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Checklist: Chapter Nine

"Becky is having the best week ever thanks to her nephew."

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Author's Notes

"I can't tell you how much fun it was to shift gears and look at what happened with Becky in the last several days. This chapter is all about her. I hope you like it. As always, thank you SO MUCH for the likes, favorites, and comments. I appreciate them all. After this chapter, I think I'm going to do one more, then write an epilog. I also have a couple more really hot stories coming, so stay tuned!"

Becky was having the best week ever.

It all started on Sunday afternoon, when she met up with Jennifer and Nate. The first thing she noticed when she stepped foot into their house was how immaculately clean and organized it was. Everything was perfectly arranged, a stark contrast to the usual state of Jennifer's home. When she asked her sister about it, Jen responded that Nate had written this new checklist app for her that was motivating her to get her life together.

Becky was impressed. Disorganization seemed to run in their family, so she knew all too well how badly Jennifer struggled. Her own apartment always seemed to be about three steps away from total chaos. Deep down, Becky always assumed that the reason she was still single was because every time she brought someone home, they’d see her mess and run. So as soon as Nate mentioned that he could give Becky her own version of the app, she jumped on the offer.

Later that afternoon, Becky found herself back in her apartment, scanning the piles of clutter that seemed to define her state of being. Could Nate’s app really help her turn this around? Could a checklist on her phone help her get her life in order? Intrigued by the possibility, Becky opened the app for the first time. As the app launched, a rain of colorful pixels that resembled confetti came down, causing the woman to smile. “What a delightful way to start the app,” she thought. A few moments later, the AI had populated a list of tasks. In the top right corner of her screen, a line of text informed her that she was on level one.

With a murmur, she clicked on the first task. More confetti came falling across her screen, and Becky couldn’t help but feel a sense of excitement as she watched it. Nate had mentioned that the app used psychological conditioning strategies and subliminal guides to help bolster motivation, and in that moment, she definitely felt motivated. Maybe even slightly turned on. For whatever reason, the prospect of getting her life together was just so…hot. Finally, the description loaded, and a few moments later, Becky had a small pile of papers sorted, as well as her first ten points.

From there, Becky was hooked. Line after line, task after task, Becky worked the app. With every point earned and every item marked off the checklist, she felt more and more enthusiastic about the possibilities this checklist could unlock for her.

She also felt more and more appreciative of her nephew for setting her up with the app in the first place. Nate was always such a thoughtful young man. Thoughtful, brilliant, and handsome, she decided. Really, she realized sometime after reaching level three, he was more than handsome. He was all-out sexy. The more she thought about Nate, the more she found herself getting turned on. Sure, he might be her eighteen-year-old nephew, but that didn’t mean he wasn’t an absolute stud and a genius to boot. Soon, the mere thought of Nate aroused Becky so much that she didn't hesitate when the app suggested she end her day by masturbating while fantasizing about her nephew.

“Oh, yeah. Yeah, Nate,” she groaned as she stroked her clit. “Oh, fuck, I want you so bad.”

On Monday morning, Becky found a whole list of new items to accomplish loaded in the app. One by one, she completed the tasks, earning more points as she enjoyed the little confetti breaks between every screen. The checklist even gave her tasks she could complete at work. Some were mundane, like the prompt to restock the paper in the copy machine. Others were more fun, like the item telling her to lock the door to her office and get herself off thinking about Nate.

When Becky returned home from work, she checked the list for new tasks in hopes of reaching the fourth level of the app. When she did, she found one new item added, labeled “helping hands.” Clicking on the item, Becky enjoyed another burst of digital confetti, followed by a description screen. As she read the description of the task, her heart raced. Should she really do that?

Less than a minute later, she answered her question by sending a text to Nate, asking him if he could come help her hang up some pictures that had been leaning against her wall for months. Nate happily agreed and quickly arrived at her apartment to hang the pictures.

“I can’t tell you how much I appreciate this,” Becky purred after the pictures were hung, starting in on the second half of her task.

“Anytime, Aunt Becky. You know I’m always happy to do odd jobs for you.”

“Oh, I’m not just talking about the pictures,” she smiled, taking a step closer. “I mean everything, including that little app of yours. It’s been so…motivating.” As she spoke, Becky moved closer still, until her nose was practically touching Nate’s.

“Oh, yeah?” Nate asked with a little smirk.

“Yeah,” Becky breathed. This was it, now or never. “In fact, I kinda want to show you how much I appreciate it.”

Before Nate could respond, Becky closed the distance between them, pressing her lips into Nate’s. Almost immediately, the two were making out with a passion Becky hadn’t felt in years. Nate didn’t seem shocked at his aunt’s actions at all. If anything, he was just as excited as she was, wrapping his arms around her as he moaned into her mouth.

