It was Halloween. Jessie and James’ house had been decorated with props of Gastly, Haunter, Duskull, and Dusclops. Nobody in the neighborhood knew they were members of Team Rocket and they intended to keep it that way. If anyone knew they were members of that crime syndicate, someone would have egged their house a long time ago. And in the real world it was bad enough, but having fresh Exeggute all over your porch was way worse to deal with.

But Jessie had been sitting home this Halloween. She was ready to go out, dressed up as a sexy Nurse Joy, her costume gave an inviting look into her bustline, revealing her ridiculous cleavage. But after having a fight with James, didn’t want to deal with it. He was dressed up as Officer Jenny, wig, makeup, pushup bra and all. He was indistinguishable from the real thing and loved the way the tight skirt flattered his ass. His legs looking so sexy in the shiny leggings didn’t hurt either.

“Hey Jessie, who do you think is hotter, me or you?” he said, flaunting his ass in front of her and gave himself a spank.

“How about you go jack off before you go out in public like that, because I can see you pitching a tent right now.”

He blushed and look down. The panties he was wearing were so tight and felt amazing on his dick. Then he started fondling himself. “Can you give me a hand here?” he said. “You’ve got those natural big tits and...”

“What, do you need help on how to jerk yourself?”

“Well I’ve always wanted to do things with your rockin cleavage and...”

“James, if you’re so hot then go beat it in front of the mirror, okay?”

“You know with that attitude Jessie, before you know it you’re going to be a crazy cat lady.” Meowth took offense at that comment.

“And what about you, always dressing up in women’s clothes?” Meowth said.

“Oh you both are so mean to me!” James said. “Fine, I’ll trick or treating on my own.” With that, he left, his ass and legs sauntering as sexily enough to make any woman jealous, slamming the door shut behind him.

“Wow, what a diva,” Meowth said.

“Well most divas don’t go out in the middle of the night with a boner in their skirt.” But all that talk from her was a front. As much as she hated to admit it, she was a bit jealous of what an amazing rump he had.

“So he’s more like a street walker?”

“Yeah, I wouldn’t put it past James to do that.”

“Hey, let’s go out on our own.”

“Nah, I don’t feel like seeing the twerps anytime soon, and you know they’re out and about.” She yawned to herself before sitting back on the couch. “James can get a spanking all on his own this time.”

“Jessie you’ve let yourself go.”

“Oh can it. A girl needs her beauty sleep every now and then.”

“Whatever, I’m gonna give that report to the boss.”

“That’s a good kitty.” She turned on the TV louder than normal, ready to drift off to sleep. Then she heard the doorbell ringing. It was muted a bit by how loud the TV was, but it kept on ringing, and Jessie couldn’t nap at all. She eventually got up and answered the door.

It was Ash and Brock. Ash was dressed up as a Pikachu and Brock was dressed up as an Onix. She hoped they didn’t recognize her.

“Trick or treat!” Ash said.

“Nurse Joy?” Brock said.

“No you stupid twerps!” she said, before she had a chance to catch herself for revealing her identity.

“Hey, you’re Jessie!” Ash said. Brock actually opened his eyes hearing that, and stared at her ample cleavage.

“Yeah, so have some candy and get the fuck out of here,” she said, going back to get some candy just to get these two out of her house.

“Oh I see some candy right here,” Brock said, going right inside and grabbing her juicy ass under the big skirt of her Nurse Joy costume. She was only wearing a thong so even under the costume, she felt his hands grabbing all over her big butt.

“Brock, that’s evil pussy!” Ash said.

“Fine, more for me.” That remark made Ash feel left out and jealous, and he went in too, shutting the door behind him.

“Goddamn you are one smoking hot woman!” Brock said, not letting go of her ass. “Come on and get a feel for it too, Ash!”

“Okay!” he said, grabbing her juicy rump alongside Brock.

“Get your hands off me, you twerps! Meowth, give me a hand here!” Then she realized that with the TV on so loud, Meowth couldn’t hear her in the back. “When I get my hands on my Pokemon, you two are gonna be in for it!”

“I’ve wanted to see these tits for so long,” Brock said, getting right in front of her and pulled down the front of her dress, fully exposing her big bouncy tits. Ash got behind and, hiking her long skirt up, started feeling all over her ass.

“Why do you work for Team Rocket anyway?” Brock said. “A hot body like this isn’t fit for a life of crime.”

“Shut up you!” she said, hating how flattered she was by that remark after her earlier spat with James. Not helping things was that Brock had started kneading her full bosom, skillfully massaging them with his big hands. Behind her, Ash was pulling down her thong, shamelessly feeling up her long sexy legs and her bubble butt fully exposed before him. He always liked seeing her in her skintight Team Tocket uniform, but actually seeing her bare ass up this close was a treat.

