AUTHOR’S NOTE (2021/06/04): This story was formerly titled All Is Fair (and May’s Pink Surprise before that). I’ve changed the title for the third and final time, but would like to reassure you it is in fact the same story as before and the first chapter remains largely unchanged.

Synopsis: Gary Oak, pokémon researcher and heartthrob extraordinaire, never yearned for anything his arch rival Ash Ketchum had, not until a chance encounter introduces him to Ash’s new girlfriend.

DISCLAIMER: This is a work of fan fiction borrowing characters from the Pokémon universe, which is trademarked by The Pokémon Company. I do not claim ownership over any of the characters or settings and make no money from publishing this story.

WARNING: This work of fiction is Rated MA and only suitable for mature audiences. It may contain explicit language, adult themes and graphic descriptions of a violent and/or sexual nature.

Doing The Oakey Pokey

by j.j. scriptease

Chapter 1 – May’s Pink Surprise

Gary lounged on the beach under a tall umbrella, leaning back in his deckchair with arms folded behind his head. The day couldn’t get any better. Chic sunglasses winked from atop his brow, pervading an air of cool as he gifted beach goers the sight of his toned abs. Chewing gum on one side of his mouth, he pointed at a beautiful girl modelling along the shoreline. “That one.”

“Hm!” Brock frowned with appreciation. “Not bad.” He lay reclining beside Gary, also clad in nothing but beach shorts. A girl in a blue bikini slid into view and Brock singled her out among the crowd. “That one.”

“Nice,” Gary said. He pointed at another young lady, flaunting long legs in a one-piece costume. “And that one.”

Brock nodded, impressed. He gestured towards a woman who bore a striking resemblance to Officer Jenny. “Heh, that one.”

“Just your type.” Gary drew Brock’s attention to a trio of bikini-clad beauties throwing a beach ball to one another.

“Which one?” Brock asked.

“All of them.” Gary smirked. “At the same time.”


“Would I lie to you?”

“Come on. Not even you’re that good.”

Gary let out a sarcastic laugh. “You realise you’re talking to someone who spent all their Trainer years stalked by a loyal band of cheerleaders, right? And in case you’re wondering, I’d point them all out if they were here too.”

“Show off.”

“Hey, you’re the one who wanted to play this game.”

Brock pouted. “Yeah, well, it’s not fun anymore.”

Gary laughed. He appreciated Brock’s envy. The wealth, fame, exceptional genes – and having a world-renowned pokémon professor for a grandfather – almost felt like cheating sometimes.

What a lot of guys like Brock didn’t realise though was how boring his life could be. Gary appreciated the art and softness of the female form as much as the next red-blooded male but, at some point, it all started to blend into a generic muddle of boobs, butts, and limbs.

Even the most stunning girls made him go ‘meh’ the second they started grovelling. Their willingness to lie back and throw their legs apart took all the fun out of the chase. What good was a trophy if it was just handed to you?

Gary felt a ping of regret reminiscing about the proverbial ‘one that got away.’ “Say Brock, what ever happened to that girl you used to travel with? You know, the redhead,” he said, pretending not to remember her name.

“Uh, you mean Misty? She headed back to Cerulean City a while back. I used to see her every now and then but sadly we’re not that close anymore.” A disturbing thought occurred to Brock. “Don’t tell me she’s on your list too.”

“Ha. I wish,” Gary said, matter-of-factly. “She’s fair game, right? You wouldn’t have a problem, would you?”

“Me? No. Although, I should warn you… She only has eyes for Ash.” He shrugged dismissively.

“Figured as much. She had some serious legs though. Don’t know what she ever saw in that dweeb.” Gary smiled at a sad memory. “You know I even wrote a song for her?”

“Are you serious?”

He cleared his throat.

“I wanna suck

Misty’s breasts

Like no one ever has…

To touch them is my real test –”

“Er, I’m going to stop you right there.” Brock facepalmed. “That’s terrible.”

Gary cracked himself up.

“What’s so funny?” came a voice from behind them.

They glanced over their shoulders, and sure enough, the boy who’d just graced their conversation stood there.

Brock was ecstatic to reunite with a friend he hadn’t seen in years. Gary and Ash were more like frenemies than companions, but he had to admit, seeing a familiar face stirred a little nostalgic sentiment.

Teenage Ash looked like a ganglier version of the boy Gary remembered – except now he wore an even more ridiculous league cap. He and his Pikachu dressed in matching beach shorts. It might’ve been cute when he was ten, but it was plain dorky now.

“So, you guys are like best friends all of a sudden?” Ash asked, sounding left out.

“Let’s just say we’re bonding over… common interests,” Brock let on.

“Why don’t you join us?” Gary asked, never passing up an opportunity to outshine Ash. “All you have to do is look around and tell us which of these sexy beach babes you’ve used your String Shot on, so to speak.”

Ash scratched his head, confused. “Why would I do that?”

Gary facepalmed. “I mean, who got your Weedle wet? Whose Jigglies have you Puffed? Who’s stroked your Ekans?”

“Who’s shined your Onix?” Brock tried one.

“Uh…” Ash stroked his chin. “Are you guys speaking in code or something?” Both Gary and Brock fell out of their deckchairs in disbelief. “Hey, are you guys making fun of me? I expected as much from you, Gary,” Ash said. “How about it then? A pokémon battle! We’ll see who has the last laugh then.”

“You haven’t changed one bit.” Gary sighed. “No can do. I thought I already told you, I’m not a Trainer any more. I’m a pokémon researcher.”

