HTTYB - Day 18, Part 10 (Patreon)

Yeah, so... after several months and almost a dozen chapters, day 18 is finally done. I'd like to think it started off pretty wild with that whole bath scene, and then got crazier during the last few chapters as Olivia issued her punishment. But this chapter is the craziest. I mean, maybe not, depending on what you like to read about, but this undoubtedly is the height of Reese's humiliation. The ending is literally almost poetic, took me a lil bit to write

Now with "today" complete, there's only one day left in their story (and then on to version 3!)

Hope you all enjoy :)

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Wednesday, June 2 (cont.)

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“Where did you say Reese was again?”

Jarrone was a loyal enough friend to question Olivia’s motives and wonder where Reese was as he followed Olivia into her room, but at the same time, she was too charismatic for him to say no to.

“He’s at another one of his friends’ house,” she explained, sighing and climbing onto her bed before turning on her TV and getting comfortable. She’d invited him over under the guise that she’d started playing Call of Duty but wasn’t very good and needed someone to pair up with. Luckily for her ruse, she had a Playstation and Jarrone had an Xbox, which gave her an excuse for why they couldn’t just team up online. Jarrone had been somewhat suspicious considering how out of the blue her text had been, but he’d been friends with Reese since middle school, before Olivia had gone off to college. So they knew each other at least a bit more than just being acquaintances. “Are you gonna help me or what?” she asked, lightly laughing, as she picked up her controller and turned the console on.

“If you give me a controller too, yeah,” he answered, looking around her room.

“Oh yeah, crap. I forgot where I left it,” she said, biting her lip and looking around the room with him for a few seconds, until her eyes lit up. “Wait, I think it fell down in the crack next to my bed,” she mused, and turned to reach down into the small bit of space between her wall and her bed frame. Her butt popped into the air in the process, her yoga shorts getting tightly stretched over her giant cheeks. She obviously knew what she was doing, and fiddled for a few seconds, pretending that she couldn’t quite reach the controller, as Jarrone nervously glanced at her giant butt, looking away right before she turned back around.

“Here!” she grinned, and tossed him the other controller, before going to lay back down on her bed, stretching her long, tan legs out in front of her and crossing her feet. “You gonna stand and play the whole time?” she laughed, drawing attention to the fact that he’d stayed in the middle of her room instead of getting comfortable. “You can use my chair if you’re afraid of cooties,” she teased, and pointed over to her desk chair.

“That’s not—“ he grumbled, sighing frustratedly as he turned to head towards her chair. She laughed at his reaction as her brother’s friend took a seat and leaned back. “I’m just trying to—“

He was cut off as one of the wheels on her chair gave out from under him, and he quickly jumped back up just as the chair toppled over behind him. She’d taken out one of the screws on purpose just so that that very thing could happen, but Jarrone wasn’t cynical enough to assume it was intentional. She grimaced, glancing between him and the fallen chair.

“Um, sorry… I think,” he apologized, even though he knew it couldn’t have been his fault.

Olivia sighed and shook her head, “It’s whatever, I can fix it later.” She scooted over a little bit, making room for a second body. “Guess you’re gonna have to get over your fear of sitting next to girls,” she joked again.

“Olivia, it’s not... I mean I don’t mind sitting on the floor, I’m just trying to be like, respectful, and—“

“Seriously dude, I’ve known you for how many years?” she asked, starting to get irritated now. “You’re literally one of my brother’s best friends. What are you trying to be respectful of, boundaries? I’m the one saying it’s fine if you sit down with me—which there’s also nothing wrong with as long as you’re not a creep. We’re not strangers.”

“I’m not a creep,” he protested, “I meant being respectful to Reese. Like, you’re his sister and all, so… you know…”

There was a moment of silence as Olivia let Jarrone’s awkward words hang in the air. “No, I don’t. I asked you if you wanna play Fortnite, not if you wanted to make out.” The boy blushed at her blunt delivery. And she felt a tinge of guilt too, since she was half lying when she said she hadn’t asked him if they wanted to kiss; that was definitely the direction she was trying to head, if he wasn’t so antsy and standoffish.

