The Red Rocket Crashes Into Pallet

BY : Magmos
Category: Pokemon > Het - Male/Female
Dragon prints: 1832
Disclaimer: I do not own anything here. All the settings and characters are ultimately owned by The Pokémon Company or Nintendo. I make no money off of this.

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Pain. That one simple word summed up everything about Jessie’s world at the moment. It wasn’t an excruciating kind of pain, the kind that made you scream and cry for it to stop. No, this was more the kind of ache that comes from either a bad night of drinking, or a good boxing round. It was the kind of pain that ensured that, while you weren’t suffering, the next few days were NOT going to be fun.

As she opened up her eyes, a new word entered into the description, dark. It was pitch black in every direction she could see and then some. Absolutely nothing, not even the white of her vest and skirt, was visible. As she massaged her head, she tried to retrace her steps as to what led her to her current situation, leading her to groan at the stupidity that led to her current situation.

It had been a routine day for her and her team. Following the twerps as they tried to get that brat with the hat into another league to lose, and stumbling upon someone who had some good Pokémon to steal. In this case, a miner who used a pack of Electrode and Voltorb as explosives. She didn’t even remember entirely what the plan to steal those explosive little bastards was, though she DID remember that it involved those big bulky suits that bomb squads used, three Ball Guy masks, and a net laced with super glue.

Things had been going well for awhile, heck, even the brat’s Pikachu was out of commission due to a bad stomach bug, but then that lunatic of a miner ordered all those overgrown poke balls to use explosion, which of course screwed the whole thing up beyond repair, launching James and Meowth into the stratosphere, but oddly enough sent Jessie flying into a nearby mine. Though much to her enjoyment, she did see the twerps get caught up in the blast as well.

The villainous redhead couldn’t help but chuckle at the memory, the sound alerting someone else in the cave. Someone with a VERY familiar and equally unwelcome voice.

“Hey! Who’s there!? Misty? Brock? Are you guys alright?” Jessie let out a groan in aggravation, realizing right from the first word just who that was.

“No luck there twerp! It’s me!”

Silence filled the darkness as neither party spoke for a moment, a silence that was broken by the other voice speaking up again.

“Me who?”

Jessie could feel her eyebrow twitch slightly. “Me who…ME brat! The beautiful woman who’s been following you and your friends for years now!?”

“…Misty’s been stalking me for years? Doing a bad job of it since we see each other every day…”

Jessie found herself stuttering in an odd combination of shock and fury at hearing that. Finally, she collected herself enough to just speak clearly, though with an annoyed growl. “I’m assuming you have a flashlight in that backpack of yours. Pull it out and point it at me.”

After a bit of rummaging, she saw a beam of light come from another side of the cave, revealing the spiky haired and Pokémon League hat wearing head of Ash Ketchum. After moving the light around for a moment, the beam of the light settled on Jessie, causing his eyes to widen in shock as he leaped back.

“Team Rocket!?”

Jessie smirked as she stood up and pointed a gloved finger at Ash. “That’s right twerp! Now, if you don’t want any trouble made double, you’ll hand over your Pikachu and the rest of your Pokémon!”

Ash just stared at the older woman with a confused look on his face. “Um…I don’t have them. I left them all at the Pokémon Center, remember? It’s why you guys thought it would be a good idea to steal all those Voltorb and Electrode before when I wouldn’t be able to help.” He then moved the light around the cave as he started to look for something. “Where’s the rest of your team at anyway?”

Jessie could feel her forehead begin to sweat as not only was her bluff called out, but called out in a way that ensured that even attempting it the way she did was a stupid idea. The fact that it was ASH of all people doing it just made it worse. Sighing with resignation, she just sat back down on the rocks.

“Probably in the next city over if the force of that explosion was any indication.” She spoke glumly. “So, why don’t you just find the exit so you can haul me off to jail and I can wait for James and Meowth to break me out?”

The beam from Ash’s flashlight zoomed around a bit more, eventually settling on a wall that looked to be made of a bunch of rocks and boulders piled atop each other, telltale signs of a cave in. “I…don’t think that’s happening any time soon.”

The duo just stared at the pile of rubble for a long moment before turning to look at each other. Their eyes widened as they suddenly realized the full extent of their situation, the knowledge causing them to leap away from one another and point fingers at the other and scream.

“YOU MEAN I’M SUCK IN HERE WITH YOU?!” their voices echoed out in the cave.

Jessie’s face took on an insulted sneer as she heard what Ash had to say. “What’s that supposed to mean brat!? You’re stuck alone with a gorgeous woman! This should be a dream come true for you!”

Ash just glared at the older woman. “Oh yeah, real dream come true for me! Being stuck with one of the people trying to steal Pikachu every other day! I’d rather be stuck here with a pack of Primape!”

The two continued to glare at one another before turning away with a simultaneous huff. “Well fine!” Jessie spat. “You just stay over there, and we’ll try and ignore each other till we’re rescued!”

“Works for me!” Ash shouted back, and settled in for a hopefully short wait.

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It was not a short wait. In fact, it was a wait that was still going on hours after their tiff. The entire time the two just sat on opposite ends (or what they thought were opposite ends at any rate) of the cave, growing more and more bored as the minutes passed. Just when both trainers felt their minds starting to crack, a loud sound came from one half of the duo that echoed through the area.

*Gurgle. Gorgle.*

Ash shined the light at Jessie, the Rocket member’s face almost as red as her hair and scratching the back of her head in embarrassment.

“Heh heh. It’s…been a bit since I last ate…”

Ash just stared at her for a moment before shutting off his light. A few clicking noises echoed from his side for a few seconds before the light returned, but rather than a focused beam is spread around, showing more of Ash as he stood up and walked over to Jessie. As he came closer, she could see that the flash light he’d been using was one of those fancier ones that can switch some bits around and be used as a lantern.

After reaching where Jessie had sat, Ash plopped his backpack on the ground and began rummaging through it, eventually pulling out a bag of dried fruit and jerky and handing it to the older woman.

“Here. Not gonna make you starve in here.”

Slowly, as though she were expecting the bag to burst into flame, Jessie took the offered bag and opened it up, taking a quick whiff of the contents. She then pulled out a piece of dried mean and tossed it in her mouth, chewing it a bit until the flavor hit her tongue in earnest. As her eyes watered in happiness at the first bit of real food she’d had in awhile, Jessie tore into the bag, scarfing down everything she could.

While Jessie gorged herself on dried food, Ash had opted to pull out another, smaller, flashlight and take a look around the area a bit more. The cave was actually a fair bit larger than he’d expected, with plenty of space for the two of them to use. The best thing he found though was that the cave had a small river running through it.

“Well,” Ash started as he remembered what he could about wilderness survival involving water, “we shouldn’t get too thirsty here at least!” He then turned back to Jessie who was currently licking at the now shredded remains of the bag. “We might still go hungry though.”

Jessie had the decency to look somewhat embarrassed at her lack of table manners, but she quickly covered it up with haughty airs, her nose pointing up in the air. “Humph. Well excuse me for not being able to eat decently every day. Not all of us can make money off of Pokémon battling.”

“You could though.” Jessie’s eyes widened a bit as she heard that. “I mean, you and James aren’t the best I’ve seen, but you could win more than a few Pokémon battles if you actually focused on it and trained.”

Jessie just stared at the younger trainer for a moment more before turning away, trying desperately to maintain an aloof air. “Hmph. Like the guy who keeps choking in the league’s matches would know what he was talking about!”

Ash glared at Jessie’s backside hard enough for the other trainer to feel it and turned away as well. Quiet returned as the two trainers ostensibly refused to talk to the other. Eventually though, Ash broke the silence.

“So, why DID you join Team Rocket anyway?”

Jessie jumped a bit at the sudden question and turned to look at Ash who was still staring at the wall. “Why do YOU care, brat?” She spat out.

Ash just shrugged. “I’m bored, and it looks like we’re gonna be here awhile. If you’ve got any other ideas to keep ourselves busy other than talking, I’d love to hear it.”

“Jessie just stared at Ash for a bit before sighing and lying down on her back. “Well, if you must know, it wasn’t actually my first choice.” She looked a bit wistful as she remembered her past attempts at employment. “I’ve tried so many other things. Tried to be a nurse, but the classes were full and all I could get was the training courses Chansey go through. Failed that. I tried to be an idol, which went just as badly.”