“You’re a chicken is what you are!” Ash and Pikachu mimicked flapping wings.

Gary waved them off. Ash might’ve grown outwardly but he still sounded ten on the inside.

“Anyway,” Brock said. “What we were trying to ask is if you’ve scored with any of the wonderful ladies out here.” He winked.

“Oh! Well why didn’t you just say that then?” Ash rubbed the back of his head sheepishly. “No, can’t say I’ve ever done that.” Gary smirked in the background. “But,” Ash continued. “I do have a girlfriend now.”

Gary snickered. “You finally got around to asking your Pikachu out, huh?”

“Very funny, Gary,” Ash said. “Actually, she’s right over there.”

Just as he pointed towards the beach, her head broke through the water’s surface, drenched tresses clinging to the sides of her face. She took in a huge gulp of air and wiped the water from her eyes, brandishing raw, sapphire pearls that sparkled brighter than the ocean she’d emerged from. The soaked brunette smiled genially as remnants dripped from her jaw, beaming against the backdrop of crashing waves and racing hearts.

Her massive breasts were next to emerge, jiggly mounds of flesh dragging water up with them, trickles running down their slopes and through her cleavage. A thin slingshot bikini adorned her near-naked form, red-white strips only broad enough to tape over her nipples, leaving the bulk of her bosom gleaming under the sun.

She strutted onto the shore, hourglass hips parading in slow, seesaw motions, sure to hypnotise dozens of beach-dwelling eyes. The stunning brunette glimmered on the coastline, a ruby amongst grains in the sand.

As Gary and Brock picked their jaws off the ground, Ash grabbed her attention with a wave. “May, over here! Come say hi to my friends.”

She flashed pearly whites and jogged over. Gary was mesmerised by her big, bouncy, glistening, dripping-wet breasts. He’d rarely seen naturals that size on a lean, fit girl. They were large, but not grotesque, with just the right amount of spring to make all the beach balls jealous.

Brock decided his hearing or vision was lying to him. “That’s… May?” He gave her a onceover, perturbed.

“I can’t believe you haven’t hit that yet,” Gary said.

Ash flushed. “We’re saving it for a special occasion!”

“Being with a girl like that… you’d think every occasion is special.” Gary’s mind drifted for a second. As she drew closer, he and Brock scrambled out of their lazy stupor, spraying their breaths, smartening their hair and straightening their sitting positions.

“You remember Brock and Gary,” Ash said.

“Brock!” May squealed. “It’s been so long!” She pulled him into an embrace, one he was thrilled to be a part of, his pink face hidden over her shoulder. “And you’re Gary? Have we met?”

The dashing pokémon researcher flinched. “You mean you don’t remember me?” A girl forgetting him hadn’t happened since like, well, ever. Granted, he failed to recall any previous encounter with her too; she must’ve looked totally different, he reasoned. “I still get a hug though, right?” He flashed his best smile and stretched out his arms.

“Er, let’s start here.” The bashful girl offered a handshake instead.

Now she was turning down his hugs too? What the hell was going on here?! Gary shook her hand all the same, not letting his disappointment show.

“You look really good, May,” Brock said.

“Aw, thank you! I’m digging your new look too. The afro’s definitely better than the spikes!”

“I don’t know,” Gary said. “Spikes aren’t bad if you know how to work them.” He flicked his own to emphasis the point.

“I guess,” May said. “Know someone who does?”

Gary face-faulted. The cheek of this one! He’d be insulted if he didn’t love it.

She tugged on Ash’s arm. “Hey babe, why don’t you come take a dip with me?”

“No point coming to the ocean if you’re not going to get wet,” Ash said. “Nice catching up with you guys. Well, nice catching up with you, Brock. We should grab a bite some time. Gary, smell ya later!”

The spiky-haired researcher panicked. “Ash! Wait!” The pokémon trainer whipped around, confused. “I changed my mind,” Gary said. “I’ll have that pokémon battle with you.”

Ash practically leapt for joy. “All right!” He pumped his fist. “We’re going to be ready, aren’t we, Pikachu?”

“Pika pi!”

“Heh. Good luck. You’ll need it.”

As Ash and his girlfriend walked to the shoreline hand in hand, Gary zoned in on the brunette’s pert exterior. His heart was racing, his head spinning, his mind all over the place. Confusion, trepidation, excitement, all combusting in his veins at once. A tilted smirk crept onto his features.

Finally, a challenge.

. . .

May leaned against her fist, nodding off as she gazed at the lonesome picnic basket. The baguettes she’d worked so hard on were going to waste. Ash’s insatiable desire to be the greatest pokémon trainer ever butted into her hopes for an intimate lunch.

Still, it was unlike him not to work up an appetite all afternoon, especially with the energy he exerted coaching his little fighters. The imminent confrontation with that Gary guy was more than a pokémon battle to him.

May grasped the sentiment, having had her own share of rival coordinators, but it was disconcerting when she couldn’t even talk him into food. Every time she beseeched him, his response would be the same: ‘Okay, in 5 minutes’, ‘Please give me 10 minutes’, ‘Just 2 minutes, I promise this time!’ Or so he said, an hour ago.

Her PokèNav plopped with a new message.

Dawn was online, a good friend and fellow pokémon coordinator. They often swapped tales of their achievements in recent Contests. But Dawn let on her smilie-obsessed excitement was owing to something entirely different this time. Something special.

