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Chapter Text

Okay, this is heavily based off of another fanfic by tommyGunn called 'Issei's MILF Conquest'.

In short this is of an aged up Ash Ketchum having a harem and banging the milfs of the Pokemon world bringing them into said harem... surprised this hasn't happened sooner.

Disclaimer: There's not too much of a story gonna be told here outside of the summary. This is a smut fic, short and simple.

Second Disclaimer: This chapter is really just to start up the story, so it might be a little off in terms of writing... more or less short.

Eight years after Ash had become the champion of the world, and achieved his dreams of becoming a Pokemon Master, things could not have been better for him. He eventually moved out of his mother's house and into his own now that he was old enough. Not only that, but he had also come across the many girls he met during his travels.

It started out innocent enough, then as the years went by, things got a little 'heated'. Not only had Ash practically grown up, but he finally settled down with his girlfriend... s. Yeah, first it was one, then it was three, then it was several. And with this harem of his, also came the aforementioned 'heated' moments.

Long story short, his home was eventually turned into a mansion just to fit every girl in his harem and there were many nights filled with passion and lust... maybe also during the day.

As of now, the Sinnoh League Champion Cynthia had come to challenge the young Pokemon Master to a friendly match. Though, what she's there for is something more.

(Ketchum Household, Battle Room)

"Garchomp is unable to battle. The winner of this battle is Ash Ketchum and Pikachu." Dawn calls out.

"You did good Garchomp. Get some rest." Cynthia says while petting the down dragon Pokemon before calling it back to its Pokeball.

"Not bad, Cynthia. Almost had me there." Ash says while walking up to the blonde woman.

"That's surprising, coming from the Master himself."

"He didn't get his title for nothing." Dawn says while standing up. "Though, he's been focusing more on some 'other' things lately. Right, hun?" She says while rubbing her belly.

"Yeah, but I still keep up my training. Right, Pikachu?" Ash says.

"Pika, Pi." Pikachu agreed.

"I see." Cynthia says before humming to herself. "Well, Ash, if it's not too much trouble, could I perhaps talk to you alone?"

"Oh yeah, sure." Ash says before Dawn and Pikachu left the room. "What is it you wanted to talk about?"

"Well, since you beat me, I believe I should reward you appropriately for so." The woman explained.

"There's no need to do that. I had fun battling you."

"Yes, well I don't think that's enough. Being of that, I believe I should extend my visit here for the time being."

"If you insist. What kind of reward?"

"Well, I was wondering if perhaps you have a guest room for more... 'privacy'?" She then says while leaning over a bit, causing her cleavage to jiggle slightly.

Ash blushed a bit, shaking his head. "P-Privacy for what exactly?"

She then took a step towards him, face to face with him. "I'd gladly show you. ~"

If he was still ten years old, he probably would've missed the obvious signs, but now that he was older... and have had done it so many times before, being of how many girls he's already married to at that point. He only smirked a bit.

(Ash's Room)

Once they arrived in the master bedroom, they hadn't wasted time and were already in the middle of making out. Ash already proved to be the dominant one as his tongue overpowered Cynthia's easily.

The blonde put her hands up his shirt and started feeling up his abs and chest. He returned the gesture by groping her ass and giving it a good squeeze. He showed how much he had learned from beforehand and deepening the kiss. She didn't know how he did it, but she could feel her body temperature starting to raise with each passing second, and she loved it.

They eventually stopped kissing a string of saliva connecting their lips. "Goodness." Cynthia says.

"Felt good?" Ash asked as she nodded. "You haven't seen anything yet."

Without warning, he then picked her up and hoisted her onto his shoulder. Then went over to the bed and plopped her down on it, causing her bust to jiggle afterward. He pinned her to it before she could do anything else and grabbed her orbs and started squeezing them with glee.

"Oh, so sudden." She moaned out.

"You're one to talk. Who was the one that asked for this?" He says before he

"Perhaps that's fair, but how about we do this properly." She says before removing his hands, then undoing her top and allowing her breasts to bounce out.

"Hell yeah." Ash says before grabbing them and fondling them.

"You like them? Go ahead, dear. Touch them to your hearts content."

And touch he did. He continued to play with her bust in every way he could. Rubbing them fully, letting them bounce for a second before grabbing them again, pulling them apart from each other before squishing them together as Cynthia moaned happily. He could feel his pants tighten around his crotch the longer he did this.

"They're so big and soft." Ash says while practically drooling.

"Keep going. It feels so good." Cynthia moaned out.

He played with them for another second before he leaned down and took one of her nipples into his mouth and started sucking on it. He would continue to do so, causing the Sinnoh champion to feel her face get hotter as she continued to moan aloud into the soundproof room.

After a bit, the blonde champion moved her hand downwards and grabbed the tent forming in the Master's pants and started rubbing it. Moments later, he pulled away from her breast before getting on his knees. He didn't waste time in undoing his pants and pulling out his monster of a cock. Cynthia's eyes widened as she started touching it.

Ash then sat down on her stomach, placing his rod right between her bust. He then grabbed both of her orbs before he started thrusting between them, his tip just barely reaching her mouth. She smiled as he continued to thrust, feeling the softness of her jugs around his member causing it to harden further as the seconds passed.

The woman just sat there and enjoyed letting him use her body for his enjoyment. The bed started to squeak from how much he was bucking his hips, a goofy smile on his face while he was doing such and the older woman loved seeing it.

"Feisty too." Cynthia says.

Ash chuckled at her little comment and sped up with his thrusts. The blonde champion then started licking the tip of his member, coating the tip in her saliva. That only encouraged the Master to continue.

This would continue for about a minute before Ash reached his climax and sprayed his load all over the woman's face. She caught some in her mouth while some got in her hair, especially the part covering her eye. She didn't seem to mind though.

"Sorry I didn't warn you." He says.

"It's fine, dear. So much though, you must have been really pent up." She tells him.

"That's actually just a light load."

"Oh really. Well, care to show me more? ~"

Ash simply smiled before they got off the bed. He decided to take the rest of his clothes off as Cynthia started taking the rest of her top off. As she bent over to slowly pull down her pants with her panties, showing her lovely thighs, asscheeks, asshole, and glistening pussy.

The Master couldn't contain himself and grabbed her by the hips while she was still bent over, causing her to gasp before impaling her pussy with his shaft, causing her to scream from how quick he moved.

They took a second to adjust before he pulled back and started thrusting back in, causing her to moan out loud.

"Fuck!" Cynthia says while putting her hands on the end of the bed to keep balance. "So big."

"And you're tight as hell." Ash then reeled a hand back before slapping her ass, watching it ripple as he did.

Hearing that, he decided to slap her ass again, leaving a handprint. She continued to moan with the sounds of wet slaps and the slickness of the Master's member going into her echoing throughout the room.

After a bit, Ash decided to lean over and grab her breasts squeezing them. Cynthia tried to keep her voice to herself but couldn't do so as he started moving his hips faster.

"So good!" She let out. "Please harder!"

After a minute, Ash decided to pull Cynthia up from the bed to his chest while continuing to thrust into her. Keeping his hands on her boobs, squeezing them harder while pinching her erect nipples. She nearly lost her balance again, leaning against him for support.

"Yes, please! More! Fuck me more!" She moaned again.

"Look at you. Coming after a boy, years than you and getting this turned on by his cock. What would people think of you? What would they say?"

"I don't care! Let them talk. It doesn't matter to me. AH!"

"Wait really?" Ash then walked back to the bed and pinned her to it. "Not a care in the world?"

"NO! Besides-ah... t-then they'd know I'm with-gh... a 'real' man."

"Heh, that's something I can get behind."

He then gave her ass another slap, turning it redder than it had before. He started bucking his hips harder and faster which only made the blonde Champion even louder before she came, spraying on his still moving shaft and getting some on the sheets.

"Cynthia, I'm gonna cum. Do want it outside or-?" Ash tells her.

"No! Keep it in! Please, let it all out in me!"

"Alright then. You asked for this."

He continued to thrust into her fast as piston, enjoying it as it lasts. He'd go hard enough until the blonde nearly grits her teeth as she felt his tip penetrate her womb entrance before his cream shot into it and started to fill her up.

"Yes..." She says as he thrusted one more time. "YES!"

He gave her one more thrust. He held her in place before pulling out, his cum starting to flow out and onto the sheets, dirtying them further.

"Yes..." Cynthia says under her breath with her eyes rolled up.

"Huh, maybe you were right. I guess I was a little pent up." Ash says while pulling on her asscheek a bit which caused more to spill out. "Good thing you prepared for this, right?"

"N... No..." She says as he rosed a brow. "I might be pregnant after this."

"Wait, what!?" He then says out of shock. "But... but... oh man."

"You will take responsibility, won't you?"

"Of course, yes. I'm not gonna abandon someone with my kid."

"I'm glad." Cynthia says before lifting her head, then her eyes widened. "You're still hard."

"Yeah, it takes a while when I'm in the mood."

"I see. Well-" She starts to say before gasping as she was suddenly flipped to lay on her back. "Ash-AGH!" She then moans before he stuffed his member into her still full pussy.

"If I'm gonna have a kid either way, what's the point in stopping?" Ash says while holding her legs up by her knees.

Then he started bucking his hips once again as she moaned, feeling his hard shaft sliding across her white stained canal. He set her thighs on his shoulders as he grabbed her hips to keep pace.

"This was your plan all along, wasn't it? You wanted me to do this and knock you up, right?" He asked without losing rhythm. "That's what you're gonna get then."

They were in for about an hour, no one hearing what they were doing thanks to the soundproof room. While no one knew what might've been going on during their time in the bedroom, afterward, Cynthia asked to stay overnight, and boy did the Pokemon Master have a story to tell.

(The next day)

"YOU DID WHAT!?" Misty shouted at Ash in the livingroom. "We agreed you'd talk to us about this first!"

"Sorry, it just... happened ya know. I uh... honestly wasn't prepared for it." He explained to her.

"..." She sighed while still holding their infant daughter in her arms. "What am I gonna do with you sometimes?"

"Well, what can we do?" Dawn says while walking in and sitting in one of the chairs while cradling her pregnant belly. "After all, he does have his charms."

"That's true." May says while walking in with her smaller pregnant belly. "Still, Misty is right though."

"I know." Ash says while sheepishly scratching the back of his head.

(Several months later)

That day, the Sinnoh Champion had moved in with the Pokemon Master. Two months after that she had married Ash, now officially becoming known as Cynthia Ketchum, joining his other wives in his household.

Of course, the media were shocked to learn of such, especially when they learned that she was carrying twins, but they couldn't care less about it. When his mother Delia learned about it though, she was shocked to learn that a woman who was almost her age was now one of her daughter-in-laws, but she couldn't be any happier to learn she'd be having more grandchildren.

Right now, the World Champion was stepping into his home ready to greet his wives.

"I'm home!" Ash called out waiting for a response but was surprised to not get any. "Hello? Is anyone here?" He waited again before looking at Pikachu.

"Pikachu(Maybe they're out)?"

"Seems like it."

The electric Pokemon hopped off his shoulder to go check on his own family. The Pokemon Master put his hands on his hips while looking around before spotting a note on the livingroom table. He walked over and read it. All it said was to come to his room with a winky face.

He got curious and made his way to the master bedroom, wondering what it was he was about to walk in to see. He opened the door and a trickle of blood came out of his nose from what he saw.

"Hello, Ash. ~" Cynthia purred.

The Sinnoh Champion was on his bed, wearing a set of black lingerie. Black fur around her neck, bra holding her bigger bust, panties, elbow length gloves, knee high stockings, and a garter belt connecting them. The biggest thing that stood out was her cradling her heavily pregnant belly resting on her thighs. Seeing her caused a tent to form in his pants.

"Come on, don't keep me waiting now. ~" She says while smiling seductively.

He was astonished for a second before grinning and closing the door and was quick to take off his clothes, showing off his raging hard member. He then got on the bed and started gently rubbing her belly.

"Our babies' are getting big." Ash says happily.

"Just another month or two and they'll be here." Cynthia says before she suddenly felt a kick. "Oh, they know you're here."

"That makes me happy." He says before kissing her belly.

They stayed there for about a minute before cutting to the Sinnoh Champion laying on the bed, bra off, her husband fingering her while sucking on one of her breasts, drinking her milk. She panted while her face was turning red with each passing second, enjoying his treatment.

He added another finger to her folds, continuing to pump them in and out of her. He stopped sucking her boob before switching to the other one.

"Guess it... tastes good, right?" Cynthia asks as he stops.

"Does it? It's delicious." Ash says before he goes back to drinking her milk.

"I'm happy you're enjoying it. It's yours until I give birth."

They would later switch positions with his blonde wife on top of him, riding his member as he continued sucking her breasts. She moaned while hugging him as he hugged her back while being gentle with his thrusts to not hurt their children.

After a bit, he stopped sucking, continuing to buck his hips gently. His blonde wife ended up climaxing in his lap due to her sensitivity, while she felt more kicks from her babies.

"Cynthia, I'm about to cum." Ash tells her.

"Go ahead, let it all out." Cynthia tells him through her moans.

He nodded and went faster, but not too hard. Then he would release his seed into her pregnant pussy, much to her glee. Afterward, they laid on the bed, the Sinnoh Champion's pussy leaking onto the sheets while she made out and cuddled with the Pokemon Master.

"I love you, Ash. I can't wait for our children to be born." Cynthia says.

"I love you too, Cyn. And I can't either." Ash says back.

