Beach Conquest (Pokemon) (Patreon)

Poll Winner

Themes: Beach Sex, Rough Sex, Fucked Silly

Summary: Based on this image. After Ash wins the Pokemon World Championship, Jessie finally realizes she's been wasting her life as a member of Team Rocket. More than that though, all of these girls and women circling Ash are too afraid to make the first move, or expect him to do it instead. But Jessie isn't so lacking in confidence. So SHE makes the first move... and reaps the rewards as a certain young man shows himself to be just as enthusiastic a lover as he is a Pokemon Master.

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They have the beach all to themselves. A private beach, beautiful and pristine with not a single other human being or even a Pokemon in sight. It was just more evidence that Jessie had made the right call. Grinning, she turns to her handsome companion.

“You really do bring me to the best places, Champion~”

Ash Ketchum flushes a bit at her flirtatious tone. Or maybe he’s blushing because of what she’s wearing. The purple bikini she has on isn’t that much more risqué than any other bikini… but it is still a bikini. And it’s one that rides high on her hips too, showing more of her thighs and waist, as well as her ass.

Still, it does the job, covering up all of the inappropriate bits. It’s not lingerie masquerading as a bikini, mostly because Jessie hadn’t wanted to accidentally cause Ash to pass out from a nosebleed rather than because she wasn’t trying to seduce him. She definitely was, but these things had to happen in the right way or else they could wind up ruined far too easily.

“Heh… glad you like it, Jessie. You know, I’m still kind of waiting for the other shoe to drop and this to all turn out to be a ploy to try and steal Pikachu again.”

Jessie scoffs, but also grins, not really taking offense to his words. After all, she can tell he doesn’t really mean them… but even if he did, it would kind of be fair.

They were a classic pair of Enemies to Lovers, really. She had spent over a decade trying to steal Ash’s Pokemon as a member of the dastardly Team Rocket. And he had spent a decade thwarting her and her partner James at every turn. Frankly, that should have been the first sign, but even after all these years, it wasn’t until she and James were cheering Ash on as he won the Pokemon World Championship that she came to several stark realizations.

Number One, they were never getting Ash’s Pokemon. It just wasn’t happening. Even after all this time, Jessie and James hadn’t managed to get promoted within Team Rocket. Meanwhile, Ash had become a literal Pokemon Master and Champion to boot. Trying to steal Ash’s Pokemon was like trying to steal Pokemon from… from Cynthia! An idiotic, moronic idea to be sure.

Number Two… they didn’t even really WANT to succeed. Or at least, Jessie didn’t… and frankly, James hadn’t really either in the end. Neither of them were particularly stupid. But they were idiots. Specifically, they were self-sabotaging idiots who got into the wrong line of work and because of the sunk cost fallacy, never bothered to get out. Until finally, that wake-up call.

Shaking her head in amusement, Jessie squeezes Ash’s hands and pulls him further out onto the beach until she finally finds a good spot and begins to set up towels and a beach umbrella with his help.

“You don’t have to worry about that anymore. James and I are out of Team Rocket. Even Meowth left. And James… well, he’s kind of nobility? And his parents actually died years ago, leaving him their entire fortune. So he and Meowth went off to see what would come of that, I suppose.”

Jessie had been afraid that James and Meowth would hate her for what she’d decided to do, but in the end they’d been surprisingly understanding. After cheering Ash on in the World Championships and going back to their hotel room together, the three members of Team Rocket had sat down and talked… a lot. And in the end, James and Meowth had been in full support of Jessie.

They clearly hadn’t been feeling the whole Team Rocket thing for a while, maybe even years, but Jessie was a domineering woman who didn’t take no for an answer so they’d been too afraid of what she might to do try and signal that they wanted to leave. She still felt a little bit bad about that, but at least all was well that ended well.

Taking out a bottle of lotion, Jessie lays down on her towel and hands it back to Ash with a coy grin.

“Rub me down, lover boy?”

Ash blushes… but if there’s one thing that Jessie can count on the man to do, it’s not back down from a challenge. He nods sharply, though he does blush even harder when she tells him he can’t just kneel on the side of her.