May didn’t even have to press for details before they flooded her screen. Her eyes grew twofold as she scanned the text; Dawn recounted how a mundane trip that started with her and Kenny going to the Poké Mart ended with her back against an aisle of Super Potions and her childhood friend up her skirt.

She apologised if the story was too personal but May waved off her concerns. In fact, the brunette was invigorated with curiosity, pushing for more detail as she repositioned herself so Ash wouldn’t glimpse their conversation.

May had never wanted to criticise her friend but the infamous pink skirt screamed ‘easy access’ and it was only a matter of time until some boy tried to ease his way into it. Reading Dawn’s encounter however aroused a cocktail of unexpected stirrings, least of all envy. She was deviously grateful the blue-haired coordinator spared no explicit detail.

Soon, Dawn had to log off despite May begging her to stay. Understandably, there was no contest between instant-messaging her and hanging out with Kenny, especially after the most recent development in their companionship.

May couldn’t help imagine what those two would get up to next. She watched Ash, hard at work with his pokémon, and wondered how Dawn would feel about lending her that skirt. Would he even bat an eyelid though? When Ash delved into his pokémon trainer zone almost nothing could pull him out.

In spite of her frustrations, she hated playing the nagging girlfriend. Rather than get in the way, she put aside her own selfish needs for his attention, deciding to do something nice for her pokémon.

The effort she put into lunch had gone unnoticed, but her lovely little companions hopped and soared at the prospect of her Pokéblock recipes. She rummaged through her bag for ingredients to make a treat she called May’s Pink Surprise.

Her inventory would be sufficient if not for a shortage of Pecha Berries. Luckily, the woods they’d stopped in were part of Route 104, sat in the backyard of Petalburg City, her hometown. She’d explored the area countless times with her father as a little girl, well enough to know Pecha Berry trees could be found in the vicinity.

When she informed Ash of her planned excursion, the preoccupied trainer muttered back something unintelligible, showing little acknowledgement of a single word she’d just said. She rolled her eyes and wondered if he’d even notice she was gone.

May wrapped a towel around her waist and went about her way.

To the uninformed eye, all the trees looked the same, but May could name every single one, distinguishing them by their scent, shape and colour of their leaves. As she delved deeper into the woods, the sight of Ash and his pokémon faded into the background. Soon she couldn’t hear them at all.

Pausing, she contemplated whether it’d be a good idea to leave Ash on his own; his sense of direction was terrible, and he might’ve panicked when he realised she wasn’t there.

On second thought, nah. She was over-worrying. She did that a lot these days, often forgetting he was a big boy now, more than capable of taking care of himself. Plus, he had a gang of pokémon ready to defend him to the death should trouble arise. Reassured, she continued her expedition.

May collected Pecha Berries using the space between her forearm and belly like a makeshift basket. As she hummed along, a distant voice interrupted her tune.

“Poke-a-ho, gotta bang ‘em all!”

It sounded like singing. The melody was familiar although the lyrics baffled her.

“…you know it’s my destiny!

You fuck me and I’m fuck you…”

The song came from a boy leaning against a tree, his back facing her. She crept up and tapped his shoulder.

He stopped mid-song and whipped around, startled. His shock shocked her.

She squealed.

The Pecha Berries tumbled to the ground.

May clutched her heart, calmness settling in as she recognised his features. He stood a foot taller than her, slim, flaunting a blemish-free visage and sharp jaw. Tinted glasses posed on his brow, and big, spiky hair strutted in gelled perfection. His open collar showed off the dazzling pendant around his neck. He looked like he spent more time than her in front of the mirror, daubing on some arrogance here and there, practicing the slanted grin married to his face.

“So, we meet again,” he said.

“You’re… that guy from the beach, right?”

He face-palmed. How could she not remember his name? Again!? “Gary Oak,” he stated clearly. “The Gary Oak. And you’re Ash’s girl.”

May beamed. “That’s right.” She knelt down to regather her berries. He decided to help despite her insisting it was okay.

“What are all these for?” he asked, tilting a berry between his fingers.

“May’s Pink Surprise,” she said.


“May’s Pink Surprise. It’s a recipe. My own,” she chimed.

“Can I try some?”

“Ha! Sure. Although, I should probably warn you it’s a Pokéblock recipe for pokémon.”

“Figures.” He shrugged. “You named a Pokéblock recipe after yourself?”

“If you’re gonna help, help. Less talking, more picking up.” She winked, a polite ‘shut up’.

The pokémon researcher took a moment to research her body. While a red towel covered her bottom half like a skirt, her stringy bikini left little to imagine up top, her cleavage all but bursting on full display. This up close he could see bits of areolae poking out the sides of her straps. He licked his chops.

‘Ash Ketchum, you sly devil…’

He might’ve underestimated his childhood rival yet.

Gary fought the urge to stare, afraid dribble may escape his lips without him realising it. He still couldn’t fathom how Ash refrained from pouncing on such a busty beauty walking right next him all day long.

She asked him why he decided to practice his singing in the middle of a forest of all places. There was a hint of suspicion behind her question. Good thing he’d anticipated it.

Gary pointed upwards where a Shieldon sat clutched around a branch like its life depended on it.

Weird, thought May, how did a Shieldon wind up on Route 104?

The poor pokémon seemed afraid of heights and refused to come down. Gary claimed his singing helped calm its nerves. Judging by the sample she heard, May was more inclined to believe his singing was the reason it stayed put; it would’ve explained how the Rock-type got up there in the first place too.