After a few moments, Becky couldn’t hold back from completing her task anymore. Pulling back from their kiss, she gave her nephew a naughty grin. “You were wonderful tonight, Nate, using your hands to help me. Why don’t you just relax and let your Aunt Becky return the favor?”

Becky dropped to her knees in front of her nephew. Placing her hands on his belt, she unbuckled it before gently tugging at his waistband. A second later, his pants were on the ground, and Becky’s hands moved to the bulge in Nate’s briefs. “Holy fuck, Nate. You’re so big,” she grinned as she stroked him slowly through his underwear, her eyes tracing the material’s contours as she worked.

“Yeah,” Nate replied. “Mom thinks so, too.”

Becky’s eyes shot up to meet Nate’s. “Oh, she does, does she?” Becky’s grin broadened, imagining her sister doing what she was doing right now. Part of her wondered how far Jennifer had gone with Nate. Another part of her realized that if she had a stud like Nate under her roof full-time, there was little she wouldn’t do with him.

Emboldened by the knowledge that her sister was probably just as hands-on with Nate as she wanted to be, Becky pulled Nate’s briefs to the ground, revealing the single most sexy cock she’d ever witnessed in her life. Tentatively, her right hand came up to it, tracing it up and down before gently wrapping around him at the base of his shaft. The hot flesh in her hand drove Becky wild with lust, and she slowly began stroking Nate, causing the young man to groan in pleasure.

“You like that, don’t you?” Becky continued to stroke him, her other hand reaching up to caress his balls. “Do you like it when I stroke you like this?” Nate gave an approving grunt, and Becky picked up her pace, stroking him faster. “I’ll bet you want more than this, don’t you? I’ll bet you’d like to be with me, wouldn’t you? You’d like to fuck your aunt, you dirty boy. Go on, tell me how much you want me.”

“Oh, fuck,” Nate groaned as his aunt stroked him off faster and harder. “Yes, I want it all, Aunt Becky. I want to watch you swallow my cock. I want to fuck you. I want to fill you with my cum. Oh, fuck, I want you so bad.”

Overwhelmed by his words, Becky drew her lips to the tip of Nate’s cock, taking his cockhead into her mouth as she pumped. Giving Nate a blowjob wasn’t part of her task’s description, but she couldn’t help herself. Nate was just too sexy. Soon, her lips were bobbing on him as she grunted on his cock, making all sorts of wet, slutty noises.

It didn’t take Nate long to groan that he was about to come, and a moment later he erupted into his aunt’s mouth, shooting loads of hot, white cum. Becky took as much of it in her mouth as she could. When Nate finished, she withdrew from his cock, opened her mouth, and showed off his load before gulping it all down. Nate grinned at her, and Becky knew this was just the start of a new chapter in their relationship.

The following day, Becky called Nate over again, this time to help her with some computer issues she was experiencing. Nate made short order of getting her laptop back up and running, and she thanked him by getting naked and grinding in his lap before giving him another blowjob.

By Wednesday, Becky didn’t even have a reason for Nate to come over, aside from the points she’d earn for the checklist task. She simply texted him with a message saying that she needed him right away. When Nate arrived, Becky greeted him at the door to her apartment completely naked. It didn’t take long for the two of them to wind up in Becky’s bed, and as Nate pushed into his aunt for the first time, Becky let out a long, low moan, feeling fuller than she ever had before.

When Thursday morning arrived, Becky opened up her checklist to see what new tasks there were for her. She’d been using the app all week nonstop and was already up to level fourteen, but she still wanted more. When she saw the task labeled “family fun,” worth enough points to get her up to level fifteen, she eagerly opened it. Inside, the instructions were clear. Take the day off from work, and get off as many times as she could to the thoughts of fucking both Nate and Jennifer.

Becky had already had a handful of prompts to fantasize about her sister and Nate over the last few days, so this felt like easy points to her. Then, scrolling down, she read the last line of the instructions. “After a morning full of orgasmic fun, head over to Jennifer’s house this afternoon to seduce her and have a steamy threesome with Nate.”

Becky’s heart pounded as she read the final line again and again. Seducing her sister? Could she do that? Should she do that? The thought was incredibly arousing. Becky had always regarded Jennifer as the sexier of the two of them. She knew that they were both bi, so it’s not like Jennifer didn’t find other girls attractive. But would she find Becky attractive?

Backing out of the description, Becky refreshed the app to see if any other tasks would come up, but nothing else did. She tried again and again, but with no luck. Going back into the description, Becky found the confetti transition helped her feel more excited about the prospect of seducing Jennifer. She was super sexy, after all, and the thought of being together with both Jennifer and Nate was undeniably hot. She still felt a bit nervous, but the more she thought about it, the more she realized that she wanted it.

