Chapter 10: Twerp or Treat (Pokemon)
Synopsis: On Halloween night, Ash and Brock accidentally find Jessie and James' house without even realizing it. Needless to say, many hijinks and fun ensues.
***
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.
Jessie had been sitting home this Halloween. She was ready to go out, dressed as a slutty Nurse Joy with a low cut costume that revealed her rocking cleavage and a short little skirt which revealed so much of her lovely legs and fine ass, 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, exposing her big bouncy tits. Ash got behind and, hiking her skirt up, started feeling all over her ass only covered up in a thong.
"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.
Both of them were encouraged by this act of submission from her. Brock grunted in pleasure feeling her vagina tighten a bit on his penis. And Ash in particular had become more focused though no less quick in pounding her tight ass.
"Hey Ash, I think she likes it!"
"Yeah, her butt is so good!" He liked the feeling of her full and ample booty slapping up against his hips. He was always worried about finding the right time and the right girl for sex, but now that he was doing it for real, all he wanted was more. "I love you Jessie!"
"Shut up you stupid twerp!" That was what she said before she lost control of herself from how good it was. "Ah! Ah! Ah!"
"My little man is gonna make some ladies very happy," Brock said. His thrusting speed had slowed down a bit, he was too busy watching Ash getting his freak on. He was going at full speed with a big grin on his face.
Ash came first, releasing his virgin load of semen right inside of her tight asshole. It pushed Jessie to her own orgasm just then. Neither of the two guys had stopped thrusting inside of her. Ash was determined to get as much of his goo in her butt as possible, pumping his dick to the end of her anus with each of his movements.
And everytime he did it, Jessie's cunt vagina was getting tighter and wetter on Brock's dick. He could tell by Ash gritting his teeth that he just came, and he was ready to finish too. He picked up the pace, surrendering himself to his pleasure before he stole another rough kiss with Jessie.
His dick spasmed and twitched almost immediately as he came hard inside her wet cunt. The first gush of his hot spunk inside of her prompted her to start moaning loudly through their kiss. He pushed his cock inside of her as far as possible and then stopped, letting his hot member shoot as much cum as possible deep into her womb. Jessie tried pushing him off, but between his enthusiasm and how much she was getting off on doing it with him, she didn't try very hard and stopped pushing back after awhile.
When Brock was spent inside of her, he finally brought his face away from hers, leaving behind a long trail of spit between their mouths. Her face was flushed considerably, and she couldn't look away from him in that post orgasmic state of unashamed lust and muddled thoughts. There was still semen leaking from her vagina and asshole, spilling onto the floor and onto the dicks still inside of her.
Finally, they both pulled out of her, Brock first, then Ash. Jessie collapsed onto the couch and lay her head back, taking it all in as she was still faintly sighing. Brock and Ash looked down at her before high fiving each other on how badly they wrecked her.
When they heard the front door open, they all looked. Brock and Ash's dicks both sprung back to life as they saw who they thought to be Officer Jenny with a bag of Halloween candy. Jessie gave an awkward thumbs up to her partner in crime. But all James could do was shake his head.
Eager to defend himself, Brock said, "Officer Jenny! It's not what it looks like, I swear!"
"Jessie, what in the world are you doing?" James said.
"James?" both Brock and Ash said, incredulous. They just stared at him, admiring his surprisingly feminine figure and how well he fit the look of Officer Jenny. But what surprised them even more was that their dicks were starting to get hard again. As they looked at him, they realized he was really hot. And after fucking Jessie like crazy, they were eager for more.
"What's up with the twerps, Jessie?" James said, becoming irritated.
"Hey Ash, let's do a reversal this time," Brock said.
"Okay!" Ash said, still too horny to think straight or what Brock meant by that statement.
Before James had a chance to react, both of them pounced on him. Brock got to him first, getting behind him and pulling up his skirt. James reached behind to push him back, but Ash got in front, and grabbed both of his wrists.
"Jessie, help me out here!"
She just looked up and said, "Hey, you said you wanted to the hottest person here. Don't blame me when the beedrills come for honey."
"I never thought I'd be doing this, but wow!" Brock said. He had gotten down on his knees to blatantly ogle James' legs. He had lifted the skirt all the way up, he was surprised how soft and hairless James' skin was all over. But what he really liked was that the Officer Jenny costume included a lacy black thong with garter straps connected to shiny black stockings. Brock cupped all over the sexy legs in front of him, shamelessly rubbing his face all over them.