Gary claimed he’d stumbled upon it on his way through the woods. He asked if she could help him bring it down. The thought of doing anything for this stuck-up, self-obsessed show off didn’t sit well with her, and probably wouldn’t with Ash either, but she couldn’t look away from the frightened pokémon without guilt pelting her conscious.

“Oh, all right,” May said, setting down the berries in a neat pile.

“Great.” Gary smirked. “Here, I’ll give you a boost.” He interlocked his fingers and lowered the crude foothold.

Her hands pushed off his shoulders as he hoisted her up. Stifling a grunt, he elevated her reach towards the branch, supporting her weight with relative ease. Her fingers stretched to their limits but wiggled a few inches shy of the troubled pokémon.

Damn, she mused, this would’ve been so much easier if she’d gotten to finish her batch of May’s Pink Surprise. The pokémon would’ve practically leapt into her arms for a taste.

She needed extra height and asked if Gary was comfortable with her stepping on one of his shoulders.

“Yeah, yeah, of course!”

That had kind of been the whole point.

The pink-faced boy gawked as he found himself staring up her towel. Her snug bikini bottom fashioned a cameltoe right above his head, eclipsing the sun in all its luscious glory.

As the unbeknown rescuer concentrated on easing down the pokémon, he concentrated on the curvature of her vulva, tempted to reach out and chomp on the succulent fruit, if only his neck was as long as a Girafarig’s. The thong-like attire rode up her taint, gifting him the sight of bare underbuns – big, pert and toned to perfection.

Too perfect not to get distracted – his hands suddenly wobbled.

“Whoa!” May cried. “Easy, easy. I’m almost there!”

“Hurry!” He was losing his balance.

Wobbling precariously, she urged him to stay strong just a little while longer. ‘Almost… there…’ Her hand reached and reached, fingertips wiggling towards the frightened Shieldon… ‘Come on…!’

She grazed the branch –


The two-person tower came crashing down.

One yelp and one hard-landing later, she stirred only to find herself lying on top of the researcher.

Gary lay still as a board as he miraculously woke up in her bosom. The heavenly breasts pulled away despite his murmurs not to go, despite his willingness to suffocate a happy man.

The gleeful Shieldon rolled onto its feet then scampered into the shrubbery, safe once more.

“Thank goodness,” May sighed.

Then she remembered her awkward predicament.

With cheeks redder than a Pikachu’s, she apologised for landing on top of Gary.

Then… awkward silence.

Their eyes engaged in a slow, pensive dance. Gary struggled to read her intentions. He normally waited for a cue. But with this girl, things didn’t happen the way they normally did. Throwing tact out the window, he grabbed the back of her head and pulled her down onto his lips.

May was taken by surprise, groaning in discontent as his mouth smothered her complaints. His arms restricted her attempts to pull away and his lips closed any distance she achieved. Fuming, she was ready to call him every name in the book, but when her mouth opened, his tongue accepted the unwitting invitation.

The slimy sensation was icky at first, his persistent organ slithering all over hers. But then she noted a tang of strawberry. She loved strawberries. The remnants of his chewing gum most likely.

Her furrowed brow relaxed, her mind slipping into a dreamy haze, her tongue shifting from running away to chasing his. His hands pulled away from the back of her head, no longer sensing the need to hold her steady. She ignored the opportunity to break free, deepening the kiss instead.

He rolled his hands over her shoulders then ran his fingertips down her bare back. She was still in dreamland, bobbing for strawberries, when he snuck into the warm space between her waist and towel. He felt round the smoothness of her butt cheek and gave it a good squeeze, shocking her into full consciousness.

“You jerk!” She slapped him and backed away, refastening the towel around her waist.

“Heh.” Gary stood up, massaging the handprint on his cheek. “Can’t say that happens to me often. Or ever.”

She crossed her arms, unamused. “Who the hell do you think you are?”

“Gary Oak. Only everything you long for. Admit it. You were loving it.”

“Shut up. You tricked me.”

“Please. I only started the ignition, but you kept revving and revving, didn’t you?”

She huffed, wishing she’d smacked him hard enough to dismember that smirk.

“What are you so pissed about?” Gary asked. “It was only a kiss. Not like you haven’t done that before, right?” To his surprise, she turned away without reply. “What? Are you serious?” Gary laughed to himself. “I swear Ash is so -”

“Gentlemanly,” she cut in. “He’d never try to pull what you did.”

“Is that right?” He took it as a compliment. “Why are you still standing here?”

“What?” She looked confused.

“I mean, if you’re so offended and disgusted, why haven’t you run back to Ashy boy yet?” As he expected, she didn’t have an answer, so he decided to provide one for her. “See, what I think…”

He took a step closer to her. “Is you like being here. You like me looking at you.” He took another step forward. She took a step back. “Coz unlike Ash, I appreciate an exquisite specimen when I see one.” He eyed her from head to toe. The standoff continued to move, him approaching, her retreating. “You and I are alike, May. We want the same thing. And you know it.”

May backed into an oak tree. Cornered. No place to run.

She denied his every word, outwardly at the least. He was just a creep. Albeit, not the worst looking creep, but a creep nonetheless.

He had the air of someone accustomed to getting everything they wanted, an undeserving snob with the world at their feet. She was in a loving relationship with someone who made a difference to the world every other day. Light-years spanned between him and Ash.

Sure, deficiencies crept into their relationship like any other, but under no circumstances would she downgrade to a self-centred jerk. Even as his tall, imposing charm closed the gap between them to an inch.

