Jessie's Mutiny

Team Rocket followed Ash as he journeyed through the Hoenn region. His adventure eventually brought him through Route 117 between Verdanturf Town and Mauville City. He, Max, May, and Brock stopped at an inn for the night. Due to the lack of vacant rooms for 4, May, Max and Brock were assigned to the room just opposite of the private room for Ash and Pikachu. Long after they fell asleep, Jessie, James, and Meowth climbed up to the rooftop of the inn, right above the room where Ash and Pikachu were sleeping.

“The twerps should be fast asleep by now.” Jessie explained. “But let’s not take any chances.” She pulled out a small bag full of green powder and gingerly handed it to James.

“Huh? What do I do with this?” he went to open the bag, but Jessie grabbed his other hand in time.

“Be careful with that!” she snapped. “It’s Sleep Powder from a Vileplume. It will knock them right out. Dump it in this room, I’ll work on the other room.” James and Meowth nodded their heads in unison, and Jessie slowly made her way across the rooftop to above the room May, Max, and Brock were in. Careful to not get the powder on her skin or breathe it in, Jessie slid open the window and dumped the powder inside. The draft blowing in carried the powder over the occupants of the room and put them into an even deeper sleep. She smiled darkly as she saw her handiwork. May’s expression became much more relaxed and her breathing slowed down, as with the others.

“There! Ha ha!” James exclaimed triumphantly, letting the cloth pouch drift away in the breeze. “Now let’s grab Pikachu and get out of here!”

“JAMES, YOU IDIOT!” Meowth shouted, leaping up and punching him in the stomach. “Ash wasn’t in his bed! He’s still awake somewhere!”

James curled over in pain from the punch, and when he recovered, he went to strangle Meowth in retaliation. Jessie’s ice cold glare, however, ended their scuffle prematurely.

“Quit your fighting and grab Pikachu!” she ordered. “I’ll take care of the twerp.”

“Y-yes, ma’am!” the two frightfully said in unison. Jessie climbed down into the window and passed by the sleeping Pikachu as she made her way to the door. Stepping into the hallway, Jessie heard activity coming from the center of the hallway. Ash came stepping out of the bathroom, shielding his eyes from the bright light illuminating the hallway. Jessie suddenly realized something, and took one look back at the doorway, contemplating her next actions. There would be no other opportunity like this for a long time…

By the time she came to a conclusion, Ash closed the distance between them, and the instant his eyes noticed her purple thigh high boots, she immediately grabbed him and put a hand over his mouth.

“Quiet.” She hissed. “James and Meowth are taking Pikachu right now, and the others have been knocked out with Sleep Powder. If you act quickly, you can stop them. I am not working with Team Rocket or James or Meowth this time around.”

“What? Why are you helping me out?” Ash whispered when she took her hand away.

“That’s not important right now!” she replied. “Go and do what you do best! I’ll stay out here until you’re done. It’s best that they do not see me.”

Ash ran into his room to see James and Meowth jump out the window with Pikachu in their arms, still fast asleep from the sleep powder. Quickly sifting through his clothes, Ash grabbed one of the Pokeballs and enlarged it by pressing the button on the front, just in time to see Team Rocket’s signature Meowth-shaped hot air balloon rising up from among the trees in the surrounding forest.

“Ha ha ha, looks like we have Pikachu now!” James announced. He paused for a long period, as if waiting for something.

“Any time now, Jessie!” he called out impatiently. “We can’t do this without you!”

“I think da twerp musta gotten Jessie!” Meowth pointed out. “We’ll come back for her later! We finally got Pikachu!”

“Oh no, you don’t! GO, TORKOAL!” Ash threw the Pokeball out, which opened up and released the Torkoal, a yellow turtle with a black shell that released clouds of smoke. Meowth scowled as he realized that they were right in the firing range of Torkoal’s attack, and their wicker and cloth hot air balloon would not stand a chance against concentrated fire.

“James, get out of here now!” he shouted, kicking James in the head.

“This is not Formula-1! This is as fast as we can possibly go!”

“WHAT?! Uh… James? I think we’re toast.”

“Torkoal!” Ash shouted. “Use your flamethrower attack!”

“KOAL!” Torkoal opened his mouth and released a thick jet of fire that was aimed at the gas tanks on the hot air balloon. James quickly moved to the side to avoid getting torched himself, but in the process, he lost grip of Pikachu, who fell out of the basket and into Ash’s arms, who ran and made a diving catch like a professional baseball player. He hung in the air for a good two seconds before tumbling across the ground. The gas tanks on the hot air balloon exploded above them, and sent Meowth and James flying to the stratosphere for the nteenth time.

“And this was such a great plan, too.” James sobbed. “But now it looks like we’re just-“

“Wait a minute!” Meowth interrupted. “We forgot Jessie!”

“I know! And it’s just not the same!”

“WAAAAAAAAAHHH!” The two could be heard wailing in despair as they disappeared from sight. Ash got to his feet and brushed the dirt off his pajamas, still very confused about what was going on.

“Hopefully Jessie can answer my questions. Thanks, Torkoal. Return!” Ash held up the Pokeball to Torkoal, who vanished back into the orb in a flash of red light. Holding Pikachu close to his body, he returned to the inn.

“Ok, Jessie, what’s going on?” he asked when he returned to his room. Jessie was sitting on the bed, her shapely legs crossed. “Why aren’t YOU trying to capture Pikachu?”