Like I said, this was really just a buildup chapter, so sorry if it wasn't as well written. But I think I made it clear what the next chapters are gonna be like.

So, I hope you look forward to this.

Chapter Text

Any ideas for Pokemon to be married to Pikachu? I'm not gonna write a sex scene with Pikachu, but I do think that he should get some love too.

Also, if you have some suggestions for naming Ash's kids, you don't have to, but you can still tell me.

(Valencia Island)

We start our chapter on the beach in front of the laboratory where the Professor Philena Ivy resides. She while wearing her usual lab coat and swimsuit was out on the beach, in the middle of cutting some netting that a small Poliwag had gotten caught in while a certain young champion was helping. Once the Poliwag was free, it swam away.

"Thank you coming over to help out, Ash. These poachers are a pain to deal with." She tells him.

"It's okay, Professor. Always happy to help." He says as they stood up.

"I didn't think you'd come out to help. I figured you'd be busy spending time with your wives or... well, being the World Champion and all."

"Well, I still like traveling every now and then. Least when I'm not busy anyway. They don't mind me going out on my own every once in a while. Though, where are the triplets?"

"They have time off for a few days."

"Well, guess everyone deserves a break." Ash says before heading back to her lab.

(Sometime later)

After doing a few more chores, Philena had decided to head back to the beach, setting up a towel and umbrella, pulling out the sunscreen and ready to apply it. Her Pokemon were resting, and she was hoping to get a tan, believing that she was alone for a moment especially since she had a private beach, until she heard a splash.

As she looked back at the water, she was immediately mesmerized by the sight of the Pokemon Master rising from the water, shirtless and only in his swim trunks. When she saw fit and athletic body soaking from the water, she couldn't help but blush and was unable to look away.

It wasn't surprising to see since it was well known that he had practically traveled the globe for years so of course he'd have a gym body, though now that she was seeing it in person, she couldn't help but pop a nosebleed from seeing it.

She would continue to stare, watching him go back into the water and swimming to a different spot before rising again. It seemed that he was exercising. After a bit, she wiped the blood from her nose before getting ready to get a tan, until she looked back and saw him leaving the water and getting a mischievous idea.

"Oh, Ash." She called over, catching his attention. "Are you busy right now?"

"No, not at the moment." Ash tells her.

"Good, then if you don't mind..." She then holds up the bottle. "Would you mind helping me with the sunscreen?"

"Uh..." He says before looking around. "Sure."

He then walked over to her, a little dense as to what he was walking into at first. That was until she started slowly taking off her lab coat, making sure he was watching her and he was. He blushed as he watched her drop her lab coat onto the towel while showing off her endowed body.

She handed him the sunscreen before she got down on the towel and laid on her stomach, which gave him a view of her bubbly ass. The champ stared for another second before shaking his head, now starting to get an idea of what she was trying to do, but not jumping to conclusions.

Ash got on his knees, applied the sunscreen to his hands then started to rub them on her back which made the professor hum in pleasure. He made sure he rubbed it all in, giving her a little bit of a massage as he did. Finishing off with the crevices where her suit stopped.

"Dear, I think you missed a few spots. ~" Philena says before referring to her shoulders and swinging her legs a bit to give the hint. "Would you mind getting those for me? ~"

That was more than just a hint, he understood straight away what she was trying to get him to do with her and a smile slowly grew on his face.

Ash added more to his hands and then began rubbing. Beginning with her shoulders and neck, making sure to take his time getting a good feel in while she continued to hum in delight. He then moved to her arms rubbing them sensually up to her wrists, again continuing to take his time.

He would move on to her legs, rubbing her toned thighs with the sunscreen. Gently pressing into them, still playing it like a massage as he moved down to her ankles much to the professor's enjoyment. While doing so, he looked back up, seeing her swimsuit riding up her asscrack, getting an idea of what to go for next.

"Okay, now-OH!" She started to say before he suddenly grabbed her large ass. "Ah, I-I was, about to ask you about that. ~"

Ash continued to rub them, giving them a nice squeeze every few seconds. Philena giggled as he did so, which only encouraged him to keep it up giving her ass a few light slaps. He then went to her exposed sides to use to the last of the sunscreen in his hands before he stopped.

"Sorry, Professor, I think I missed some spots again." He tells her.

"And where would that be?" She asked before he held the bottle in front of her.

"Right... here!"

Ash then squeezed the bottle, squirting sunscreen onto the front of the professor, making her gasp in shock. Before she could say anything, he moved his hands over to her and started rubbing her chest, making sure to get her collarbone and part of neck in the process.

She hummed some more as he brushed his hands across her fair skin, then gasped as he suddenly moved his hands down into her swimsuit, groping her large breasts. She exhaled before biting her lip to keep herself from letting out any sounds of pleasure too soon.

He saw and pulled her up onto her knees before continuing to fondle her bust from under her swimsuit. Philena could feel her face starting to turn redder as more of her body heat started kicking in the longer he continued. She smirked a bit, getting excited in hopes of what else he'd have in store.

He enjoyed the feeling of her nice and firm orbs in his hands, the tightness of her suit making it seemed like it was trying to keep them from leaving. He soon removed one of his hands, leading it down, moving it into her suit and start rubbing her pussy lips, making her moan out loud. She thought she'd be prepared for it, but she was still caught off guard, especially when she felt something poking her from behind.

"So..." Ash says while moving his face up to Philena's ear. "How long did you plan to wait before asking?" He whispers, causing her to turn her head and look at him.

"Was it that obvious?" She asked.

"I'm a married man with kids. I may have been blind back then, but not now. You could've just asked me if you wanted to."

"Well, I didn't think that'd be fun. I had heard that you had gotten with the Champion of Sinnoh so, I hoped you wouldn't mind."

"Oh, I don't. That being said, your assistants aren't gonna be back for a few days, right? Let's make the most of this."

Ash pressed his lips against Philena's, muffling her moans. She put a hand on the back of his head as he dominated her mouth with his tongue while he continued moving his hands, still fondling her boob and rubbing her entrance under her swimsuit.

She tried to match his tongue's effort with her own, but it was hard, especially when she felt him start grinding his boner against her ass. He stopped rubbing and pulled his hand out of her suit and examined it, watching the strings of her juices connecting his fingers falling apart.

"Ah, this wet already?" He asks after pulling back.

"I... can't help it."

"Then what do you say we skip the foreplay?"

"I'd love that. ~"

Ash stopped fondling Philena's breast but held her by the waist to keep her from going back down. When he pulled back a bit, she looked down and her eyes widened seeing his large member sticking out from his trunks, not expecting it to be so big. He moved the crotch part of her suit, revealing her pussy lips, aiming his member at them.

"Ready?"

"Yes, please. ~" She begs.

He listened and slowly inserted his shaft into her folds, the combination of her juices and the sunscreen lotion acting as lube and making it easy for him. As soon as his tip entered, she nearly grunted, but once he was fully in, she gasped due to his size. She huffed for a moment.

"Just tell me when I can move." He says to her.

"There's no need to wait on this old lady." She huffed. "You can go ahead and do it now."

Oh, he was not gonna take that in stride.

Ash pulled back and thrusted back in, repeating it and causing the professor to moan. Her legs shook slightly with each thrust, feeling her crotch starting to heat up. She knew what it was and was trying to hold in her climax so that she didn't do it so soon, especially before he does.

She grits her teeth before moaning again as her bust bounced up and down, surprisingly still not coming out of their prison. He would also reel back and smacked her ass with his hand. The World Champ was proved that he wasn't just a Pokemon Master, making her body feel like as though it was set on fire, and she was loving it.

"Hey careful now. We may be on a private beach, but some trainer might swim by and hear. ~" He whispered seductively into her ear.

"Oh, you're so cruel." She playfully whined.

Hearing that, the champ decided to amp it up and wrapped his arms around her waist, pulling her back against him before he started going faster. Her bust bounced faster and eventually popped out of her suit before she came and sprayed her juices on his balls and on the towel, causing her eyes to roll back and her tongue to hang out.

"I'm about to cum, Professor." He tells her.

"Yes! Fill me up! Make me a mother!" She yelled out.

Ash obliged with Philena's plea and started going harder. He gave her one hard thrust, penetrating her womb entrance, and started unloading his balls into her. She leaned back into him, her knees sprawling out in front of them as she felt his warm seed in her belly.

After a bit, he pulled out of her and her entrance leaked out of onto the base of his shaft, leaving her panting and drenched in sweat.

"Feel good?" He asked while holding her in his arms.

"Yes... yes, it was... amazing." She says before looking at him. "I can see why so many women like you now."

"Well, that's part of it." The champ then looked down at his still hard member. "Still think you can keep going?"

She looked down at his member and thought for a moment. "How about we go clean up?"

(Later in the shower)

"Oh! Oh fuck yes! Ash!" Philena shouted.

While in the shower, Ash started fucking her in the ass. As the water came down on their bodies, one of her legs was up on his shoulder while she leaned against the wall for support as he was bucking his hips into her.

"Shit and I thought your pussy was tight." He tells her while putting a hand on her waist. "Still, I feel bad you didn't find anyone sooner. Who could resist a body like this?"

"Don't worry about it, just... fuck me!"

He later on would fill her ass with his seed as well, but they still weren't done.

(The next day)

"Are you kidding me, Ash? Another one?" Misty says over the phone.

"I'm not." Ash says back.

"For the love of..." She pinched the bridge of her nose. "This is what I get for marrying a lover's boy. Just promise you'll at least not be back a day later?"

"Yeah, I can promise that. Don't worry."

"Good."

"So, you're not gonna punish me?"

"Who said I wasn't gonna punish you?" She then says before smiling darkly. "Just wait until you get back and see what the other girls and I have planned for you. ~"

She heard an audible gulp from the other side of the phone. "I'll keep that in mind. Love you."

"Love you too, hon."

Misty then hangs up before sighing. She figured at this point that punishing him would be pointless, but she couldn't go back now. Ash was gonna be gone for a few more days so he'd have plenty of time with his new future bride.

(Several months later)

Sure enough, Professor Ivy had now joined as one of Ash's wives, officially now married to him. However, she couldn't live with him, but he promised to visit her every now and then and vice versa, especially since she now was barring his child.

As of now, they were sitting on a towel on the professor's beach at night, the champ having her in his lap while both were dressed the same, they had when they first fucked. This time though, the professor's swimsuit was stretching a bit from her breasts that were bigger and her round bulging belly that was being rubbed gently by her husband.

"So, do you think it's gonna be a boy or girl?" Philena asked.

"I don't know, but whatever they turn out to be, I'll gladly take care of them." Ash says before kissing her on the cheek.

"That's what I like about you."

After a bit, the master helped his wife stand up before they walked over to the water until they were thigh deep. The professor then reached down and moved the crotch part of her suit to the side, and her husband then inserted his shaft into her pregnant pussy from behind, nearly making her yelp as she did.

"Ready?" He asked.

"Of course, my love."

Ash hugged Philena before bending down and they started swimming around in the water. They didn't go too far, but enough to see some water Pokemon around, none of them noticing they position they were in.

After a bit, they went to a nearby rock formation, the professor flipping over to face the champion while he was gently thrusting into her and sucking one of her breasts.

"Careful, Ash. If you drink too much, our baby might not get any." She says as he stops.

"I can't help it. It tastes so good." He tells her. 

He leaned and started kissing her as she kissed back, the child kicking in their mother's belly. He soon came in her canal before they separated and stared at each other lovingly. He was ready to have another kid and couldn't be prouder to be a father to yet another.

Have a suggestion for who's next? Remember to comment and follow.

Chapter Text

Okay, so there is really only one person commenting on these, but good enough. The next one was only Juniper, but I figured, why not add one more?

So heads up for this: You're gonna be seeing a small bit of yuri, and more dialogue before we get to the juicy parts.

(Unova Region)

Ash Ketchum was currently in the Unova region on a date with one of his wives, Iris. They decided to visit her old home: the Village of Dragons, and to meet with the elder. As much as they would like to bring their son, he wasn't old enough for travel just yet, however, they planned on doing so once he was old enough.

When they were done, they made their way to a nearby town to spend the night. They came to one of the diners in the town and were waiting to be seated. Meanwhile, at one of the outdoor tables, two very familiar women were looking through the menus before one noticed and tapped the other on and gestured over to them.

"Well, look who it is." One of them says, catching the attention of the other two.

"Professor Juniper? Dr. Fennel?" Ash says, surprised.

"That's us." The blonde professor says happily. "Been a while since we've seen you."

"Sure has. You two look great."

"We could say the same thing about you." Fennel says while the champ scratched the back of his head.

"I'm surprised we haven't seen either of you sooner. What brings you two here?" Iris asked, curious.

"Simple. We're here on a little honeymoon." Juniper says while holding up her hand, revealing her ring.

"Wait, you're..."

"Uh-huh, and gladly so." The professor says as the lavender haired woman blushed a bit.

"Congratulations." Ash tells them.

"Excuse me, sir." A waiter came by. "We have a table ready."

"Alright. Sorry to cut this short." The champ tells them.

"It's fine. We can talk later if you want."

(Later)

After dinner was done, the couple met up with the professor and doctor and were doing a bit of catching up. The women talked about how they got together a year back, things slowly happened, and they eventually got married a few months before that day.

Not much worth noting happened before they went to the hotel for the night. Ash decided to go down to the bathhouse hot springs before bed. However not long after entering, an employee came around and looked at the signs.

"Blasted kids playing pranks." He says before fixing the signs to say which side was for which gender.

