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Lisa's Ploy	By : Lennox Category: +S through Z > Simpsons Views: 6562 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own The Simpsons. The characters are the property of Fox/Disney and I am not associated with the creators or owners of the show. This story is a work of fan-fiction that is written for non-profit and entertainment purposes only.

Chapter List
- 1-Lisa's Ploy
- 1
Lisa's Ploy
“So Lisa, if you press on Bart’s elbow…” Wayne Slater began. He lifted the boy’s arm into the seemingly harmless grasp of two of his sister’s fingers.
“Owww,” Bart winced in discomfort.
“…here, he’ll tell you anything you want to know.”
“I admit it,” Bart cried to a smiling Lisa. “I let Milhouse lie down in your bed!”
That scene had played out in Lisa’s mind for several days. She felt betrayed by her brother for giving his friend access to her private domain. And Bart had only said he was lying down on her bed. Had he been lying to her and telling her the bare minimum under Wayne’s simple torture? Milhouse’s crush on Lisa was far from subtle. She knew, deep down, that there was no way the blue-haired boy would be content with just her bed.
Lisa had begun to formulate a plan; one that would teach both Bart and Milhouse a lesson. She lay in the darkness of her room (on sheets that Milhouse had not been on) and ran her idea through her mind over and over again. She wanted to make sure she had every detail planned out before she would set it in motion. For this to work; everything had to go just right and the most crucial steps would be out of her control. But she was confident she could make it work. Lisa flung back her bed covers and swung her legs to the floor. Lisa stood up and walked out into the hall.
Bart winced as he heard his bedroom door open. The light from the hallway spilled into his room through his door and right onto his face, waking him up from the sleep he’d only just begin.
“Bart…” Lisa whispered as she eased the door closed behind her. Bart slowly opened his eyes to his sister’s approaching silhouette.
“Hey sis,” he said with a sleepy smile. “You want a quickie before you go to bed.” Sex was usually the only reason that the siblings would enter each other’s rooms.
“Maybe,” Lisa grinned as she walked up to his bed. She watched Bart’s arms shift down under the covers and a familiar bulge began to repeatedly rise and fall above his crotch.
“Here, allow me, big brother,” Lisa said as she reached under Bart’s sheets. Bart pulled his arms out and slipped his hands under his head. He loved it when Lisa called him that.
“By all means, sis,” he smiled. He felt Lisa’s soft and gentle fingers wrap around his hardening shaft. It twitched at her touch, quickly standing proudly in her grasp.
“So what’d you want to do tonight?” Bart asked. Lisa didn’t answer straight away. She knelt by the bed and placed her chin upon the palm of her hand.
“Can’t a girl just give her brother a handjob?” she asked. Bart tried to not let his sudden disappointment show. He was hoping she’d want to ride him, or they’d at least share a sixty-nine. Lisa gently released her fingers from Bart’s stiff cock and she eased her hand down against his thighs. She cupped Bart’s balls in her hand and gently closed her fingers around them. Bart spread his legs for her and waited patiently to see what she had in mind. But he quickly felt the discomfort of Lisa closing her fist around him.
“Uh… Lisa…?” he nervously said.
“Yes, big brother?” Lisa asked with a smile.
“What, uh… what are you doing?” he winced and felt Lisa’s fingernails digging into his flesh.
“Bit more effective than Wayne’s elbow squeeze, isn’t it Bart?”
Bart’s mind raced for a few seconds before he remembered what his sister was referring to. He quickly pushed himself up on his elbows as Lisa pulled back his covers. She wanted him to see how she had him.
“Okay okay okay…” Bart was starting to panic. He knew that Lisa would never intentionally hurt him, but the pressure of her closed fist was becoming unbearable.
“Tell me, Bart,” Lisa began. “What does Milhouse do in my room?"
“I don’t know…” Bart was starting to panic. Lisa wasn’t happy; it wasn’t the answer she was expecting. “Is that what this is about? I’m sorry! I won’t let him do it again.”
“Try again,” she squeezed a bit harder.
“Lis, I don’t know. He told me he just wants to lie in your bed but… ow ow ow. I… I sometimes hear him rummaging around in there through the wall… Lisa, I really don’t know. I just… I just let him do it.”
“How often?” she asked.