“Straddle me. That’ll make it easier and ensure you cover every part of my back.”

“… Sure, alright.”

Jessie lays down properly and then goes a step further by untying her bikini top, letting it fall on the towel. She’s now topless, though her breasts are still pushed into the towel and not visible, technically. Still, she can tell Ash notices from how he stiffens as he climbs on top of her, straddling her waist.

To his credit, he doesn’t comment. Instead, he squirts a generous helping of lotion into his palm and brings it down on her back, beginning to massage the lotion into her body as Jessie moans.

That was the kicker, really. Ash Ketchum did not lack in confidence. Even if he’d basically wound up being quite the short king, stagnating at a height that left most women towering over him despite being a full-grown man, Ash had never let that get to him. Instead, he seemed to make it his strength, allowing others to underestimate him so he could turn the tables on them.

Really, what he lacked was experience, plain and simple. Not experience with Pokemon, of course. The man was a Pokemon Master and now a Pokemon Champion as well. He was the cream of the crop when it came to training Pokemon and fighting alongside them. No, Ash lacked experience… with women.

Which was crazy, really. He had SO many women in his life. Every single place he went, Jessie swore he found a new girl to follow him around and basically make big doe-eyes at him. He was basically the Pokemon Trainer equivalent of a sailor… with a woman in every port and every town and every city and… well, you get the point.

Except, unlike those rascally sailors, Ash hadn’t done anything with all of the women that were drawn to him like a moth to flame. He’d had like… one kiss in his entire life and that was it. And Jessie should know, because she’d literally been following him around to try and steal his Pokemon for the entirety of his journey.

This part, Jessie didn’t feel bad about. Because if any of those fine women, many of whom were probably more worthy than her in the end, had wanted to make a move… they could have. If they didn’t understand by this point that Ash didn’t know a thing about romance or sex and he needed to be swept off of his feet instead of the other way around… then that was on them.

Jessie moans as Ash rubs the lotion into her back. Then, just as he’s finishing up and climbing off of her… she twists and flips around, looking up at him as he freezes up in place at the sight of her full, bared breasts just… in his field of view. Her rock hard nipples were driving her crazy rubbing against the beach towel and all that, but now they’re out in the open and being played with by the cool sea air.

Smiling coyly, Jessie glances at the discarded lotion bottle.

“Do my front now, please?”

Ash hesitates for only a moment before swallowing and nodding rapidly. He gets some more lotion in his hand and begins to do her front, starting with her sides and her abdomen… but eventually, when she gives him an encouraging nod, moving his hands to her breasts.

He has no clue what he’s doing of course… but that’s never stopped Ash Ketchum before. Jessie moans under his inexperienced yet enthusiastic touch, her arms going above her head as she arches her back and pushes her tits into his fondling grasp. She loves it. She loves how rough he’s getting with her, how he’s just going to town on her chest like there’s no tomorrow.

“Nnngh… that’s it, Ash. Feels… so good…”

When she’d first approached Ash after breaking away from Team Rocket, he hadn’t believed her at first, not really. But she’d proven it to him… with her mouth on his dick. Yes, she’d sucked him off before they’d even gone on a first date. Yes, that was a little slutty of her. But let’s be honest, she owed him quite a lot for all the headaches she’d given him over the years. And what better way to prove her sincerity then by debasing and humiliating herself?

She’d even gone so far as to swallow for him and while she wouldn’t say that cinched it or anything, he’d at least been willing to give her a chance… something that Jessie knew infuriated all of the other women in his life to no end. But then to be fair, if they really wanted to be with Ash, where the fuck were they when he was becoming Pokemon Champion? It was disgraceful.

“You like that, huh? You like when I play with your tits, Jessie?”

Eyes lidded, she grins up at Ash as he tries his hand at dirty talk. It’s a little rough around the edges, but it’s made all the better by his authenticity.

“I love it, Ash~ I’m getting nice and wet for you… and I can feel you getting nice and hard for me.”