Towel around his waist, Ash slowly got into the water and laid against the edge. The heated water instantly relaxing his muscles the moment he entered. He sighed while leaning further back into the water until his shoulders were in.

"This is nice." He says to himself.

He was sitting in for like a minute before he suddenly heard some muffled voices coming from the entrance, much to his curiosity. However, as he listened closer, he realized that those were not male voices.

'Wait... what are they doing? Isn't this the boy's side?' He thought before looking at the silhouettes. 'They're getting undressed, they don't realize. Shoot!'

Thinking quickly, Ash quickly got out of the water and looked around, running over to one of the rocks and sitting behind it, out of sight. Then the two girls entered the hot springs, still talking. That was when he recognized that it wasn't just any girls, they were Juniper and Fennel.

At the moment, he was still wondering what the two of them were doing on the boy's side of the hot springs, not listening to what they were saying and more focused on making sure he was hidden.

However, his curiosity still peeked his dignity and he peaked around the rocks. They had on towels that clung to their skin showing off their beautiful curves. Juniper's bust was just slightly bigger but Fennel's thighs and ass were thicker, something that kept him from looking away.

They were still chatting to each other as they entered the water, which he still was too mesmerized to listen to. Then it snapped in his mind what he was doing and quickly looked away while hiding again. Although, he couldn't get the sight of their bodies out of his head and felt his boner form under his towel.

'Crap, this is probably the worst time for that.' He thought. 'Come on, they're a married couple. You can't do that to them.'

"I-I don't know." He suddenly heard Fennel say.

"Come on, don't you wanna try?" He heard from Juniper as his head perked up.

"Aurea, what if someone comes in and sees us?"

"I'm sure we'll be done before then. If not, then we'll just have to make it quick, won't we? ~"

When he heard the tone of Juniper's voice, he only got even more curious. Was there something he missed when he was busy staring at them? He did only listen in at that moment, so there was no doubt something he missed. Though based on what they were saying, were they... they wouldn't, would they? In a place like this?

Before he finished his train of thought, he heard a gasp and quickly looked back. Fennel was leaning back with Juniper having one hand under her towel, moving in a very suggestive motion. The blue-haired doctor was seen biting her lower lip as if trying to keep herself from making any noise while her wife was enjoying the sight.

"Does it feel good?" Juniper asked.

"Yes... yes, it does." Fennel would say back quietly.

Ash's eyes nearly bulge out of their sockets as he was watching the scene unfold, his shaft fighting against the prison that was the towel. Then when they started kissing, the doctor reached up and started groping the professor's chest through her towel, rubbing them and giving them the occasional squeeze.

That was too much. Despite the fact that he had so many wives and has had sex multiple times, that didn't stop him from getting turned on from something like this. He decided that he couldn't take it anymore and uncovered his member.

'Forget it, I can't just sit here and do nothing.' He thought to himself.

Ash started jerking his member off to the two women in the hotspring. The sounds and the view alone were enough to make him hard so he didn't have to do much.

Then he watched as Juniper helped Fennel out onto the surface and moved her head down between her legs under the towel. He knew exactly what they were doing and continued to jerk off to the sight, leaning to their moans and becoming harder because of it.

At this point, he was hoping that Iris was still awake so she could help him when he got out. Or at the very least, maybe in the morning. He continued to watch them before they stopped, and the blonde professor hovered over her wife.

"Doesn't this just excite you? The mere feeling and knowing anyone could walk in and see at any moment. ~" She asks.

"It does, and I love it. ~" Fennel moaned back.

'They just had to talk like that too.' The champ thinks to himself while looking away.

"Well, if that's the case, why don't we talk to our little watcher here?" The professor says as the champ flinched.

"Huh?"

"Yes, I mean you, Champion." Juniper continued to say while looking where he was.

"Shit." He says while looking back. "How long did you know?"

"About since we got in."

"You weren't hidden that well." Fennel explained.

'Aw man.' Ash slumped a bit.

"So, did you enjoy the show?" Juniper would then asked as she got on her knees.

"What?" He asked before realizing something. "W-Wait, you're fine with me watching you?"

"No, it was actually quite exciting." 

"... Oh..." He wasn't even shocked by what he heard. "I mean... do you want me to leave?"

"Actually, you can stay if you'd like." Fennel responded.

"In fact, we wouldn't mind if you were to join us." Juniper then says.

"... Say what?" Ash says, dumbfounded. "You mean, like..."

"I think you know what we mean, hon." The blonde professor tells him.

He was about to open his mouth to say something but closed it. He thought for a moment, looking back at the two and sighed to himself. He couldn't help it. At this moment, he figured it wasn't worth trying to leave and taking the risk of someone seeing his boner through his pants. Plus, it was two hot women, so it was hard to say no.

So, without a word, Ash dropped the towel from his waist and stood up while turning around, his body now fully exposed to them along with his boner. The two blushed at the sight.

"Oh my." Fennel says.

"I think he's interested." Juniper says.

(Later)

They wasted no time. Towels were removed, Ash had Juniper pinned against one of the walls, making out with her and fondling her boobs, while Fennel was behind him, stroking his shaft and fondling his balls while licking them.

The champ was enjoying his spoils, his tongue roaming around the professor's mouth, getting a taste of her wife's juices in the process. He was also enjoying the doctor down and licking the underside of his shaft, causing it to stick up against her wife's folds, essentially doubling the pleasure for the other two.

Well, he learned that they wrong when they said it was exciting to risk getting caught. He was getting turned on just by the mere thought that anyone could come in at any moment and catch them doing this. Although, it didn't seem like anyone was coming in yet, so they were in the clear.

Eventually, the young man stops the kiss and pulled away a string of saliva connected to their lips. "Mmm, not bad. ~" Juniper with a smile.

"I've been learning after a bit of experience." Ash tells her.

"So big. I'm surprised we couldn't see it sooner." Fennel says while still rubbing his shaft.

(Later)

The women were now on all on the floor, the doctor on top of the professor, Ash was on his knees, eating out Fennel's entrance while fingering Juniper. The two women were huffing and quietly moaning to themselves as he continued to pleasure them.

"That's it, keep going, Ash." Juniper moaned out.

"Yes, don't stop." Fennel also moaned.

The champion continued to lick and finger them as best as he could, making sure they were enjoying it as much as he was. The professor giggled before she started kissing her wife right in front of him, they made sure to be extra lustful with it.

Ash got the idea that they were doing it on purpose. He stopped his licking and fingering before leaning himself up and bringing up his member. He started looking up and down between the two of them, figuring which one to do first. The other two were too busy to notice him grab and spread Fennel's ass and slowly inserted himself into her folds, causing her eyes to widen.

He continued until he was fully in. "Oh, fuck..." Fennel moaned after separating from her wife.

"Damn." The champion huffed a bit.

"Are you okay, honey?" Juniper says while hugging the other woman.

"Y-Yes, I..." Fennel panted a bit.

"Just give it a second. It takes time to get used to."

They took a moment to adjust before Ash began thrusting in and out of Fennel, causing her to moan out loud. Her asscheeks rippled each time while she was rubbing her body against her wife's, mainly squishing their breasts against each other.

"Well? How are you feeling so far?" Ash asked her.

"A... A-Amazing, this feels... so good." She moaned.

Hearing that, he continued bucking his hips, feeling her get tighter each second while the other woman watched with a small smile. Juniper held her breasts up and allowed Fennel to take one nipple into her mouth, the sight of such made the champ get harder in the doctor before going faster.

"Easy, now. Don't go too hard on her." Juniper tells him.

"Sorry." He slows down a bit.

After a bit, Ash felt her came and spray on his crotch. Her entrance tightened, squeezing his member as if trying to milk him dry. That seemed to warn him of his own coming up.

"Do you want it inside?" He asked.

"Ah, y-yes. Please." Fennel says after pulling off her wife's breast.

Following her request, he continued thrusting until his tip got through her womb entrance and then fired his load right into her, filling her up to the brim. She gripped the professor's arms tightly as he released rope after rope of his semen. He pulled out when he was done, causing her to collapse while his load gushing out of her entrance onto her wife's.

"Fuck..." She says while panting. "I-It feels... so warm..."

"Take it, it feels good?" The champ asked as she nodded.

(Later)

Juniper was now on all fours, Ash already having his member in her entrance, thrusting away as she had her face in her wife's crotch eating her out while drinking the excess cum from it. The professor was moaning while licking as Fennel had her hands on the back of the rocks keeping balance.

He gave Juniper's ass a slap, causing it to ripple with his thrusts. He felt her climax on his crotch and tighten around his shaft. After already going for a little bit, he felt himself get closer to his own.

"I'm gonna do it again." He warns them.

He started going faster before blowing his load into the professor, filling her up next. She moaned straight into her wife's pussy before he was done and pulled out of her, the extra baby batter squirting out of her onto the floor.

Ash wiped sweat from his brow before looking at the two panting women. Fennel still had her entrance leaking with his semen, Juniper's not being much different. He knew that they were probably gonna be joining him at this point.

(Several months later, Ketchum Household)

It came as no surprised that Professor Aurea Juniper and Dr. Fennel were now a part of Ash's harem. They were still married, but now they were added to his marriage. Iris was a little annoyed because they were supposed to be Unova for a date and he ended up sleeping with two women.

Misty at that point had given up, having a feeling that this wouldn't be the last time and knowing there was nothing she could do to stop her husband. If it happened again, it happened again.

And to add, Fennel's Munna had mated with Pikachu. It came as a bit of a surprise, but not an unwanted surprise.

As of now, the two women were in the living room in their underwear, everyone being out doing something that day, their breasts having grown since then and their bellies big round and carrying their husband's children.

"Looks like they're getting bigger again." Aurea says while using a measuring tape on her wife's belly. "It's only gonna be a few more months."

"I hope they'll be okay." Fennel says while using taking her milk pump off one of her breasts. "It's been hard moving around with these two. You're lucky you only have one."

"Yes, however, I wouldn't mind doing this again. Besides, we can finally have children to call our own."

"It is exciting."

A moment later, they were making out on the couch, their bellies rubbing against each other while Aurea had her hand down in Fennel's panties, fingering her, while in return getting her breasts massaged through her bra.

"Honey, would you mind helping me? ~" Aurea asked.

"I don't mind at all." Fennel says while helping her undo her bra, causing her boobs to bounce up now free from their prison.

The doctor stared in awe for a second before taking them in her hands and started sucking on one of her wife's breasts, drinking the milk from it. The professor giggled while she kept her hand moving in the same sequence.

They were going for a little bit before the front door open.

"I'm ho-" Ash started to say.

He and Pikachu saw both of his newest wives freezing mid-session. He popped a nosebleed and a pitched a tent at the same time while his Pokemon quickly hopped off his shoulder and ran off to find his own family. The champ just simply wiped his nose.

"Bedroom, now."

(Later in the master bedroom)

The three of them were all on the bed on their knees, clothes all discarded, and Ash had both Aurea and Fennel on either side, thrusting his member between their bellies while taking turns sucking milk from either's breasts.

"Goodness, dear. You're so needy today." Aurea tells him.

"Agreed. Careful not to drink too much." Fennel tells him.

They would do this for about a minute before he came, covering their bellies in his cum. Some even got on the breasts that weren't being sucked on.

After a moment of cleaning up, Ash was behind Fennel, her in his lap having his member thrusting into her folds as he was kissing her. She came in his lap, moaning into his mouth as her wife watched while masturbating. He soon came in her as he pulled away from her lips.

Now he was in the same position with Aurea, making out with her as well. This time he was caressing her swollen breasts, trickles of milk squirting out of her nipples as he did so. She also climaxed in his lap moments before he came in her entrance.

Afterward, they laid in bed, the Pokemon Master and his two wives cuddling beside him with their bellies resting on top of his and their entrances leaking.

"Honestly, with all these other girls, we thought you'd be too busy for us." Aurea tells him.

"I always have time for all my girls, you two included." Ash tells them.

"We couldn't be any happier to hear. We love you, Ash." Fennel says with a smile.

"I love you both too."

Chapter Text

Honestly, I might be considering making a Pokemon version of this story... completely not canon with this story of course, but still, a thought.

(Ketchum Household, Battle Room)

A battle had taken place earlier between Ash and the Kalos League Champion: Diantha, damage already taken place on the battlefield, his Lucario and her Gardevoir in their mega forms. However, the psychic Pokemon turned back into their normal form and collapsed shortly after.

"Gardevoir is unable to battle. The winner of this battle is Ash Ketchum and Lucario." Dawn called out as the Grand Duchess went to her fallen Pokemon.

"Are you okay, Gardevoir?" Diantha asked, getting a nod in return.

"Good job, Lucario." Ash says while walking down to his Pokemon who turned back to normal form.

Diantha had come over to visit just like Cynthia did, to challenge the World Champion to a battle to test if she had a chance against him. Of course, she figured she was gonna lose, but that didn't stop her from wanting to test his strength. Things weren't very eventful after the fight... until nighttime that was.

(Later that night)

Diantha was awake and in thought. Before she arrived there, she heard about the recent news about the World Champion not just marrying the Sinnoh League Champion, but also a professor and doctor from Unova who were already married to each other. It came as a surprise to most that they would go for someone that much younger than them, although it got her thinking of something herself.

After she had left the room, her Gardevoir left her Pokeball. Checking to make sure her trainer was gone, she left without being noticed. The psychic Pokemon ran into the Pokemon Master's Lucario who also just so happened to be wandering around as well. The jackal rose a brow before Gardevoir put a hand on her cheek.