“What?” Bart wasn’t listening. His eyes were glued to his sister’s wrist behind his shrunken cock. His arousal had vanished completely in his panic and discomfort.
“How often does he do it?” she asked again. Her voice was stern and strict as her grasp on his was firm and tight.
“I don’t know… once every week or so?” Bart lied. He did know, roughly. He had an envelope full of $10 notes hidden in the back of his closet, the admission he charged his best friend to violate his sister’s privacy.
“You get him around here tomorrow afternoon,” Lisa could hear the anger in her voice. “I don’t care what you say to him, but I want Milhouse in my bedroom by the time I’m home from school.” She released her grasp on Bart’s balls. The boy quickly pulled up his pants and moved as far away from his sister as possible.
“Why?” he asked.
“Because I’m going to fuck him,” Lisa said nonchalantly.
“What…?” Bart wasn’t sure he had heard her correctly. “Lisa… it’s Milhouse we’re talking about here. You’ve never wanted to…”
“Well, I’m going to now, Bart. You’re not going to tell him but you will get him here.”
“Come on Lis. I don’t want you sleeping with Milhouse any more than you want me sleeping with Allison or Janey. Why would I bring him over here?”
“Because,” Lisa climbed onto the bed, “you’re not going to fuck me until he does.” Bart was speechless. His mind was racing but he couldn’t come up with an argument or a defense. Lisa placed her hand gently on the side of his face. “I’m going give Milhouse what he’s always wanted, Bart. And you’re going to set it up for him.” She moved closer and she placed a soft and gentle kiss on her brother’s lips. “I’ll see you in the morning.” With her point made and part of her plan cemented in place, Lisa slipped of Bart’s bed and back out into the hall.
*****
Milhouse didn’t need much convincing for another secret visit to his crush’s room. Bart had barely got the offer out of his mouth before his friend had shoved ten dollars into his hand. Milhouse could barely contain himself as he rode the bus next to his friend, but Bart was lost in his thoughts while he stared aimlessly out the window. He knew he had fucked up by betraying his sister’s trust and he knew the price he was about to pay. His sister and secret lover was about to bed his best friend. Bart knew this would make Milhouse’s entire month, but the stabbing pain his chest was almost too much to bear.
‘It’s just one time,’ Bart tried to convince himself. Lisa was always set in her ways and ideals. He wanted to act strong and defiant and hope that she was bluffing, but he didn’t want to risk losing his incestuous relationship.
“Thanks, Bart, you’re the best!” Milhouse almost bounded up the stairs in the Simpson home. He rounded the corner and almost threw his hand onto the knob of Lisa’s door. Milhouse was immediately met with the familiar scent of her room as he stepped inside.
“Home sweet home,” he muttered to himself. Milhouse flung himself onto Lisa’s bed. He buried his nose into her pillow and inhaled as deeply as he could. The blue-haired boy filled his lungs with Lisa’s smell and quivered as he slowly exhaled. Milhouse closed his eyes in a silent moment of reflection. He felt no guilt in slipping into Lisa’s room. As long as she didn’t find out and he didn’t make a mess, was there even a problem with what he was doing? Milhouse finally sat up and took in his surroundings. He wondered what he could do in her room, where he could explore on this visit. Perhaps he could look through Lisa’s closet? Maybe read her diary on the desk? Or should he check her draws for new pairs of panties?
Downstairs, Bart sighed on the couch. His elbow was on the armrest with his closed fist supporting his head. He glanced over at the clock. Milhouse had been up in Lisa’s room for several minutes now. He knew that he’d come down when he was done, but Bart also knew that Milhouse would take his time. The sound of the front door opening quickly snapped the boy from his thoughts. He turned around just in time to see Lisa walking into the house in the arms of his school bully.
“Lisa! What the hell is he doing here?” Bart pointed his finger squarely at Nelson Muntz. His blood immediately boiled at the sight of his arm around his sister.
“Shut up, Simpson,” barked Nelson. He dropped his arm from around Lisa’s shoulders to behind her back.
“Yeah, shut up Bart,” Lisa snorted before she jumped lightly at the pinch on her ass. Bart gritted his teeth and he gripped the back of the couch in his hands. His face fell as he suddenly realized what Lisa was doing. This was her ploy; this was how she punished him.
