This is a request from ObeliskX, sorry it took so long.

Ash x Misty

"You think you can out-swim me, Misty, leader of Cerulean Gym?"

"Easily, I've trained more water-type Pokemon than you," Ash retorted.

Ash was back in Kanto visiting his old friends, and made his first stop in Cerulean City to visit Misty. They were in the midst of yet another argument. Since they were unable to agree on who was the better swimmer, they decided to have a contest to see who truly was the best. In order to ensure there was no cheating, they let all of their Pokemon out along the edge of the pool. While they were preparing themselves for their race, the Pokemon began to talk with each other.

(In Pokemon Talk)

"It's nice to be back in Kanto, I've been to so many new places that it is finally nice to be back home," Said Pikachu.

"Yeah I can't imagine all the places you've been, Just going around Kanto was enough adventure for me," Misty's Starmie replied.

"It's also nice to see Ash reaquainted with Misty," Pikachu continued, "She is by far the best girl Ash has traveled with. Always was able to keep him in check. The only problem is her irrational fear of bug-type Pokemon."

"What were the other girls he has traveled with like?" Starmie asked.

"Well, there was May, she was alright. She had to drag her annoying little brother around though. Then in the Sinnoh region he traveled with Dawn, she was obsessed with contests. I feel bad for her Pokemon. And when Ash traveled through the Unova region, a girl named Iris traveled with us. She was hellbent on becoming a Dragon Master, but she couldn't even take on a simple ice-type Pokemon. Finally there's Serena from Kalos. She was so into Ash, but he was too oblivious to notice. Poor girl," Pikachu said.

"Wow, he certainly has been around the block a couple of times then, hasn't he," Starmie replied.

"Nope, Ash hasn't done anything but merely befriend them. He is just too focused on training and battling," Pikachu said, shaking his head.

"Well, what if we were to change that?" Starmie suggested.

"I don't know about that, Ash is my best friend, I'm not going to force him into something he doesn't want to do," Pikachu replied.

"Who's to say he doesn't want to, but he just doesn't know that he is able to. I know Misty has thought about these kind of things with Ash," Starmie stated.

"Well, I guess it's worth a try…" Pikachu agreed reluctantly, "But how are we going to make them?"

"Leave that to me," Starmie replied.

It was at this point that Ash and Misty had begun their race, and it was close. Ash held the lead for the majority of it, but near the end of the pool Misty began to pass him. Right as they were about to reach the end of the pool that Pikachu and Starmie were on, Starmie unleashed an Ice Beam attack that bound Ash and Misty together by their arms and legs. Starmie then lifted them out of the water with Psychic and placed them on a bed of towels laid out along the side of the pool.

"Starmie what are you doing?" Misty asked alarmingly.

All Starmie could do was flash its gem in an attempt at explanation. Ash was not trying to escape like Misty, he was instead taking in the shape of Misty's body, being so close to her that he could feel the heat off her body. Ash noticed her small, but perky, breasts, and how tight her bathing suit clung to her body.

"Ash, do something!" Misty yelled, but Ash just kept taking in all of her features.

Before Misty could say anything else, Ash planted a kiss on her mouth. Misty was caught completely off-guard, and tried to resist. As Ash kept his lips planted on hers she began to calm down and actually enjoy it, so she started kissing back. They battled with their tongues for control of each others mouth. While they were doing this, Ash was able to slide his swimming trunks off, exposing his manhood. Misty then pulled the bottom part of her bikini off, and began to grind on Ash's dick. After a few minutes of this, Ash was finally able to line up his erection with Misty's pussy. He pushed in slowly at first, letting Misty get used to the foreign object inside of her. She nodded when she was ready and Ash pushed all the way in. The position they were in was awkward due to the cuffs, but they were able to make it work. Ash first got onto his knees, allowing his cock to push in further than before. Misty then began to ride him, moving faster than before. Ash could feel himself reaching his limit, but he did not want to stop this soon. Misty on the other hand, was enjoying herself too much to care how long he lasted, she cherished each moment she got of the experience. Before Ash could tell Misty to stop, he felt his climax build up and shoot into her. Misty was caught off guard by this, and could only let out a small moan. It was at this time that the ice cuffs finally melted and they were free, but they held each other in a tight embrace.

"That was incredible Ash," Misty said, "You must have had a lot of practice in your travels."

"Er, yeah," Ash replied, blushing a little at his bluff.

They then got dressed and continued to talk for the rest of the day.

"Well, I should go," Ash said as the sun set.

"Why?" Misty asked, "It's almost dark, you should just stay here for tonight."

"I guess I could," Ash replied, catching the gist of what Misty meant.

They both went back into the gym to continue the fun of earlier that day.

After a long time, I finally got this one done. Sorry yet again for the delay. Keep an eye out for my next story, because I cannot guarantee a time frame for it to be done.