Gary leaned one arm against the tree, slightly above the shorter girl. Her body language might’ve fended off most but it would take more than crossed arms and a turned head to make him look the other way. He lowered his voice into her ear. “So, May. How was it? Your first kiss ever?”

The feisty girl mumbled something he wouldn’t ask her to repeat.

He let her unsavoury remarks roll off his grin. As far as he could tell, he had her on the ropes. “C’mon, May. You can’t even look me in the eye and tell me to go away can ya?” He practically dared her to.

May couldn’t believe he had the gall. She wasn’t about to fawn over his stupid, cocky, miserable, intoxicating smile. How many hints did she have to throw at him? Criticism kept bouncing off his impregnable shield of vanity. How annoying.

She really wanted to hit him where it hurt. What better way than to trump his silly challenge? Looking into his eyes and telling him to get lost was hardly the impossible task he made it out to be. Yet, she found herself needing to prepare before taking the plunge. She inhaled subtly then looked up at his piercing orbs.

The words caught in her throat before fumbling out feebly. He chuckled, unconvinced. Inching his body closer, he let his strawberry-scented chops hover at the tip of her nose, teasing as he asked her to try harder in a low, sensual purr.

She cleared her throat, uncomfortable with his proximity, but determined nonetheless. Her flimsy eye contact betrayed weakness and Gary sought to pounce on it.

His lips dipped lower. Tantalizingly lower. May whipped her head to the side, keen on avoiding another blunder. However, offering her neck in the process threatened to be just as detrimental.

His lips pecked her up and down. She stifled a gasp at the soft, wet touches. The tip of his tongue teased her flesh with light strokes. He painted a thin coat of saliva on the side of her neck, let the cool breeze sizzle upon it, then reinforced the sensation with another swipe of his tongue.

She grew into the rhythm despite groaning her discontent. Encouraged by her feeble resistance, his chops clamped on her nape and sucked the breath out her lungs, a shot of adrenaline to her heart.

The sounds of his suction met her exhalations. She’d never anticipated this reaction, granted she’d never had anyone test the sensitivity around that area. He cradled her throat with a gentle hand as his tongue indented her erogenous zone, his lips spreading farther, wider, covering more ground in their aggression, yearning to suck the skin of her bones.

The tugging of her flesh tickled in ways that made her body giggle. Although she reminded herself this wasn’t her boyfriend Ash, her sensory nerves refused to discriminate.

She could tell her assaulter was addicted to her flavour. He was practically making out with her collarbone. She fretted against the graze of enamel. Paranoid he’d bite. But when he finally did, it lit her skin on fire, a scorching sensation stirring her loins ablaze.

His hot breath poured into her ear. “May, your body’s so soft.” His touch trailed down her arm. The tiny follicles lining her limb heightened from the electric charge in his fingertips. Suddenly, she felt shy about not having a shirt on, his gaze barrelling down the heart of her bosom. “Bet they feel even more amazing than they look,” he whispered.

May was on the verge of retort when he recaptured her lips. The taste of his hot, cherry passion washed down her words. It was a soothing addiction, overwhelming her in deep, brash strokes. His smouldering presence filled her mouth, a finger running down her cleavage, the soft friction rousing her hairs.

No, thought May, breaking the lip lock. She glanced left and right, panic in her eyes. “We can’t…what if someone –”

He steered her face back to his and planted hot lips on hers. “Yes, we can.”

She’d be careless to believe that, but common sense made little sense in times like these. The kiss grew more frantic, heads tilting, lips absorbing one another. He squeezed her ass over the towel, moaning at its tautness.

An illicit tingle zipped through her veins as he copped a good feel, their patience plummeting. The purrs of his desperation were contagious. Some semblance of decency urged him to stop, albeit with muffled conviction, and fear of losing what wits she had left.

His hunger was insatiable, targeting her nape and collarbone when her lips became unavailable. Her own hands were inspired to rummage around his biceps while his emphasis fell upon her thighs. He seemed hell-bent on testing her loyalty, and at this pace, she was failing wonderfully.

“Wait,” she exhaled, but did nothing to stop him kissing her neck. He groped her right breast whilst preoccupied her with his lips. His breathing grew heavy in her ear as he appreciated the weight and suppleness of the large mound, pinching and stirring it in circular motions. “Hnggg…” May bit her bottom lip, losing herself to the sensation. “Hey,” she muttered, “What if someone, what if Ash –”

“Ssshhh…” He kissed her.

So invested was the pokémon researcher, he didn’t seem to care if Trainers happened upon on them, or her boyfriend for that matter. Why couldn’t Ash show this much interest in her body?

Gary brushed aside one bikini strap with his thumb, unveiling the big, perky nipple that had hardened underneath. She blushed at being indecently exposed, and more so at his divulging her state of arousal, the pink nub pointing tall and erect.

To think, she and her boyfriend had never got this far. Ash was absorbed with his pokémon right now, none the wiser to his fiercest rival one-upping him in the cruellest way imaginable. If only he’d spared a moment to consider her needs.

A selfish excuse, maybe, but how else could she justify wanting anything to do with Gary Oak? Ash was not without his positives; he made her feel special, but Gary made her feel wanted.

She knew it had to stop at some point. The when and how eluded her.