“Now you’ve got it, Bart,” Lisa smirked. She read his face; she knew he had figured it out. “Nelson and I are going upstairs. You can make sure we’re not interrupted.”
“If anyone else comes into that room, then it won’t be just one Simpson I’ll be pounding today.” Nelson shook his fist towards Bart. The boy said nothing, following his sister and bully with his eyes as they walked towards the stairs.
“Wait, one last thing.” Lisa reached under her dress and pulled her panties down her legs. She stepped out of them and tossed them over the railing. “Be a good brother and put these in the laundry for me. I won’t need them.”
“Shit,” Milhouse started to panic. His heart was racing as he heard Lisa’s muffled voice through the wall. “Shit, shit, shit, shit, shit.” He spent several precious seconds panicking instead of considering his options. His feet felt like they were frozen to the carpet. He knew he should’ve just run to Bart’s room and ducked behind the door. But in his alarming fear, Milhouse instead ran to the nearest hiding spot. He jumped into Lisa’s closet and pulled the door closed. He froze when the bedroom door opened and Milhouse was forced to leave the closet door ajar to avoid being discovered. He watched through the gap in the door, his heart in his throat, and his jaw dropping. Milhouse gasped, and quickly covered his mouth when he watched Nelson walk into the room with Lisa. Lisa immediately turned and pushed Nelson up against the back of her bedroom door. She used the school bully to push the door closed as she placed a kiss on his lips. Nelson quickly reacted. He wrapped his arms around Lisa and lifted one hand to place against the back of her head. Milhouse watched Lisa and Nelson’s connected lips parting ways so their tongues could slip between them. He felt like he wanted to throw up yet he couldn’t turn himself away.
“You, by the bed now,” he heard Lisa say. Milhouse watched as Lisa pulled Nelson’s shorts and briefs to the floor and his eyes fell upon his bully’s growing cock. Nelson peeled his vest off his shoulders and let it fall on the floor. He stepped out of his clothes and sat down on the edge of Lisa’s bed.
“Take this off,” Lisa whispered, tugging at his shirt.
“After you,” Nelson folded his arms with a smirk. But Lisa pulled Nelson’s arms from his chest and placed his hands on his hips.
“You do it,” she grinned. “I took my panties off downstairs, remember?”
“I don’t think I could ever forget that,” Nelson said. His hands gripped the hem of Lisa’s dress and he pulled it up over her body. Milhouse’s eyes went wide as her body was revealed to the room. Lisa lifted her arms above her head and her dress was tossed aside. Wearing nothing but her pearl necklace, she dropped to her knees between Nelson’s legs.
“Now,” she muttered, loud enough for Milhouse to hear. “Let’s see what this monster of yours tastes like.”
Milhouse couldn’t watch. He slunk back into the darkness of the closet and buried his face in his arms. She’d just called Nelson’s dick a monster. He could barely hear the soft sounds of Lisa’s blowjob, her lips slurping and smacking along Nelson’s shaft.
“God, it’s so good,” he heard Lisa moan. “And it’s so big. I don’t know if I can fit it all into my mouth.” Milhouse’s heart sank. He tried to hold back his anger and his sadness, his rage, and his tears. This couldn’t last long. He’d have to remain hidden and wait it out.
“Well you’re gonna try," Nelson grunted. Milhouse couldn't watch. Nelson placed his hand on Lisa's head and forced her down his dick. Lisa took his length with ease but forced the sound of her gagging from the back of her throat. Lisa slipped one hand between her legs and began to rub herself as she pulled herself up along Nelson's cock. Nelson closed his eyes and tilted his head back. He left his hand on the back of Lisa's head and placed his other hand behind him on the bed. He savored the feel of her tongue and the sounds of her throat. Lisa's lips parted to allow a muffled moan to escape her mouth. Nelson opened his eyes and looked down passed her head at her hand between her legs. Lisa had begun to fuck herself with her finger, using it to mimic the movements of her head on his cock.
"Geez, Lisa. You're really getting into this, aren't you?"
"God, yes," Lisa groaned. She had pulled her mouth off his cock and quickly wrapped her spare hand around him.
"It's so thick. This'll split me in half." She jerked Nelson's cock as she took the tip of him back into her mouth. Her tongue flicked against the head to lick up his leaking pre-cum. She gazed up at him, just as Nelson placed both his hands on the side of her head.