Ash actually turned to her with a confused look on his face. “Really? How? I mean, I can see how the nurse thing wouldn’t work out with your attitude, but with how often you’ve fooled me and my friends you seem like a pretty good idol just for the whole acting part.”

Jessie actually smiled at hearing that. Granted, the bit about the Nurse attitude irked her, but she’d LONG come to terms with the fact it really would’ve been a bad match for her just on personality. “Well thank you for saying that brat, that might actually mean something if you and the other twerps weren’t as sharp as a bag of hammers.” Her smile only widened as Ash just turned his head indignantly. “Anyway, everything else I tried I failed miserably at, so I ended up just following in my mother’s footsteps and joined Team Rocket.”

Ash stared at her with wide eyes at hearing that. “Your mother was part of Team Rocket!?”

Jessie’s smile took on a much sadder look. “Yeah. She was. A class A agent too. The ‘Ideal of Team Rocket’ as the old boss used to say.”

Ash was quiet for a bit as he thought on what he could possibly say about that. Finally, he just said the first thing that came to mind. “She…she must be very proud of you then.” He then winced as he saw Jessie’s smile fall completely. A strong sense of shame filled him as he realized that, due to her MANY failures in trying to catch Pikachu, Jessie was probably not on the best of terms with her mother. Granted, he wasn’t ashamed of stopping her from stealing his friend, but he didn’t like the idea of twisting a dagger in a wound like that. Before he could apologize though, Jessie said something the completely floored him.

“I wouldn’t know. She went missing when I was still a little girl.”

Ash’s mind just went blank at hearing that. Looking at the younger trainer with a small frown on her face, Jessie continued on. “I don’t remember all the details, but I remember the old boss had sent her out to catch a rare Pokémon.” The frown deepened as Jessie was clearly struggling to keep composed. “The last thing she wanted from me was just a photograph of me smiling, but I was so upset at her leaving me behind like that, I couldn’t do it. I just couldn’t stop crying no matter how much I tried. Then, she went missing in an avalanche while chasing down some rare Pokémon I can’t even remember the name of.” She stopped there, breathing a bit deeply as she tried to recollect herself.

Ash could only stare at the older woman in no small amount of shock. He knew James had had his own tragedy in life, but he never even considered Jessie may have had a past like that, and he couldn’t help but sympathize with the red head. Finally, he cracked a bit himself.

“I’m sorry.” Jessie, a few tears trailing down her face, turned to look at him. “I…I can’t even imagine what that must’ve been like. If…if that…if that had happened to my mom I don’t know what I’d do…”

Jessie sniffled a bit as a small smirk returned to her face. “Oh? Are you close with your mother brat?”

Ash nodded. “Yeah. I am. My dad wasn’t around when I was growing up, so for all my life I was all my mom really had.” He smiled a bit as he traveled on his own path down memory lane. “I still remember when me and Pikachu left Pallet. She’d gotten everyone she could together to see me off as best as they could. Then she told me, in front of half the town, how she’d packed me extra underwear.”

Another moment of silence came between the two that lasted until a loud snort came from Jessie, followed by a muffled noise coming from her mouth before she just burst out laughing, rolling around on the ground and holding her sides.

“PFFFT HAHAHA! EXTRA UNDERWEAR! AND IN FRONT OF THE WHOLE TOWN!? HAHAHA!”

Ash just smiled and continued. “Well, in her defense, Pikachu DID zap everyone right before that. Don’t think she was thinking too clearly.” Jessie just started to laugh even harder at hearing that, her feet now kicking alongside her rolling.

Eventually though, she did calm down enough to actually talk normally again. “Ha, ha, hoo. Nice to see me, Meowth and James aren’t the ONLY ones to get zapped on a regular basis like that. Thanks brat, I really needed that.” Ash just smiled, not even bristling at the brat comment.

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A day had passed since their conversation, and the two trainers had since gotten more things figured out about their situation. First, the food situation, while bad, wasn’t dire. The cave was full of mushrooms that, according to Jessie, were perfectly edible. Combined with the remaining dried food Ash had, their food should last them a good while if they rationed properly. The river had a few Pokémon swim through it, but it was pretty much nothing but Magikarp which ensured they’d be more trouble than they were worth trying to eat.

Secondly, the river’s exit and entrance were too cramped for the humans to try and crawl through. So any escape attempt through there was doomed to failure.

Finally, the river wasn’t the only water source in the area. There was also a large hot spring in the cave that would allow for more comfortable bathing than the cold river.

Sadly though, entertainment options were still quite limited, which led Jessie to ask something very personal.

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“So, you and the twerpette, anything happening there?”

Ash and Jessie were around the hot spring, Jessie in the spring and bathing, and Ash off to the side a bit waiting his turn and pointedly trying NOT to look at Jessie. Hearing that question, the Ketchum lad’s head tilted in confusion.

“Anything happening? What do you mean?”

Ash could almost feel Jessie smirk at that. “You know, anything happening? I mean, you two were traveling all alone the Orange Islands for a good bit. Just a boy and a girl, no one to distract each other or get in the way...”

“…I don’t follow.”

Jessie could feel her eye twitch as amusement gave way to irritation from the dense wall that was Ash’s mind. “I’m saying, have you and that scrawny redhead travelling with you ever had sex!?”

Ash’s eyes shot open wide as he tumbled backwards from shock, landing into the spring. After flailing in the water a bit, he turned to look at Jessie, whose hair was currently down and partially covering her face.

“WHAT!? N-N-NO! We haven’t! I never!”

Jessie’s smirk widened as she took in how flustered Ash had become, clearly enjoying how embarrassed the person who’d caused her no small amount of headaches was. Finally, she waved him off with a wet hand. “Calm down runt, I was only teasing. Still though that is surprising.” She then looked contemplative, her hand now stroking her chin. “With how long you two have been traveling with each other, you’d think you would’ve at least kissed by now.”

Ash’s face took on an interesting red hue as he turned around and started twiddling his fingers. “Well we haven’t all right? Is that so weird?”

“A little bit.” The older trainer said bluntly, causing Ash to sink a bit into the water. “I mean, I know I make fun of how scrawny she is, but she IS cute in her own way. Are you gonna tell me you aren’t just a LITTLE interested?”

“Well…I…” Ash stammered out before finally opting to just bite the bullet. “Yeah. Yeah I am. I’m VERY interested. Ever since I saw her in that Kimono back with those giant robot Pokémon I was interested.”

Jessie just nodded and leaned back. “Hmm. She DID look good with her hair down, huh? What about that mermaid outfit she had during your second trip to Cerulean City?” She let out a chuckle as Ash’s head started to let out steam. “So why haven’t you said anything to her?”

The younger trainer let out a sigh. “I’ve…thought about it…but…I don’t want to risk losing her. She’s one of my best friends. I could handle her saying she didn’t like me, but I couldn’t deal with her deciding I made things awkward and leaving.

Jessie just stared as Ash for a moment before letting out a quiet snicker, causing Ash to glare at her with a harsh look.

“Sorry,” she forced out, “but that just sounded like some REALLY melodramatic angst from a fanfic author who bit off WAY more than he could chew.”

Ouch.

“Well what about you and James!?” Ash shot back, pointing at the bathing redhead. “Have you and him ever tried anything!?”

“Nope,” Jessie spoke without a second’s hesitation, “but not because I couldn’t bring myself to ask. James…let’s just say that your squinting friend is more his type and leave it at that, shall we?”

Jessie couldn’t help but giggle at Ash’s confused look at hearing that. “Poor dear, so young and so unused to the world and its secrets. I should do my duty for those less mature than I, and help guide you, shouldn’t I?”

Ash just grumbled out as he slid more into the water. “Don’t know what you’re talking about, you’re not that much older than me.”

Jessie just smiled wider as she slowly stood up from the water, causing Ash to realize something that he’d somehow managed to forget in all this.

Jessie had been bathing.

He then realized something very important about that fact.

Jessie was very, very, naked, and on full display.

