New Year's with Jackie - Chapter 1

This chapter isn't too grossly descriptive until the last few paragraphs but it's definitely gonna be for the next few chapters 🤷🏽‍♀️ But if you've read all parts of this series so far you know that's kinda a theme with it lol

~

Christmas morning for Denver’s family was uncomfortable for everyone involved.

After Jackie accidentally dropped her gift to her brother and her parents saw the dildo she’d tried to give him, she’d gotten in a fight with their mom and dad that lasted for half an hour. They, of course, found her present to Denver to be disgusting and perverse. She, of course, insisted that it wasn’t that big of a deal, and that she knew they wouldn’t understand which is why she’d tried to hide it from them.

Denver even came to her defense, fabricating a story about how he’d gotten in the middle of some crazy and awkward gift mixup at work in which his coworker had accidentally given Denver a similar present meant for their partner instead. He hadn’t told his parents the story but he’d told Jackie about it, so that must’ve just been her way of teasing him about it. Denver knew that helping bail his sister out of her trouble would help him in the long run, and Jackie was definitely appreciative that he lightened her burden of guilt. But he couldn’t take back the past. Even though their parents eventually relented, deciding that their daughter was a grown woman and they couldn’t punish her, Denver and Jackie hadn’t been able to change their mind. Prank present, gag gift, white elephant; it didn’t matter in their eyes what she wanted to call it. It was inappropriate to give to her brother. “I’m sure you didn’t mean anything wrong by giving him something like that,” their mom had sighed. “But it was still a bad call. We should all just move on and I’m sure your dad and I will forget about it eventually.”

They tried to move on, but breakfast was still eaten in an awkward silence. Jackie’s reputation was tainted in the eyes of her parents now. Even if that reputation had always been a lie to begin with, she couldn’t bear the feeling of her parents’ disappointment in her. She fought not to tear up right in the middle of the kitchen table. When Denver glanced up at her to see how she was doing, she glared at him through watery eyes. Christmas was ruined. He’d ruined it. So now she’d have to ruin him.

As much as Jackie was itching to get back at Denver though, she was still mature enough to not let her vengeful feelings interrupt the holiday. As the hours went on in the day and the four of them met up with the other side of their family later that day, the uneasy spirit of their parents died down a bit. But not all the way. It’d be a while before they could see their daughter normally again.

That night, after everyone had gone back to the house, Jackie held her brother back for a moment as their parents headed inside. “I’m sure you already know what has to happen,” she whispered through gritted teeth.

Denver swallowed nervously, unable to look her in the eyes. “…Yes.”

“That was easily the lowlight of my fucking year,” she continued. “You know how conservative Mom and Dad are, I… I just can’t believe you let that happen.”

“I’m sorry.”

She took a deep breath, looking down to the ground. “I know you are. And I haven’t forgotten that you tried to help me this morning at least, after you fucked everything up.” She sighed again, looking up into Denver’s eyes with a serious expression. “But that was exactly the kind of behavior I was trying to eliminate the last couple days and train you out of. So tomorrow morning I’m gonna help you pretend to leave in the morning and then go hide your car again so I can keep you for another few days. And since I’m gonna be up all night reliving that morning in my head, I hope you’re up all night too, thinking about what I have in store for you.”

With that, she headed inside and left him standing out in the snow, wallowing in fear over what the near future had in store for him.

* * * * * *

Denver said his goodbyes to their parents early the next morning. His mom wished he could stay a couple days (and he had packed a couple pairs of clothes with the intention of doing exactly that), but she didn’t press him too hard since they saw each other every couple months anyways. It saddened him though, only getting to spend a day with his mom and dad before heading back to his sister’s hell. But at least she’d given him that day.

Jackie waited until she heard their mom start her shower, knowing that her dad had gone back to sleep after saying goodbye to Denver. Then she ushered her brother out to his car and opened the driver-side door for him. “Get in,” she nodded, but stopped him before he could sit down. “With your face up.” He paused, wondering if she was telling him to do what he thought she was telling him. “Yes, I’m gonna sit on your face,” she groaned impatiently, “did you forget how you shrink?”

Moving more anxiously, trembling from the knowledge that he only had a few more seconds left of being full sized for the next however-many days, he climbed into the car. Sliding his body towards the floor but leaving his head and upper torso resting upwards on the seat, the rest of his body was contorted and crammed tightly into the space near the pedals. He winced, staring at his car ceiling, when he heard his sister whistle. He turned his head to her, just as she looked around one last time to make sure nobody was watching, and then shimmied her pants down… and her underwear.

He gasped, “Why are you taking off your underwrmmmphhh!” Before he could even get the question out, she reached her leg over to the center console and pulled the rest of her body over her brother, before her ass fell on top of his face and muffled the rest of his speaking.

“Seriously, after what you went through a couple days ago, and you got fazed just from seeing me pull down my pants?” She chuckled, “The next week is gonna be real tough for you if just seeing my vagina was enough to scare you.” Wait, the next WEEK? he thought fearfully, as his sister readjusted herself so his nose wedged itself deeper into her crack. Two days had been brutal enough, but seven full days of torture was more than a step up from what he’d been through already.