The Kalos Champion was only going for a nightly walk around the mansion, not planning to anything more than that. However, that was stopped when she saw the door to the family bathroom open up and steam pour out of it.

And so, the Pokemon Master walked out while sighing, done drying his hair and holding a towel in his hand with another around his waist. He immediately stopped when he noticed the woman.

"Oh, Diantha. I didn't think you were still awake." He says casually.

She didn't answer, staring right at his fit and athletic body with a red tint spread across her face. He stared back, noticing her body through her night gown and the same thing happened to him while also awaking a certain friend under the towel.

(Later)

It happened so fast. Diantha found herself completely nude on the shower floor with Ash french kissing and fingering her entrance. She had her hand stroking his shaft as she was trying to fight with her tongue back, but his easily overpowered hers.

"Oh god." Diantha moaned after pulling away.

"Feel good?" Ash asked as she nodded. "Then you're gonna like this next part. ~"

He then went down and started licking her entrance, causing her to gasp and moan as he did. She rested her legs on his shoulders while he lapped at her folds, getting a taste of her juices and sending a wave of pleasure through her body.

Diantha held his head in place while leaning back against the floor, feeling her face and body heating up with each lick. Her body completely soaked from head to toe from the water raining down on their bodies. He furiously moved his tongue inside of her folds, making sure to taste every bit of it.

After a bit, they changed positions, her being on top of him sucking and stroking his shaft while he was licking at her entrance. She couldn't get the whole thing into her mouth, but she was still putting in her best effort. Unfortunately, she wasn't able to match with the Pokemon Master.

'So big.' She thought to herself, still sucking.

Ash gave her ass a slap while pressing more of his mouth against her folds, licking every bit of her inner walls. Diantha had climaxed from what he did, causing her to stop for a moment as the world champion swallowed each drop. She pulled off of his member and panted for a moment.

(Some more time later)

"I wasn't expecting you to be eager to do this." Diantha says while lying on her back, legs spread.

"It's easy to get used to." Ash says as he was rubbing his member against her folds. " I learned to accept it."

"Will you stop teasing me already?"

He shrugged before he pushed into her entrance, causing her to gasp before gritting her teeth in pain. They took a moment for her to adjust before he started bucking his hips, her struggling to keep her moans in.

Ash was hardly thinking about how tight she was, being used to it already. He reached down, putting his hands under her thighs and cupping her ass, making it easier to keep in pace without trouble.

"Still feel good?" He asked her.

"Yes... just mph... so big."

"It gets easier after the first time."

Ash took one of her breasts into his mouth and started sucking on it, which eased her slightly. That didn't stop her from climaxing on his shower floor. They continued like this for a little bit before the world champion felt his member starting to twitch.

"I'm gonna cum. If you want it inside-" He says before Diantha wrapped her arms around him and pulled him into a hug, locking her legs around his.

He got the hint and sped up his hips. He would soon blow inside of her and filled her womb with his load. Her neck craned as her eyes rolled back from the feeling. After a second, he pulled out of her, causing his warm semen to floor out onto the floor.

"So much..." She moaned.

"How about we go somewhere more comfortable?"

After a moment, Ash lead Diantha out of the bath and into the halls, with only their underwear and nothing else, much to the Kalos Champion's embarrassment. She was worried of the idea that someone would see, but the man of the house seemed confident and wasn't worried in the slightest.

As they passed one of the windows, she could've sworn that she saw her Gardevoir out in the gardens with Ash's Lucario, doing what she and the world champ were doing earlier.

Once they reached the entrance to the master bedroom, Ash opened the door and allowed Diantha to go in first before going in afterward. If there was a small chance she was gonna be pregnant earlier, after that night, it was inevitable.

(Several months later)

After that night, Diantha Ketchum was welcomed into the family. Once word got out, people were shocked that he managed to get yet another older woman added, but also another league champion. It got them wondering who might be next.

Not only that, but it turned out to be true that her Gardevoir and the Pokemon Master's Lucario had gotten together as well. Imagine that.

Right now, our hero was with his new wife in his room, drinking milk from her now grown boob, rubbing her pregnant belly, while she was stroking his member.

"They've been getting real feisty lately. Really take after their daddy." Diantha says to him.

"I'll make sure to raise them properly. Plus, they're already gonna have a lot of siblings." Ash says.

They stopped and Ash put Diantha in his lap, inserting his member into her ass before he began thrusting. He was massaging her bust to keep her at ease, a bit of her milk trickling down the back of his hands while also taking it easy. This would go on until she sprayed her juices on the sheets before he came in her ass.

The Ketchum family is getting bigger and bigger. The Pokemon Master was looking forward to seeing more of his children come into the world and could only wonder what the future would hold for him next.

Little short this time, but eh.

As for next time, I already have an idea as to who to add next.

Chapter Text

Ash's family seemed to be growing without end. Many of his wives have already given birth, some still had yet to do so. Not only that, but Pikachu's eggs had hatched along with his other Pokemon's eggs, and that added to the family as well. 

Safe to say, his house wasn't very silent, whether it'd be him having 'private time' with one of his lovers, or the cries of his children that hadn't turned a year old yet.

At the dinner table, Serena's mother Grace was visiting to come check on her daughter and to see her grandchildren. Her daughter was one of many who the Pokemon Master had gave twins, which made her happy. However, it did bring up some thoughts. And right now, she was staring at her daughter who was holding her grandson, but also something else.

"I'm still surprised that you're pregnant again. Don't you think it's a little early?" Grace asked.

"Oh, uh..." Serena says while looking down at her pregnant belly. "It's gonna be fine. I know Ash will treat them well." She then says before looking over at her husband who was rocking their daughter to sleep, Pikachu hopping past with a baby Pichu and Buneary on his back.

"Yeah, he's busy from time to time, but he's not a bad father. He's already got a lot anyway." Misty says before her daughter started crying in her arms. "Up, that's feeding time. Sorry." She then got up, her belly showing off her second pregnancy and left the room.

(Later)

Grace was walking through the halls after paying a small visit to her grandchildren. Her mask of happiness faded. Seeing her daughter so happy with a man she loves enough to have more than one child made her happy, but also sad at the same time. She remembered the day her own husband left her after learning she had become pregnant.

Part of her wished that she had what all the girls in this mansion had. Not only a man to love but to at least have another child. Though, she figured that helping take care of her grandchildren would be the same.

As she passed one room, she slowed to a stop. She turned her head to see one of the rooms was open a crack, a small bit of sound coming through it. She opened it a bit and peaked through, being shocked by what she was.

Her daughter: Serena was on the edge of the bed, wearing the performance dress she used to wear when she was younger, moaning as Ash was in front of her with his pants down, bucking his hips into hers. He held her legs up while she had her arms wrapped around his neck, her belly pressed against his own.

"Oh, Ash. Please don't stop. ~" The blonde moaned out.

"I won't." He says before he started kissing her.

Grace couldn't believe what she was seeing. The fact that not only her daughter would wear her childhood dress for such a thing, but that she was having sex even while pregnant. It came as a shock to see, but... it sorta turned her on.

She continued to watch, mesmerized by the sight and starting to imagine herself in her daughter's position. After a bit, they came to a stop, and she watched her son-in-law pull out. From there, she could see how big his member was.

At that point, she decided to slowly close the door before rushing away to one of the guest bedrooms. Her face was red and she could feel her heart racing, not only that, but she could feel wetness in her lower regions.

She pulled down her pants, seeing how much she was, but while she felt shame... she slowly reached down and started rubbing against her wet folds.

(Early morning)

Ash groaned as he started to wake up. He had a familiar feeling of morning wood, however, he felt wet and heard a little bit of a slurping sound. He slowly started to sit up and saw a big lump moving in his bed. He assumed it was one of his wives and smirked a bit.

'Alright, let's see who it is this morning.' He thought to himself.

He reached for the sheets and lifted them up, wondering who it was. Then to his shock, he found his mother-in-law: Grace underneath, in her underwear, licking his shaft.

"G-Grace!?" He shouts in shock while crawling back a bit. "W-What are you doing?"

"I'm sorry, Ash. I know this seems unethical, but I couldn't help myself." Grace tells him.

"W-Where did this come from?"

"I saw you with my daughter yesterday and I couldn't help myself." She then crawled up to him.

"Woah, woah, wait, what about Serena? Are you really okay with doing this to her?"

"Please, let's keep this between us. Just this once, okay?"

Ash sweated for a moment in thought. Knowing how lonely she was from not having her husband for so long, he felt bad for her.

Now that he could see her body barely covered and mostly exposed, he could see her well-endowed body with her bra holding together a good amount of cleavage. He thought she was beautiful, but didn't want to stare at her, especially with her daughter around.

He took a look at his clock. It was still early, the sun was practically still down which meant that no one else was awake yet. Plus, he did have soundproof walls so no one would hear.

"Screw it." He said to herself.

He then mashed his lips against her and started french kissing her. Grace was caught off guard for a moment, but as she sunk into the kiss, she could immediately feel the arousal going through her body.

He took one of her hands from his face and moved it back down to his shaft. She got the hint and started stroking his member, making it grow harder in her hand. He also reached back and grabbed a handful of her ass, causing her to moan into his mouth.

She was surprised that he was so quick to accept it, questioning it a bit in her mind, but couldn't care less about that right now. His other hand reached up and unclipped her bra, pulling it off and causing her bust to bounce freely.

After they pulled away, Ash grabbed Grace's boobs and started fondling them. Her face was turning redder and redder with each second, rubbing his thumbs against her nipples, pressing them in and licking them, causing her to moan aloud.

"Ah, goodness... keep going, Ash." She says while putting her free hand on his head.

He sucked on one of her breasts while rubbing her other tenderly, getting a firm feel of them. Just as before, she started to feel her body turn hotter, especially down in her neither region as she kept rubbing his tower.

'This is so wrong, yet, feels so good.' She thought to herself.

He stopped what he was doing, and they decided to change positions. Ash sat on the edge of his bed with Grace on her knees in front of him, both naked while rubbing her breasts against his member.

'It's so big, how had I not noticed it before?' She thought to herself while giving it a lick.

"Grace, this feels amazing." The champ says.

"I'm glad."

Grace continued licking his shaft, giving it several kisses to add. His member then squirted and sprayed like a fountain, getting all over her face, breasts, and some in her mouth. She let it sit for a second for a small taste before swallowing it.

"Sorry I didn't warn you." Ash tells her.

"It's fine dear."

"Let's get to the main part a little earlier." He then got up from the bed.

"Alright, just be easy on me. It's been a long time since-OH!" Grace was caught off guard as she was pulled against the master's chest, then felt his tip against her folds.

"I plan to make this the best for you." He says before slipping his member into her entrance causing her to nearly scream out loud. "I'll make sure you enjoy it."

He then began bucking his hips as his mother-in-law continued to moan, her boobs bouncing about as he did. Once again, the heat continued to flow through her body, and she was falling into a state of euphoria.

So many years she's been neglected. So many years she hadn't felt so good. So many years and she finally was getting it again. Only this time, it felt better. Her ex-husband wasn't this big, nor did he give it to her this good.

"Oh... oh fuck!" Grace cried out. "So GOOOOOOOD!" She then came and made a puddle on the floor.

Her eyes rolled back and she had a goofy smile on her face as her son-in-law continued to fuck her like no tomorrow. Her pussy tightened around his member. She wanted this, wanted this to keep going and wanted him to take her as his.

"I'm about to cum Grace." Ash tells her.

"YES! Please, fill me! Make me a mother again!" Grace says.

His eyes widened when hearing that, however, he was too wrapped up in the moment to stop. He lifted her off her knees and started thrusting faster and faster as she moaned even harder. Then he came. He didn't pull out, spraying his cum inside of her, drenching her inner walls and her womb with every bit he had.

He eventually stopped and let her lay on the edge of his bed before pulling out of her, a waterfall of his seed mixed with the puddle of her juices. She was left a panting, sweaty mess.

Ash got worried. He just came inside his own mother-in-law. Sure doing this with older women was hot, however, he was worried of how Serena would react should she hear about this. Not like there wouldn't be any way to hide if she was carrying his child.

He saw that he was still hard as hell, not only that, but it was still dark out. He only sighed before helping Grace back up for another round. If there wasn't any going back, he decided to accept whatever fate lied for him.

(Several months later)

Against Grace's words, it was not kept between them. She was the next in line to join Ash's harem and become his newest wife.

Serena was pissed to learn that her husband had sex with her mother, and he had to go through a bit of a lecture... and some punishment because of it. However, she couldn't change what happened and, in the end, she was glad that her mother wasn't lonely anymore and had someone to love her just as much as her.

Delia was the most shocked. Her and Grace were very close friends, so to learn that her friend was now married to her son and technically her daughter-in-law now, it came as a shock. Still, knowing that her son was able to make even her happy, she was happy.

Right now, Serena was sitting on a chair in the living room while breastfeeding her newborn son.

"Morning Serena." Misty says while entering, holding her own newborn daughter.

"Good morning." The blonde says. "See you're doing good so far."

"Pretty much, yeah. Still mad at him?"

"A tiny bit. Wondering if it's ever gonna stop though."

"I wouldn't count on that any time soon. Where is he now anyway?" Misty says while looking around.

"Oh, he's just... busy."

Busy was right. Ash was in his bedroom, Grace lying her back against him as he was gently thrusting his member into her pussy, rubbing her pregnant belly and swollen-with-milk breasts while kissing her. After a bit, they stopped kissing with a string of saliva connecting their lips.

"Oh, Ash. I've never felt so happy in my life." Grace says.