As the water trailed down her body, tracing her more than generous curves, Ash could only stare mesmerized by the sight. Her legs seemed to be miles long and smoother than melted butter, her hips were wide and looked so very nice to hold with a soft plush and oh so spankable ass behind them and a neatly trimmed tuft of red hair covering her snatch, her stomach thin and taught with plenty of exercise, and her breasts stood firm and large.

Ash was suddenly reminded of that same feeling he had when he saw Misty in that Mermaid outfit. The whole situation left him too stunned to really speak any further as he felt his face heat up to temperatures hotter than the hot spring he was in.

Jessie’s red lips just smiled further as she reached down to Ash’s face and wiped around his nose, pulling her limb back with a bit of red blood that had dripped out. “Well now,” she spoke with no small amount of amusement, “at least we know you and James don’t have much in common.” With that, she strode out of the spring, gathering her clothes and leaving the younger trainer in a blushing stupor.

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Hours later when the two had gone off to bed, Jessie, now dressed in her standard Rocket outfit and her hair styled in her trademark solid curl, found herself unable to sleep. Staring up at the ceiling of the cave, she found herself thinking about her conversation with Ash back in the baths, and feeling something she wasn’t used to feeling.

Guilt.

Oh, it wasn’t particularly strong, not one of those things that would leave her scrubbing at her hands screaming “out damned spot”, but it was enough to bother her a bit. There they were, the runt bleeding his heart out to her, and she just made fun of him for it. Honestly, she’d done a lot of bad things to people, but that just seemed particularly petty even by her standards. Grunting in frustration, she got up and strode over to where Ash had set up his own sleeping area, decision in mind. She was going to help the kid out with his lady troubles.

“Alright twerp,” Jessie began as she walked around a boulder that was blocking her off from Ketchum, “Lemme give you some…” Jessie’s face then turned a dark shade of red as her eyes widened and pupils shrunk. With a bad stumble, she bolted behind the oversized rock again, only to slowly peek out from behind it.

There was Ash, his pants around his ankles, and jerking himself off. While that alone would’ve been enough to cause Jessie to freak out like she did. No, that would be due to one small detail.

Unless she was hallucinating, Ash was hung like a goddamned Tauros.

As she got a second look, she found that she really wasn’t seeing things. Attached to the somewhat scrawny young man’s pelvis had to have been the largest dick she’d ever seen in her life! That thing looked to be as long as his thigh, and as thick as Jessie’s wrist!

“Rgh…” Ash moaned out, his eyes closed tight as her jerked himself off. “Misty…that’s it Misty…”

“Holy shit…” she whispered to herself as she watched Ash rapidly jerked himself, a bit of drool trailing down her mouth as she stared. “If he’s that big, it might be for the best he’s never fucked the twerpette. That thing would split a girl as scrawny as her in two!

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As Jessie stared, Ash was lost in his own fantasy. The start always varied a bit in location, but tonight it was rather simple. Just a nice little hotel room, with one other occupant lying on the bed.

On said bed was Misty, clad in a red and yellow bikini that clung to her body like a second skin and showed off her body fantastically from her long smooth legs, her flat stomach, to her modest chest, nipples poking up from under the cloth. With a sultry smile, the orange head lifted up a hand and gestured for Ash to come closer which he did with no small amount of haste, clamoring onto the mattress and crawling on top of it until he was atop Misty, the two trainers looking right at each other.

“Well Mr. Pokémon League Champion,” she began with an excited purr, “you’ve beaten the Elite 4, won the Pokémon League, and now you can have any girl you want.” She then moved her raised hand down till it was on the front of his crotch and began rubbing his rapidly growing member. “Why don’t you make me your starter woman?”

With a loud groan, Ash bent forward and pressed his lips against hers, an action Misty returned with gusto, the water trainer’s tongue darting into Ash’s mouth and engaging his tongue in a wrestling match. The two pressed against each other, Ash relishing in Misty’s smooth body as both trainers moaned into each other’s mouth.

Ash broke away from the kiss, a trail of saliva connecting to two, and leaned back to unbuckle and pull down his pants. As he was doing that, Misty crawled out from under him and, with one pull, untied and let fall her bikini top, revealing a pair of small breasts topped with bright pink nipples. As the cloth fluttered to the mattress, Ash’s member burst out from the front of his pants and pointed towards the now wide eyed imaginary Gym leader.

“Oh wow Ash,” she whispered as she traced the top of Ketchum’s dick, the tips of her fingers just barely touching the rock hard flesh below them, “you’d have to train just about any woman to be able to handle this thing; I sure hope the two of us will be able to do it.”

Ash was almost completely lost in the feeling from Misty touching his dick, but one word managed to get through his head. “Two? What do you…” Before he could continue, he felt a pair of gloved arms wrap around his chest, followed by something warm and soft enveloping the back and sides of his head.

“Oh, don’t worry Misty,” Ash heard a familiar voice speak, “between the both of us, I’d say we’ve got the twerp here well in hand.”

Looking up, Ash saw a familiar face, looking down at him with a smile formed from her red lips and a flirty wink on her face.

“J-Jessie?”

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“Jessie….” Ash groaned out in reality, a drop of pre trailing down his member.

Jessie’s eyes widened in shock at hearing that. Granted, her vanity ensured she was proud that she was in his fantasies, but she wasn’t exactly expecting to find out he fantasized about her. As she continued to watch, she could feel a familiar, and much neglected tingling in her nether regions, causing the curvy redhead to whimper slightly in aroused frustration. It had been a LONG time since she’d so much had been able to get a few moments away from Meowth and James for a little private time, let alone actually getting laid, and the sight, sounds, and musky smell in front of her was reminding her of just how long it had been.

Taking one more look at Ash’s face to see if he was paying attention and seeing he was still lost in his own little fantasy, Jessie went to work. She started by unzipping her white Rocket jacket, exposing a VERY tight fitting black top that did nothing to hide her erect nipples which she then pulled up with one quick jerk, exposing large breasts topped with dark red nipples with a good bounce. With one gloved hand, she began massaging and rubbing the mounds on her chest as her other hand reached down to her skirt, pulling up the small cloth and sliding her covered hand into her now dripping panties, and slid her middle finger into her soaked snatch while her palm rubbed up against her clit.

“Oh fuck yeah,” Jessie hissed as she leaned back in a spot that would allow her to keep watching Ash while she jilled herself off, “back in the saddle.”

Her hand on her breasts was nothing short of active, squeezing and massaging a breast, pinching its nipple, moving to the other and repeating the process and back again, each squeeze causing her breasts to spill out from between her fingers.

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In Ash’s fantasy, things were rapidly heating up. Ash had found himself pinned against Jessie due to the older woman’s surprisingly strong grip, his head nestled in between her soft tits, while Misty was face first in his crotch, nuzzling his member and lightly kissing the throbbing organ.

“What’s going on? Why is Jessie here?” The trainer from Pallet whispered. Sure, every now and then his fantasies would include another girl he met (or two, Heaven knows the Joys and Jennies always came as a set for the young man), but Jessie had never been included before.

Said older redhead let out a sultry giggle as her gloved hands started rubbing Ash’s chest. “Well, Misty and I got to talking, and we both decided that a champion like you should get some EXTRA special treatment…”

“Mmm.” Misty moaned as she gave the head of Ash’s member a particularly passionate kiss, breaking away with a loud smack. “MWAH!” She then looked at Ash with a heated smile. “So we decided who better to ensure that treatment than the two girls who know you best?” She then gave a cute out as she looked at Ash. “You don’t have any problem with that, do you Ash?”

Ash was quiet of a moment as he tried to comprehend what he’d just heard. Any further thoughts however, were cut off at the root as Misty lowered her head down to the head of his dick and wrapped her lips around the sensitive organ’s tip, her tongue swirling around it like a piece of candy. This caused the Ketchum lad to lean into Jessie who took advantage of the now distracted trainer by grabbing his hands and placing them on the sides of her breasts, encouraging him to squeeze her melons and press them against his head.

“Nope! No problem!” Ash said cheerfully as he turned his head to the left and began kissing and licking as Jessie’s left breast, causing the older woman to giggle from the sight and slightly ticklish sensation.