Milhouse lifted his head from his arms when he realized how hard he had become. His blue shorts were sporting a bulge between his legs. He cursed himself for feeling turned on and excited at a time like his. He sighed, and silently rested his head against the closet's back wall. "God, yes," he heard Lisa say. He looked up at the small open gap in the door. Through it, Milhouse could only see the edge of Lisa's desk. He stood up as quietly as he could and took a step forward. Milhouse knew he would hate what he would see, but his curiosity was starting to get the better of him. His cock twitched in his briefs at the possibility of what was happening in the bedroom. This was the girl he loved and adored, but watching her with someone else was a pain Milhouse found himself willing to endure. He eased the closet door open just a tiny bit more so he could see Lisa's mirror above her desk. He was just in time to watch the reflection of Nelson forcing Lisa's head back down his cock. Lisa made no attempt to resist or fight him, with no sign of discomfort or displeasure. She was eager, she was keen, and Milhouse could do nothing but watch the girl of his dreams sucking on his bully's cock.
Milhouse didn't notice his hand on his bulging shorts until he had already started rubbing himself. His fingers, one by one, slid back and forth over his erection. The boy sighed in defeat. He silently cursed himself for resorting to such a measure. He lifted his feet from his shoes and slipped his thumbs into his shorts and briefs to push them down his legs. Now barefoot and bottomless, he pressed his hand against the closet wall beside the door for support, and found his hand on his cock, reluctantly rubbing himself at the reflection.
"Goddamn Lisa..." Nelson grunted. His climax was building, he was getting close. Lisa squeezed him with her lips as she was brought down on his cock over and over again. Leaking pre-cum dribbled onto her tongue with almost every thrust of her face. It was a feeling that Milhouse could only imagine. He watched Nelson bring Lisa down one last time and hold her face between his legs. He offered no further warning before his twitching cock sprayed a thick load of cum into Lisa's mouth. Lisa swallowed it straight away. Milhouse could see her closed eyes as she relished his seed, listing to the loud and exaggerated sounds of her gulping it down. Nelson finally released his grip on her head and Lisa pulled her head from his cock. She leaned back until he sat on the floor, breathing heavily and swallowing Nelson's final spurt.
"Whoa..." Nelson sighed. "Why weren't you this keen back when we were dating?"
"That was a long time ago," Lisa smiled. "Do me a favor, and open that top draw." She pointed at the chest of draws beside her bed.
"What am I looking for?" he asked, leaning over to pull the draw out.
"The blue one," Lisa said. Nelson pulled a small blue tube from the back of the draw and inspected its label.
"Lubricant?" he read.
"Lubricant." Lisa nodded.
'I don't want to see this,' Milhouse thought to himself over and over. But his eyes remained glued to the gap in the door. He watched as Nelson squeezed a healthy amount of the gel into his hand while Lisa lifted herself onto her knees. She leaned forward and reached her hands behind her to pull apart her rear cheeks. Milhouse quickly yanked his hand away from his cock. He felt it twitch as the sight of Lisa's ass and pussy had propelled him to the edge of orgasm. He swore under his breath; he could see everything. Both Lisa and Nelson had their backs turned to him, so Milhouse eased the closet door open just a little bit more to risk a greater view. He wanted nothing more than to just jump out and dive between Lisa's legs. Her pussy and ass looked so inviting to him, and he would have given anything for a single lick of both of her holes.
Nelson smeared the lubricating gel around Lisa's asshole. The girl almost shrieked as the cold slime was wiped against her skin. His fingers traced the circular rim to coat it in lube, while his cock twitched in anticipation between his legs.
"That's not going to be enough Nelson," Lisa teased him. "Smearing just the outside won't do at all."
"You got it, Lisa." Nelson squeezed more of the gel out onto his finger and pressed his finger against the girl's rear hole.
"Oh God," Lisa groaned as she felt her ass open up around the intruding finger, and shivered as the cold lubricant was smeared around inside her. Nelson turned and twisted his wrist to coat the entrance to Lisa's ass in lube, before pushing until half his finger was inside her. Nelson couldn't deny the rush of power he was feeling by having Lisa below him like this. His cock was twitching, begging to inside.
"I think I'm going to go a little faster," Nelson grinned. It was more of a statement than a warning to Lisa. But he was true to his word.
