HTTYB - Day 19, Part 1 (Patreon)

it's back woooooooo.

sorry it took a few extra days. been working on the christmas exclusive, but also i have a plan (which hopefully will succeed!) to release a full-length chapter (or more) of a story every day for a week leading up to christmas. idk why but i already committed to it lol. will still be posting things this week too though.

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Thursday, June 3

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The caffeine in Reese’s system petered out eventually, and his exhausted body finally succumbed to the sensory overload a little after 5 in the morning. The boy was able to get in a bit less than 2 hours of sleep by the time Olivia returned to free him. She’d still found the time to go on her early morning jog during the last hour of Reese’s punishment, but made sure to get back before their parents woke up so she could retrieve her brother.

The sound of his best friend fucking his sister became so ingrained into Reese’s brain after that many hours, that he was actually woken up by the sudden silence of the speaker getting turned off. His dazed brain didn’t even register why he’d woken up and was struggling to piece back together where exactly he was, until the blanket covering his hamper-cage was pulled away and he realized it was morning now, and Olivia had come back for him.

She picked the wicker basket up and carried it to her room, setting it down in the middle of her floor before closing the door. When she pulled open the top, hoisting Reese’s body up with it (since his wedgie was still attached to a hook on the underside of the lid), she felt a quick pang of sympathy. He wasn’t technically a skinny or slender boy, but his size made him still appear small and weak, especially in his half-naked state. Her bra cups that were secured around his head only further dehumanized him, and the term “prisoner of war” flashed in her mind at seeing her little brother in such a helpless state. A quick glance over to her broken $1,500 laptop eased her mind a bit; he can handle a single night of torment in return for what he did, she told herself, but unhooked him anyways and set him on the floor in front of her.

Olivia brought a staple puller to unfasten the edges of her bra from each other, since she wanted to be careful and ensure that the ‘booby helmet’ (as she now called it) would still work if she needed to use it in the future. She hoped she wouldn’t need to, but it was best to be safe nonetheless. “I’ve gotta pee really badly,” she told him as the staples dropped to the floor, a bit antsy from how long she’d been holding it in. She should’ve gone to pee before getting her brother

The panties that had been stuffed around his head fell to the floor as the cups came undone and fell alongside them. Reese squinted from the sudden burst of light that signaled his first time being able to see again in nearly 10 hours. But once his pupils had adjusted, he looked up to Olivia with wide, hopeful eyes, filled with joy over finally being done with his punishment. Next came the duct tape around his wrists and ankles, which she was cautious to be slow with so their removal wouldn’t hurt him too much.

Once his arms and legs were free, he got on his feet and immediately gave his sister a hug, grateful for his freedom after the torturous night. She continued releasing him, being even more deliberate with untaping his mouth since she knew his lips would be more sensitive.

“Alright, I really can’t really hold it in anymore,” Olivia winced, halfway through with uncovering his mouth. “You can finish taking it off,” she added, darting out the door towards the bathroom.

He hadn’t liked Olivia going slowly even though he knew she was trying not to hurt him, so he grabbed the end of the duct tape that was already off and ripped it the rest of the way. His instinctive reaction was to sigh with relief, but since his mouth was still jam-packed with Olivia’s sock, it only came out through his nose, strained and wheezy. Despite how salty and dirty the sock had been last night, it was completely flavorless now, thoroughly soaked with Reese’s saliva after so many hours of marinating in his mouth. Getting out her sock was the last of Olivia’s punishments he had yet to rectify (other than putting some clothes back on), so he reached a couple fingers up and pinched onto some fabric. Reese didn’t even need to open his mouth to grab the sock since it had made it physically impossible for his jaw to close. But as he tried pulling the sock back out, it seemed that it had gotten jammed so tightly into his mouth, he wasn’t even able to dislodge it. He tried grabbing other areas and pulling on them too, but he didn’t know where the end of the tubing was so he only ever pulled at the sides.

By the time Olivia was done using the bathroom, he was yanking so hard to try and free himself that he had to brace his legs to keep from jerking himself forward. His sister came back into her room just as he tugged at the sock so hard that he lost his balance and stumbled forward into her legs, colliding with one of her thighs.