Her expression softened and she tried taking a different approach to coax him into staying. “Look, I’m sorry if I made you feel uncomfortable or something. If you only like hanging out with my brother, I guess I understand. You can leave if you want and I can find someone else.” Her choice of words had been deliberate, just enough to guilt trip him without making it look like that was her intention. But it was, and it worked.

“No, that’s OK, it wasn’t anything against you or anything,” he tried to reassure her, and then paused, rubbing his temple as he considered his next move. “I guess you’re right though,” he said, slowly wandering over to Olivia’s bed. “I just, you know, I—“ he stammered, and Olivia was just barely able to keep an innocent looking straight face. Her brother’s friend was a cute enough guy, and he’d never seemed shy to her growing up. But seeing him stammer around her suddenly made him adorable too, and she was even beginning to feel a tiny bit turned on already from watching him fall back into her trap. “Even though I know you didn’t say anything, it’s still like… I mean, I’m coming over at night and you’re inviting me up to your room; I didn’t even say hi to your parents. It sounds like Reese doesn’t even know I’m here. I wasn’t trying to say you had any kind of intentions or anything but I mean you can at least see where I was coming from, why I might think it’s kinda sus, right?” he asked hopefully.

Olivia smiled and relaxed her shoulders, “Totally.” Jarrone felt instantly relieved, and her smile was so reassuring. Even if he was trying to keep a respectful distance, she was obviously a beautiful woman, and seeing her calm again made him feel at ease too. “Like I said,” she continued, “I didn’t wanna make you uncomfortable, I just figured since we’ve known each other for so long, you shouldn’t feel bad about relaxing and just hanging out. So I hope you can see where I was coming from too.”

“Yeah, that makes sense,” he nodded, gingerly sliding onto her bed in the spot next to her, but still keeping a safe distance. She was fine with that though; there was still plenty of time to work her way with him.

* * * * * *

Olivia and Jarrone continued to play through several matches together, and it didn’t take long for him to let his guard down and relax around her. She was easy company, so much so that he didn’t mind having to put in most of the work for their games. She kept apologizing for either being unable to kill other players or because she got killed herself, but she also made him laugh enough that he didn’t get frustrated.

But after an hour of matches with varying amounts of success, they finally seemed to have found their groove. There were only 20 players left and neither of them had died yet—and Olivia had even gotten a couple kills on her own. She was so focused and determined she was sitting up straight with her eyes locked squarely on the screen. The game had just been a ploy to get Jarrone to come over, but now she was genuinely invested and wanted to win.

When she’d gotten her third kill of the match she cried out in joy, and sprung forward on her bed so that she was laying on her stomach with her upper body propped up on her elbows. She wanted to be as close to the TV as possible, her excitement and anticipation climbing with every second. But at the other end was Jarrone, who was now finding it difficult to concentrate on playing. Olivia laying on her stomach with her feet casually kicked up behind her, her big butt wiggling with every move she made. Even with him trying to keep his distance, it was impossible for him not to pay her any attention. He’d always been an “ass man,” so friend’s sister or not, how could he continuously ignore one of the thickest butts of anyone he knew?

The two of them soldiered on, and the amount of players gradually dwindled down until there were only four people left: Olivia and Jarrone, and another duo. Olivia was so close to the first win she’d ever had with the game, her body was practically trembling with adrenaline.

Three players now. With the advantage, Olivia and Jarrone cornered the final player into a corner, gunfire surrounding them and trapping them in. They tried fighting back, but there was clearly no way for them to come back.

“YES!!!” Olivia jumped up onto her knees, screeching and cheering as the victory animation played on screen. It wasn’t a noteworthy game for Jarrone, but Olivia’s exuberance rubbed off on him and made him smile, glad to see how happy she was about her first win.

