Raise the Ante

by jessicarocket

During a night of heavy drinking, Jessie and James decide to play a game.

This fic was inspired by and based upon a beautiful comic by lalalastill dreaming. MANY, MANY thanks to her for allowing me to use her lovely headcanon for this story. Her work is outstanding, so please check her out on Tumblr and Deviantart if you haven't already: .com and .com

Thanks for reading! All feedback and welcomed and greatly appreciated!

James carefully scanned the inside of the malasada truck, ensuring everything was in its proper place and that the deep fryer was indeed when turned off and securely closed. Since luck never seemed to be on their side, he often found himself worrying that their hard-earned business could burn down in the middle of the night as a result of one of their typical oversights.

Just outside the door, he heard his partner speaking in a tone that make it abundantly clear she was quickly losing patience. "James, what are you doing in there? Let's go!"

He smiled to himself as he dragged his eyes across the space one last time and flicked the light switch. "Coming!"

After locking up, James stuffed the keys in his pocket and and trotted toward his teammates. They made their way back to their secret base in comfortable silence, save for the sounds of their shoes scuffing against the concrete. The sun was just beginning to set as they approached downtown, lights sparkling against the canvas of amber and pink. Although the trio had seen quite a few Alolan sunrises and sunsets by now, the experience never ceased to take their breaths away.

As they reached the outskirts of downtown, Jessie caught a neon sign in the corner of her eye and felt her interest pique. Turning her head slightly to get a better view of the sign, she saw the words Discount Liquors and stopped in her tracks.

An impulse filled her mind and she called excitedly to her partners."James! Meowth! I've got an idea!"

James and Meowth froze and gazed at each other, exchanging the same wary expression. Those words often meant trouble was brewing.

James turned to fully face Jessie and couldn't help but smile when he saw the devious look on her face. She was especially charming when she was plotting something, and James was well aware of the fact that he was powerless against her whims. Regardless of where she would lead him, he couldn't help but follow, full steam ahead.

"What is it, Jess?"

Her sly smile spread wider as Jessie crossed her arms and replied cooly. "I think after our recent business success and the bounty of Alolan Rattata we delivered to the boss yesterday, we're long overdue for a little fun." She gestured her head toward the liquor store behind her.

Eagerly rubbing his paws together, Meowth replied "Good t'inkin', Jess!"

In their unusual dramatic flair, the trio cheered loudly and leapt into the air before taking off toward the store at a full sprint. Wobbuffet suddenly emerged, enthusiastically shouting his name in an attempt to join in the excitement despite the fact that he hasn't the faintest idea what was going on. By the time he got his bearings, his teammates were already stumbling through the door, leaving him scrambling to catch up while shouting "Wobba!" in a desperate plea for them to wait.

It didn't take the trio long to spot their poisons of choice. For Jessie, it was a bottle of Everclear. She liked to keep it simple and effective, with the goal of getting drunk as quickly as possible. James was initially drawn to a fancy brand of bourbon he recognized from the elegant balls of his youth, but instead grabbed a bottle of cheap whiskey out of spite, grinning at the thought of how appalled his father would've been by that choice. And for Meowth, a six pack of PBR, which he had developed a taste for during his time as a street cat.

The team nearly fell into old habits by attempting to smuggle the bottles of alcohol out of the store, but their eyes met as soon as they started to stuff the bottles under their shirts. They collectively remembered there was enough cash on hand thanks to a profitable day of donut sales.. Without a word between them, they seemed to instantly agree that they should do the honest thing for once and not tempt any additional bad karma. They needed all the luck they could get for future endeavors.

As the trio made their way to the checkout counter, a thought suddenly hit James and he bolted across the store, a flurry of lavender hair bobbing through the isles. His teammates were momentarily puzzled when he scrambled back with two forty ounce beers cradled in arms in lieu of liquor. Reading the confusion on their faces, James smiled sheepishly and mumbled "bottle caps" with a shrug. Jessie and Meowth rolled their eyes and sighed, neither willing to admit they found this oddly endearing.