"I'm glad you do. What kind of husband would I be if I didn't make sure my wives were happy? Especially my kids."

He then lifted one of her breasts up and took it into his mouth, drinking her milk. She only moaned in bliss as he did so. Not long after did he come inside her canal and paint her walls with his seed.

Chapter Text

Okay, been getting some requests for some women, but I wanna do some other milfs before then.

(Sinnoh, Dawn's old home)

Ash was with his wife Dawn visiting her mother with their child: Satoru. They did this every now and then with the other mothers so that their kids could see their grandparents. Though things were differently during the visit.

Johanna had heard that Serena's mother: Grace had remarried and had grown curious about who the lucky man was. She was shocked that not only was it was her son-in-law that she had married to, but that she was already carrying his child. Hearing that, she couldn't help but wonder...

As of now, Dawn was just leaving to visit Professor Rowan for a bit, leaving her husband and mom in the house and her son. With this, her mother was a little worried. There was only so much she could do with her son-in-law besides talking and they had already gotten mostly caught up on things when her daughter was there.

When Ash was busy trying to get her grandson asleep, she decided to go into her room and close the door. Huffing a bit, she pulled down her pants, skirt, and panties and went to the bed and lied on her side. Then she moved her hand down between her crotch and started rubbing her folds.

She hummed to herself at first before she started moving faster while groping herself. Her lips quivered as a bit as she could already feel her nectar starting to soak her entrance. She had done something like this before, but this time was different.

"Ash..." She muttered to herself.

Slowly, she was starting to imagine it was Ash's fingers. Was it immoral? Maybe. Did she know it? Yes, but she couldn't help herself. Years of not having a man to satisfy her needs and yet her daughter found someone who was getting more love from a handsome man than her. 

She moaned one second before covering her mouth, still muttering the name of her son-in-law. A thought ran through her mind as to whether he would do the same with her and if her daughter would be alright with it. He already done it with one of his mothers-in-law, so maybe he'd do the same for her?

As she was thinking that she suddenly felt another pair of fingers touch her nether region. She jumped before looking behind her.

"A-Ash!?" She gasped in shock at seeing her son-in-law being the one touching her. "What are you doing?"

"I was just passing by after going through the bathroom and couldn't help but overhear what was happening in here." He says casually. "Seems like you could use some help."

"W-Wait, we can't! You're my daughter's husband, I couldn't-AH!" She almost gasped as he started rubbing her entrance.

"You say that, yet you're the one moaning my name while doing this." He tells her as she looked back at him. "Besides, I'm sure Dawn wouldn't her mother to be lonely, yes? Just sit back and let me do the work."

Before Johanna could protest, Ash kissed her which made her eyes widen in shock. He then inserted two fingers between her slit and continued to finger her as she moaned into his mouth. It wasn't long before she felt the difference between her fingers from his, the stimulation going from her crotch straight through the rest of her body.

She could feel her face starting turn red and moaned louder into his mouth as he started groping her breast with his free hand. It all happened so sudden and so fast, she felt as though she was turning into puddy in his hold.

"G-Goodness..." She says after getting free from the kiss.

"Feels better when it's not done by yourself, doesn't it?" He tells her before turning her over onto her back.

"W-Wait, what about Satoru? He might hear."

"Let's try to be quiet then."

Ash then moved down to Johanna's crotch, her pussy sopping wet. He then started rubbing her supple legs, giving her inner thighs tender kisses as she covered her mouth with one hand while the other hand was tightly gripping the sheets. He made his way down to her lower lips and gave them a lick which made her tremble.

He would keep lapping at them as she leaned back while moaning into her hand. It was so long that she had almost forgotten what it felt like to be eaten out, but somehow, she knew it felt better than when she last felt it.

It didn't take long before she came, spraying on his face and into his mouth. He gulped it down before wiping his face and looking down at his panting mother-in-law.

"So... interested in going any further?" He asked.

She looked at him, then nodded. Suddenly the shame of her daughter finding out about her doing it with her husband vanished.

After a bit of recovering, Johanna sat up and took off her shirt and then undoing her bra, letting her large bust bounce. Ash couldn't help but pop a nosebleed upon seeing them. He stood up and removed his shirt, causing her to stare at his young and healthy torso before his pulled down his pants, causing his member to fling out as she gasped.

"I-It's so big." She says. 'Bigger than his.'

"If it's too much, we can stop."

"No, no it's okay, just..." She says before turning around and getting on her knees, lifting her hips up in the air. "Don't go too hard."

Ash simply nodded and stood at the edge of the bed, grabbing Johanna's beautiful ass. He aimed at her entrance and slowly pushed inside, causing her to gasp and moan as she felt his shaft starting to stretch her canal. Once he was fully inside, she was left panting.

"Just tell me when I can move." He says.

"... G-Go ahead... please."

He nodded before pulling back and thrusting back in gently. She at first tried to keep quiet once again but she couldn't stop herself from moaning. It was only a few seconds and yet she could already feel herself about to climax a second time.

Perhaps it was her being sensitive from earlier, but she was loving it. Never could she remember the last time she felt this good. So many years gone by, not one man to satisfy her and yet this younger man who was married to her daughter and gave her a grandchild was making her feel beyond amazing.

"Please, go faster." She says.

"Sure thing."

He started going a little faster, which caused her to moan louder. Her face turned redder as she could feel her ass ripple with each slap from his crotch. He reeled back and gave her ass a light slap which made her gasp while trembling more.

Deciding to switch things up, he stopped for a moment before pulling her of her hands, then moving his hands under her thighs and lifting her off the bed. Before she could ask, he continued thrusting into her entrance, causing her to moan aloud.

Not long after, she came, spraying onto the floor as her eyes rolled back. Johanna realized something in the middle of it all. No wonder she couldn't remember the last time she felt this good, because it didn't feel this good the first time. It felt so much better. Her old husband had never made her feel this way.

This continued for another minute before Ash felt his member twitch. He made sure to warn her, but she either didn't listen or didn't care, maybe both. As he penetrated her womb entrance, he climaxed and started filling her. She continued to moan as she felt his warm seed going into her body.

They stayed there for a moment before sat on the bed and let her rest against his chest. He knew she was gonna be next and had hoped that Dawn wouldn't mind, but he had a feeling she wouldn't.

Then the moment was interrupted by the sounds of crying.

"Oh, crap." Ash then pulled out before laying her on the bed. "I'll be right back."

Johanna lied there as he put his pants on and left the room. She gasped as her pussy squirted, her son-in-law's baby batter leaking out onto the sheets. The crying ceased, much to her relief, though she part of her realized something. With this much, she was wondering what she'd do about it.

After about a minute, she was just recovering and reached for her bra before Ash came back in.

"Turns out Satoru just needed a diaper change. He's back asleep now, so we should be good." He explained.

"Oh, good." She says before seeing him walk back over while undoing his pants. "A-Ash."

"It sometimes takes a while before I become soft." He says while dropping his pants as his hard member flopped out. "Dawn's not gonna be back for a while so..."

He then pinned her to the bed and started kissing her before inserting his member into her still leaking entrance. Safe to say Johanna's room was filled with moans and the bed creaking for another hour, her grandson resting quietly and sound asleep as if not hearing a single noise.

(Several months later, Ketchum Household)

Dawn was annoyed that their visit with her mother ended in her husband banging and impregnating her mother, but less so since like Serena, she was happy that her mother was no longer lonely. She could deal with the aftermath. However, it was clear that punishing him wasn't getting him to learn a lesson, so the girls slowly gave up.

Johanna had of course married and moved in with Ash, becoming one of his wives. She was happier than ever before, not just that she was getting to see her daughter and grandson more, but that she was going to have another child.

Was Delia shocked again? Yes, but was quick to accept it as usual.

Right now, Johanna was in the kitchen cleaning dishes while no one was home. She was wearing an apron over her maternity dress which had her pregnant belly protruding from it. She wiped some sweat from her brow and was about to continue before she gasped as her husband's hands suddenly groped her enlarged breasts.

"A-Ash, don't sneak up on me like that." She says before he started massaging them through her clothes.

"Sorry. Seeing one of my beautiful wives working alone I just couldn't help it." He says before undoing the apron and removing it. "Plus, you seem exhausted so why don't you take a small break?"

"I guess it wouldn't hurt." She says before being caught off guard when she was turned around and then sat on the kitchen counter, shocked upon seeing his member already out. "W-Wait, now?" She says as he lifted her skirt up, revealing her sopping wet pantyless pussy. "C-Can't we wait until-" She stopped and moaned as he pushed into her.

He started his routine of thrusting in and out of her as she moaned aloud. The feeling disturbed their children and they kicked for a second, causing her to gasp between moans. He pulled down the dress, freeing her breasts before he started sucking one of them, drinking milk from it.

Johanna just simply smiled and welcomed the pleasure. She was feeling so much better than her previous marriage. This time she had someone who she could love and would love her back, and even Dawn as well.

As Ash came inside of her, she couldn't help but look forward to giving birth to twins. Happy to know that they'd have a loving father.

Chapter Text

Someone suggested that I include Misty's sisters and I'm not gonna write a chapter of them since they're not milfs unfortunately, but I will maybe mention them later on.

If anyone gets the reference of the children's names in the story... I don't know.

(Ketchum household)

So, where does this story take our champ? Well, right now he was currently home. He had just got done putting the son he had with Daisy: Gary's sister, to bed, he was confronted by one of his wives and his brother-in-law.

"I'm sorry, huh?" Ash says, dumbfounded.

"Were you not listening? I said I want you to come and try to help our mother in... your methods." May says, albeit a little nervous.

"Uh... I didn't think I'd ever hear you say that of all things. You really want me to come and... ya know... add your mother to the family?"

"I know it sounds weird, but we need your help more than anything. It's been a year since her and our... 'dad' divorced, and she hasn't exactly fully recovered since then. We just want her to be happy and you already helped yourself to two of your other mothers-in-law so I figured this shouldn't be much trouble."

"So, you'd be alright with me making love with your mother?" He asked before she nodded.

He looked at Max: his brother-in-law who was as of now a teenager and Pokemon Trainer. "Hey, I think it's a little weird too. Just... help her okay? I don't like seeing my mom sad after so long. Even if it means bringing her into this house."

"Uh... well. Okay, if you say so. I'll do what I can."

(Hoenn, May's old home)

And so, they took a boat over to the Hoenn region. The three arrived with Ash and May's son and daughter: Landon and Marina. Their mother: Caroline Maple put on a happy front and even cooed upon seeing her grandchildren after a while.

They spent time talking together, catching up on missed time. Again, the mother of the Maple family was putting up a smile as if nothing happened, but Ash could see right through her mask. Even when seeing her grandchildren, she had trouble truly showing happiness. It almost reminded him of the time she thought her husband was cheating on her.

He hated seeing it. Her and Norman seemed so inseparable and yet years later, they still ended up divorcing. He thought it was disgusting. Caroline was beautiful in every sense and was even a lovely wife and mother at that, so he couldn't see why anyone would give someone like that up. If he ever came across that man, he'd make sure to give him a piece of his mind.

"Mom, me, Max and the kids are gonna head out for a bit." May says while picking up their kids.

"Oh, are you gonna be gone long?" Caroline asked with curiosity.

"No, we'll be back soon enough. Take care." Max says as well before they left, closing the door. "You sure this is a good idea?"

"Hopefully it is. Ash knows what he's doing." May says before they started walking away.

Once the siblings were gone, their mother was left with the champ. Caroline went up to her room, not having anything to say to her son-in-law. Ash decided to follow her up after a bit, finding the door wide open. He took a look inside and saw her with an open photo album, pulling out pictures before taking a box cutter to the one in her hand.

"Caroline?" He asked.

"Oh, hi Ash." She says before tossing the piece she cut out into the trash. "Sorry for not saying anything earlier."

"It's cool, but what are you doing?" He asked as she took out another photo.

"Just putting the trash where it belongs." She says while cutting Norman out of the photo as best as she could before tossing it in the trash as well. "This is the best I can do anyway." She says before pulling out another.

"I see."

After a second, she sighed before just tearing it two before tossing it. "Is there something you need?"

"No, just... you don't seem like you're doing very well."

"I assure you I'm perfectly fine."

"You don't have to hide it. You can tell me."

"I..." She was about to deny him again before thinking about it for a second. "Fine, you got me. I'm just really upset right now, especially since I was recently reminded of you-know-who."

"I can tell." He says before taking the album out of her hand and setting it on the nightstand. "How about we don't look at these and talk about this." He then sat beside her.

Caroline rubbed her face, wiping a tear before he could notice, but he did notice. "I just don't get it. It's been so many years, and he decides that apparently, I'm not good enough anymore. All the moments with had with each other are suddenly meaningless." She huffed. "What's wrong with me?"

"Hey, nothing's wrong with you." Ash says as he takes her hand in his, catching her off guard at first. "It's not you that's the problem, it's him. He just doesn't see how good you are and how good he had it."

"I-I don't know."

"Well, I do. I know you deserve better. And if he decided that you were not enough for him out of the blue, then he doesn't deserve you."

"Do you... mean that?"

"Of course, I do. Which is why I'm doing this."

Before Caroline could react Ash suddenly leaned forward and planted his lips on hers. She appeared shocked when he did before he pushed her down onto the bed, keeping kiss intact while still holding her hand.

He wrapped his other arm around her waist, moving his tongue past her lips and into her mouth. She felt a strange tingle going through her body that she hadn't felt in a long time. They separated in need for air after a bit, a sting of saliva connecting their lips.