She whipped around and pounced on him, squeezing him in a hug of gratitude. He chuckled awkwardly as her breasts squished against his chest, and attempted to hug her back. After a few moments of holding him close to her, she broke away, but held onto his shoulders and grinned at him. Their faces were only a few inches apart, and Jarrone almost lost his breath at how beautiful she was up close. But here she was getting overly cozy with him again, and he felt he needed to say something. “Olivia, I don’t—“

She leaned forward and cut him off with a kiss, gently allowing her lips to shut him up. He was caught off guard, both by her actions, but also by how soft her lips were. He was too transfixed to push her off, and his dick even started to harden. She broke away again with a sly smirk, and crawled off the bed, keeping direct eye contact with him the whole time. “It’s getting kinda late, so if we’re gonna keep playing I’d rather get into something more comfortable,” she purred, lifting her shirt up over her head and letting it fall to the floor. Jarrone gulped nervously as he couldn’t keep his eyes from shifting down to her boobs. Insanely gigantic and easily bigger than his head, they were practically begging to burst out of her bra. The suddenly swung low, creating a chasm of cleavage as she bent over to pull her shorts down, until she kicked those aside too.

“I’ve got a confession to make,” she said, standing up tall again and giggling at how completely frozen her brother’s friend was, unable to take his eyes off of her. “It was kinda dishonest of me to imply when you came over that I didn’t have any ulterior motives, cuz I definitely did,” she continued, tiptoeing back over to her bed at a tantalizingly slow speed, swaying her hips for extra emphasis with each step. “So if you’re maaaaad at me,” she teased in a hushed voice as she got back onto her bed, crawling over his body, “then you can still leave. I wouldn’t wanna make you do anything you wouldn’t wanna.” She stopped once her head was only a foot away from his, a seductive smile forming on her lips as she awaited his response.

His eyes traced their way down her face, catching a glimpse of her massive tits as they lightly swung over his torso. Even further back, her bronze, beefy thighs came together at her hips, where her ass was just out of sight. His dick was getting so hard that it strained against his pants, just at the thought of what her butt would look like without anything on. Which was obviously not even counting the rest of her. Jarrone’s brain was telling him no, but his dick was saying something else, it was screaming something else. His heart rate was through the roof at how achingly close he was to one of the hottest girls he’d ever seen in his life.

Olivia was still smiling at him, but she couldn’t tell if he was gonna remain ‘loyal’ to her brother or not. “Sooooo… is that a—“

The boy jumped up, grabbing her head in his hands and returning her kiss with more gusto than he’d ever shown anyone before. After so much build-up and anticipation, Olivia unleashed more passion than even she was expecting, jumping into his lap and burrowing her tongue past his lips, a sloppy sound coming from each of them. He scrambled to pull his shirt and pants off as she ripped rushed out of her lingerie so fast they nearly ripped.

But Olivia knew what prize her brother’s friend wanted the most, and she slowly turned around, getting over onto her hands and knees to bare her ass for him. Jarrone was so mesmerized that he audibly whimpered, taking it all in for a few seconds before spreading her cheeks and lurching forward, eating her out with the kind of reckless abandon that only a teenager could have.

Olivia gasped as she felt his tongue lick circles around her anus, and her elbows crumpled beneath her as she reached her hand down to one of her nipples and begin playing with it while focusing on how Jarrone made her feel. Seducing her brother’s friend had been a thing in itself, but the fact that he was clearly experienced just made her all the more grateful for choosing him. She turned to look over at her hamper, stationary and unassuming, and a smile grew on her lips as she thought about the fact that he’d been forced to listen to them for the last hour, and now was about to have to listen as she fucked one of his best friends. This was the kind of payback that went beyond what taking any amount of his money could achieve—and that’s how she knew that he would never forget it. She moaned shakily, sighing in a rising state of ecstasy. It was definitely more than was realistic, but she wanted to make sure her brother heard everything.

“Aren’t you worried your parents might hear us?” Jarrone asked, but ignored his own precaution and dove back in.

Olivia laughed and shook her head. “They’re all the way downstairs. And they’re watching TV. And I have music playing from a speaker right next to the door too.” She turned her head to look at him, a sly expression on her face. “Don’t worry, the only people who can hear us right now are right here in the room.”

* * * * * *

Reese writhed in agony as he listened to his sister fucking the brains out of his best friend. At the beginning, he’d been immensely grateful for his friend’s loyalty, but apparently Olivia’s sexual draw was stronger than his friendship.

They both had an incredible stamina too; Reese had hoped that maybe he’d only have to listen to them fuck for 10 or 15 minutes, but they lasted at least twice as long as that, and then he had to deal with Olivia’s impassioned and prolonged moan as she climaxed. And then climaxed again.