The Rockets then strolled out of the store and walked aimlessly through the bustling downtown area, unsure what their next move would be. At this point, the sun had nearly settled behind the horizon and the city lights appeared to shine even brighter. Without a word, Jessie powered ahead of the group, clearly with a mission in mind. After years of experience, James and Meowth knew better than to question her motives. Instead, they elected to obediently follow her lead, doing their best to keep up with her brisk pace.

Jessie guided the group down a quiet dirt road, and James and Meowth soon recalled that this particular path led to a secluded stretch of beach. Though night had completely fallen by the time they arrived, the full moon softly illuminated their surroundings, creating a tranquil ambiance. Jessie plopped down on a sandy spot near the bank of the ocean and her teammates joined her seconds later, all three simultaneously craning their necks to study the canvas of stars above. The cool breeze against their skin and the sound of waves crashing against the shore soothed their tired souls.

After a few moments of comfortable silence Jessie sighed and said, "I'll never get tired of this place."

James smiled widely at her dreamy tone, a feeling of warmth slowly spreading through him. He had never seen his partner as content as she had been in Alola, and in turn he had never felt as peaceful as he did during this particular journey.

After a few minutes of content reflection, Jessie decided it was time for some indulgence. Grabbing the bottle of Everclear abruptly and removing the lid in one swift motion, she tilted her head back to take a large swig and almost immediately lurched forward in a fit of coughs. Opportunities to drink were few and far between for their team, and while Jessie would never freely admit to being a lightweight, she wasn't completely accustomed to the burn of strong liquor.

A look of concern filled James' face as he gently rubbed her back. "Take it easy, Jess."

Jessie inhaled deeply and straightened herself back up, attempting to minimize her blunder and deflect all attention from it. "I'm fine. Are you two going to join me or not?"

Quickly reading the irritation in her tone, James and Meowth retrieved their respective beverages and, as they did in all things, tried to catch up with her. James gleefully admired the bottle cap for a moment before stuffing it in his pocket and gulping the beer as quickly as possible while grimacing at the taste. Meanwhile, Meowth bit directly into his can and downed the contents shotgun-style.

It didn't take long for the trio to feel the effects of the alcohol, and within minutes they were singing loudly while dancing in circles. Their recently strokes of good fortune only intensified the giddiness. It wasn't often that they were able to drink in celebration rather than to drown sorrows, so this level of bliss felt quite foreign.

Jessie and James were pulled from their carefree reverie by peculiar sounds coming from their feline teammate. Coming to a halt, their heads snapped in Meowth's direction, where he was struggling to remain standing. He appeared to be trying to say something, but the only intelligible words were "meowth, meowth, meowth... meowth, meowth…"

Their eyes locked as they blurted, in unison, "Is he… speaking Pokemon?"

A moment later, a sharp laugh left Meowth's mouth as he fell face-first into the sand. James bolted to his side, rolling him over to reveal a serene smile and a bit of drool. Jessie squatted behind James, peering over his shoulder.

"I think he's okay; just asleep." As the words left James' mouth, he turned to Jessie and realized her face was mere inches from his own. A feeling of electricity shot through him, rendering him speechless as he admired the perfect symmetry of her face.

Jessie plopped down next to him and sighed loudly, declaring, "I'm so bored." After a moment's pause, her face lit up. "We should play a game!" She turned to glance at James, a sly smile creeping across her face.

James felt his pulse accelerate, though he wasn't entirely sure why. "Um… what kind of game?"

Her smiled widened. "Something like… poker. I have a deck of cards in my bag." For emphasis, she shoved her hand inside the bag, quickly retrieved the deck and waved it in the air.

James raised an eyebrow. "Jessie, you know we don't have nearly enough cash for any sort of game that involves gambling."

"I know. That's why we'll bet our clothes instead."

James froze and gulped loudly. He swore he'd detective a hint of a sultry tone, but his alcohol-clouded mind was having difficulty thinking clearly. "You mean, l-like… strip poker?"

Jessie giggled softly, relishing the surge of power she got from turning her partner into a flustered mess at the drop of a hat. With a smirk, she murmured, "Exactly."