Misty meanwhile took this as an opportunity to keep going. Slowly her head slid down, swallowing up Ash’s member inch by inch, all the while humming slightly, causing vibrations to trail down Ash’s member and make the only male trainer in the room moan into Jessie’s tits. As she neared the base, she started pulling back up, dropping the humming and opting to suck instead, a loud slurping noise coming from her hollowing out mouth as she pulled up before reaching the head and moving back down, humming once more.

Jessie meanwhile, had removed Ash’s hands from her breasts and slid away from the younger man before pressing him down to the bed and straddling his stomach, looking down at the wide eyed trainer who was currently looking at the older woman’s figure in awe. With a smug grin, Jessie leaned over until her breasts were dangling right in front of Ash’s face.

Ash reached out and grasped a breast in each hand, both breasts being large enough that if Ash was using both hands on one he wouldn’t be able to cover it entirely, and began squeezing them randomly, drawing a light moan from Jessie.

“C’mon twerp.” She whispered in a heated tone. “Have some fun.” She then leaned in closer, putting her breasts mere inches from his face. With a loud gulp, Ash leaned his head up towards her red tipped nipple, wrapped his mouth around the hardening nub and gently sucked at it, causing the redhead above him to let out an appreciative moan.

“Oh yeah…good boy”

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Back in reality, Jessie was finding herself frustrated. One hand was down in her panties, two more fingers had joined her middle one in thrusting in and out of her dripping snatch, a soft squishing noise resulting from her efforts. Her hand that had once been pawing at her tits was now lifting up her left breast, bringing its nipple up and allowing her to latch her red lips onto the nub, slurping and sucking at it almost as loudly as the noises coming from her pussy. All the while, the woman in question let out muffled whines and moans as that desired release stayed JUST out of reach.

With a final frustrated grunt, Jessie let her arms drop, one final slurp coming from her lower lips as her fingers pulled out and her breast bouncing back into place on her chest.

“Damnit!” She moaned as her boot clad legs squirmed in unsatisfied aggravation. “It’s not enough! I need a bit more! But what!?” A loud drip drew her out of her aggravated distraction and back to Ash where she saw his member was now leaking surprisingly thick pre cum like a cracked pipe. The smell wafted through the air and filled her nose, causing a shudder to go throughout her body as her pussy spasmed in a min orgasm.

“You’ve got to be kidding me,” she moaned through the bliss. “How does he smell so GOOD!?” Her mind made up, Jessie crawled over to where Ash was sitting, the younger trainer still too lost in his fantasy and his own ministrations to notice her, and knelt down till her mouth was just above his dick. With a gulp of saliva to steady her nerves, she opened her mouth and leaned down…

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Back in Ash’s imagination, Ash had found himself on his back and his saliva coated member exposed to the air. Misty and Jessie were kneeling by his erect mast, each with a hand on his dick and gently stroking him as they carried a conversation.

“So,” Misty began with an even tone as she looked Jessie square in the eyes, “which one of us goes first?”

Jessie took on a mockingly contemplative look, her free hand placing a finger just on her chin as her eyes looked up. “Well, clearly it should be me. I mean, I’m pretty certain our not so little Champion here would split you apart if you tried to put him in while he was hard.”

Misty glared at the older woman and moved to try and straddle Ash, only to see that Jessie had a point. Just the head of Ash’s cock was large enough that trying to push it through the younger red head’s lower lips would be an uncomfortable experience and even if she managed to force it in, Ash’s length (which ended just under her belly button) would ensure he’d break her as he was. With a cute pout on her lips, Misty moved off of the Pallet trainer and Jessie quickly took her place. The older redhead quickly placed the tip of Ash’s member against her lower lips and slowly lowered herself, enveloping his cock in between her warm and wet walls.

Ash let out a groan at just how GOOD it felt to be in Jessie’s inviting pussy. Only the head of his dick was inside her, but it felt absolutely wonderful as she somehow made it feel like her pussy was sucking on his dick! His member twitched and throbbed as Ash felt his balls tighten for the first of hopefully many rounds of cum to fire into the Rocket trainer’s depths…

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“OH PHUCK!” Jessie screamed around Ash’s dick, her voice muffled by her mouth being wrapped around the younger trainer’s dick. Her eyes rolled to the back of her head as the taste of his pre filled her mouth, one of her hands back in her panties and finger fucking herself wildly once more while her other hand was on the ground, assisting her shaking knees in keeping her up.

“COM ON!” She continued to scream in her muffled voice, “COM FUR MEH! COM OHN THRP! COM!” She let out an excited squeal as she felt Ash’s member expand, just before it filled her mouth completely with one burst of hot cum, her cheeks bulging slightly from the sheer volume as a trail leaked out from her lips and down her mouth. Her pussy quivered heavily as the combination of the debauchery of what she was doing, the (surprisingly decent) taste of Ash’s thick load, and the ministrations of her fingers thrusting into her finally caused her to orgasm, her snatch all but spraying her juices under her with almost as much force as Ash’s dick was firing right now.

“OOOH PHUCK!” She shrieked, causing more of Ash’s jizz to fly out of her mouth as her body shook wildly as every inch of her being felt as though one of Pikachu’s lightning bolts had gone through her. Instinctively, she began gulping down Ketchum’s cum as quickly as she could, still sucking wildly to coax more of his seed out. Finally, he tapered out and with one final suck Jessie pulled back, the head of his cock leaving with a slight pop.

“Ohhh FUCK I needed that!” the curvy redhead moaned as she felt her body stop shaking. With one last gulp to make sure her moth was now empty, she looked up to see something she probably should’ve expected, but was honestly hoping not to.

Ash Ketchum, with his eyes almost bulging out of his head in shock at what he was seeing. The two trainers just stared at each other for a long moment before Ash broke the silence.

“Umm. Jessie…what were you doing?”

Jessie, managing to dredge up what dignity she could, just gulped down the cum still in her mouth, readjusted her clothes, and with all the grace she had, bolted to the other end of the cave without so much as a word, leaving Ash in a very dazed, and yet oddly satisfied state.

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The next few days in the cave for the two trainers were an awkward affair to say the least. Ash and Jessie kept their distance from one another for the most part, most of their interaction being limited to quick hellos and mutterings as they both tried to avoid eye contact with each other. Granted, no one would be able to blame them for that, the whole situation would make for an odd conversation at the best of times; let alone being trapped in a cave. Still, it did make for a rather lonely situation for the duo.

Eventually though, an issue arose that necessitated some discussion.

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The two trainers sat across from one another, neither looking directly at the other but closer than they had been the last couple of days. In between them lay a small collection of plastic bags holding various dried foods. As the two stared at the pile, Ash spoke what they were both thinking.

“We are running out of food.”

The trainers both let out a long sigh as they realized their situation had truly gotten to the point where things were getting bad.

“Okay,” Jessie began as she took another look at the food, “if we manage this stuff carefully, and focus more on the mushrooms in the cave, we might be able to last a week and some change. After that…” She didn’t feel the need to continue on. Both the Rocket Woman and the Pallet Trainer knew what that would mean and could only hope they’d get out soon.

As Ash stared at the food and tried to figure out the best way to ration out the food, Jessie found herself thinking back to that VERY awkward day, particularly the discussion they’d had before things got uncomfortable to talk about.

“Kid’s that hung, and he’s never had sex before. Now it seems like he’s gonna die before he can even get a chance to use it.” Jessie’s brow furrowed as that thought ran through her head. “How the hell is that fair? Someone that gifted should get a chance to enjoy what Arceus gave them! I should…I should…oh the hell with it, I was gonna do this the moment I saw that beast in his pants.” Her mind made up, Jessie stood up and walked to Ash. As the younger trainer stared at the taller redhead, she gestured for him to stand up, which he did.

As Ash stared up at the Lady Rocket, he opted to voice his concerns. “Um, what’s up Jessie?”

With a sigh to steady her nerves a bit, Jessie placed both of her gloved hands on the younger trainer’s shoulders, ensuring she had his full attention. “Look twer…er…Ash, our situation is bad, right?” Seeing Ash nod, she continued on, “we’re both probably going to die in here, and I know you haven’t had sex yet, right?” Ash blushed heavily but still nodded. “Well, I can’t say it sits right with me letting someone who’s been…willing to put up with me and James for so long go out like that, so I’m gonna make you an offer.” She then lifted her right hand off his shoulder and cupped the side of his face. “I’m willing to fuck your brains out so you don’t die a virgin in here. What do you say?”