And again.

And again.

Normally Olivia never really cared about dirty talk, but for Jarrone she pretended to and turned it up to 11, complimenting him on everything from how big his dick was to good she was making her feel. And then when he’d finally had an orgasm of his own and Reese thought it might be over, he heard his friend commenting on how his sister was so unbelievably hot that he’d only need 5 or 10 minutes before he got it back up again. So he went to go use the bathroom as Olivia cleaned herself off a little bit and then checked her phone.

When Jarrone came back into the room, Reese heard Olivia greet him again, except he could tell from where her sound was coming from that she wasn’t on their bed anymore. “Ready for round two?” his friend asked, clearly filled with far more lust and confidence than when he first came over.

Olivia giggled her approval, and then Reese felt a huge thud above him as his sister hopped onto her hamper, causing her brother’s secret prison to creak and groan under her weight. The sloppy sounds of them making out again continued, with Olivia making sure to moan extra intensely to taunt her brother. After a few minutes of that, Olivia hopped back off, giving Reese relief for only the few seconds before she bent over with her forearms on the lid, leaning her upper body against the hamper. “Do my ass this time,” she breathed, and then lowered her head all the way down between her clenched fists, readying herself for his cock. “And please, Jarrone… I really want it rough tonight,” she whimpered, just a few inches above where her little brother was hanging inside. “I need you to fuck me as hard as you possibly can.”

“Oh, you like it rough, huh?” he asked, and slapped her ass hard enough to leave a mark. She yelped out of surprise as her body bumped into the hamper, rattling her brother’s cage. “Well with an ass like yours, I don’t think I’d be able to stop even if you begged me to.” And with that, he slid his dick inside, not even taking the time to be slow with it. Olivia whined from the feeling of her anal cavity suddenly expanding, her body trembling with excitement. And then it happened. The first thrust.

Olivia’s legs crashed into the side of the hamper as Jarrone pushed his dick fully inside of her. He pulled back out, and then again, this time a little faster. Again, a little faster. A rhythm formed as he began pounding his dick all the way up her ass, and with each new thrust, Reese’s hamper shook again, letting him actually feel the energy behind his oblivious best friend’s fucking motions. And right above him, Olivia’s head lay on its side on top of the hamper, the volume of her moans going up and down as Jarrone’s shaft went in and out.

Their speed picked up, to the point where every single second, the entire room seemed to shake for Reese. He wiggled and he squirmed with every ounce of energy he had, more uncomfortable and fear-struck than he’d ever been before, but he couldn’t even begin to escape his binds. He didn’t just try yelling, but actually screaming, making his voice as loud as he possibly could and dreaming of a fantasy where his friend might actually hear him. But Olivia’s socks provided such an air-tight muffle that a pencil dropping on the carpet would’ve been louder than Reese’s pathetic, wretched soul. Olivia had buried the knowledge of his presence so thoroughly that Reese could’ve hung in that hamper for years without a single person knowing. “I hope you had fun tonight,” she whispered, just low enough that she knew only her brother would be able to hear her. “Cuz I know your friend did.”

Moments later, Jarrone buried his cock so far up Olivia’s ass that he couldn’t hold himself back anymore, and his dick exploded in a fiery rage that shot his seed so deep inside her that she came at the same time, panting despite not even doing most of the work. The two of them collapsed on top of Reese’s confinement, sweaty, exhausted, and content.

* * * * * *

Jarrone left to head back home not long afterwards. But even though she was technically alone with her brother again, she declined to say or do anything. She’d turned the music off, so she could relax in the quiet, and she was on her phone working on what she hoped would be the final cherry on top for the night.

A little before midnight, their parents eventually went to bed, which was conveniently just as Olivia was finishing up on her phone. Hearing that the house was now quiet, she slipped her door open, grabbed her portable speaker and phone, and turned back to the hamper.

Reese was just as alert as ever as he felt Olivia effortlessly lift him up, carrying him downstairs and through the house. He was only set down for a moment as Olivia propped open the door to the garage, before picking the hamper back up and carrying him outside. There was a quiet hum from the air conditioning unit as it spread cool air throughout the rest of the house, but not much else could be heard.

