(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.