James continued to gape back at her as she added, matter-of-factly, "Think about it. We're still wearing our Bewear outfits, which are basically identical. So, we're starting off on equal footing."

Snapping himself back to reality and forcing his jaw shut, James replied "Well, if you really think about it, you technically have an additional piece of clothing to lack. So in all actuality you have a bit of an advantage."

Jessie eyed her partner suspiciously, unsure of what he was referring to. When James picked up on her confusion, he blushed deeply as he mumbled, "You know... " His face turned a deeper shade of crimson as he gestured over his chest.

Jessie's threw her head back, a sharp laugh erupting from her lips. Resting her gaze back on James and noting how adorable he looked when he was flustered, she quipped, "Good. I prefer to have an advantage."

James emitted a slight whine as Jessie scooted toward him and dealt their cards. He felt vulnerable and cornered, and yet those feelings were mixed with a hint of something else. Was it excitement? As hesitant as he was to enter this activity with his best friend, he felt an odd rush of adrenaline at the thought of her removing pieces of clothing. He prayed his hazy mind could focus on the game enough to at least have a fighting chance against her.

Their pair examined their cards carefully. Peering at James for a moment, Jessie took another swig of liquor and confidently declared, "I bet my hat, shoes, and socks. And you?"

James met her gaze and shuddered slightly. However, he was thankful to start with a bet that was rather tame. He managed to force out a choked "I m-match."

Jessie confidently slapped her cards face-up on the ground and James followed suit a moment later, only to find himself woefully outmatched. With a sigh, he removed his hat, shoes, and socks and tossed them aside, silently chiding himself for already getting off to a bad start.

Another round later, Jessie found herself outmatched by James and removed the same articles of clothing he had, leaving them somewhat tied again. With a careful analysis of her new set of cards, she proposed, "I bet my shirt."

James smiled inwardly when he was greeted by four aces in his hand. There's no way she'll beat this! With an odd surge of confidence he so rarely experienced, he replied, "I'll raise you a shirt AND pants."

Jessie was momentarily taken aback by this uncharacteristically confident display of behavior from her normally demure partner. Between the alcohol coursing through her veins and the smug look on James' face, Jessie's heart pounded and an impulse took over. "I MATCH!" she shouted. She wouldn't let him win.

When their cards were laid bare, she was horrified to see James had won the round. Knowing exactly how to wipe the smug look off his face, Jessie shot her partner a seductive look as she slowly, torturously lifted her shirt inch by inch. And it worked, as the intensity of her gaze had him blushing and squirming uncomfortably within seconds. By the time she set to work on her pants, James was a sweaty, flustered mess and she savored the influence she had over him. James was transfixed, taking in each inch of her silky skin as her pants slid slowly down her thighs.

He was eventually broken from his trance by Jessie clearing her throat loudly. With a startled yelp, his entire body stiffened as he stuttered "S-sorry! I don't… I mean, I er…"

Jessie chuckled as she dealt cards for the next round and was pleased to see her luck return, especially considering how few items of clothing she had left to lose. After winning two rounds and enjoying the sight of James shyly removing his own shirt and pants, she suddenly felt an odd pang of nervousness. Regardless of what happened in this final round, one of them was going to left in a very compromising state of undress. Though the thought excited her beyond reason, it also terrified her. Were they ready for this? Was this a bad idea?

And with that final round, Jessie found it was her who had lost.

"WHAT?! I LOST?!" she shouted, fists clenched in fury. She tossed the cards aside and crossed her arms, trying to ignore James' beaming smile and joyous laughter. Then, another idea crossed her mind, and she knew exactly how to gain her dominance back yet again.

"So... we both know what's coming next." she purred, eying James seductively. With a dip of her shoulder, she let one of her bra straps slide down her arm.

James immediately tensed and swallowed loudly. "D-do we… ?"

Jessie felt a surge of adrenaline at the sight of her partner's flushed, sweaty face. At that moment, she decided to prolong the tortuous teasing as long as possible. "But it would only be fair for you to give me a hand with this, " she murmured with a wink.

James retorted, a slight whine to his tone, "Wait, why? I won the game fair and square!"