"A-Ash what are you doing!?" She says out of pure shock.

"Showing my mother-in-law love, if that wasn't obvious."

"B-But we can't! I-It's not right."

"It's perfectly fine." He tells her as he starts lifting her skirt. "I said you deserve love, so let me give it to you properly."

Then he moved his hand into her panties and started rubbing her entrance, causing her to gasp before shutting her mouth, trying not to let out any sound. Her face started heating up the more he rubbed.

She didn't protest and let him do as he pleased. He reached under her shirt, brushing his palm over her slim before groping one of her breasts. She gasped again as he fondled her boob before giving her kisses up her neck.

"A-Ash, please... what if May and Max come back?" Caroline tried to say.

"Don't worry, they'll be gone for a while. We have time." Ash says before he stops and removed his hand from her panties and looked at the juices covering his fingers. "Seems like you're enjoying it anyway." He says before licking them clean.

She looked ashamed to acknowledge that he was right but didn't fight against it. A minute later and their clothes and underwear were strewn on the floor and Caroline was sucking on Ash's member while he sat on the edge of the bed.

'Why is it so big? Norman was never this big before.' She thought to herself as she continued sucking.

The taste of his precum alone was addicting and left her wanting more. She would then start fondling his balls, making him exhale while leaning back a bit. That made him think her ex-husband was even more stupid to give up someone like this.

A minute later and the champ gave her a warning that he was nearing his end which she heeded and pulled out and started to jerk him off. He came and sprayed his load on his face and in her mouth, some dripped down onto her collar and down between her boobcrack.

'So much too. How is this possible?' She thought.

"You wanna get to the main event?"

"Yes, I think I am."

After cleaning her face, Caroline sat on her bed while holding onto Ash's shoulders as he aimed his member for her folds. He pushed his cock slowly into her, causing her grip to tighten before he was fully inside her.

"Oh, fuck." She muttered under her breath.

"Am I alright to move?" He asked her before she nodded.

He then started pulling back and thrusting back in as usual which she moaned to. She was still surprised that she was doing this with her son-in-law but also because she was feeling so good from it.

With each second gone by, she could feel more than just a tingle going through her body. She looked the trash with the cut out photos, but Ash turned her to face him.

"Hey, don't let him get into your head. Forget about him." He tells her.

She couldn't help herself and pulled him into a kiss, hugging him tightly. He hugged back while lifting her off the bed as she wrapped her legs around his waist, and they started moving their hips together.

It wasn't a feeling she missed so much as it was a feeling that was much better than anything she had felt before. She started to fall into a state of euphoria as she climaxed on his crotch while moaning into his mouth, in bliss as she was being pounded by the younger man.

"So..." Ash says after pulling away from her lips. "You wanna me to come inside?"

"Yes! Please do it!" Caroline begged.

He pushed her back onto the bed and continued to move his hips like a jack hammer. One last slam and he came, filling her womb with his seed and leaving her moaning in bliss. She loved feeling each and every last drop inside her.

After a while, he pulled out of her, his cum squirting out of her. He then looked back at her as she looked up at him with loving eyes.

"Feel better?" He asked.

"Yes... yes, I do."

(Later)

"I don't know. Do you think this actually would work?" Max asked as he and his sister were walking home.

"Hopefully it did." May says as they answered. "Hey, A-" Before she could finish they heard the sounds of moaning and a bed creaking.

"... Okay... I think it worked." The boy says before turning and walking out.

(Several months later, Ketchum Household)

And just like that, Caroline Maple was now Caroline Ketchum, now married to her daughter's husband. The Pokemon Master had turned another one of his mothers-in-law into one of his wives. Had Norman heard about this? Well, they didn't know for sure, but if he did, they wouldn't care to find out.

The maple siblings were glad to know that their mother was happy once again. Max still felt a little weird that his brother-in-law was now also his father-in-law, but he could get over it for the time being.

Now, Ash was in his bedroom making out with Caroline while rubbing her big and round pregnant belly as she bounced on his shaft. He stopped kissing her and moved his head down to her breast and started sucking it.

"Yes! Drink, my milk, Ash. ~" She says happily.

May was watching from the side while holding their son in her arms. In truth, she was waiting for her turn, but seeing her mother enjoying herself was a happy sight for her. She decided to go up to her.

"Mom, could you help feed your grandson?" She says while holding her son out to her.

Caroline took Landon into her arms, the one-year-old latching onto her free boob for milk. The feeling caused her to climax on her husband before he came in her.

Ash was starting to wonder if there was some kind of pattern he wasn't seeing, but he still enjoyed himself none the less.

Chapter Text

Okay, here by popular demand.

(Pewter City)

Ash and Misty had gone to Pewter City to visit their old friend Brock and his kids. They were busy catching up on old times, but that would change soon enough.

The three of them and one of the gym leader's sons were hanging out on a nearby bench in the city, all with ice cream.

"Seriously, I wouldn't believe it if I didn't see it. I cannot imagine how I would've been back then if I heard about what you were doing." Brock says.

"Well, thankfully, old you didn't. Arceus knows he wouldn't have shut up about it." Misty says.

"Well, isn't this a coincidence." A voice caught their attention and they seemed surprised by who they saw.

"Lorelei!?" Misty says, more shocked.

"Been a while." The Elite Four member says while walking up to them.

"Been a while is an understatement. It's been a lot longer." Ash says.

"What brings you out in Pewter City?" Brock brings up.

"Just doing a little bit of visiting. Seems the champion is doing the same here." She says to them.

"You got that right." Ash says.

"S-So, uh... h-how long do you plan on staying?" Misty says nervously.

(Later)

The redheaded member of the Elite 4 decided to join the trio with the visit. As they talked Misty was a little nervous. Ash couldn't help but mentally chuckle. Even though they weren't little anymore, she still idolized the woman after so long.

Speak of the devil, the champion couldn't help but stare. Lorelei was simply beautiful for her age and her outfit really showed off her body. He did look away so that he wouldn't be seen as immoral, though he didn't know that she noticed.

After a bit once night fell, Lorelei asked to have a battle with the champion tomorrow which he eagerly agreed to. 

As sunset came, Ash and Misty were busy swimming laps in the pool of the motel they were staying in. Brock had already returned home for the night, so the couple were left to themselves. The water gym leader in her blue bikini had swum into her husband's arms as they embraced each other before sharing a passionate kiss.

That was before they heard the pool door open and they stopped before looking and seeing a familiar redhead walk into the area.

"Sorry, was I interrupting something?" Lorelei asked.

"Not really." Ash says casually.

"Y-You're not." Misty says, still a little nervous.

"Good. I was just coming here to relax a bit." The older woman says while walking to one of the empty chairs.

She then proceeded to remove her clothes, revealing an ice blue cross bikini. As she went over and sat by the edge of the pool, catching the champion's eyes for a bit, which the water gym leader caught and had a bit of a feeling that she knew what was next.

Sometime later when night fell, Misty had gone up to her room for the night, leaving her husband and the Elite 4 member alone, already expecting the outcome but also feeling a bit of excitement at the same time.

Ash was just swimming around aimlessly before rising from the water, only to be caught off guard when he saw arms wrap around him from behind and two large orbs press against his back. He knew that it couldn't have been Misty so that left only one thing.

"Lorelei?" He asked.

"Correct." She says before he turned to look at her. "Not the reaction I was expecting."

"This isn't the first time this has happened to me. I've gotten pretty used to it by now. What brought this on?"

"I saw you staring at me, handsome. Besides, I heard you already have two champions so I figured you wouldn't mind."

"I don't." He says before taking her arms and surprising her as he spun her around, now holding her in front of him. "Though you're pretty bold to be going after a boy so young."

"You're one to talk. Especially with all those other women who might be older than I."

"Maybe I am one to talk."

She giggled a bit before they moved their faces closer and started kissing. The ice trainer decided to wrap one of her legs around his body and start grinding against his crotch. He already knew what was to come next.

(Lorelei's room)

Ash laid on the bed, Lorelei's crotch in his face, her thong moved a bit as he gripped her ass whilst lapping his tongue at her entrance while she rested her breasts against his stomach and bobbing her head on his member which was sticking out of his swim trunks. It wasn't anything new to him at this point and he embraced it.

He made sure to get as much of a taste he could. While doing so, the redhead pulled off giving it a few more licks.

"So big... I can see why those other girls like you so much. ~" She says in a seductive tone.

"There's more than just that. I'd be glad to show you." He says.

"Oh, I will, but don't think I won't offer the same."

She then lifted her breasts up and plopped them around his member, continuing to massage it with them while licking before putting her mouth over it again, her bikini offering more of a hold that added to the pleasure. He barely even flinched, continuing to lap at her folds for more of her juices.

He decided to give her ass a small slap as he pushed his tongue deep into her entrance. Having much experience, he knew what spots to hit.

After a small bit, he felt her climax and spray all over his face and into his mouth, causing her to moan into his member. The vibrations caused him to cum inside her mouth. She downed every drop he had, making sure not to leave any behind before pulling off.

"Oh my." She says to herself.

"Good enough for you?"

"Yes, it does feel good, but what do you say we skip the foolplay?"

He couldn't say no to her offer.

They now changed to a doggy position, the champ had one hand on the ice trainer's ass, using his other to rub the tip of his member against her entrance.

"Come on, stop teasing me already." She tells him with a smile.

"Sorry, just making sure you're ready." He says back.

"Trust me I am. It's gonna take a lot to-AH!"

She was interrupted when he started to push his member into her entrance, causing her to moan. He felt her canal tighten around him and mold itself to fit him.

"I figured. Good thing, I am a lot." He says into her ear.

With confidence, Ash grabbed her hips and pulled back and started his routine of bucking his hips into Lorelei as she struggled to keep her moans in. He watched as her ass rippled and her boobs jiggled with each thrust, making sure each was powerful and made her feel as good as he made his wives.

The bed creaked with each thrust, the only other sound being of clapping filled throughout the room. Thankfully the rooms in the motel didn't have thin walls so having someone hear them was out of the question.

He upped it by reaching forward and grabbing her arms, pulling them back as he continued. They would continue to do so for the better part of almost an hour, the ice type Elite 4 member came, spraying all over his member.

"Lorelei, do you want me to cum inside?" Ash asked her.

"Yes! Yes, fill me, Ash!"

He started thrusting faster, causing one of her boobs to bounce out of her bikini. He then let out his cum and started filling her womb with it right up to the brim, her pussy walls tightening to milk every drop it can out of him.

After a bit, they turned and laid in a spooning position. The champ's member still inside of her as she panted with her face red.

"So, think you're still up for that battle tomorrow?" Ash whispered into her ear.

"Might be... challenging, but I'm... not backing down." Lorelei says between her panting.

"Good to know. I won't hold back either." He says while giving her ass a light slap. "I'll have to go so that Misty doesn't feel lonely."

"I know but..." Lorelei says before wiggling her hips a bit. "Who says you need to leave so soon? ~"

He smirked before wrapping his arms around her, then without pulling out, turned so that she laid atop of him before he started bucking his hips once more.

(Several months later, Ketchum Household)

After about a month, Lorelei had now become one of Ash's wives. She was welcomed graciously by the other wives, but especially by Misty. Being that she was a part of the Elite 4 in the Kanto Region, of course news would spread.

Like always though, they didn't care. The ice type trainer was happy now with the world champion as her husband and was especially happy to become a mother.

Speaking of which, in the family bathroom, Ash was sitting happily as his newest wife was using her now bigger breasts to massage his member while licking it.

"Do you like it? Does it feel good? ~" Lorelei asked in a seductive tone.

"Yeah, it feels so good." He tells her.

After a bit, they switched to her in his lap, his member thrusting into her entrance. One hand on her pregnant belly and his other holding a boob up as he sucked, drinking her milk.

"I can't wait to meet our baby soon. They're gonna love their daddy." She says while caressing his cheek.

"I'll make sure they do. They're gonna have a lot of fun with their other siblings as well."

He stopped drinking and kissed her passionately while still bucking his hips into hers. He came into her entrance and as he did so, he had some thoughts in mind. This would eventually continue, though who would it be next?

Okay, I'm gonna announce the next one before we get to it.

Up next is Lana's mother. A little problem is that she doesn't have a name so... any suggestions for her name?

Chapter Text

So, looking at the comments, I think I'm gonna go with the name Kopiko. Thanks to KGBeastboy for the idea.

Also just to make it clear Lana's sisters aren't part of the harem.

(Alola, Lana's old home)

After all that happened, Ash was hanging out with Lana's family with their daughter. Her sisters Harper and Sarah were happy to see their niece, her mother Kopiko was no different. All completely wholesome... for the most part.

Everything was completely fine upon arrival, and their meet up seemed just as regular as the last, with a little difference. After a small bit, Ash couldn't help but stare whenever he saw Lana's mother around, stealing a glance every now and then.

He didn't notice it before, but now he started to take notice of how beautiful her mother was. Maybe it was because of what happened to him and his other mothers-in-law, but he also noticed that she was acting somewhat different.

Lana noticed and had a feeling of what was gonna happen. It had been a long time since her mother divorced with her father, so she appeared to have gotten over him. She already knew what was coming next.

"Are you sure you'll be alright?" Ash asked.

"We'll be fine." Harper says.

"We'll make sure to take care of Leena too." Sarah says while being the one with his daughter in a baby carrier.

"I've got everything I need." Lana says while holding up her baby bag. "Are you gonna be alright?"

"Oh, it's okay dear. I'm sure everything will be fine." Kopiko says while happily waving.