She paused and looked down at him, quickly seeing what the problem was, and giggled at the fact that taking her sock out had even been an issue for him at all. “You need some help there bud?” she asked, a bit mockingly, but he ignored her tone and nodded eagerly, his desperate puppy dog eyes matching the vibe he gave off of a stuck, helpless puppy who needed their master to get free. She gently but firmly held onto his head to keep him still with one hand, and used the other to dig her thumb behind his top teeth, right up against the roof of his mouth, and wiggled out a little bit of the top of her sock, where the foot was supposed to enter. Once a sliver of it was free, she was able to pinch it between her thumb and forefinger and pull a bit more out. She pulled it upwards, and Reese suddenly found himself lifted several inches off his feet. “Damn, that really is stuck,” she murmured; he could only look at her with optimism in his eyes, hoping that she hadn’t packed the sock in too much.

In a big, strong motion, she yanked upwards with way more strength than he’d been able to muster, and dislodged even more of it, although her brother’s body was treated a bit like a rag doll in the process. But that forceful heave had been sufficient to get enough of the sock out that the weight of Reese’s body was now able to do the work, and he found himself slowly slipping down as the soggy sock slowly snaked out of his mouth. Olivia gave the sock a gentle shake to speed it up, and watched as the former element of her workout routines unsheathed itself from her little brother’s mouth, until he fell back to the floor with the soaked black gym sock hanging overhead.

Immediately after becoming free, he fell to his knees at Olivia’s feet and hugged her calf, then bent down and serenaded the top of her shoe with a flurry of kisses, ignoring as the spit from her sock dripped onto his bare back from above. “Thank you thank you thank you,” he croaked in between kisses, as she raised an eyebrow at how subservient the overnight debacle had suddenly made him. “I’m so sorry for breaking your laptop,” he said, “I’m sorry I didn’t trust you Olivia, it’ll never happen again.” And she believed him; clearly his discipline had done its job.

“Okay, okay, don’t be so weird about it though,” she said, nudging the bottom of her leg forward to indicate he could back away and stand back up. “So I know that normally you’d be getting ready for school right about now, but I was doing some thinking while I was out on my jog. I’m pretty sure I’ve mentioned it a couple times, but I was planning on heading to the beach house with Jordan and Elle later today.” Their family co-owned a place on the coast, which Olivia would visit with her friends every couple months, and even more in the summer. The place was a lot more snug and quaint than their regular house, but it was still a nice kind of home away from home, which was especially nice whenever she wanted to get away from her family for a bit.

“But I realized there’s a problem,” she continued. “Since you still haven’t passed your last class—and tomorrow’s literally the last day of school—I’m worried that if I left you alone, you’d be tempted to slack off like you did for the rest of this year, and then you wouldn’t finish the make-up work on time. Which would mean I would’ve wasted aaaaaaall that time over the last few weeks helping you out for nothing. So because of that, I basically have to see your shit through to the end myself, just to ensure I didn’t waste my time. I mean, I wanna help you graduate too, cuz I love you and all, but I didn’t expect that I’d invest as much time as I did.

“As I’m sure you can imagine though, I don’t wanna interrupt my vacation while you lag around here and do whatever. Which means the only fair option would be that you come along with us, and put yourself to good use. Like I don’t really have that many ideas yet; maybe you can be our personal chef and make us dinner, or when we head down to the beach you can run back to the house to get something if we forgot it. I don’t know. I’m sure Jordan and Elle can help think up some ideas too, and we’ll definitely have to think up a few more fun games to play with you.” She smirked at that comment; it had been fun trying to squeeze her brother into her clothes a few times recently, but she still had a couple more she wanted to try out.

“But basically, yeah. You’ve already been doing so much for me anyways these past few weeks in return for my help, so this’ll be your final day on the job. My last day of working for you, your last day of working for me.” She paused, then added, “Although since it’s your last day, we’re probably gonna end up putting you to work a lot.”

Reese didn’t even need to hesitate and think about it; he just nodded as soon as she was done talking, his eyes unwavering. “OK, that sounds fair to me,” he said earnestly. There was a moment of silence between them; Olivia was a bit surprised with how quick his response had come. She assumed he’d agree to it since he’d done almost everything he asked since she started helping him, but she expected at least a little bit of ambivalence. Even a hint of frustration. But there was none of that.