If Ash was blushing before, that was nothing compared to the ketchup like hue his face had taken on at hearing that offer. Granted, he probably shouldn’t be THAT surprised at the offer after what all had happened a few days ago, but he still wasn’t expecting someone who’d been among his regular opponents to just out and ask that!

Still, he’d be lying if he said he hadn’t been thinking about it on a regular basis ever since the…incident. Feeling Jessie’s lips wrapped around his dick was one of the best feelings the younger trainer had felt in a long while, and the sight of her climbing out of the bath was still etched into his young mind. Had it not been for the combination of those two facts, he might have had the willpower to say no, as it stood though…

“Yes.” Ash whispered as Jessie just smiled at the younger trainer’s answer.

His answer was a given before she could even ask.

With a sigh of relief, Jessie’s hands moved to the front of Ash’s jacket and grabbed the blue cloth before pulling the younger trainer upwards a bit, causing him to stand on his toes. “Okay, just follow my lead, alright?” Without giving him a chance to answer, she firmly pressed her lips to his, drawing a light moan from both trainers. They held the kiss for a long moment before Jessie pulled back, leaving the two slightly out of breath as they stared at one another before Jessie, her body now burning, lunged back in, causing the duo to fall backwards onto the stone cave floor, the older woman atop the younger man as Jessie’s tongue forced its way into Ash’s mouth, quickly dominating Ash’s own organ.

As Jessie dominated their lip lock, Ash had found the courage to let his hands wander the redhead’s body. His bare fingers traced up and down the back of her exposed midriff, massaging the warm, smooth skin. With an annoyed grunt, Jessie grabbed one of his hands, broke off the kiss, and glared at the younger trainer.

“Look twerp, we’re about to fuck each other’s brains out. Show a little bit more drive here.” Her hand then drug Ash’s lower till he was palming her white mini-skirt clad ass. Seeing his eyes widen a bit, she squeezed his hand to try and encourage him to start groping her a little bit. “Okay?” Ash just nodded and continued to squeeze at her surprisingly soft ass.

Seeing he didn’t need guiding anymore, Jessie let her hands start wandering Ash’s body, feeling up the younger man’s surprisingly firm form. Her curiosity peaked, she broke off the kiss and began pulling at his shirt and jacket till both articles of clothing were pulled off the young man and thrown to the side without a care.

“Oooh!” Jessie cooed in an excited twitter as her gloved hands started to roam Ash’s chest. “Looks like the twerp isn’t so twerpy after all!” Indeed, while Ash wasn’t carrying a six pack, his body was still rather well toned. One doesn’t go through the trials and misadventures the average trainer does and not build SOME muscle after all, and Ash had been through more than what most trainers did.

Feeling emboldened at the praise, Ash’s other hand moved down to join its twin at Jessie’s ass, where it gave her still clothed booty a firm slap, drawing a gasp from the woman atop him. He then grabbed hold of her mini skirt and pulled it upwards, exposing her barely covered, black thong clad ass, before yanking off his gloves and grabbed hold of her jiggling ass cheeks, his fingers sinking into the soft flesh.

“And you’re not nearly as hard as you act.” Ash spoke as he thoroughly enjoyed the feeling of Jessie’s ass in his palms. He honestly couldn’t get enough of the plushness of the redhead’s ass, feeling it spill out between his fingers, the jiggling even a light slap could cause, it was almost addicting!

“Mmm.” Jessie moaned at Ash’s ministrations. “Not bad for your first time Ash, but you know another part of me is feeling a little neglected here.” She gave her chest a good shake hoping he’d get the hint. Ash, his usual thick headedness apparently cleared up at the moment, quickly got the hint and moved his hands to the front of her white jacket and pulled up on the zipper, loosening up the piece of cloth till Jessie could just yank it off, leaving her in her black under shirt. Her very, VERY tight undershirt.

The black cloth clung to Jessie’s chest almost like a second skin, her hardened nipples poking through the top only further enforcing this with the only thing left to the imagination being the color of the skin under it. Ash quickly dispersed said mystery by grabbing at the bottom of her shirt and pulling it up, causing her large breasts to bounce as they were exposed to the cool air.

Ash just stared wide eyed at the firm orbs on Jessie’s chest. Oh, seeing them in the bath was one thing, but up close like this, he was better able to appreciate what he was seeing. Each of Jessie’s breasts was a fair bit larger than a Poke ball, and topped with bright pink nipples. The younger trainer almost drooled at the sight as Jessie just smirked at his dumbfounded face.

“Well?” She asked as she leaned down, putting her breasts closer to Ash’s face. “Why don’t you have some fun?” With a rapid nod, Ash moved his hands to her chest and gently, almost fearfully as though the older woman would vanish, grasped her breasts and began kneading them, the excess tit flesh spilling out from between his fingers, the feel of her hardening nipples pressing against his palms and the sound of her gentle moans encouraging him.

“Mmm. Good boy,” Jessie groaned out as she felt a growing dampness in her neither. “Tell me, how do they feel?”

“They’re…they’re amazing…” Ash whispered in awe, “They’re so soft, but still firm. I could just touch them all day.”

Jessie’s grin widened as one of her hands moved behind Ash’s head and pulled him up a bit. “Well then, why don’t you see how they taste?”

Ash, not needing any coaching for once, leaned his head up and buried his face as best as he could in the valley made by her tits, nuzzling the warm soft skin with a soft groan. He then began licking and kissing at every inch he could, wet smacking sounds echoed through the cave as Jessie just closed her eyes and enjoyed Ash’s work. Slowly but surely, Ash’s lips found themselves wrapped around Jessie’s right nipple, sucking and pulling at the sensitive nub with enough force to cause her tit to stretch slightly if he pulled back.

Feeling the telltale sign of arousal trailing down her thighs, Jessie pushed Ash away, forcing him back onto the stone floor of the cave.

 “Hey, what gives!? I was just…” Any further complaints were cut off by Jessie placing a gloved finger on his lips.

“Shhh. Don’t worry twerp.” Jessie cooed as she scotched down till the trainers were eye to eye again. “It’s just time for me to have some fun. Trust me, you’re gonna love this.” With that, Jessie leaned down and kissed Ash again, but much lighter this time, more a peck than anything, before moving down his jaw and down his neck. All the while, she continued to peck and suck at his skin as she went, leaving red lipstick marks as she went. When she reached his chest, she opted to mix things up a bit and added her tongue to the mix. She lapped at the sweat beginning to form on his chest, trailing at every inch of his torso she could reach before she reached the top of his pants.

The older woman licked her lips as though she were at a banquet as she stared down at the massive bulge in Ash’s pants, a dark spot forming at the tip with the unmistakable scent of pre-cum wafting from it. Without a word, she quickly unbuttoned and unzipped the younger man’s jeans before yanking them down, allowing his member to bounce free.

“Oh, hello again!” Jessie spoke to the bobbing shaft cheerfully before looking back towards the trainer from Pallet. “Tell me Ash, have you ever heard of a Titfuck before?”

Ash looked contemplative for a moment before his face blanched in disgust; the thought of what should be incredibly painful acts involving Jessie’s nipples running through his head. “Not really. Doesn’t sound like it’d be too comfortable though. I mean, how would I even fit?”

Jessie gaped at the other trainer for a moment before bursting into a quick giggle fit. “Somehow, I can’t help but think I have an idea what you think it is.” With that, she grabbed her breasts and spread them a bit, making sure Ash’s dick was in between them. “Let me show you what I’m talking about.” Her breasts were then pressed together, enveloping Ash’s member in their warm softness. The male trainer’s eyes rolled into the back of his head, a loud moan rolling out of his throat as he felt what could only be described as warm soft pillows covered up his dick and begin rubbing it up and down.

“Oh god, Jessie that feels amaz…” A sudden slurping noise and new yet familiar sensation caused a shock of pleasure to fire up his spine. “AH!” Looking down, he could see that the head of his dick had been poking out from between Jessie’s breasts, and the redhead in question had taken some initiative and wrapped her lips around the fleshy tip, throwing in a light blowjob in the mix.