Olivia set him down for good in the corner of the garage, and then went over to where their dad stored his bundle of old or tattered blankets, mostly just kept for emergencies. “So, this is where you’re gonna be spending the night,” Olivia announced, tossing the blankets on the floor beside where Reese was. “I don’t wanna keep you up in my room—for reasons you’re about to find out—so I figured out here would be a good a place as any. Unfortunately the weather is saying it’s gonna be pretty warm tonight, and humid too, but I can’t really control that part so you’re just gonna have to tough it out. At least you won’t have to worry about your clothes getting stained by all the sweating you’re about to do.” She snickered at her cruel joke, and continued on by grabbing her speaker and setting it on top of her hamper, facing down so that all the sound would be pointed to where Reese was hanging.

“I might as well just let you know now, remember when I gave you that water before gagging you a few hours ago? Well, I didn’t want you falling asleep on me tonight and escaping your punishment, so I crushed a couple of dad’s caffeine pills and mixed them in. So you’re gonna be up aaaaaaall night, whether you wanna be or not.” Reese twisted about in a fit of frustration; the one thing keeping him going for the last few hours was the idea that he might be able to fall asleep eventually, but apparently that wouldn’t be an option anymore. “But don’t worry, cuz after I made your best friend fuck the shit out of me, I edited a playlist on my phone for you to listen to and keep you company. Except it’s just one song—well, technically a recording, actually.” She pressed the play button on her phone, and suddenly the sound of a familiar moaning and groaning started playing over Reese’s head. “After Jarrone went to the bathroom during the halftime show, I set my phone up to record our second session, and then after he left to go home I spent some time editing it down on my phone. It starts right after I asked him to fuck my ass, and ends just after he came inside me. And then starts all over again.” Sure enough, Reese listened as the speaker played his friend making the comment about Olivia liking it rough, and then the steady sound of their skin clapping together as he started pounding her.

She squatted down next to the lid, leaning in close to make sure her words were crystal clear to her poor little brother. “I hope you remember every. Single. Detail. Of this night,” she whispered, and stood back up. “Because this is what you deserve.”

And with that, she picked the blankets up and threw them over the speaker to block off the sound waves from traveling in any direction other than her brother’s prison. It also allowed her to turn the sound up higher than normal since she could be sure that nobody would be able to hear it upstairs and across the house. Which is just what she did: holding the volume up button until the speaker was at its max, blasting the noises of her fuck-fest into her brother’s ears, while it was less than half as loud for her. She gave her little setup one last look of satisfaction, and then turned to head back inside without even saying goodnight. She paused just outside of the garage door after it closed again, and was impressed with how little she could hear, knowing that by the time she got back upstairs, she wouldn’t be able to hear anything at all. Her plan had worked. Every single step. So now she could have a relaxing night’s sleep knowing that her brother was taken care of.

A few tears dribbled down the prisoner’s face as the sounds of Olivia having raw, impassioned sex nearly deafened him.

All at the hand of his best friend.

All while sweat began dripping down his half-naked body.

All while a wedgie still stretched tightly against his ass and bit into his skin.

All while he was gagged and tied up with his hands and legs behind his back.

All while his sister’s bra trapped him in a pitch-black space,

in a pitch-black basket,

in the corner of a dark garage,

in the dead of night.

All while Olivia’s pair of salty, acidic socks burned his taste buds and left him parched.

All while the panty-stained scent of his sister’s pussy flowed freely in and out of his nose.

All while a flurry of chemicals whizzed about his brain to ensure he was awake enough for every moment.

All for the next 8 hours.

Olivia was right. He would remember tonight; every second, every sound, and every smell. Every taste and tremor. Every feeling, both physical and emotional. Fear, desperation, anger, anxiety, sadness, betrayal, hopelessness, but most of all…

Guilt. Because he had brought this upon himself. Inside his head, his voice echoed Olivia’s words. He couldn’t escape them.

This is what you deserve.

This is what you deserve.

This is what you deserve.

You are going to remember every single aspect of tonight.

And that’s exactly what you deserve.