'It could have been any two trainers…but it had to be these two,' Jessie thought to herself as she put on some lipstick. She always liked to look hot when doing Team Rockets dirty work. James and Meowth were out doing something else, leaving her to take on Ash and Misty, who were alone on one of Kantos most desolate mountain trails. 'I'll simply defeat them in battle, and then take their pokemon,' she thought to herself with an evil laugh.
"Uh-oh, it's Jessie," Ash said as he saw her up ahead.
"Psst, Ash, gimme your Butterfree," Misty whispered to Ash, "while you two are battling, I'm gonna get her good."
"That's low Misty, even or you…I like it, here you go," Ash said, handing her the pokeball.
"Alright kid, I challenge you to a pokemon battle," Jessie sad with a grin on her face.
Ash looked around, "what, no dirty tricks."
"No, not today," she said holding up a pokeball.
"Pikachu, go," Ash said and Pikachu leapt in front of him. Misty sent out Ekans. A battle broke out, and Pikachu missed a thundershock, allowing Ekans to wrap Pikachu. Jessie was getting the uperhand, but she didn't notice Misty hiding behind a tree.
"Butterfree, string shot," Jessie heard Misty say, and turned her attention in Misty's direction. The String hit her right in the face covering her eyes and mouth. Muffled yells came from her as she tried to pull it off, but Misty ran up to her with rope and grabbed an arm, while Ash grabbed another arm, and they pulled both her arms behind her back. Misty quickly tied her hands together, and Jessie tried to kick them away, but missed because she couldn't see.
"Staryu, spin around her," Misty said as she tied some rope around Staryu. Staryu began spinning around her incredibly fast, pinning Jessie's arms tightly to her body. The rope stopped just under her boobs, pressing her shoulders up high. Misty then grabbed the end of the rope, put a sneaker against her butt, and tightened it even more. More muffled sounds were coming from her as she wiggled around trying to get free. It was no use though, the knots were tight.
"What should we do with her now," asked Ash with a grin on his face.
"Let's hear what she had to say," Misty said pulling the string off her mouth, revealing smooth red lips.
"You dumb kids, UNTIE ME RIGHT NOW!" she yelled, still wriggling around trying to get free.
"Why should we," asked Ash.
"Because I'll kill you two of you don't," replied Jessie.
"And how are you gonna do that all tied up," asked Misty.
"Err, why you two," Jessie said angrily, now more than ever trying to break free.
"Let's go for a walk," Misty said, pushing Jessie in the butt with her foot.
After a half hour of them bringing Jessie up the mountain, with her fighting all the way, she yells out, "Can you at least take the string off my eyes."
"No," says Misty, "but it looks like it's falling off, so I brought a blindfold." Misty wrapped a blindfold around her head. "Where are we taking you?" she asks Jessie. "You know, I wonder what you'll look like in my clothes," Misty asks her, pushing her aside into the woods. "Ash give us a minute."
"You can't be serious," says Jessie.
A few minutes pass, and Ash hear Misty call him over. He comes in, and sees a very angry Jessie wearing one of Misty's spare sets of clothes, with the exception of those hot thigh high boots.
She is dangling from a tree, with her feet just touching the ground, and she is bent over slightly, so the first thing Ash sees is her tight ass barely fitting in Misty's shorts. They barely go down a fraction of her leg, and don't cover all of her ass, revealing Jessie's thong. Then he moves to the front of her, noticing Misty shirt tight around Jessie's large breasts. Her cleavage is showing, almost down to the nipple, and this shirt is so small on her, it doesn't cover her side boobs at all. Her shoulders are completely exposed in Misty's tank top, round and high up.
"This is ridiculous, get me outta here," Jessie yelled, trying to wiggle free. With every shrug, her shoulders went higher and boobs bounced out a bit.
"I wonder what's tighter, the clothes or the ropes," Ash jokes.
"I know I can make the ropes tighter," says Misty, pressing both feet against Jessie's tight butt, while pulling on the rope.
"Just turn me into the police already," Jessie yells.
"Oh, but we have some fun planned for you," says Ash.
"Like what," asks Jessie, annoyed.
"I got some itchy powder," says Misty pouring some into her pants.
"Why you…get this stuff out of here," says Jessie, squirming around with her teeth barren in anger.
"It isn't over yet," says misty, and she grabs Jessie thong, pulls it up as far as it'll go, and ties it to the ropes, so it will not slide down.
"Ahh. What is wrong with you two," Jessie yells, receiving the worst thong wedgie of her life.
She kicking at her butt with her long legs, perhaps trying to scratch it with her foot or het the wedgie down; it was no use though. A few hours passed, with Ash and Misty teasing her.
"Wow Jessie, the moon is beautiful tonight," Misty says.
"I hate you says Jessie," shaking her head, trying to get the blindfold off.
The next morning, they bring her into a village. She demands that they take the blindfold off so she knows where they are going, but they don't. They turn her into the police, and she is locked into a pillory in the center of town. She is still blindfolded and wearing Misty's tight clothes, more pissed off than ever.
"This would be a nice place to stay for a couple of days," says Ash, sitting on top of the pillory.
"Won't you two just get out of here", yells Jessie.
"Uh-oh, it looks like the itchy powder has worn off," says Misty, poring some more down her pants before bringing her thong back up. This makes her tight ass move up higher, and she is wriggling it around in irritation. Misty than spanks her for good measure.