With a muffled giggle, Jessie began pushing downward, her breasts flattening a bit on Ash’s pelvis, and allowing more of his member to fill her mouth. After going as low as she could, she rose back up, a loud slurping noise filling the air as her cheeks hollowed form her sucking on the other trainer’s tip before going back down.

As she went, slowly picking up speed, the sound of the sucking from her mouth and the slaps of her tits slapping into Ash’s thighs echoed through the caves.

Ash, not yet used to the new sensations he was feeling, felt a familiar tingling I his testicles, the organs tensing up as his member expanded slightly. “Jessie! Jessie I’m…I’m cumming!” He tried desperately to warn her. Instead of pulling back, Jessie slammed down, her face nuzzling her own tits as she swallowed down as much of Ash’s cock as she could. With a jerk of his hips and a loud moan, Ash fired round after round of hot cum into the red-haired woman’s mouth which she greedily gulped down. Eventually he tapered off and his hips fell back to the ground, leaving the trainer from Pallet gasping for air.

Jessie, with one final slurp to make sure she left nothing behind, released her breasts and pulled her mouth off of Ash’s softening member with a light popping noise. With a smile, she looked at the younger trainer. “Thanks for the heads up runt. Most guys I’ve been with weren’t that considerate.

“No…no problem…” Ash gasped out. “I heard…that it doesn’t taste too good to drink that stuff.”

Jessie just chuckled as she stood up. “Well, I wouldn’t say YOURS tasted too bad, but you’re right. Still, rather not let that gunk mess up my hair.” With a flick of her wrist, her skirt fell to the ground, followed by her panties before she strode over to Ash’s head and straddled his face, both her knees falling to the side as she lowered herself as far as she comfortably could. “Now then,” she spoke in a husky whisper, “why don’t you return the favor?”

Ash gulped nervously as he took a good look at Jessie’s snatch. He didn’t know what to expect to see, but the sight and smells were certainly intriguing him. The lips and folds were a bright healthy pink, with a thick musky smell that Ash had to admit was rather nice. With a bit of determination, Ash lifted his head up, stuck out his tongue, and hesitantly licked at the very edge of Jessie’s pussy lips.

As the flavor hit his taste buds, Ash’s eyes widened as a hunger he wasn’t aware he had filled his mind. The moment the flavor of Jessie’s juices filled his mind, every instinct in his being demanded he get more! With a deep breath, he pushed his face right into Jessie’s snatch and began licking at every inch he could, no rhyme or reason beyond gathering more of her fluids.

“Oh yeah,” Jessie moaned, leaning back a bit as one hand kept her propped up and the other massaged her right breast, “that’s a good boy. Keep licking and you’ll get a nice little present.”

If Ash heard her he didn’t give much indication of it as he continued to lap and suck at her lower lips till any of her fluids were long gone. Desiring more, he moved his head more towards the center of Jessie’s vagina, his tongue slipping in as far as he could get it. Finding the apparent source of that amazing flavor, he began swilling said tongue in her depths, gathering up as much of her arousal fluids as he could, the sound of slurping and Jessie’s happy moans filling the cave as he went.

In an odd coincidence, as Ash plundered Jessie’s trove, his nose had started rubbing against the sensitive nub of her clit. A series of shocks ran through Jessie’s spine, causing the older woman to shudder in bliss and start rocking her hips trying to get him to do it again.

Ash, in a rather stunning display of intelligence, noticed that Jessie’s juices flowed a bit more every time his nose brushed that nub. That knowledge ingrained in his head, the Pallet trainer began trying to rub Jessie’s clit as much as he could while lapping at her depths.

This proved to be something of a mistake, as this caused Jessie to throw what little caution she was taking to the wind. With a feral growl, she spread her boot clad legs wider, dropping herself onto Ash’s face snatch first and grinding away at his face, her hips rolling back and forth wildly.

“OH YEAH! THAT’S IT ASH! THAT’S IT! MORE! MORE!”

This left Ash in a bit of a panic, his legs kicking as his hands slapped at Jessie’s thighs hoping to get her attention.

“JEPHY!” He screamed in a muffled voice. “GEH OOF! I CHNT BREAF!”

Seeing how Jessie wasn’t inclined to listen, and with his vision beginning to blur, Ash did the only thing he could think to do. Start trying to focus on licking and sucking the nub of Jessie’s clit as much as he could in a desperate attempt to get her to get off and calm down. Thankfully for Ash’s sake, this was enough to finally push the redhead over the edge.

“OH FUCK, OF SHIT, OH FUUUUCK YEEEES!” As Jessie screamed, she stopped her rocking against Ash’s face and arched her back, her pussy quivering wildly as she utterly drenched Ash’s face in cum. Finally, she collapsed backwards, allowing the younger trainer to breath once more as both attempted to catch their breath. As Jessie gulped down breaths of air, she turned to the side to see that, much to her happy surprise, Ash’s member had returned to its fully erect state.

“Well well, nice to see all that energy can be put to other use twerp.” Jessie purred as her gloved hand slowly rubbed Ash’s length. “So, you good for taking this further?” Ash, still dazed from the lack of air, could only give a thumbs up in response.

With a heated grin, the older redhead stood up again and lowered herself down till the tip of Ash’s dick was pressing against her entrance. She then looked Ash right in the eye. “So twerp, this is it. If you want to back out now, this is your last chance.”

Ash closed his eyes for a moment as he thought about this. “Is this really something I want to do? I know I’m probably gonna die down here, but its JESSIE from Team Rocket we’re talking about here! Before this, we’ve never had two kind words for each other!” He then opened his eyes and looked at Jessie’s curvy form, a light pout on her face as she looked at the younger trainer apparently having second thoughts. “Ok, I DO want to do this!” Without so much as a word, Ash grabbed Jessie’s hips and raised his hips up, sliding the head of his member past her folds.

Jessie let out an odd combination of a relived sigh and pleasured moan as she slowly dropped her hips down to meet Ash’s own, the older woman wincing a bit as she felt herself be filled more than she’d ever been used to, finally letting out a winded grunt as the younger trainer bottomed out inside of her.

“Holy SHIT kid!” She groaned in a mix that could only be called pleasured pain. “Thank god it’s me you’re doing this with! You’d have spilt that poor girl you’re usually with right in two!” She rotated her hips a bit, relishing in how full she was feeling. “Mmm. Should’ve done this YEARS ago!”

Ash moaned in agreement, the pressure from her warm velvet depths clamping down around his dick. Reaching up to grab Jessie’s tits again, gently massaging the large fleshy orbs, he attempted vainly to jerk his hips up.

“Jessie, c’mon!” He pleaded. “This feels too good! I want to keep going!”

“Oh ho?” Jessie chuckled, looking down at the younger man and raising a hand up, hiding her mouth with the back of the gloved limb. “All this time trying to steal your Pikachu, and all I needed to do was just mount you to make you start pleading for me…” The red-haired lady was cut off as Ash let out a low growl and tried to push her up. “Fine, fine. I’ll stop teasing you.

With that, she gently pressed both of her hands on Ash’s chest to better keep herself level and slowly, agonizingly slowly as far as Ash was concerned, lifted her hips up until just the tip of his member was still in her folds. Then, without warning, she slammed her hips back down, drawing a happy moan from Jessie as she was filled again, and a slightly pained groan from Ash as his hips hit the ground. Of course, the feeling of being wrapped up tight in Jessie’s dripping hot snatch again ensured he wasn’t going to complain.

Jessie would then repeat the motion, the sounds of both trainers’ hips meeting each other clapping faster and faster as she gradually picked up speed. Her breasts bounced wildly all the while, nearly hypnotizing Ash as he stared at her glorious orbs.

“You…you know…” Jessie panted out as she looked at the younger trainer below her, “you’re free to play with them if you…oooh!” anything else she had to say was cut off as Ash rose up, wrapping his arms around her bare back to better help him up, and began nuzzling Jessie’s tits as best as he could, alternating between sucking, licking, and rubbing as he went. “Good boy! You know how to make me feel good, don’t you? Oh yes…Oh yes!” Anything else she had to say fell into babbling and moaning.