Somehow she’d cool from her hot and bothered state and disengage before the point of no return. She could do that, she told herself. This was nothing more than two agitated kids scratching each other’s backs. Yeah, that’s it. Just a little longer then she’d break it off, rush back to Ash and forget it ever happened. No harm done. Yeah…

Gary had other ideas.

He handled her breast like someone who’d done it a hundred times. She wondered if he whispered in all the girls’ ears how they owned the best pair he’d ever touched.

Genuine or not, his flattery rubbed her all the right ways, heightening her arousal, spurring the thought he wanted no one else like he wanted her in that moment. He massaged her tit round and round, pressing, nipping at the bountiful flesh.

Was this really happening? Did she really want it to?

Her body certainly did.

He lowered the side of his face onto her chest then the tip of his tongue circled her areola. It was cold and wet, yet hot against her skin, fuelling the fire in her epicentre.

He loved tormenting her. Her nipple was ripe and swollen, puffing out for attention, but the audacious tease traced around it again and again. Finally, his mouth enclosed her areola, trapping steamy breath over her breast before his tongue flicked into action.

He started with faint strokes. Even the slightest of touches had her nipple exclaiming. The half-licks appeased her for seconds at a time. Not enough. She needed more.

Her body offered a subtle thrust into his mouth. She knew he got the message when he caught her nipple between his teeth and sucked it hard, drawing a gasp of shock and ecstasy.

Her sensitive nub had never lived such pleasures and she struggled to hold it in as his chops licked and tugged on her breast. The sneaky researcher wasn’t done there. In the midst of everything, a hand found its way to her towel and began to unwrap it from her waist.

‘No, not there’, were the words that sprung to mind, but never made it past her lips.

Truth was, she wanted to know what it was like to be touched there. Not-so-innocent curiosity perhaps, but Arceus, if Ash wasn’t going to do it, someone had to.

Gary yanked the towel from her waist and threw it behind him. Only May’s skimpy bikini remained clinging to her figure, concealing her nether regions in a narrow triangular strip, tan lines spreading beyond the scant material. He could barely eye her crotch for more than two seconds without reaching for a touch.

May surveyed their surroundings again, as if this particular development warranted extra caution. “Oooh…” she blurted out, then covered her mouth immediately, bashful as his middle finger stroked the tiny strip covering her pussy. Another outburst like that and they might get caught. “Hey, we better stop,” she whispered, looking around.

“You really want me to?” He could tell she didn’t.


He smirked. Now she knew his name. After today she’d never forget it. He prodded the area covering her entrance, fingertip poking at the fleshiness of her pussy lips. “Heh, did you use a Water Gun attack or are you just happy to see me?”

“S-stop it,” she said, hiding her red face. “I have a boy… a boyfri-frie…”

“You’re saying it doesn’t feel good?”

“That’s…” she stammered. “That’s not the point.”

“Heh, you want it bad don’t you? It’s not all that surprising, you know. ‘Never’ is a long time to go without any action.” He spoke coolly while teasing her crotch in broad vertical strokes. “You’ve wanted this for a long time, haven’t you? Someone to appreciate this banging body you’ve worked so hard to whip into shape.”

It wasn’t right, entertaining these devilish thoughts behind Ash’s back. But Gary wasn’t wrong in anything he’d said either. She couldn’t pretend she wasn’t enjoying his touch any less than she was hating it.

“You’re absolutely gorgeous,” he poured honey into her ear. “You deserve someone who’s going to pay attention to that.” He emphasised his point with wet kisses on the side of her turned face. “Someone who appreciates these big, beautiful tits.”

May was flustered by his words, his proximity, his sweet scent and sweeter sentiments, his husky tenor lighting up nerve endings she’d never had activated before. No one had been so direct, so lewd about the parts of her body they craved most. Far from being disgusted, she played it silent and coy, even as she felt his finger sneak beneath under bikini bottom…


“Whoa, so tight,” he muttered.

May shifted with a purr as he pushed more of his finger inside her, the first digit to ever breach her virgin walls.

He worked her tightness through quickening rhythms, aided by her overflowing excitement. “So fucking wet too!”

Her pussy made squishy sounds from the fast pumping of his digit. At this rate he’d drain all the fluid in her body. Spurt, spurt, spurt, and her timid moans in between.

Adrenaline tainted her fear of being caught, perverting it into some kind of warped exhilaration. She couldn’t say for sure what point her concern swayed from offending Ash to hoping no one would interrupt them. As he thickened the penetration with a second digit, she all but resigned herself to the inevitably of sin.

She was going to get fucked by her boyfriend’s fiercest rival, wasn’t she?

Distant voices caught them off guard. Startled, she pushed Gary away and covered up her treacherous pussy.

“Would you relax?” He chuckled, holding up fingers drenched in May sauce. “They’re not even near us.”

She heard the random voice move along and disappear. He was right, but it didn’t matter. “Still too risky. There’s no time for this. Sorry.” Wait, why was she apologising?

“No time?” He laughed off her excuses. “If that’s all that’s stopping you, you could’ve said so.”

He dropped to his knees and pulled aside her bikini bottom. She blushed furiously, knowing his line of sight sat level with her exposed pussy.

Gary licked his chops. “I mean, you did say I could have a taste of May’s Pink Surprise.”

“What!? Hey, that’s not what I mea- ah!”

Suddenly, May was looking down at the top of his head, face buried in her crotch. She clutched his shoulders intending to push him away, but after a few licks, her hands clasped him in place instead.