"Oh God that feels good," Lisa moaned. The intruding finger was fucking her at a slow and comfortable pace. But one wasn't enough for Nelson.
"Let's see you take two," he said. Nelson pulled back his hand to smear two fingers with the lubricant. He pressed them against Lisa's hole and slipped them inside her. Lisa took a loud, deep breath and clenched her teeth as she felt herself stretch. Nelson didn't stop this time. He pushed both his fingers inside of her, watching in awe as his knuckles disappeared under Lisa's rim. Nelson found that they were moving inside a little easier. He started moving his fingers in and out of her, just going a little bit faster to watch her squirm.
"Fuck Nelson... if that's how your finger feels..." Lisa gasped. Nelson grinned as his fingers moved in and out of her hole with ease. He could feel her clenching down on him, almost as if her ass was trying to pull him deeper. Nelson pulled his hand back and positioned himself behind her. His cock in his grasp and pressed against the small gaping entrance.
"Enough of that. I didn't come here just to finger you."
"No," Lisa sighed as she looked back at him. "You didn't. "Just... go easy, Nelson. It's my first time back there "
Nelson let out a soft moan as he nestled the head of his dick to Lisa's ass. He pushed forward, applying just a little pressure and eased the head into her asshole. He slid his hands to her full cheeks and grabbed them tight to spread them apart. He admired the way his shaft was pressed into her puckered hole. Nelson took a deep breath, then gently started pushing.
"Oh god!" Lisa whimpered. She closed her eyes and lowered her head to the floor. She grabbed and squeezed her fists down on the edge of the rug. She felt a mixture of discomfort and pleasure as Nelson slowly pushed his shaft in, stretching her tight little hole open with his cock. He fed her hole every inch and buried his length inside her warm hole. Lisa felt herself involuntarily clenching around his intruding member, squeezing him like a warm and tight glove.
"Holy fuck, you're so tight," Nelson grunted. Her anal ring was squeezing the base of his cock like a vice. "I hope you're ready for this," Nelson grinned. Lisa silently nodded. Nelson pulled his hips back just enough to keep his cockhead inside her ass, before pushing himself back in.
Milhouse could only watch as Nelson pushed his way inside. He watched Lisa grip the rug beneath her in her hands, and her toes clenching as Nelson pushed his cockhead into her ass. "Just... go easy, Nelson. It's my first time back there." Lisa's words were like knives to Milhouse's heart. He stumbled backward against the wall and sunk back down to the floor. This wasn't just a fuck, this was her first fuck. His mind betrayed him as his memory played her words over and over in his head. He could recall the trembling excitement in her voice; Lisa wanted this. He watched Lisa though the gap in the door. Her body was jerked back and forth with each thrust that Nelson forced upon her ass. His hand found his cock again and he started to jerk off. Already he hated himself for doing it, but he couldn't deny he wanted to cum. He sat up and opened the chest of draws beside him to pull out a pair of Lisa's panties. His depression was overtaken by his need for release. At least in his mind, he could picture himself in place of Nelson. Milhouse pressed the panties against his nose and took a deep breath. They were clean and smelled of laundry liquid, but the faint smell of Lisa was still stained on the fabric. He quivered and silently exhaled, dropping the underpants onto his wrist and quickly wrapping them around his cock. Milhouse positioned himself so that he could only see Lisa and he started jerking off into her panties as he watched Lisa being fucked through the door.
The discomfort that Lisa felt had faded once her butt had adjusted to Nelson's cock. The schoolyard bully could only moan as he continued defiling her backdoor. Her ass delightfully squeezed his cock. Nelson was in heaven. Lisa's ass hugged every inch of dick as it was pushed in and out of her hole. The slapping sounds of his hips against her cheeks echoed throughout the room, and his cock leaked pre-cum inside her stretched hole. He watched her ass as he shoved his manhood inside. Nelson drove his cock as deep as he could reach, giving Lisa every inch he had.
“Oh my God,” he groaned.
"No! Someone help me!" Lisa's false pleas were enough to pull Milhouse from his fantasy. He saw her hands behind her back with Nelson's foot pressing down upon her wrists.
"Oh yeah! You nasty brainiac. Take my big fat cock in your nerdy little ass."