The cave was filled with countless sounds at this point, from Jessie’s moans, Ash slurping and sucking at her firm breasts, and the slapping of their hips meeting one another now reaching a speed that made their fucking sound more like a fast clap. Unfortunately, Ash’s inexperience combined with the mixture of sounds, smells, and sensations was causing a familiar clenching feeling in his testes to build.

“Jessie! Jessie!” He yelled as best as he could between Jessie’s soft yet firm mounds. “I’m coming!”

Jessie, who was nearing her own release by this point, looked down at the younger trainer with wide eyed panic. “Wait! Don’t you dare! I’m not there yet so don’t you…” She was cut off as she heard Ash let out a long groan and a familiar warmth filled her depths, causing her eye to roll back in pleasure. “Ooooh fuck!”

Ash then collapsed, breathing heavily as Jessie glared down at him with an annoyed look. The younger trainer looked away with a fair amount of shame at the circumstances.

“S-sorry Jessie. I just felt so good and…” Jessie placed a gloved finger to his lips and silenced him before letting out her own sigh.

“It’s fine Ash. It’s your first time after all, can’t expect you to be some super stud just because you’re hung.”

“So…can I try again?” He asked with no small amount of hope. The older woman couldn’t help but chuckle at how excited he seemed.

“Sure. Just let me rest a miIIIN!” Jessie felt one of Ash’s hand grab her by a shoulder and proceeded to flip her onto her back, her boot clad legs flailing in a panic with Ash climbing atop her with his dick still buried in her snatch. “Wait! I’m not ready yet! Let me just rest a biIIIIIT!”

Ash, without a word and his face expressing grim determination, began thrusting wildly into Jessie’s depths, each thrust came quicker than Jessie had been going before and was hard enough to cause the redhead’s tits to jump upward. Jessie herself could do nothing but shriek in pleasure as Ash hammered away at her, her boot clad legs wrapping around the younger trainer and ensuring his every thrust would be shorter and quicker.

“OH FUCK YES!” Jessie screamed, her head flying back as her tongue dangled out of her mouth. “MORE! GIVE ME MORE YOU BIG DICKED LITTLE BASTARD! MAKE ME TASTE IT!” Before too much longer, Jessie felt a welcome quivering from her lower lips, causing their grip on Ash’s intruding member to tighten as she felt her long awaited orgasm hit her, her juices flooding out in a deluge mixed with Ash’s cum. “OH ASH!”

Ash, still sensitive from his own orgasm minutes before, quickly followed suit. His member expanded slightly before firing off one last stream of his seed into her depths, mixing with the sloppy mess beginning to leak out between them.

The two trainers found themselves collapsed in a sweaty, panting mess, limbs numb, brains fried, but generally feeling more content than when they had started. With no small amount of effort, Ash lifted himself up, and looked Jessie in the eye with a smug grin.

“Well? Did I do better?”

Jessie’s only response was to return that grin with one of her own before grabbing Ash by the head and pulling him towards her, pressing their lips together surprisingly tenderly considering who she was. Eventually she pulled back with a more genuine smile.

“Yes, yes you did.” She whispered, laying his head into her still heaving bosom as the two just enjoyed the afterglow.

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The day continued on as such, with the two continuing to “get to know” each other, over…

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Jessie was now lying on her side while Ash, sitting just above one of her legs while holding onto the other and propping it up on his shoulder for better leverage, thrust into her.

“That’s it Ash!” She moaned. “Just…like…THAT!”

With a loud scream, her pussy clamped down on Ash’s intruding member, drawing another orgasm out of him and mixing their juices into a puddle under them.

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And over…

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Ash, lying on his back, had his feet lifted into the air by the older redhead’s grip on his ankles causing his hips to hang in the air, his dick in Jessie’s depth as she slammed her hips into his.

“Jessie!” he screamed, “I…I’m gonna…”

“That’s it twerp!” She hissed, “Let it all out! I’m not stopping till you’re dryer than a Cubone’s helmet!” Her teeth clenched as Ash fired another burst of hot cum into her depths, causing her own orgasm to hit, her pussy clamping down once more.

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And over…

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Inside the hot spring, one could hear the sounds of moaning and light splashing. Inside, Jessie was leaned back against the edge of the spring, her water straightened hair hanging out the side while the rest of her floated in the water. Ash meanwhile was atop her, his head once again nestled between her breasts as he gently thrust in between her legs, almost as though he were falling asleep.

“Mmm.” Jessie moaned as she gently stroked Ash’s hair. “Not a bad way to spend the day, huh twerp?”

“Mmm hmm.” Ash muttered out as he nuzzled Jessie’s melons.

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All in all, it was a very productive day.

As day broke (Well, as much as day can break in a cave at any rate) the next morning, the two trainers could be found in a single spot for a change, nude and wrapped up in a large sleeping bag with Ash snuggled into Jessie’s side, both wearing quite content smiles on their faces. Eventually, Jessie’s eyes fluttered open, leading to her stretching a bit as she met the new day.

“Good GOD but I needed that!” She thought to herself quite happily. “Been too long since I got laid like that! Wish I knew how hung this twerp was before, could’ve had a lot more fun LONG ago!” Any further thoughts were cut short by a sudden noise. It wasn’t a particularly loud one, but it was fairly consistent and coming from the cave in. With a bit of concern, she started nudging at Ash. “Hey. Ash. Wake up.”

“Mmmph.” The younger trainer mumbled through sleep induced delirium. “Not right now Jessie. Let’s wait till after breakfast to have sex again…”

Jessie rolled her eyes with a slight smile at hearing that. “No you dummy, wake up. Something’s happening.” With a loud yawn he slowly rose up and followed her over to the collapsed entrance whereupon they both pressed their ears to the collection of piled rocks. After a moment they heard something they hadn’t heard in a few days.

“Hello!? Is anyone in here!? Ash!? Jessie!?”

The voice of a third person.

Both trainers’ eyes went wide as they heard that. Remembering their food situation caused both trainers to start hammering on the rocks and scream. “YES! WE’RE IN HERE! RIGHT HERE!”

“Ah! Great!” The third voice spoke cheerfully. “I was getting a little worried that this was gonna change from a rescue to a retrieval!” The voice was then muffled as a brief struggle could be heard before another, much more familiar voice could be heard.

“Ash!?” the voice of Misty echoed out in a relived panic. “Is that you!? Are you okay!?” Another struggle broke out as James’ voice then chimed in “Jessie!? Tell me you’re alright! I can’t go disguise shopping without you! I can’t negotiate discounts like you can!”

Both trainers broke out into wide grins at hearing those particular voices. “Yeah, we’re okay!” Ash shouted. “Low on food, but that just started to become a problem!”

One final struggle broke out as the first voice reasserted itself. “Confound it, back up and let me work before you make the situation WORSE! Okay, listen up you two, it’s gonna take me a bit to get things set up on this side to get you out. So, you go ahead and clean up what you can while I do that. Last thing we need is a damned Drddigon rampage because they found too much trash in their territory.”

Taking a moment to look at each other and realize they were both still nude, the two trainers blushed heavily. “Good idea!” Jessie shouted as she and Ash ran for their long discarded outfits. “Just tell us when you’re ready!”

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Thankfully, it hadn’t taken long for both trainers to make themselves look presentable, and it took less time to gather up any refuse that shouldn’t be left in a cave. Unfortunately, this left them in a rather uncomfortable silence as they stood next to each other, trying to look casual about having spent most of an entire day screwing each other’s brains out.

“…So…” Ash broke the silence awkwardly. “About yesterday…I just wanted to say thanks.”

Jessie attempted to wave him off. “It’s no problem; I just didn’t think you should die a virgin is all.”

Ash nodded slightly but continued on, “Still, I appreciate it. Never thought my first time would be with one of the prettiest girls I know.” Jessie went stiff at hearing that, her face turning tomato red, but Ash continued on. “So, do we just…go back to being enemies after this? Like nothing happened?”

Jessie closed her eyes and took a deep breath to steady herself before answering. “I don’t know. Look, just give me a bit to figure out where things stand with me, and I’ll get back to you on that. Okay?”

Before Ash could answer, the third voice chimed out as though he were speaking through a megaphone. “OKAY! CLEAR SOME ROOM IN THERE! WE’RE GONNA BLAST THIS WALL DOWN IN 3, 2, 1! EXPLOSION!”