Lana's thoughts only grew bigger. She left with her sisters and daughter, already knowing what was gonna happen. After all, she knew what happened the last few times when three of his other wives left him alone with their mothers.

Once they had left, after shutting the door, Kopiko walks past Ash while brushing her hand up his arm. He noticed but didn't say anything. This had only been one of the few things she had done since he got there. It had only been seductive glances up until that point, maybe 'accidentally' bumping into him with her breasts, but nothing that went too far.

Sometime later Ash was reading a newspaper. It talked about Professor Samual Oak retiring soon which he had already known beforehand, especially since Gary was said to take over for his grandfather. There was also some news about him, but it wasn't anything new so he didn't pay it any mind.

He got up to walk to the hallway, his wife's mother was walking from the other direction, and he was intending on walking around her. While going around it made her bump into a table and knock over some books.

"Shoot, lemme get that." He says before she stopped him.

"No, no, it's fine. I'll get it."

Kopiko tells him before she leans down to pick them up. As she did, her ass pressed against his crotch. He hadn't flinched a little when she did it, but it did cause him to freeze for a second. Even through her skirt, he felt his little friend start acting up as soon as contact was made.

"Oh, my bad dear." She says after putting the books back.

She moved away while standing up. He didn't let it go though, moving back against her while reaching up and grabbing her breasts, causing her to gasp as she was pulled against him.

"How long do you plan to keep this up?" He asked her.

"I was wondering how long it'd take you to notice." She says while looking back at him with a smile.

"Oh I noticed ever since you started." He says before giving her boobs a squeeze through the fabric of her shirt. "Just didn't think it was appropriate to act like that in front of your daughters and granddaughter. But now that we're alone, what do you say we make the most of it?"

"Please do. ~"

(Sometime later)

They went to the living room, and strip down. Ash and Kopiko were already kissing, his cock thrusting between her hot and thick thighs. He licked every part of her mouth, his tongue messing with hers every now and then while his hands gripped her ass and her large breasts pressed against his chest while her juices started coating his member.

It led to them falling onto the couch, still kissing. After a while, they stopped and pulled away, a string of saliva connecting their tongues.

"Someone seems eager to have fun with their own son-in-law." Ash says.

"You're one to talk after marrying three other mothers." Kopiko says.

"Fair point."

He pulled away and moved down, spreading her legs before he started licking her entrance, sending a jolt through her for a moment. He continued to lap at her entrance as she held his head there, moaning throughout the room.

He didn't have to lick for long as after about a minute, she moaned louder as she came in the champion's mouth. He happily gulped it all down before pulling away and looking up at the woman who was panting a bit.

"I-I'm sorry. It's a long time." She says, a little embarrassed.

"It's okay, it happens. If you want, we could skip the foreplay."

"I would like that."

He then moved his arms under her and lifted her up in a bridal carry, which made her giggle as he walked out of the living room and down the hall.

Ash brought Kopiko to her room and had her laid on the bed before getting on top of her and started kissing her again. He grabbed his penis and angled it at her entrance, slowly pushing it into her which caused her to moan into his mouth and hold him tighter. After taking a moment to adjust, they pulled away again.

"Tell me when to start." He says to her.

"You do it now. Show me how you please my daughter."

He smiled took her hips and pulled back before he started thrusting back inside. It didn't take long for her moans to echo throughout the room. She could feel her entrance canal spread and reshape itself to fit to his shaft each time the tip hit her womb entrance.

He moved his hands up and started playing with her large melons, adding to her pleasure. He'd move away and down to them, taking a nipple into his mouth before sucking on it. Just like his other mothers-in-law, Ash made sure that Kopiko wasn't left out and make her feel as good.

Several minutes went by, the two of them continuing to bang with no sounds but moans, wet slapping and the creaking of the bed. She came on his member, spraying his crotch and his ballsack with her juices while he kept thrusting.

"Yes, Ash! Give me you're children!" She yelled out.

That encouraged him to buck faster in her. His tip made it into her womb before he came. She let out her loudest moan as she felt his warm seed in her belly. Her pussy tightened around his member like a vice grip, wanting to squeeze it of every drop he had before he was done.

"So, does it feel good?" Ash asked while pulling back a bit.

"Yes, that was amazing." She says.

He took a moment to wait and pulled out of her, his cum squirted out onto the sheets. He was starting to get up before Kopiko tightened her grip on his shoulder.

"Hold on now dear. My daughters aren't home yet. Would you mind treating me to more? ~" She asked.

He only smiled before turning her onto all fours and aimed his member at her asshole, pushing it inside. Hours would go by with her moans echoing through the house.

(Several months later)

So, like that, Ash had turned another one of his mothers-in-law into one of his wives. Lana wasn't much upset, knowing that it was partially on her for leaving her husband with her mother. Harper and Sarah weren't deterred when they heard, only happy that their mother had found a lover even if it was their brother-in-law.

As for now, the family were on a private beach to spend time with each other, Leena being left with Kiawe to be babysit her.

"We found a spot!" Harper and Sarah both say at the same time.

"Coming." Lana says, stopping midway to rub her big and round belly.

She was wearing adjusting her aqua blue bikini around her grown breasts and was currently pregnant with twins. Ash walked up and put an arm around her.

"Are they doing good?" He asked.

"Yeah, they've been really calm though."

"That's good to hear."

Then his other hand was grabbed before wrapped around to touch a bigger belly. He looked and saw Kopiko smiling at him. She wore a frilled bikini with the same color that made good cleavage out of her milk filled jugs while showing off her belly which was filled with triplets.

"Honey, do you mind helping me with the sunscreen? ~" She asked him.

He nodded before heading to their spot together with the two of them. Keeping to his promise, Ash made sure to get the parts of their bodies they couldn't reach, those of which being her thighs, backs, and the undersides of their bellies. To say he didn't take pleasure out of it would be a lie.

Lana at some point went out into the water. Her sisters were playing with each other while she was just relaxing nearby. She looked out onto the beach and saw her husband still with her mother, only sighing as she knew what they were doing.

Kopiko laid on her back as Ash was sucking on her breasts, drinking her milk while rubbing her belly and gently thrusting into her entrance. Having five more kids along the way, he would do whatever it took to raise them alongside his others.

Though, his journey of gathering older women weren't stopping here.

Chapter Text

Just a heads up, Ash hasn't left Alola at this time. You'll see why just about... now.

Ya know what's funny? Me and my friends never finished the Pokemon Journeys anime.

(Kiawe's family farm)

After his visit with Lana's family, Ash decided to head over and visit Kiawe just for old times' sake. He was still gonna be in Alola for a sometime and wanted to see his friends before he had to return home.

Like before, things were all normal, he had caught up with his friend on things that were happening in their own lives, and nothing seemed out of place. That wasn't completely the case.

Like with Lana's mother, Ash couldn't help but notice how beautiful Kiawe's mother Sima was despite her age. He had stared at several points whenever no one was looking. How could he not? Unlike several of his mothers-in-law, Sima was not afraid to show off her body especially with her attire.

As all things had been, he started to notice some things she'd do. He knew because she'd only do it when she knew it was only him watching. Stuff that he definitely understood of by now after now having so many wives. He knew she wanted him.

Kiawe seemed oblivious to what happened the last few times Ash was left alone with a woman and that soon come to bite him.

(Later that night)

Ash was getting back after doing a late-night delivery. He insisted to take this just so Kiawe and his little sister Mimo could get sleep. It took a while to take care of, so the moment he got back to the farm, he already knew that everyone had to be out like a nightlight. Well, not everyone.

"Hey, Ash." He heard and turned in the direction of the voice.

"Hi, Sima. What're you doing still up?" He asked.

"Was just doing one last checkup on the Pokemon. What about you? How did the deliveries go?"

"It went pretty good actually. No complaints and everyone seemed happy."

"That's good to hear. Thank you."

"No problem. If you don't mind, I'm just gonna head to bed." He says, walking to the door.

"Hold on." The woman quickly says while stopping him.

"Huh? Something else you need?"

"I do actually." She says before stepping closer, putting her hand on his chest. "Not here though. So, if you wouldn't mind, could we perhaps go somewhere we could speak in private. ~"

He knew that tone. It was one he had grown familiar with over the years, and he knew what she was trying to do.

He didn't waste time, taking her by the waist and pulling her to him, mashing his lips against hers. She was shocked, but immediately eased into it as she wrapped her arms around his shoulders. He wrapped his arms around her waist, pulling her closer while pressing her boobs against his chest.

They stayed there for a little bit, their tongues entangling around each other as they made out. They separated for air after a minute, saliva strings formed between lips.

"Woah. Not bad." She says.

"You weren't either." He says back. "About speaking in private..."

(Sometime later)

Somewhere in the forest nearby the farm, Ash was standing with his pants down, Sima crouching in front of him while bobbing her head on his cock. He had a hand on the back of her head while she had her hands on his hips to keep balance. The only sound being the occasion wind, but mostly the sound of wet slurping and humming coming from the naughty mother.

The champ could feel his member getting harder with each second. She was making sure to put in all the effort she could to please him in any way she could. She could already taste the precum and was eager to get him to release.

After about a minute or two, Ash could feel his climax coming up and was quick to warn Sima which got her ready. They continued for another little bit before he came in her mouth. The sounds of her gulping added to the pleasure. After a bit when he was done, she pulled off of him before opening her mouth, revealing she had swallowed it all.

"Damn, not bad. You're really something." He tells her.

"That means a lot from Alola's first champion." She says before standing up and turning around, bending over, and lifting her skirt to reveal no underwear but a wet vagina. "Why don't you show me what you can do? Handsome. ~"

Ash simply smirked before getting on his knees and grabbed her asscheeks, giving it a nice squeeze before pulling them apart. He then started licking her pussy lips, causing her to gasp. The champ wasn't holding back, slithering his tongue all around her lower lips.

"Shit, keep it up, babe." Sima moaned.

Her eyes squinted as she moaned into her hand, feeling a tingling sensation running through her body. The champion kept licking, tasting her sweet juices onto his tongue entering his mouth. He moved closer and enveloped his mouth over her pussy lips, tongue going into her and licking all over her vaginal walls.

He kept licking over and over again before reeling his hand back and slapping her ass. She came, squirting her juices into his mouth. He gulped down every bit before pulling back, giving it a few more licks before standing up.

"Not bad. You're something." She said to him.

"I've been practicing." He says back before grabbing her hips and rubbing his member against her entrance. "You haven't seen anything yet."

"Oh, you naughty-AH!" She started to say before he pushed his shaft right into her and moan and lean over, putting her hands on the tree. "Oh, fuck... fuck, it's so big."

After a second, Ash pulled back and started bucking his hips back into her, causing her ass to clap with each second. Sima moaned as he kept pounding her, the tingling sensation increasing in her crotch each time.

The champ, despite already having done this many times before, could never get over the feeling, especially how tight she was. He huffed as he continued slamming his hips into hers, watching her asscheeks ripple each time.

It continued before he saw her boobs bounce out of her top. He smirked before leaning down and grabbing them in each hand, then start fondling them without losing rhythm in his hips. She couldn't take much more before she came.

"Fuck! Fuck me harder, Ash! Turn me into one of your whores and give me your children!" Sima moaned out.

Ash kept going, thrusting harder and faster into her. Her vaginal walls started to squeeze his member as if trying to milk him. Her eyes rolled back as her tongue hung from her mouth as he kisses her neck.

After a bit, he gave her a few more hard thrusts before stopping, giving her bust a good squeeze. His seed sprayed out into her womb, filling it up within seconds of his climax. Once he was finished, he slowly pulled out of her, his cum dripping out to the ground.

"That was amazing." Sima moaned out. "It's been so long since I've felt being filled."

"Glad to help, but I'm not finished yet." He says, moving his tip up to her unfilled asshole.

"Oh, I hoped you'd say that. ~"

He then pushed into her ass and the moans would continue throughout the night.

(Several months later)

So, what was to be expected? Well, Sima had now become one of Ash's wives. Kiawe was shocked at first, especially since his mother had married a man who was younger than even him, but overtime got over it, since his mother was happy.

Mimo was quicker to accept her new stepfather for aforementioned reason, but also because she learned that she might be an older sister soon.

As of now, Sima was on the farm, sweating after having just gotten done checking up on the Tauros. She huffed while rubbing her back. She still wore her usual outfit, however, the difference being her large and round belly that was carrying her new husband's child and her top seemed tighter on her swollen tits.

She only smiled before rubbing the top of her belly, before another pair of arms wrapped around her and rubbed her midsection. She only smirked before looking behind her.

"You know, you shouldn't be working while pregnant." Ash says.

"I'm perfectly fine, hon. I can take care of-" Sima says before getting cut off by a kick in her stomach. "Strong... just like their dad. ~"

"How about you take a break? Spend some time with your husband?"

"That sounds nice."

He then began kissing her before he moved his hands up to her large jugs to massage them. She removed them before she pulled back.

"Hey, not out in the open-"

She started to say before he started kissing her again. He then turned and lifted her in a bridal carry, causing her to gasp in his mouth. He then began walking into the forest.

In the forest, Sima was sitting on the ground, nude, Ash's hand down and fingering her. He was bucking his hips, thrusting his member between her thigh and calf, while he was treating himself to her boobmilk.

"Honey, take it easy. Save some for our kid." She tells him.

He just kept drinking while fingering her, until she came in his hand.

After a bit, Ash lifted Sima up, back against the tree, thrusting his member into her entrance. She moaned as they held each other, as if they were a loving couple for years. She moaned while smiling in his hold.