Sliding the other strap down her arm, she held his gaze as she continued to playfully tease. "Well, you surely could do with some practice."

James scoffed and crossed his arms. "Oh, I see. You think I have no clue how to do this?" With his eyes squeezed shut, he meekly added, "Well then, come closer."

To say Jessie wasn't expecting this was an understatement, but she held her ground as she slowly crawled toward her partner. "Er… sure," she replied, trying to hide her confusion.

Jessie crawled nearly into James' lap, leaving less than a foot of distance between them. She inwardly smiled when she realized James was still holding his eyes tightly shut. The fact that he was trying to so desperately to respect her and her body despite their closeness and effects of alcohol touched her in a way that threw her off balance for a moment.

"It would probably help if you opened your eyes, James."

Sweat now trickling from his temples down his cheeks, he sputtered "Y-yeah! Okay!" and slowly pried his eyes open to discover his companion was perched directly in front of him. He held his hands out awkwardly, unsure of what to do next. What if she felt violated by him removing her bra? Or what if she felt offended if he refused? This seemed to be a no-win situation for him.

Leaning closer, their faces now close enough to feel the other's breath, Jessie proposed, "You know, James. You should really be able to do this, just in case things get serious with a girl you like."

With his fingers now awkwardly fumbling at the clasp of her bra, James nervously whispered, "In… case?" while his mind silently screamed 'That's exactly what is happening right now, my dear!'

Feelings of nervousness and uncertainty overwhelmed James, leaving him feeling almost paralyzed. Hands shaking and voice wavering, he leaned back and blurted, "Jessie! I can't do this!"

Jessie stared back at him blankly, shocked by his outburst. "What? Unhooking a bra? Try harder!"

James was now visibly shaking, and his tension would have been palpable to Jessie even if she weren't inches from his face. "No, I mean… I can't use you to practice this." After a shaky breath, he mumbled, "Not if we're just playing a game."

Jessie studied his face for a moment and felt a pang of empathy for her partner, deciding she had taken the playful teasing far enough. "Oh, I see! This doesn't feel… real enough enough for you?" she whispered, leaning in to plant a soft kiss against her companion's lips. Breaking away slowly, she drank in his wide-eyed look of surprise as she added, "Feels quite real to me." A soft blush crept across her own cheeks, and she prayed he wouldn't notice.

James' look of shock quickly morphed into an expression Jessie couldn't quite read, but she thought she saw a hint of tears welling up in his eyes. Her musings were cut short by a pair of arms winding around her shoulders abruptly as James crushed his lips against hers. As both partners relaxed into the kiss and allowed it to deepen, James deftly unhooked Jessie's bra with one hand as the other gripped her shoulder tightly.

Backing away a fraction of an inch, Jessie whispered playfully against James' lips, "You did it! Well done."

James somehow managed an equally playful reply, despite his breathlessness. "Told you I know how to do this." He winked and both fell into giggles, recalling James' extensive experiences with traditional women's clothing.

When the laughter faded and silence returned, the all-encompassing electricity between them peaked as they stared into the other's eyes, unable and unwilling to focus on anything else. The world around them seemed to disappear as their faces tilted and their lips met again.

Jessie grabbed James roughly by the shoulders and pushed him backwards, pinning him to the ground underneath her as she planted a trail of soft kisses down his neck. His soft moans and breathy sighs lit Jessie on fire, and she felt she might combust if she didn't possess this man in every way possible.

Sitting up to straddle James' hips, Jessie glanced down at him and felt the fire in her core intensify even further. She watched his eyes sweep over her, an expression of adoration and awe clearly etched across his features.

"Touch me, James," she whispered. To her pleasure, he was eager to oblige, gliding his hands slowly from her hips to her waist. He paused for a brief moment to read Jessie's expression before deciding it was okay to glide his hands further to her breasts. With a moan of approval, Jessie flashed James a wicked smile before hooking her thumbs under the waistband of his boxers and tugging swiftly. She let her eyes wander over his now fully nude body, grinning at what had finally been revealed to her.

As Jessie leaned forward to capture James' mouth again, an odd screeching sound startled both partners and sent them plunging back to reality. Their heads snapped in the direction of the sound, and both found themselves frozen in shock as they saw their feline companion was awake and fully aware of their situation.