The cracks in the cave in shined with a bright white light before a series of loud…well…explosions blasted out, sending the rocks and boulders scattering around in a fragmented frenzy of pebbles and dust. As the air cleared, Ash found himself shoved to the ground by two different weights.

The first was the familiar yellow furred form of Pikachu, the poor electric mouse sobbing in sheer misery over not being able to help him before, and the other was an almost equally weepy Misty. “Ash!” the shorter redhead in the cave screamed out as she clung to the Pallet trainer. “Thank goodness you’re alright!”  All Ash could do was just pat Misty and Pikachu’s backs and repeat how he was fine.

Not that Jessie was much better off. The moment the smoke cleared, she found herself wrapped up in one of the tightest bear hugs she’d ever go through as James clung to his teammate sobbing like a lunatic, with Meowth just looking on with a happy grin. “Oh Jessie! Please don’t do that again! Team Rocket just isn’t the same without you bossing me and Meowth around!” Jessie just pat her teammate on the head with a happy smile of her own.

The happy reunions were cut a tad short by the third voice, now revealed to be the Miner with the Electrode and Voltorb that drew Team Rocket in the first place. “Whoowee, nice to see a happy ending here! Lots of ways this could’ve ended tragically I’ll tell you what!”

Hearing the miner’s voice, combined with reuniting with their team’s leader, seemed to flip a switch in James and Meowth’s heads, causing both to turn on the other groups in the cave with fire in their eyes. “Alright then,” Meowth shouted, “Enough with the sappy stuff!”

“That’s right!” James chimed in, so frazzled that he started speaking lines that Meowth should be, “Now, hand over those exploding medicine balls you call Pokémon before ERK!”

James quickly found himself cut off by a gloved fist meeting the back of his head. Looking behind him, Meowth saw the quite irritated form of Jessie with a clenched fist. “Jess?! Whaddya think you’re GRK!” Another fist upside another head, and Meowth found himself joining James in cranial injury induced dizziness.

With an annoyed huff, Jessie grabbed her teammates and drug them away from the cave. “Learn to cut your losses you two. It’s been a rough couple of days, I’m done here.” She turned around to give one final wave towards Ash before marching off.

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“Brock, does something seem off about Ash?” Misty asked the third member of their group.

Days after the cave in, our familiar travelling trio of Ash, Misty, and Brock found themselves traversing the roads once more, looking for a new gym for Ash to challenge for a badge and eventually entrance into the Pokémon league! That said though, something was off about the group at the moment.

Ash, who was normally the first one in front of the group and leading them to their next destination (for better or worse with his sense of direction), had opted to hang behind the group. Aside from that, he was also being uncharacteristically quiet, barely saying much at all.

Brock just gave a little shrug. “Eh. He had a pretty close call back in that Cave. He’s probably still processing that. Just give him a couple more days and he’ll probably be right as rain again.”

Misty said nothing beyond turning back to look at Ash with a bit of concern before returning to the road. Of course, had she been paying more attention to the younger man in the group, she might have had a better idea on just what was going through his mind.

“Good grief, has Misty’s ass always been that tight!? And those legs, how does she keep them so smooth!?”

Specifically, the fact that his mind was filled to bursting looking at Misty. Indeed, his time with Jessie in the cave seemed to have finally awoken the sleeping dragon that was Ash’s hormones in full. Oh sure, he had noticed before as his masturbation habits could attest, but having actually had sex now seemed to make him FAR more aware of the appeal of women than he’d ever had before. Between Misty, meeting a Nurse Joy and Officer Jenny to get evaluated and give statements, and lacking any opportunity to “relive” himself, he’d quickly found himself becoming VERY flustered VERY easily to the point he was now desperately trying to keep his distance from Misty lest he risk doing something stupid.

“Hey Ash!” Misty’s voice broke his inner thoughts, causing Ash to look up at Misty who was now pointing at a sign. “Looks like we’re almost to Rose city!” She then clasped her hands together as her eyes sparkled in joy. “Finally, a nice hotel room! With showers! No more camping for a bit!”

Ash however, found himself distracted by the mention of showers as the mental images of Misty IN said shower ran through his head. The water trailing down her smooth body, dripping off her pink (as far as he knew), erect nipples, he couldn’t help but whimper a bit as he felt his pants become more constrained.

“Too bad there’s no gym though.” Brock mentioned as he stared at the sign. “Still, a private room with an actual bed would be nice.

“PRIVATE ROOM!?” Ash screamed in his head. “A private room means privacy! Privacy means neither Brock or Misty would be around! Brock and Misty not being around means I can FINALY deal with this!” Without so much as a word, Ash dashed forward like a Crobat outta hell, Pikachu just barely hanging onto his shoulder.

Misty and Brock just stared at the departing trainer for a moment before Brock spoke up. “Guess he’s dying for some decent room service.” Misty just massaged her brow and let out an annoyed sigh.

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About an hour later, Ash finally found himself in a nice little hotel room. Pikachu had found himself a corner to curl up in on the bed, Misty and Brock were in their own rooms, and in a few minutes he’d be set to deal with things in the bathroom and hopefully deal with his pent up issues. Just as he was about to stride off and “take care of business however, the phone in his room began ringing. With a twitchy eyebrow, he grabbed the phone and answered with every ounce of politeness he could manage.

“Yes…” He answered trying desperately not to sound irritated.

“Go to room 206 now.” The garbled voice on the other end spoke plainly. “Come alone.” The phone then clicked as whoever was on the other end hung up. Growling in no small amount of aggravation, Ash stormed out and all but sprinted down several halls till he found the room in question. Without so much as a second thought, he grabbed the handle and pushed the door open.

“Oh my, aren’t we forward?” A Very familiar and VERY welcome voice filled his ears, causing Ash to pause a moment and look into the room.

There on the bed, clad in her boots, gloves, and a surprisingly lacy set of black lingerie consisting of a pair of black panties and a matching bra, lay Jessie who was looking up at Ash with an amused grin on her face.

“Jessie? What…” Ash stammered out only for the older redhead to put a finger to her lips and hush.

“Shhh. Close the door and lock it.” As he did so, she continued on. “I’ve done a bit of thinking, and I’ve decided, that time in the cave is NOT going to be the last time you and I screw each other. So, here’s the deal. Any time I’m not busy with Rocket business, I’ll look you up for a good fuck. No strings attached like “Give me Pikachu and I’ll give you anal”, just a man and a woman playing the games men and women play. That sound good?” Ash just nodded rapidly, the tent in his pants leg jutting out for Jessie to see. “Well then, why don’t you see if you can take of my lingerie with your teeth?

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For the record? He could.

End of Chapter

 

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So, does anyone care to explain to me just why this particular ship is so rare? Like, seriously, this just confuses the ever living hell outta me. I’ve legit found more fanfics where Ash enters into a relationship with Pikachu than I have Ash and Jessie. Seriously, there’s like…twelve fanfics for that ship. Even Japan is pretty bare on that end, with ONE doujin that has her giving him a titfuck, and then has him and James banging Misty.

Is it because of the age difference? Can’t be. I’ve seen PLENTY of fanfic where Ash at least bangs a MILF from the series, let alone what other shows get up to.

Is it because they’re enemies? Like that’s ever stopped shippers before, especially with THIS franchise.

Honestly, the only thing that makes sense to me is that people are terrified of pissing off Rocketshippers. Which, yeah. That’s a legit fear right there. Some of you may be too young to remember, but Rocketshippers could be their own special brand of crazy back in the day. You’d think Jessie and James were tragic heroes and not, y’know, animal poachers and criminals. (Don’t get me wrong, I love Team Rocket but let’s not mince the fact that they ARE the villains in the show)

Well, anyway, I’ve done my own part to help tip the scales a bit more. Hopefully it was a good read. As always, review if you have commentary. I may get snippy, but I ultimately DO enjoy criticism. Also, this fic is entering the backburner pile, so while It’s not done, it’s also not getting much focus. Now, if you’ll excuse me…

The author closes a massive metal door with a sign attached that reads “Rocketshipper Protection Chamber. (Formally the site of Filthy Frank’s Weeaboo Protection Chamber)”



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