baby's dash," Dean snapped as he pulled the driver's door closed behind him, making sweeping motions with his hands at the steaming travel cup. "What were you born in a barn? Get that coffee off her dash before it leaves a mark!"
With a fond chuckle, Jay obliged and took the cup and packet onto her lap. "Alright, honey, your car's OK," she promised, shooting the older Winchester a teasing but reassuring look.
Through an obviously fake cough, Gabriel added unhelpfully, "For now."
Dean shot the archangel a withering glare that made him sit back, even more amused, with his hands held up in surrender. "Nothing by it, Dean-o, nothing by it. Now come on, let's get-a moving!"
"We gotta wait for Cas yet," Dean told them, turning back around and slotting a tape into the deck.
Led Zeppelin's Ramble On was just starting as Sam folded his massive frame into the Impala and announced, "Cas is gonna meet us there, he...has stuff to do?"
"What exactly does an angel cut off from Heaven, have to do?" Jay wondered, but she didn't miss the small flicker of hurt in Dean's expression.
"Hey!" Gabriel protested. "I got plenty to do, thank you very much."
Jay shot a snort over her shoulder, to which she earned a swatting from the archangel.
"Right, well, come on Baby," Dean murmured to the wheel as he hefted up the handbrake and started the engine.
Throughout the journey, Jay and Gabriel traded witty remarks back and forth, pausing only for Jay to eat a gummy bear or throw one in Gabe's direction.
Dean was adamant about getting to Georgia before nightfall but Jay managed to convince him to pull over at a service station to get some food and more beer. Reluctantly, he had rolled his eyes and pulled into the car park.
Jay was the first one to dash up the short stack of staircase and into the large building, heading straight for WHSmith's where she grabbed a large armful of gummy bears and thrust them all in the arms of the slightly bewildered cashier.
He totalled the amount, sneaking dubious glances towards the vast amount, and packed them all into a plastic bag.
"And this!" Jay heard Gabe announce behind her, before a hand came around her waist to dump a porn mag and a massive bag of lollipops on the counter.
"Gabe-!" she moaned but was interrupted again by Dean coming up behind her to throw another porn mag and a cased box of pie into the cashier's hands.
"Add this, too!" he called as he joined Gabe outside.
"Dean-!" she groaned, but was this time cut off by Sam appearing by her shoulder to drop a newspaper and a box of salad on the counter.
"Thanks, Jay," he thanked as he bounded off to the other boys' sides.
"OK...now that's..." Jay struggled as she twisted around to face the boys. "I don't know which of those is unhealthier than the other."
Dean grinned and clapped his hand on his brother's shoulder. "Sammy gets off in his own way."
Sam shrugged him off but there was a smile tugging absently at his lips. "Get off, Dean. I'm checking the papers for any cases and yes, I like to eat healthy because have you seen how many chemicals are in pie?"
"No, I haven't," Dean replied. "I just read pie."
Jay smiled at her boys before turning back to the cashier and accepting the two bags and vaguely bemused look he handed to her.
2007
The third hunt Jay joined the brothers on was in Ohio, investigating a strange suicide off a high floor at a university.
It was one of the university professors; an old bloke who took the swan dive for no reason anyone was aware of. Via further digging into student rumours, the trio had managed to uncover adulterous secrets that left all three of them debating whether or not his mysterious death was really something that desired investigating.
And then they were told about the legend surrounding room 669- which immediately made Jay giggle- the girl who died in there or something. Jay passed it off as bull but they dug it up anyway and she sat back while Sam and Dean searched around for some bones to burn.
Even by the second day, Jay was finding the brothers' actions towards each other hilarious.
She was lounging quite happily on the motel sofa, nursing a bottle of beer, watching the two bicker about Sam's missing laptop and Dean's slashed tires.
Jay didn't think she'd ever laughed so hard when they actually started wrestling on the bed.
There was another incident that involved a frat boy swearing up and down that he was abducted by aliens and...probed...a lot.
They were sitting down at a table in the bar talking to the frat boy and Jay was having real trouble hiding her stuttering laughter as he continued to tell them about his experience with the aliens.
Frankly, Jay thought it was fucking comical that the aliens made him slow dance! And she told him as much, much to Sam's disapproval.
Before Bobby arrived- at her pleading- there was one other case in the same town when an animal tester (Jay couldn't remember the actual terminology) was eaten by an alligator.
It wasn't until Bobby showed up that any of it started to make sense.
"You got a trickster on your hands," he'd told them.
"That's what I thought," Dean told them straight away.
"What?!" Sam had exclaimed. "You did not!"
Jay just giggled and shared an amused look with Bobby.
By that point, the three men still didn't know what it who Jay really was but she had no inclination to tell them just yet.
Bobby explained what a trickster was to them and so they went out to hunt the thing with their stakes. Sam and Dean seemed positive that the trickster was the janitor they spoke to at the university, the one that Jay hadn't met yet.
When Sam, Bobby and Jay arrived at the university later that night, after Dean's ingenious plan to trick the trickster, their stakes were poised as they entered the hall.
Jay could clearly see the trickster sitting in one of the seats of the bleachers. At her entrance with Bobby and Sam, the trickster turned around and-
The Princess of Hell felt her breath hitch and her heart stutter.
The trickster's expression changed from smugness to something akin to wonder. A frown pulled at his eyebrows for a second but then the trickster displayed the only genuine thing he had since the first time he met Sam and Dean, he smiled. It was a small smile that only quirked his lips a little but it shone in his eyes and echoed through the room until the blood roared in her ears and lights shone too brightly in her eyes.