He grabbed her bare ass for leverage and practically French kissed her wet snatch. His fingers dissected her nether lips and his tongue glided along their inner linings, sending a tingle up her spine, and when he reached her aching clit, May cried out for all the heavens to hear.

He pulled back to warn her to shush.

Yes, yes, she nodded hastily, anything to make him continue.

As his tongue re-acquainted itself with her clit, she held it all in, every utterance of ecstasy, every curse word in the book, every Legendary pokémon believed to exist. She contained herself in strained groans while pleasure mounted on the back of her knees. In response, he swung one of her thighs over his shoulder, aiding her balance but also drawing closer to her sweet spot.

May’s eyelids drooped, making it harder and harder to stay vigilant of oncoming Trainers, pink fog thickening all around her. She lost touch with reality. Her feet were off the ground, her head past the clouds.

All she felt was his tongue pushing in and out of her damp entrance. His tongue flicking at her nub. His tongue thrusting wave after wave through her body.

All she heard was her lover slurping up every ounce of ecstasy gushing down his gullet. How she hadn’t drowned him yet she’d never know. How she was still conscious for that matter.

It felt like she was hanging on by a thread, numb to everything except intense pleasure. It possessed her, forced her hips to gyrate, her muscles to tense, her claws to dig into his shoulders, her pussy to clamp his tongue tight.

It screwed her eyes shut as rapture exploded from her core, rippled to her extremities and elicited a silent scream.

May looked down with a flushed expression dotted in sweat. He gazed into her hazy blue eyes and lapped up her cum. She tasted herself when he gave her another deep kiss.

Although the orgasm had consumed her energy, his affectionate lips and vigorous tit massages moistened her pussy again in a matter of seconds.

Her hands roamed beneath his shirt and his bulge grinded on her navel as they immersed into a full-blown make out session. Although May anticipated what was coming next, her heart fluttered when she felt him undoing his pants.

If anyone would’ve predicted her first time was going to be up against a tree in the middle of Route 104 with her boyfriend’s scumbag nemesis, she would’ve called them crazy, amongst other colourful expletives. But here they were.

She had no illusions this was about anything more than sex for Gary. Well, that and one-upping Ash. May never knew the conception of their rivalry, only vague details of its existence, and while she’d never act with the intent to hurt Ash, the intent to experience ultimate pleasure was beyond her will to resist, even in the midst of a war between the two boys.

It was ugly. Love could be ugly too. Everything could be fair.

His pants dropped around his ankles.

She gasped as he scooped the back of her thighs and hoisted her off the ground.

Then she felt it. Big. Round. Probing at her entrance.

Too big, she imagined, as it prodded blindly for the way in. Granted, with their hot and heavy bodies wedged together, neither of them had the vantage to make the consummation seamless.

His eager dick slipped and slid over her juices, occasionally grazing her clit to blissful effect. It thrilled and frightened her. The longer he prolonged it, the more anxious she became, nervous someone might spot them, nervous she’d miss out on cheating.

“Do it,” she begged. “Now!”

Gary was taken aback. He’d underestimated the effect of his own charm. Grinning, he reached under her elevated thighs and aligned his erection with her entrance.

May exchanged eye contact with a Taillow soaring overhead. In that brief glimpse, she saw guilt reflected in its eyes. The bird pokémon flew out of view, and a second later, May lost her virginity.

Despite his slow and meticulous efforts, she grimaced with every thrust, parting her further away from innocence. Her pussy stretched open with almost as much pain as pleasure.

Two fingers couldn’t have prepared her for the enormity to come. He pressed her back against the tree and kissed her throat, tasting the moans vibrating in her voice box. Between laboured breaths, he murmured shock and elation at her tightness.

May would’ve complimented his size in return but pants and moans worked her mouth beyond coherence, her hungry snatch feeding on more and more cock, salivating around his girth.

He was so damn big, granted, she didn’t have anyone to compare him to. One thing was for sure though, Ash wouldn’t have the balls to fuck her raw in the woods. The thrill magnified every sordid sensation perverting her. She never wanted her boyfriend’s enemy to stop fucking her.

While May grew more accustomed to penetration, Gary grew less patient in his thrusting. Fingernails digging into her thighs, he ploughed past the thin crotch area of her slingshot bikini, pounding her pussy at a furious pace, a battering ram on fire.

Each thrust knocked her ass against the tree, dragging her back up its bark. The discomfort was a small price to pay for the pleasure being pumped into her.

It alarmed her how fast she’d gone from sexually frustrated to taking more dick than she could handle. He immersed himself to the hilt of his cock, pulled back, then shoved it in again, and again, and again, a squelch and a cry each time. It was as though he was trying to shove his entire body through her virgin gash.

She felt every last bit of him and then some. He brushed aside the strap of her bikini top to free her neglected nipple, if just to watch both of her breasts bouncing in tandem.

Pressing his body against hers, he squished her chest as their moan-full mouths reunited. The sloppy kiss was rocky from the turbulence of his thrusting. Drenched in each other’s sweat and saliva, they fucked like wild pokémon in heat.

Her pussy showered lust all over his shins and the roots of the tree. Several pumps and squelches later, May broke the kiss to scream euphoria at a second orgasm.

Gary warned her he was close to his own and wanted to sprint to the finish. The ricochet of wet smacks doubled in speed and intensity, the ripples bobbing her head up and down, dishevelling her bandana.

She wrapped her arms around his shoulders, weeping in ecstasy as he climbed within touching distance of her cervix, filling her snatch to the brim repeatedly.