"What da hell are youse two doing?!"

Neither Jessie nor James could do anything more than blink in reply, both wearing matching looks of dumbfounded surprise.

"I can't believe you're doing dat nasty shit in front of Me-owth. Do youse two have no decency?!"

Jessie and James continued to stare back at him blankly, mouths agape. With a frustrated groan, Meowth rested his head in his paws.

The silence was broken by a soft moan, and against his better judgement Meowth risked another glance at his partners. To his horror, Jessie had once again pinned James against the ground, rejoining their mouths in another heated kiss as they picked up where they had left off. They were both too intoxicated by alcohol and each other to focus on anything else.

"NO! STOP IT! Yous two are sick!"

Meowth's frantic screams faded into the distance as he sprinted away from the beach. At that point, he didn't particularly care where he ended up as long as he didn't have to witness what his teammates were doing.

Jessie awoke with her head throbbing and stomach in knots. The sun's morning light felt painfully bright despite the fact that she had yet to open her eyes. 'Ugh, I feel like I've been hit by a train."

As she yawned and moved to stretch her aching body, she became acutely aware that a pair of arms were wrapped around her waist. She also could have sworn she felt someone else's breath against her forehead. Slowly opening her eyes and doing her best to shake away the sleepy fog, she found herself gazing at a familiar face. She couldn't help but feel warm and content in his arms, and she smiled at the way his lavender hair was stuck to the side of his face. Closing her eyes and surrendering the the peaceful warmth consuming her, she was suddenly jolted with the realization that she was completely nude. Letting her gaze fall lower, she noted that James was equally nude. Her entire body tensed as bits and pieces of the night before entered her consciousness.

Jessie's instinct was to bolt, fearing she had made a fatal error and sullied the most stable relationship she'd ever managed to have. Her heart began to pound, intensifying the pain in her head and causing her throat to release an involuntary grumble. This was enough to stir James, and Jessie held her breath as he slowly opened his eyes and peered directly into hers. A sleepy, lopsided grin crossed his face as he tightened his hold on her waist. Jessie was unable to sufficiently mask her wide-eyed panic, and after a moment James detected her anxiety. That was all it took for him to realize their mutual nakedness as the mind-movie of the previous night began to play in his head.

James whimpered softly and braced himself for the worst. He desperately searched for the right words to ease the tension and came up frustratingly empty. The pair held each other's gaze for another brief moment, though it felt like hours to both of them, and Jessie elected to use her typical self-preservation tool: avoidance.

"Ok, so we made a mistake. Let's just forget this ever happened." She turned her head away from her partner and made a move to get up, but this proved difficult as James tightened his grip on her. Snapping her head back toward him, she saw a look of desperation on his face, pleading with her in a way he couldn't vocalize.

Jessie scoffed, feigning irritation. "What, James? What do you want?"

He was finally able to latch onto some words, weakly replying, "Please, Jess. Please don't leave."

Something about the look in his eye and the tone of his voice gave her the strength to embrace the discomfort of vulnerability. For once, she wanted to tear down a wall and not mask her feelings behind apathy or anger. So, she settled back into James' arms and bravely held his gaze.

"I don't want to forget," he whispered, eyes brimming with tears.

"Me neither," Jessie blurted, eyes widening as she shocked herself with her own emotional transparency.

In a desperate attempt to silence her confusingly loud thoughts, she cupped James' face and pressed her lips against his, frantically. He met her with equal force, both of them desperately trying to express the feelings they were still too afraid to vocalize.

It was Jessie who reluctantly broke the kiss, gazing fondly at James' face. She found herself pleasantly stunned by the new things she was learning about her long-time partner and best friend.

"If I remember correctly, we scared Meowth away last night. I'm sure he's fine, but maybe we should go find him?"

James nodded with a soft chuckle. "I think a heartfelt apology may be in order."

The duo carefully stood and dusted off the layer of sand and poker cards suck to their bodies. After slipping back into their slightly soiled clothing, they set out to find their teammate, hand-in-hand.