Many Pokemon avoided the area, not wanting to be bothered. They started making out once again while the champ started thrusting faster until he came into her pregnant cunt, pulling out as his cum dripped out of her.

"Thank you, Ash." She says as she was let down.

"Anytime, Sima." He says back to her as he lent down to get their clothes.

"Hold on, hon." She stops him. "Done already?"

They were in the forest for hours that day. Sima had all of her homes filled.

Chapter Text

Okay, for the one who asked about Kiawe's dad, I think it should be obvious by now that the married MILFs are divorced in this story. I just didn't feel the need to mention it.

Ash still hasn't left Alola yet at this time.

(Aether Paradise)

After getting back from meeting up with Kiawe's family, Ash was now up and going to meet with Lillie's family before planning on going back home. Since Lillie had already been there long before him, her mother already got to have time with her three grandsons.

Sadly, Gladion wasn't there, but he promised to visit some other time.

However, after what happened beforehand, she was prepared for her mother to possibly be next on the list to join her husband's harem. He already did it with three of his mothers-in-law, which just recently turned into four from what Lana told her.

Being that her mother was divorced, still young and in her prime, the chances were low that it wouldn't be the case. And so, when Ash arrived, she could already see Lusamine starting to give him some 'looks' that were she knew all too well.

However, what she didn't notice was that one of the workers at the Aether Foundation was sharing the same thoughts as her mother. A certain lavender-haired woman named Wicke: the assistant branch chief of Aether Paradise, would be eager to talk to Ash, seemingly wishing to know more about him. He knew what she trying to get at.

(Later that night)

Everyone had left for their rooms for the night, Ash on the other hand was wide awake. He was walking around just to burn some energy for the night. He had met and talked with a few of the workers who were up for their shifts. Some of the female staff

While walking around he ended up bumping into someone and went crashing to the ground on his back. He groaned in pain before looking down at who landed on him.

"Ash? Oh, I'm sorry. I should've watched where I was going." Wicke says.

"It's fine. Small accident." Ash said.

He already started to feel his thing acting up slightly, especially since he could feel her breasts pressing against his chest. Her shirt felt thin, though no proof whether it was or not. When they got up, Wicke looked down, catching a glance at the bulge already formed in the man's pants. Ash quickly turned and started to walk away.

"I'm gonna go take a shower." He tells her.

"Wait." Wicke says, stopping him. "I was actually going to take one, but you know... I could wait."

He could see the blush on her face from miles away. "I mean if you want to go in first, I'd be fine with that."

"Well, no you don't have to wait. You can go first."

He stared at her. There was more than one shower, she could easily go into another one if she wanted to. However, the champion knew what she was... failingly attempting to pull.

(In the bathroom)

The water was running from the showerhead, outside two baskets had a pair of clothes in them each, and inside, the champ was having fun.

Ash was behind Wicke, head turned, making out with her, groping her massive boobs, and thrusting his member between her beautifully thick thighs while the water ran down their bodies into the drain.

The champion was groping his potentially (most definitely) future wife, his fingers were practically gone in her flesh. He was enjoying the feeling, that and her curvy figure that made her stand out from the other girls.

"Sheesh, your boobs are huge." He says after pulling away.

"I didn't realize you were so-MFH... perverted. ~" She says back.

"Really? I'm perverted?" He says before pinching her nipples, causing her to moan. "You're the one who's been attempting to seduce at the man married to your boss' daughter."

"O-Oh... you noticed?"

"Is that a real question?"

Ash then pulled her nipples, making her moan even louder. Thrusting between her thighs made him rock hard, almost making him cum on the spot just from it alone. It had been a while since he had felt like that from anyone's legs alone.

"I was expecting Lusamine to try this, but you're not an unwelcomed surprise." He tells her before reeling a hand back and slapped her ass.

"I couldn't help it. Learning all that all those women got to have you, then the thought of her taking you and having your child next over me-AH!" Wicke moaned as he pinched her nipples again.

"Aw, you got jealous? ~" He asked, not waiting for an answer. "How about we skip the foreplay, then?"

He then pulled away before bending the woman over and then aiming his member before pushing it into her entrance. She yelled in pain as he slowly pushed himself inside her, spreading her inner walls and shape them and fit his tower. Once he was fully in, he waited a bit in order to adjust.

After a second, he asked if she was ready, and the moment she nodded he pulled back and thrusted forward. She continued moaning while her hands were on the wall for balance, feeling her pussy walls spread each time the Ketchum's cock flowed in and out of her.

Ash was getting a nice view of the older woman's huge ass rippling each time his crotch slapped against it and her boobs swung from the impact. The wet skin slapping from the water of the shower added to the lewdness and turned him on further.

"So... so good..." Wickie moaned.

"If I had a dime for every time I heard that, I'd be one of the richest men on the planet." He says while slapping her ass again. "You said you wanted to have kids with me, right?"

"Yes! Yes, please. Give me your seed and breed me like the others!"

"Alright. You asked for it."

With that, he started thrusting faster, enjoying the sounds of the woman moaning as he dominated her.

After about an hour, the man was starting to feel his climax coming, though didn't feel like warning her since she told him she wanted him to. He reached over and grasped her boobs, pulling her away from the wall against his chest and thrusted faster and harder, making her cum hard, her entrance squeezing his member tight.

Then he came, filling her womb with his seed. She moaned loudly upon feeling waves of warmth enter her body. Wicke was left panting as his cum leaked out of her, down onto the shower floor, and down the drain to never be seen. As this was going on, they hadn't notice someone entering the room.

He pulled out of her causing more to squirt out, going down the drain as well. The woman was left in a state of euphoria, her legs seeming weak. Ash laid her down so she wouldn't fall and hurt herself. Unfortunately, he was still hard, so he was getting ready for another round before he felt hands on his shoulders.

"Not bad, I must say. ~" He heard Lusamine behind him. "Seems you still have some energy left."

"Yeah, I do." Ash says, guessing who it was as he turned around, saw her nude, and smirked. "Not looking bad yourself."

"Thank you, sweetheart." Lusamine says before wrapping her arms around him. "Now, would you mind helping me feel... young again."

He chuckled before they kissed, him reaching down to grab her ass as they did.

She had a slimmer body than most of his women, and her breasts were a C-cup at most. He still remembers that Lillie used to have smaller breasts before she got pregnant with their first son which made them bigger than her mother's and only during her second pregnancy when she was having twins did hers become so much bigger. He was eager to see them grow.

While they were still kissing, he reached between her ass and rubbed both her asshole and vagina with his fingers and thumb. The blonde moaned into his mouth as he did, the running water unable to hide how much wetter she was becoming from his touch.

After a bit, they pulled away, the blonde panting a bit. As the Pokemon Master looked at her, he knew what he was gonna do next. He removed his hand from her snatch and lifted one of her legs while aiming his tip at her entrance.

"I wonder what my daughter will think of this." The woman says with a smile.

"I think she'd be happy to be a big sister. Especially seeing you happy after so long."

Ash wasted no time and pushed his member into her entrance, making her head arch back while moaning as he felt her entrance spread to welcome him. He stopped for a bit just so Lusamine had time to adjust.

After a bit, he started thrusting inside of her as she continued to moan. Wicke watched as he fucked her boss while fingering herself as his seed squirted out some more. He kissed at the blonde's neck, making sure she felt even more than just him fucking her pussy.

It had been another hour of them in the shower, him banging her over and over again, causing her to climax several times through it. He reached down and picked her up by the ass and kept thrusting, making her cum a fourth time.

"Oh fuck!" Lusamine moaned out.

The rest of her body fell limp on his chest as he kept thrusting into her entrance. He could feel her entrance tighten around his shaft, begging him to release into her awaiting womb to create new life. Unfortunately, she came fifth time, yet he still hadn't.

Not long later, he could feel his climax approaching and was ready to make this woman his. A little more time later and he gave her several hard thrusts before he came, filling her with his baby batter until it overflowed, until it started to leak out and land on the floor, going down the drain.

Lusamine panted as she felt warmth in her belly, feeling excited at the idea of having another child to raise. He kept going for a bit, still having a good amount even after cumming inside one of her workers.

It was about a minute later before Ash was done cumming and pulled out of her, causing a waterfall of his semen to flow out of her and down the drain. He hoped the drain wasn't gonna get clogged with how much was going down it.

"So, feeling good yet?" Ash asked her.

"Oh... I feel so much better than good, dear." Lusamine says while still laying against him.

He smiled before he felt someone touch his arm before feeling two big orbs pressed against it.

"Ya know, it might be possible that I won't get pregnant on the first time." Wicke says with a seductive gaze. "Do you think maybe we could go again? ~"

How could he say no.

(Later)

They had left the shower and went to the blonde's bedroom to have a more comfortable place. Ash was on his knees behind Wicke who was not just leaking semen from her entrance, she was leaning down and licking the drizzling entrance of her boss: Lusamine, both of whom were moaning loudly.

The sounds of their moans were kept in the room thanks the soundproof walls. The man had filled both women with his seed in the past two hours, seeming still full of energy and had yet to run out.

Speaking of which, he came another time inside of Wicke making her moan into the other woman's pussy as he did. After a second, he pulled out and sprayed the rest on her ass and back. He then pulled her away from the other woman, laying her on his side.

Lusamine was left on her back gasping for air before ash crawled up to her and then inserted his member into her already soaked pussy. Part of him wondered if he had done it enough, but he was still hard so they might be there for a while.

(Next morning)

Lillie was peeking through the door to her mother's room and only sighed. She could see her husband snoozing in the middle a jizz covered bed with the two women on either side of him, their entrances dripping with his baby batter.

She stood back while closing the door. She knew to expect a new sibling or siblings in the near future that were gonna be younger than her youngest sons and knew she was gonna have to prepare to explain this to her brother.

(Several months later, Ketchum Household)

Ash was in his bedroom, Wicke bouncing on his member while he was sucking on her milk filled breast. As they were doing this, he had a hand on her big and round belly. Not only that, but Lusamine was on the other side of the bed, watching with an even bigger and more gravid belly, holding up a camera while fingering herself. The women were wearing lingerie of course now with the champion as his new wives and couldn't be any happier.

Lusamine not only had her small breasts grow three times, but to the shock of her other children and others, she was said to be carrying quadruplets. It was something she was much proud of and showed off to the other mothers-in-law that were married to her new husband, knowing she was having more than all of them. Wicke didn't mind though, having twins would be enough.

"Yes, keep going... don't stop, Ash." The woman in question moaned.

After a bit, Ash pulled away from her boob and kissed the woman while still gently thrusting into her entrance. He then came, spraying his semen into her entrance. He still kept thrusting slowly until he made sure he filled her enough before pulling out of her.

He then laid her on the bed before looking at Lusamine who he got hard again upon seeing. He stood and walked over, put down the camera before kissing her and picking her up, going over to the unoccupied pillow and laying her on her back before pulling away.

"So, how do you feel now?" He asks her.

"Couldn't be any happier." She tells him. "Being a mother again and having so many kids with a strong man, such as yourself."

"Heh, good to know."

With that, he pushed his member into her entrance and started gently thrusting into her. She started to moan in delight as she felt her new husband's member going in and out of her, something she was not gonna forget. As he was moving his hips, he moved his head down and started drinking her milk.

Ash already had a lot of kids already, but he didn't mind having more. Heck, he was looking forward to meeting the next woman or women that would be joining his family and having kids with him. Whatever would happen, his family was only bound to get bigger again and again.

After a bit, he came in Lusamine, filling her with more of his seed. He rubbed her belly as he did, feeling several kicks. It was only so much longer until the due date.

(A few months later)

Gladion was sitting in the living room of his brother-in-law's home, staring at two of his new baby sisters in his arms who were asleep. The day his mother gave birth; he had three new little sisters who had black hair and a blonde little brother, all four of them had the Z marks on their faces from their father.

He felt mildly uncomfortable since they were also his brother-in-law's kids too. He looked over at Lusamine who was sitting while breastfeeding his little brother while Ash was next had his little sister in his arms. Wicke was standing next to them while holding the twins she had with him and seemed to be begging him for more kids despite it not being long since she gave birth.

The blonde man could only sigh not knowing how else to react.

"Aren't they just the cutest?" He heard as he looked back and saw Delia, his mother-in-law.

"Yeah, they are." He says in a low voice.

After achieving his goal of becoming a Pokemon Master, Ash's new goal seemed to be to have the biggest family he can. Gladion didn't hate having new siblings, and he was glad that his mother was happy too. He just needed to get used to this new life.

"You know, it kinda makes me jealous." Delia says as he turned to her. "Sometimes I wish his father was still here just so I could give my boy the joy of having more siblings... or just have another child myself, but sadly I don't think I will. Oh well."

Gladion thought it was odd of her to say something like that before she walked away and started talking to Sima and Kopiko who were holding their new babies. As she did, he stared at her, blinking for a second.

Like the other mothers his brother-in-law had gotten with, she still appeared to be young, youthful and very much attractive. He looked at Ash, then looked back at her.

Maybe...

If anyone wants to see that last part going anywhere, leave a comment below.

Other than that, I'm sorry this took so long to get out. Hope you enjoyed

Chapter Text

Okay, ya know what, I'm gonna end this here. I really have not only lost interest in this story, but I don't really like it anymore now looking back. It is not good, I do not think I can continue this, I just... I wanted to have write smut about milfs, but this... I do not like how I wrote these anymore. I'm sorry to those who wanted me to write more, but I can't go on with this series.