Then, all too abruptly, her thighs slipped out of his sweaty grasps.

May touched down, feeling like she’d come off a rollercoaster, a little weary and off balance. She slumped to the bottom of the tree but barely had a moment to catch her breath when Gary aimed his cock at her face.

She flinched as a hot spurt smacked her between the eyes. Grunting, he aimed more bursts at her lips and chest. May was out of it, heaving as he bathed her in a white-hot shower of spunk, his essence sliding down the slopes of her breasts.

Gary did up his trousers with a smirk. “Always one step ahead of Ash,” he said, admiring his work. “Some things never change.”

“Wait.” May raised her hand before he fled the scene. “You can’t… you can’t tell Ash.”

Gary didn’t get it. After the spin he’d just put her through, all she could say was ‘don’t tell Ash’? “Whatever.” He waved a hand whilst walking away. “Till the next time. Try not to dream about me too much.”

As May stooped with her body dripping another guy’s cum, a sudden wave of regret crashed over her, her senses rapidly returning. “Ash…”

She tidied herself up the best she could, wrapping her towel around her waist once more, then rushed back to camp despite the soreness in her crotch.


. . .


May returned to find Ash and his pokémon had ransacked the picnic baskets. Under normal circumstances, she would’ve been pissed. All she could do after her jaunt was give a bittersweet smile.

“Hey, May. Where did you go?” Ash asked with a mouth full of sandwich.

“Oh… just to get some Pecha Berries.”

“Oh yeah. Glad you’re back. We were starting to worry about you.”

“Pika!” Pikachu climbed onto her shoulder. The rodent pokémon offered a hug when he noticed odd imprints on her neck. “Pika pi?”

May hid the hickey under her hand hurriedly. “Oh that? That’s nothing. Just a little scratch.” She chuckled sheepishly.

Ash ignored her awkwardness. “So, where are they?”

“Where’s what?”

“The Pecha Berries?”

May smacked her forehead. “Oh, that’s right. I, uh, kind of forgot them, I guess.”

“Too bad.” Ash sank. “My pokémon were really looking forward to May’s Pink Surprise. Just the right thing to get them jacked up for tomorrow’s battle!”

“I’m so sorry, Ash. I’ll see if I can make something just as good, okay?”

The day went on as normal. For Ash and his pokémon anyway. Eating, training, eating some more, training for dessert.

Meanwhile, May shouldered the guilt of her deceit.

Even as the sun went down and the moon came up, the terrible incident replayed through her consciousness. It kept her up, lying in her sleeping bag, gazing at the stars while Ash and Pikachu snored the night away. She couldn’t believe she’d discarded her virginity in such a sleazy way.

The more she thought about it, the more vivid the imagery, the sin, the passion. Before she knew what was she doing, her hand slipped through her pyjama bottoms and her imagination ran wild into the night.


. . .


Gary looked at the stars through his window, patting the Shieldon sitting on the sill. He owed all his gratitude to its Oscar-winning, damsel-in-distress performance. If it wasn’t for that, he might’ve had a harder time pinning down his target.

And what a target it was.

When he closed his eyes, he could still feel her soft, tight body pressed against that tree, still see her magnificent bosom bouncing at his behest, still hear her hot moans pouring down his ear as he drove Ash’s girl to her climax.

Pity for the time constraint. He would’ve loved to give her plenty more. Gary chuckled, just imagining the look on Brock’s face when he found out.

For the first night in a while, Gary didn’t dream about Misty.


. . .


“We won, we won!” Ash launched Pikachu in the air. Trainer and pokémon were overcome with laughter and triumph.

Gary grunted. “Lucky break. Golem, return.” Defeated, the rock-type was zapped up into its Poké Ball.

The only thing more annoying than Ash Ketchum was losing to Ash Ketchum in a pokémon battle. Watching his over-the-top celebration grated the nerves.

May’s rejoice seemed somewhat subdued, not that the overjoyed trainer noticed. She shied away whenever Gary glanced in her direction. Although he’d never admit it, Gary had been hoping to impress her by destroying her boyfriend on the battlefield, as if destroying her pussy hadn’t been enough already.

“It’s skill, Gary. Skill,” Ash said.

“Pika-chu!” The rodent agreed.

“Whatever,” Gary said. “You make me nauseous.”

Ash stuck his tongue out. “Sore loser. We’re outta here. Till the next time you want to lose to me.” Ash and May set off.

“Hold it. Where to?”

“Uh, I don’t see why you care but since Petalburg City is around the corner, we’ve decided to drop by and visit May’s folks.”

“Hm, interesting.” Gary tapped his chin. “I’m headed the same way,” he decided.

“Uh? Really?”

“Yeah. I’ve got a paper on the habitats of Shieldon to present to Professor Birch.” He jumped between Ash and May, wrapping his arms around their shoulders. “It’s your lucky day. You get to travel with me.”

“Yeah… real lucky,” Ash droned. “Just try to stay out of my way, okay?”

“Trust me, Ash,” Gary said as they began to walk. He snuck a pinch of May’s ass. “That’s going to be the least of your worries.”

She glanced at him in the corner of her eye. Her lips twitched ever so slightly.

‘On the contrary, Ash, thought Gary. ‘I won.’

. . . TO BE CONTINUED . . .

Author’s Notes: Thanks for reading! Please rate and drop a review to let me know what you thought of this fic!

Special credit goes to revolverwing for the artwork that inspired this fan fic cover! As of the time of this writing, you can find more of the artist’s work here:


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