Ash blushes at that, only then realizing that he’d been subconsciously grinding his crotch into hers for a bit now. His throbbing erection, tenting his swim trunks, has been pushing against her bikini-clad sex for almost as long as he’s been fondling and playing with her lotion-coated titties.

When he goes to pull back, Jessie quickly reaches down and fondles his junk through his trunks.

“Don’t stop, silly. I want it. I want you to do whatever you want to me~”

Ash blushes again, before nodding with a serious look in his eye. He goes back to grinding on her while playing with her tits and Jessie just moans as he does so. Finally though, he reaches down and strips out of his swim trunks, letting his cock free. For a moment, he hesitates and Jessie giggles before hooking her thumbs into the waistband of her bikini bottoms and yanking them down her legs.

Revealing her drooling slit to Ash, she lounges back on the beach towel and makes a nice, lovely show of things. Posing for him, she gropes and squeezes her own breasts, while also framing her pussy lips down between her thighs.

“How do you want me, Ash? You can have your mouth again. Or you can fuck my tits if you like. Or… you can go for the real prize and fuck me properly, down there.”

They both know he’s a virgin. That doesn’t mean Ash doesn’t know what sex is though. But Jessie had certainly introduced himself to the more practical side of things when she’d gone down on him back at the start of their relationship. Now… Ash swallows thickly and nods, before pulling her legs fully apart. His cock slaps down lightly on her gushing wet sex and Jessie’s breath hitches as he begins to rub against her cunt.

“I’ve never… done this before. I hope I get it right.”

Jessie moans, pinching her own nipples.

“Don’t worry about getting it right, Ash. Just do what comes naturally. A man and his woman, that’s what we are. And as the man… you should take your woman. Just do me one favor… don’t hold back~”

He looks startled for a moment… but in the end, Jessie gets precisely the reaction she’s hoping for when she says those words. Ash Ketchum, the man who never gave up on his dream and who never stopped fighting… gets a determined look on his face and a glint in his eye as he thrusts into her with all his might.

Jessie moans happily as Ash’s cock punches deep into her cunt. If she’d been dry or not as wet as she was, him fucking her this roughly right off the bat might have hurt her. But the truth was, Jessie had been waiting for this moment since she’d first sucked his dick… and she was honestly sopping wet by this point.

Ash encounters barely any resistance as he drives himself deep inside of her, his cock filling every inch of her cunt. Her inner walls still tighten around his dick of course, gripping and squeezing it to the best of their abilities, but ultimately he’s able to thrust in and out of her without hesitation and without even a second of slowing down.

Grabbing hold of his wrists, she brings his hands back to her tits. He doesn’t just fondle them anymore though, he kneads and mauls them, much to Jessie’s delight. And finally, without any input from her, Ash even goes so far as to drop his mouth down upon hers. Leaning forward, he captures her lips with his own and kisses her deeply, even as he fucks her there on the beach like a man possessed.

PLAP! PLAP! PLAP!

Jessie wraps her legs around Ash’s waist in turn, locking her ankles together behind his back. She wraps her arms around his neck, pulling him deeper into the kiss even as he continues to maul her fat chest to his heart’s content. His cock drives so deep inside of her with every thrust that Jessie thinks she might have screamed in ecstasy if it weren’t for Ash’s mouth muffling the noises coming out of her own.

They fuck there on the beach for what feels like an eternity but also no time at all. They boink like a pair of Buneary, going at it with no end in sight. However, all good things do come to an end and eventually Ash cums inside of her, signaling a natural stop to their fun. That’s after she’s already cum at least a dozen times herself though, so she can’t really complain.

Especially when they wind up continuing things later back at the beachside villa they’re staying in. After dinner, they retire to the bedroom and Jessie shows Ash how much more fun they can have together, while he shows her just how talented a lover he already is despite his relative inexperience.

Those other bitches really had missed out, hadn’t they? Ash Ketchum was hers and she was his, and even if it had taken an awfully long time for Jessie to realize it, she was finally right where she belonged. Impaled on Ash’s big fat cock.