“Now close the door, it’s cold outside,” she told him, and he blindly fumbled around with his arm out until he found his door handle and slammed the door shut. “Sorry for the bad news, but I actually haven’t been feeling that gassy this morning, even though I ate a bunch of stuff last night to try and prepare. Unless you know of some other way to shrink you down?” He tried shaking his head no, but was already feeling burdened by the weight of Jackie’s body. “Yeah, my neither.”

She sighed and shifted around on her face-seat to get more comfortable, sliding back a little more and tilting her hips forward a few more degrees. The move freed up Denver’s mouth, but now the bridge of his nose was being mashed against the bottom of Jackie’s sex. “So hopefully you like the smell of fresh, morning pussy,” she laughed, “cuz you’re gonna be smelling it for a while.”

* * * * * *

Even though it was gonna take a little while for Jackie to work up enough farts to fully shrink her brother, she obviously couldn’t just let the car sit in the driveway. But she also couldn’t reach the pedals with her brother’s body crammed in the way. So her solution was having him operate the gas and brake for her, and she’d sit criss cross on his face while she steered the car. Conceptually it was ridiculous, but she made sure to have Denver take it slow, never going more than 5mph. Since they only traveled a few blocks within their neighborhood (and nobody was on the road), it actually went smoothly. After they parked it about half a mile from their house, she reclined the seat and began idling on her phone while waiting for her farts to arrive. Denver waited with her of course, although while she was scrolling through TikTok, his closest thing to entertainment was the smell of his sister’s musk wafting through his nose, while her lips occasionally wiggled against his face and reminded him to stay put.

* * * * * *

“Finally!” It was close to 10am, and after over an hour of careful and meticulous work, Jackie had successfully finished the activity she’d spent all morning on. The setup for Denver’s first day of punishment was complete. It was similar to the underwear ordeal that he’d gone through on Christmas Eve, but Jackie had had to make sure his punishment went even farther, so she’d found a way to make the idea even more uncomfortable for him. She hadn’t just tied his body to her underwear, she’d wrapped the string so many times around his body that he was practically mummified, and instead of a regular pair of panties, he was now tied to the skimpiest thong she owned.

Jackie beamed down at the tiny bump on her thong that was hiding someone beneath it. Finishing a project always felt good, but it felt even better since she knew this one was for a good cause. But after thinking him over a bit more, she knew something still wasn’t quite right. Denver’s heart dropped when he saw her expression fall to a frown. “It’s good, but it’s not good enough. This is supposed to be a lot worse than what I did a couple days ago,” she sighed. Denver thought that being on a thong, and therefore wedged a LOT further into his sister’s crack, would’ve made it worse enough on its own.

“Got any ideas?” she asked rhetorically; Denver obviously said nothing in return, and just stared back up at her, fearfully impatient. “Yeah, not surprised. You haven’t said anything in awhile,” she murmured. But that was it. His muteness sparked an idea in her. “Wait, I’ve got it!”

She reached back down with the string and started wrapping it around again, but this time the ultra-thin strands were being wrapped around his mouth. “I figure since it smells pretty shitty down where you’re going, maybe you try to lighten the load on yourself by breathing through your mouth so you don’t have to smell it.” Realizing what his sister was doing, he tried shaking his head, but his mouth got wrapped up along with the rest of him, preventing him from saying anything more. He tried sucking in air to see if maybe his sister would be wrong and he could still breathe, but he had no such luck. Only his nose would be doing the work for the rest of the day.

She didn’t stop there; after his mouth got wrapped up, she did the top of his head next. In just a few seconds, she managed to blind him too. But then went even further, and started wrapping the string around his head sideways from top to bottom, covering up his ears.

Jackie sat back up and took a look at her big brother, although he was hardly even noticeable now. His body was wrapped up, his mouth was covered, and he was blind and deaf now too. She couldn’t completely deafen him of course, but it was the thought that counts.

She leaned in close, smirking at how completely helpless and immobile Denver looked. “I figured you wouldn’t have a need for all those other senses of yours. You’re only gonna be needing your nose for today,” she snickered, and then stood back up while her brother’s attempted squirms were made in futility.

Jackie picked the lingerie up and stepped her left leg through a hole, and then her right. Holding her panties just below her crotch, she bit her lip and grinned as she imagined how much hell her brother was about to go through… and then she pulled the underwear up, stretching it as high up as it could go, just for added effect, before letting it snap back down.

His sister’s calculations had been perfect, unfortunately. Because Denver was positioned right in front of Jackie’s asshole. Actually, that wasn’t even true; because of how tight the thong was, he was pretty much on her asshole. His minuscule body rubbed right up against her massive taint—not that he could see it though. Or even feel it, technically. But he could smell it. The rotting stink of his little sister’s colon flooded his only working sensory organ. The vile stench was the only thing he could smell.

And for the next couple hours, smelling every millimeter of his little sister’s putrid, shit-stained asshole was literally the only thing his pathetic little body was able to do.