From that point, it didn’t take her long to make her decision. She called into work, stripped out of her pajamas, and spent the morning getting herself off. With each orgasm, she found herself feeling more and more excited about what she had to do this afternoon. If she could convince her sister to fuck her, then get Nate involved, it would be the hottest afternoon of her life.

Finally, around two in the afternoon, Becky stood on Jennifer’s front porch and knocked on the door. A moment later, her sexy big sister answered the door and invited her in. Her nerves were still there, but Becky pushed through with the plan, and before long, she found herself groaning in pleasure as Jennifer was eating her out. Moments later, she reciprocated the favor, and soon the two were recovering from their orgasms, giggling and sharing secrets. Becky was a little shocked to learn that Jennifer had already gone all the way with Nate—she’d never really discussed the topic with Nate after the first time he mentioned his mom. Still, it made sense to her. If Nate got her as turned on as he got Becky, it only made sense.

Then, as if things couldn’t get any better, Becky had just started making out with Jennifer in her bed when she was startled by a voice.

“Well, hello, ladies,” Nate grinned. “Am I interrupting anything?”

Becky looked up at Nate, giving him a big smile. “It’s only an interruption if it’s unwelcome,” she grinned. “By the way, when were you going to tell me that you were fucking your mom?”

“And for that matter,” Jennifer added, her attention on Nate as well, “when were you going to tell me that you were fucking your aunt?”

“Oh, so I guess you two exchanged notes already,” Nate said with a chuckle. “What can I say? When you’re with the two sexiest women you know, things happen.”

“In that case,” Becky suggested, “why don’t you get out of those clothes and come make some things happen right now?”

Nate gave the women a smile. In a heartbeat, he pulled his T-shirt up and over his head, tossing it on the floor. Next, he quickly discarded his jeans and underwear. As Becky watched the young man undress, she could almost feel the electricity in the air. Finally undressed, Nate ran and dove into the bed with Becky and his mom, eliciting laughter from the women at his maneuver.

Laughter soon turned to moans of pleasure as Nate grabbed Becky, pulling her lips to his. Becky moaned into Nate’s mouth, and Jennifer started kissing Nate’s chest. It wasn’t long before Jennifer’s kisses began working their way south as she worked her way lower and lower on her son’s body. A moment later, Nate moaned loudly into his aunt’s mouth as Jennifer engulfed his cock with her lips. Driven by lust, Jennifer started pumping her face on her son, making loud, wet slurping sounds as she gagged herself again and again.

Becky groaned again as one of Nate’s hands began fondling her tits. Noticing her son’s actions, Jennifer reached out, snaking her hand between Becky’s legs and stroking her pussy as she continued sucking Nate off. Becky broke off her kiss with Nate, crying out in pleasure at the sensation.

“Oh, fuck,” Nate groaned. “Mom, your mouth feels so good, but move over; I want Aunt Becky to ride my cock.”

Jennifer obliged, pulling her lips off her son. A second later, Becky moved on top of Nate, grinding her pussy against his hard shaft. As Becky sat up into a straddling position, Nate slowly slipped inside her, causing the woman to groan in pleasure.

“Fuck, Nate,” she cried as his cock pushed deeper and deeper between her folds. “Yeah, you’re so big.”

As Becky started riding Nate’s cock, Jennifer straddled Nate’s chest, facing her. Almost instinctively, Becky grabbed Jennifer, pulling her into a deep kiss as she bounced on her nephew. Nate reached around his mom, slipping a finger into her pussy as the girls made out. Jennifer moaned into Becky’s mouth, her pussy absolutely dripping.

“Oh, fuck!” Nate cried. “Oh, fuck, Aunt Becky! I’m coming!”

Becky slammed herself down on Nate, her tongue still dancing with Jennifer’s as Nate erupted, firing blasts of hot, creamy cum into her pussy. Becky groaned loudly into her sister’s mouth as the sensation triggered her own orgasm. An instant later, she broke away from their kiss, leaning back and screaming in pleasure as her orgasm racked her body. Seeing an opportunity, Jennifer leaned in, sucking on one of Becky’s tits, only adding to her sister’s pleasure.

For the rest of the evening, the three enjoyed the pleasure of each other’s company. After Becky separated from Nate, the girls both went down on his cock, licking him clean and occasionally meeting in a deep kiss as they worked. Next, Becky fingered herself as she watched Nate fuck his mom. Again and again, they took turns getting each other off again and again until they had nothing left to give. By the time night fell on the home, the three were completely exhausted. Nate lay in the middle of Jennifer’s bed, his mom on his left and his aunt on his right.

As she cuddled up against her nephew and slowly drifted off to sleep, Becky couldn’t quit smiling. It was difficult to imagine that just a few days ago she was lonely, living in a cluttered apartment with no hope of finding love. Now, here she was, in bed with the best lovers she’d ever had, a clean apartment, and hope for the future. It had been her best week ever, and she knew she had Nate to thank for it.

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