James was feebly wriggling in their grasps, but the more he struggled against them, the harder and hornier he was getting much to his chagrin. Up front, Ash had started kissing all over James' neck. He would have kneed the little twerp right in his weak spot, but Brock held a strong grip on his hips as he was worshipping those sexy legs with his mouth. The more he sucked and licked all over them, the more his leggings now had a sexy sheen from all that spit. Ash too had started rubbing his naked thighs up against James' crotch while he was necking him. It didn't help that James' hard penis was barely protected by the thin layer of the thong. He almost jumped when he felt Ash's hand jump straight down his panties and directly grabbed the sensitive skin of his hardness.
Brock had started eating James' ass, which by now was positively spilling out of the thong he was wearing. He kissed and sucked all over the surprisingly bouncy ass cheeks, using his lips, tongue, and teeth to get a feel for the soft and supple flesh. He loved the taste of it, James' donk tasted a lot better than he ever would have thought, almost as good as Jessie's tits.
Ash himself was having a good time too. He had brought out James' sensitive penis out and started jacking it off. And James had been wearing a pushup bra to complete his look. So Ash had pulled it down enough for his nipples to be visible, but not enough to return his chest to it's natural flat state. He eagerly started sucking on the hard nipples, licking all over the artificially inflated tits, loving it. James started moaning loudly from all the loving attention from Ash's mouth and the hand still stroking his hard member.
With the attention the two of them were giving him, as much as James hated to admit it to himself, he had stopped wanting to fight them. By now, Brock had risen up behind him and had pulled the thin fabric of the thong out from between his ass cheeks. He had wedged his hard dick in between James' lovely cheeks, sliding his dick back and forth them like they were a pair of tits. And Ash had stopped sucking on his tits and looked James squarely in the eyes.
"What's...what's that look supposed to mean?" James said, sounding more flustered than he intended to. On the couch, Jessie was smiling, watching it all go down. She had snagged James' bag of Halloween candy in the meantime and was eating from it like she was at the movies.
Ash suddenly lunged forth and started kissing James. James tried to pull his face back at first, but Ash grabbed his dick again, and James was hit with sudden feelings of ecstasy. Feeling him surrender in that instant, Ash deepened the kiss, pushing his tongue into his mouth. James couldn't help but start kissing back, as much as he hated how much he was liking it. Ash found that James tasted a lot better than he expected, he loved the taste of his lipstick. Their tongues were coiling deep around each other at that point, and the both of them melted into it. When Ash broke the kiss to look at him, his face was smeared deep with the red lipstick and James' spittle.
Not wanting to be left out, Brock leaned forward and pushed his dick deep into James' anus. James moaned louder than ever at the feeling of it. Brock's dick was so big and rammed itself deep into his anal cavity. With every push, he hit the g-spot at the end of his asshole, and James' dick sprang up harder and bigger than ever.
While James was being rammed from behind, Ash had grabbed onto his chest again and started fondling his sensitive nipples in between his fingers. This time, Ash brought his erection right up against James' bare boner, and started grinding up against him. Their penises were both so sensitive, and they had both started rocking up against each other, both of them wanting to cum. Ash started kissing him again, and James moaned deep into it, kissing him back eagerly. Their dicks were locked up completely aginst each other, the hard shafts pressing up against each other's stomachs, their balls swelled up with lust mashing together this way and that, and the heat of their genitals radiaing against each other, and it all felt so good. When the both of them stopped kissing, there was a slender trail of spit between their tongues and they gazed into each other's eyes longingly.
Not that any of this wholesome kissing going on meant anything to Brock. He pushed himself deeper into James' anus harder and faster than ever before. James couldn't hold in his moans of pleasure anymore, and he in turn had started moving faster against Ash too.
"Looks like Team Rocket is blasting off again!" both Ash and Brock said at once.
Ash came first, shooting his second load of semen all over James' genitals. That didn't stop him from grinding up against him either. Then Brock brought his dick all the way to the end of James' asshole and shot his thick goo deep inside of his rectum. Unable to help himself with that anal creampie and Ash's sweet dick still rubbing all over his, James finally nutted all over Ash's genitals.
Brock pulled his dick out of James' anus, leaving behind a long trail of cum. Ash also finally allowed himself to break away from him. While Ash was staring at his dick, covered in both his own love juices and James', his lover collapsed to the floor on his stomach. His butt was sticking up with Brock's semen was still bubbling from his asshole.
"That was so good!" Ash said.
"Oh yeah it was!" Brock said.
"This is the best Halloween ever!" They both left.
"You gonna be okay there?" Jessie said.
"I'm...I'm still hotter than you Jessie..." James said.
When Meowth came out from the back, he just stared at the both of them, awestruck. He hadn't heard a word of what went down. And James was freshly messed up, but Jessie hadn't bothered to cover herself back up either.
"Well, I'm glad you two made up!" Meowth said.
***
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