"A big strong bully is taking advantage of my little girl body! Nelson! Please... don't stop!"
The way Lisa’s tight ass was squeezing Nelson was so good that he couldn’t stop even if he wanted to. His thrusts became short jabs as he was on the verge of climax. He pulled his length from her hole and slammed it back inside Lisa one last time, his twitching cock going deep as he could before he shot his load into Lisa’s asshole. Nelson’s cock twitched against her with each rope of sperm. He gave Lisa a few gentle thrusts during his final spurts, and carefully pulled his dick from her ass when he was done.
Milhouse was struggling to control his breathing. His fist was flying up and down the length of his dick, enveloped in the crotch of Lisa’s underpants. He felt like he was on fire as his personal pleasure engulfed him. His forehead was cased in a fine layer of sweat, and his climactic shivers ran through him as he emptied his load into the soft fabric. Milhouse’s once tense body fell into a slump as he came. The boy heaved silently and he rolled his head back and closed his eyes to enjoy his moment of release. But it was a moment that was short-lived. He didn't see Nelson falling back onto the floor after pulling out of Lisa's ass. He didn't see Lisa slowly stand on shaky legs. And he didn't hear her bare footsteps on the carpet as she walked to her closet. Milhouse saw a rush of light shining onto his closed eye-lids, and he froze at the sound of Lisa's voice standing above him.
“Hello, Milhouse,” Lisa smirked at him. She was still naked, Nelson’s cum slowly leaking from between her cheeks and holding her closet door open firmly in her hand.
“Milhouse?” Nelson jumped up from the floor and quickly stood next to Lisa. “What the hell are you doing in here, four-eyes?” His eyes fell to his crotch, still wrapped in the pair of panties. “You get off on watching people? Is that it?”
“Leave him alone!” Lisa quickly ordered. “I knew he was there.”
“You did?” Nelson asked.
“You did?” Milhouse asked. Lisa held out her hand and pulled Milhouse to his feet.
“Consider our little show payback for sneaking into my room all the time.”
“Payback?” Nelson asked, confused. “Show?”
“Oh, stop complaining,” Lisa rolled her eyes. “You got laid. But now there are three of us. You two boys want to show a girl a good time?”
“With him?” Nelson pointed at the embarrassed Milhouse. “Uh-uh. No way am I doing a three-way with this loser.” In a huff, Nelson turned around to gather his clothes off the floor. He hastily dressed himself and left carrying his vest and shoes. Lisa followed him with a confident gaze as he stormed out of her bedroom before she turned back to Milhouse.
“You finished with these?” she asked him and pulled her panties from his dick.
“Wait, Lisa. I just …” Milhouse started to explain.
“I know you did,” Lisa cut him off. She held her underpants in her hand to inspect them, before lifting it to her face and pressing her tongue into Milhouse’s mess. Milhouse’s jaw dropped as he watched Lisa lick his cum off the crotch of her panties.
“Not bad,” she licked her lips as she lowered them to the ground and slipped her feet through the openings and pulled them up to fit snugly around her waist. She looked back up at Milhouse.
“I'm leaking,” Lisa shrugged. “I just need something to wear while I walk to the bathroom for a shower.” Lisa reached passed Milhouse and opened up her draw. She pulled out a fresh pair of panties and a clean dress from the inside of her closet.
“Wait, Lisa… about that stuff you said to Nelson…?” Milhouse asked as he stepped out of the closet. He feared the answer, but he felt like he had to know.
“All lies,” Lisa nonchalantly said. “Well most of them. Except for the part about more lube. I only told him what I wanted both of you to hear. Don't worry. It wasn't my first time.”
"So who was?" Milhouse gulped.
"Who do you think?" Lisa rolled her eyes. "Bart and I have been having sex for months."
“So Bart set me up? You two planned this?”
“Just me,” Lisa closed the closet and walked to open her bedroom door. “Don’t worry. Bart is getting punished as well for letting you into my room. You’ve both betrayed my trust by you being in here. You had to watch me with Nelson, and Bart had to watch me bring him home. And now, Bart is sitting downstairs knowing that his best friend will be joining me in the shower.” Milhouse quickly looked up at her. He wasn’t sure if he’d heard what she just said.
"S...shower?" Milhouse stuttered.
“Yeah, shower,” Lisa grinned. “You coming?”
- 1
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