Jessie was still wriggling in their grasps, but was surprised by how gentle they were being after all the times she clashed with them in the past. She hadn’t even noticed it, but she had stopped fighting back already, feeling them appreciate her body even if they were being total perverts about it. And if James caught her doing this, she knew he’d definitely be jealous.

“You starting to like this?” Brock said, pushing her tits up with more force this time.

“Sh-shut up,” she said, not wanting to give him the satisfaction of an answer. But from that flustered response, he already figured out the truth. He started working her large nipples in between his fingers now while pushing on her full teats with his palms, and Jessie had to bite her lip to keep an ashamed moan from escaping her. Meanwhile, Ash was starting to appreciate her ass more and more, rubbing his face all over her lovely cheeks. His head was that close to her vagina that she was started to become a little moist down there.

“I like evil pussy,” Ash said with a naughty grin on his face. He didn’t fail to notice her getting wet around her full lovely thighs, or the wonderful scent of her juices filling his nostrils.

“What are you even talking about you bratty little twerp!” she said, turning around to try and look at him. Ash started licking her pussy juice off her legs and then bit into one of her ass cheeks. “Ow!” she said, still trying to give the illusion of a fight when his teeth in her bum felt a lot better than she cared to admit to either of them. He started licking and sucking all over her big butt cheeks, loving the taste of them in his mouth as he still held onto her big hips.

“This is so humiliating,” Jessie said. By now, her nipples were hard in between Brock’s fingers as he continued fondling her fat hooters. And he loved hearing her whimper from being pleasured at his touches. So he took one of her big titties into his mouth.

He started sucking on it slowly while he was fondling the other one with his hand. Jessie started actively moaning now, she couldn’t help it anymore. He was working her big tit with his lips, pinching her nipple and teasing the other one with his teeth while he used his tongue to lick all over it.

Below her, Ash was really getting into her ass, eagerly rubbing his face in between her butt cheeks. But now he had started fingering her hot and wet pussy. She couldn’t help but start jerking her hips back and forth between the assault of wonderful sensations they were giving her. So everytime, she was hitting with his face with her bottom. And he loved it, he just couldn’t get enough of her wonderful behind.

He grabbed hold of her hips so he could get his face deep between her ass and lick her asshole. The moment she felt it, she froze up. It took her by surprise so much, even after he had just been fingering her pussy. But with Brock sucking and playing with her tits at the same time, it felt a lot better than it would have normally. Her hot and wet pussy was soaking wet and ached for something inside of it again.

Brock sensed her growing desire too, because he undid the part of his costume holding his penis, now firmly erect. Ash heard the sound of his costume being undone and not wanting his face to be anywhere near Brock’s cock, raised himself up again behind Jessie.

“What are you two planning?” she said, still not wanting to give either of them any idea of how much she was enjoying their touches.

“Just having some fun,” Brock said, pinching hard on her perky nipples. “Hey Ash, you ever do this before?”

“No.”

“Really? You’ve been traveling with tons of hot chicks and you haven’t nailed any one of them?”

“No?” The only one he ever kissed was Serena, and even then he didn’t know what to make of her.

“Well then today’s your lucky day man! I know you were just eating out that ass and playing with that pussy! Consider it practice for when you decide to marry that one lucky lady.”

“Oh yeah!” He had been going along with it since Brock got a piece of her, but now he was hard and ready all on his own. “Or marry many ladies...” he quietly mused to himself.

“That’s the spirit buddy!”

“You little twerps...” she began, but Brock shut her up with a kiss. His tongue invaded her mouth while his hands were still playing with her tits. Jessie’s muffled protests soon changed to moans from the way he was using his tongue and the feeling of his fingers roughly pinching her nipples. And Ash had started lightly spanking both of her buttcheeks with both of his hands like she was his bratty little sister.

As Brock had been kissing her, he took the opportunity to shove his cock deep inside of her wet twat. She had to break the kiss to moan loudly just then. Not helping things was how Ash had grabbed hold of her hips again and rammed his dick right inside of her asshole. The both of them were perfectly rock hard inside of her.

Brock had been taking it slow with her vagina, hitting inside of her tight wetness with a deliberately measured pace, though no less strong because of it. His hands were still on her luscious breasts, and his fingers had started twisting her nipples with motions akin to the way he was using his dick on her. Not too hard, not too slow, just right.

Even though her butt was the little twerp’s first time, he was going way faster than Brock. He definitely was in the mood for it, was eager to make this moment count. At the same time it was obvious that he didn’t really know what he was doing, his thrusts were so clumsy in spite of how fast he was, and she really wished more than a few times that he would start hitting her all the way through to the end of her rectum on a regular basis. But his inexperience didn’t make her feel it any less, and she hooked an arm around his neck, clinging to him at the same time she had wrapped both of her legs around Brock’s waist.