“Why bother? We all know how this game goes. We come up with some crazy plan to capture Pikachu, you foil our plans, roll credits, right?” Jessie sighed and stood up, closing the door behind Ash and making sure it was locked without raising concern or alarm from him. “The instant I knew you were not in here was the instant I knew our plan wasn’t going to work. Still, this situation suits me just fine. You see, Ash Ketchum, after the fiftieth attempt, this was no longer about Team Rocket, and this was no longer about Pikachu. It was about you.”

Ash sat down next to her on the edge of the bed, his mouth hanging slightly open in awe.

“Me? Wh-what do you mean?” he asked.

“While I was trying to steal Pikachu from you, I began to slowly develop a personal interest in you. However, James and Meowth couldn’t know about this, nor anyone else in Team Rocket, or I would be fired. Tonight was the most opportune moment for both of our interests. There’s no James or Meowth here, and none of the other twerps can interfere.” She leaned into Ash’s body and pushed him onto his back. Ash blushed heavily as he felt her breasts press into him.

“A-are you trying to say you… love me?” he asked.

“Maybe, but I don’t want you to see me as Jessie from Team Rocket, at least for tonight.” She worked at unbuttoning his shirt first before moving down and pulling down his shorts. Ash removed his shirt and dropped it off the bed, leaving him completely naked in front of someone who he considered for the longest time to be his enemy.

“I wonder what you think of my body?” Jessie asked as she stood up. The first things to come off was her skirt, followed by her shirt. Ash’s eyes widened when her breasts bounced into view. They were huge! He didn’t know much about cup size, but he knew just by looking at them that they were bigger than his mom’s. Jessie pressed them together and brushed her fingers over the pink nipples. Ash’s cock erected in no time from the sight. She smiled at the result. He was quite large for his age; nearly seven inches in length. At least he wouldn’t disappoint her in that department; the 13-year age gap between them made her concerned that he would be inadequate.

“fu fu fu… I bet May and Misty would try to keep you all to themselves if they knew about the heat you’re packing down there.” Jessie said as she pulled off her gloves and boots and climbed into bed with him. “But I can treat you better than them. I have assets they lack… for now, anyways.” Jessie came down to eye-level with Ash’s dick. Grabbing her breasts, she spread them apart and then pressed them together so his shaft was caught between the mounds. Ash jumped in shock. The flesh was extremely soft and warm and squishy against his cock. There was no comparison to anything he could think of. All he knew right now is he wanted to continue that sensation. Jessie seemed to sense this, and she squeezed both breasts together and proceeded to move them up and down the shaft. The uncut head of the cock disappeared in the valley for one second before emerging again. Jessie continued with this pace for many minutes. Ash was unaware of pretty much everything else around him, from the cold crisp midnight air biting at the rest of his body to Pikachu’s snoring, who was still asleep on the chair with the rest of his belongings.

Jessie moved down until her boobs embraced the base of Ash’s dick. The motion pulled back the foreskin and exposed the sensitive pink head underneath. She bent her head down and closed her mouth around the head, sucking and licking at it.

“Ahh-UAAAHHH!” Ash let out a loud cry as he felt the hot tongue roll over the sensitive head. He had masturbated before, but never has he touched the touched the exposed head. The nerves were still raw, and combined with the hot moist interior of Jessie’s mouth, he found himself on the verge of orgasm. Quickly, he pushed Jessie away and tightened his ass, trying to hold back the tide. His hips trembled and his balls burned in protest, eager to discharge his sperm like a cannon. Finally, he was able to successfully suppress his orgasm, and he slowly lowered his rear back onto the bed.

“Good to see that you’re considerate.” She said, getting on her knees and crawling on top of Ash. “I want to feel you inside of me.” Ash slowly nodded his head. There was no way in hell that he was going to say no. She was too hot to turn down! Grabbing his dick and holding it in place, Jessie sat down on his shaft. She moaned as it fit in nicely, and her inner walls instinctively gripped his meat like a vice.

“Gnnaaaahhhh!” Ash clenched his teeth and trembled violently. Jessie pulled him up and held him in her arms.

“I can feel you throbbing inside me.” She said, moving up so only half an inch was inside of her before she thrust down hard. Ash moaned into her breasts. Jessie continued this tease several times, which made him tremble in arousal. He buried his face into her cleavage and tried to hold himself back. It was still way too early to blow his load. He had to make sure Jessie came first.

Ash pushed Jessie onto her back. She locked her legs tightly around his rear as he went to pull out and thrust back into her. The soft warmth from her body was incredible! She kept his dick perfectly warm in the cool night air and pulsed and throbbed in such a unique way.

“Oh JESSIEEEE!” Ash cried out as he finally lost control. He shot several warm gooey shots of seed into her pussy. When Jessie came, her walls clamped even tighter around his shaft and prevented him from pulling out. She lifted his head from her breasts and pulled him into a deep kiss. Their tongues wrestled around in Ash’s mouth. He never did this before, whereas Jessie had done it when dating in the past, and within a minute, she exhausted him.

“What should we do about this?” Ash asked as he lay snug in Jessie’s arms. “I don’t think it would be so easy to convince the others, and if Team Rocket finds out, you could get yourself in big trouble.”

“Shhh shush, Ash.” Jessie whispered. “Just let it be for tonight. We can think of something later.” The two spent the rest of the night entwined in each other’s arms. Ash spent this time thinking about his feelings for Jessie. For the longest time he saw her as an enemy, a rival, and above all, a pest. All of that was blown away in just one night. Could all of this have just been for his attention?