She arched an eyebrow, “You don’t seem as reluctant as I figured you would. I really must’ve done a number on you last night. Kinda feel bad now actually.”

He glanced down at the floor, remembering yesterday’s events. “I mean it’s not that I’d wanna tag along with you guys otherwise, it’s just that I don’t think it’s that much of you to ask considering how I’ve been. Like last night was… pretty uncomfortable. But whenever you ask me to do stuff for you they just feel like chores. Like a little annoying maybe but it’s not like they hurt. So, you know, considering what I did, another day of “chores” or whatever doesn’t seem unfair.” He looked back up at her. “Honestly, I just felt really really, like really bad about what I did. You had every right to be mad at me. So yeah, even though I don’t necessarily love when you stick me in your clothes, or whenever you tease me a little, or whatever else—I just feel like it’d be kinda stuck-up of me to complain about it after what I did. And the fact that I literally wouldn’t have graduated without you.” He imagined how it’d feel to not be able to walk across the stage while the rest of his friends and classmates had their moment. “That’d really be embarrassing.”

“Well, won’t graduate without me. You haven’t made it yet,” she reminded him, to which he nodded again. She crossed her arms as a couple ideas popped into her head. “So you really aren’t gonna have an issue doing what I ask?” He shook his head, already knowing she was about to test him. “So… if I wanted you to kiss my ass…?” He scurried behind his sister and leaned forward, planting a firm one smack dab on her sweaty yoga shorts, right in the middle of her bubbly left butt cheek.

“Daaaaamn, even though I’ve been sweating?” she reacted as he came back around in front to see if his sister was satisfied. Wanting to test Reese a second time, Olivia sat on her legs and lifted up her arm, showing off her glistening armpit. “What if I told you to lick my armpit? Like a big one so you’d get a bunch of sweat.” His expression contorted into one of disgust, but he did as she asked and walked up to her, raising up his head and sticking out his tongue. He set it down a few inches below her pit and then slid it all the way up, across the inward curve and everything. There was an overabundance of her salty perspirant, but he ignored the taste (and the strong smell) and finished going through with it. Olivia raised her eyebrows as she watched her brother, significantly more impressed with him now. But she wanted to test him in an area she knew made him a bit uncomfortable.

“Hmmm… You mentioned the difference between tasks that are annoying and stuff that’s like actually uncomfortable, so I kinda wanna see if you’d do something uncomfortable too.” Reese’s heart started racing with anxiety. Shit, should I not have mentioned that? he wondered. “I know how much you get easily weirded out by my body, so… what if I told you to stick your nose into my cleavage and smell my boob sweat til I asked you to stop?”

He gave his older sister a look of disgust, which just caused her to laugh, but slowly stepped forward as she leaned over. Her sports bra being as tight as it was held kept her boobs from hanging too low, but they were still the biggest pair of tits he’d ever seen in his life. Even a smaller portion of her cleavage was an incredible amount compared to most other girls. He tried to not think about those things though, closing his eyes and pressing his head into the top of her boobs. The acrid, sweaty smell from her armpits returned, but with an even grosser odor because of all the moisture that had festered between her gigantic boobs while she worked out. Olivia only made him keep his head there for a few seconds though before nudging him away again; she just wanted to see if he’d go through with it.

“Alright, well you did a good job with all of those,” she commended him as she pried off her shoes, and then reached down to take off her socks. Oh… fuck. “But now…” She smirked, watching the color drain from his face as he saw her take off her shoes and socks. “After I just got back from my workout, with all my sweat and smelliness, would you really be willing to lick my feet?”

Reese was shaking as he knelt down onto the ground, but Olivia burst out into laughter and shook her head. “Ugh, I was just kidding, I’m not gonna make you do that. Makes me nauseous just thinking about it. But good to know you’d still do it, just like you said.” She rubbed his hair affectionately as he stood back up, sighing with relief.

“I don’t wanna stand around all sweaty any longer than I have to, so I’m gonna go take a shower, but I want you to join me to help me wash off. And once I’m all clean, then you can worship my feet.”