Then, everything dissipated into nothing, and that was all there was.
And in that moment, she felt her soul- quite uncontrollably- bare itself before his...
But then of course, she went and stabbed him in the chest, which didn't exactly spark chemistry.
2015
They finally arrived at the couples' retreat several hours later, long into the night and Jay was struggling to keep her eyes open.
"What exactly are our identities, here?" she mumbled through a fog of fatigue.
"Uhh, yeah, about that," Dean started, running his hand through his hair.
"Dean..." She narrowed her eyes, a warning note in her tone.
"Well, it is a couples' retreat thing," he tried.
"Ah," a female voice came from the top of a set of cream painted stone steps surrounded by tropical plants. "Mr Winchester! And this must be Mr and Mrs- umm, Trickster?"
Dean coughed around a laugh. "Yep, yeah, this is Mr and Mrs Trickster," he gestured to Gabriel and Jay. "And this is my brother, Sam, he's come about the job vacancy."
"Oh yes," the woman smiled, she was wearing a blouse with a black pencil skirt and looked to be about 40 with dark hair. "My name's Janet, your partner is inside, Mr Winchester. I hope you enjoy your stay."
"Umm, my-my partner?" Dean looked actually confused now.
"Mr Castiel?" She raised her eyebrows.
Dean's eyes went wide and Gabriel, Jay and Sam had to press their lips together hard to stifle laughter.
"C-Castiel?" Dean stammered. "He told you that...he...and I...?"
"Yes," Janet smiled. "He's just inside, he didn't get here ten minutes ago."
Gabriel wiggled his eyebrows at Sam and Jay. "Who ever said Destiel wasn't a thing."
As Gabe followed Janet and Dean up the stairs, Jay turned to Sam and mumbled, "We should never have introduced him to fanfiction."
"Yeah well, don't get him started on which of Chuck's books is his favourite," Sam groaned, making Jay chuckle. "An hour long discussion, not even including the books that Chuck never published."
"There are more?!" Jay asked excitedly, the Supernatural series had kept Jay very entertained since she'd met the boys.
Sam shot her a dark look. "So Gabe tells us..."
Jay grinned wickedly, "Well, I think I'll be talking to him about that later."
"So, Mr and Mrs Trickster?" Janet smiled at Jay and Gabriel from behind her desk.
"Umm, we're not married, it's just Mr...Trickster and Miss Singer," Jay corrected.
Behind her, Dean turned to Sam with a frown and mouthed, 'Singer?' To which Sam replied with a shrug.
"But you can just call us Jay and The Trickster," Gabe told her, wrapping his arm around Jay's shoulders.
Jay rolled her eyes. "Gabriel, his name is Gabriel."
"OK, my mistake, welcome to Riverview Couples' Retreat," she smiled at them again, reaching under the desk to retrieve three sets of keys. "Mr Winchester, you're in room 218- sorry, staff don't stay in the commercial rooms." She handed Sam the key and he thanked her briefly.
"Mr Winchester, err, Dean?" she inclined her head towards him.
"Eh? Yeah, yeah it's Dean," he told her, flashing a flirtatious smile.
She returned it and continued, "Dean. This is your and Castiel's key, and you two will be in the Cherub Room. You can find it on the first floor, its the last one on the corridor."
Dean thanked her and turned to hand the key to Castiel, starting slightly when his proximity was less than a hand-span. "Personal space, Cas, personal freakin' space."
The three left Jay and Gabe as they went to search out their own rooms- though not before Gabriel had cracked a joke about Dean making the most of that king sized bed.
"Jay, Gabriel, you will be staying in the Tropical Suite," Janet beamed at them.
"Ooh," Jay grinned. "Sounds exotic, I like it."
Gabriel looked across at her and chuckled fondly, his smile bleeding warmth.
"It's on the first floor, head that way and its the second door on your left," Janet directed them, angling her hand to her left and bending over the ornate desk to angle her hand the way she directed them.
"Alright, thanks," Jay said to Janet, grabbing Gabe's elbow tightly as she strode away in the direction she was indicated. "What the hell is wrong with Dean?!"
Gabriel just laughed. "Can't blame Dean-o, who else was he gonna couple you up with? The Sasquatch?"
Jay upturned her lip, cocked her head and raised her eyebrows in a look that considered it with a well...
With a roll of the eyes, Gabe replied, "You really want Gigantor, over this?" He gestured his hands up and down his body.
She couldn't hide the grin that curled her lips upwards and made her heart swell just a little bit.
They found their room without much trouble and made their way inside. True to its name, the room was...well it was tropical.
As soon as Jay flicked on the lights, her eyebrows rose.
"Wow," Jay exclaimed as she stepped into the room. "This. Is. Tropical."
"Well it is what it says on the label," Gabriel pointed out.
Jay's eyes settled on the king sized bed and she chewed her lip. Gabriel must have noticed because he quickly reassured her, "Oh, I'll take the floor, I don't sleep much anyway."
"Gabe," she frowned. She knew that because he was completely shut off from Heaven and relenting some of his Trickster powers that he did in fact need some sleep.
"What?" he grinned, his trickster persona taking control. "You worried for me? Aw, the Princess has developed a soft spot."
Jay just rolled her eyes and started unpacking her suitcase on the bed.
She was about half way through when she heard Gabriel abandon his own unpacking and step over to her."Woah," Gabe whistled, coming up behind her. "How many beanies does one woman need?"
Jay spun around with a scowl. "You. Can. Never. Have. Enough. Beanies!"
To drive her point home she grabbed two and pulled them over her head. "Example A," she said defiantly, and finished the rest of her packing wearing two beanies.