HTTYB - Day 19, Part 3 (Patreon)

After they dried themselves off, Olivia led Reese back to her room. She never actually told him to follow her, but he had a sense that it was what she wanted him to do anyways. After all, he was pretty much gonna be hanging with her for the rest of the day. But before they entered, Reese paused, looking down at himself. He was still just wearing a pair of underwear, but even though he’d mostly dried himself off from the shower, his boxers were still damp and uncomfortable from the water he couldn’t dry out of them. “Hey, can I go change real quick? So I’m not walking around in this all day,” he laughed awkwardly. “I’ll come back as soon as I’m dressed.”

Olivia turned around and glanced down at his privates, chuckling at the fact that he was still wearing them. “Yeah,” she nodded, “go ahead.”

He smiled and thanked her before briskly continuing past her room to head to his own. After he took off his soggy underwear, he sighed with relief; the water had made his shorts cling to his skin, feeling tighter that he normally liked. Hopefully it’d be a long time before he’d have to wear something like that in the shower again. Although if Olivia ever made him wash up with her again, he wouldn’t hesitate to put the boxers back on. Even wearing a full set of clothes was preferable to him than the idea of having to shower naked with his own sister.

After putting on a some new underwear, a t-shirt, and a much more comfortable and breezy pair of basketball shorts, he headed over to Olivia’s room and slipped inside. But the first thing he saw was Olivia with her back turned to the door, a new pair of panties having replaced the bikini bottom she’d been wearing, and her bare torso just as she had undone the bikini top. Even though her back was turned to him, he freaked out after realizing she was topless, and quickly closed his eyes and slid back outside. “Shit, sorry. I figured you’d be done changing by now,” he said, standing awkwardly outside her door so he could wait for her to finish.

Reese didn’t hear her reply, but he could hear her footsteps growing louder as she walked over to the door. Then the soft swoosh of wind against his face as she pulled the door wide open, and a half-groan half-sigh as she placed her hand atop his head and willed it in her direction, prompting him forward. He was too short for her hands to reach anything else without bending over. Reese didn’t try to fight her as she guided him into her room, but he kept his eyes closed at least since he knew she still didn’t have a top on. He patiently waited for about half a minute, expecting her to finish dressing, although he didn’t hear her make any noise. It was completely silent.

“Um… so, can I open my eyes now?” he asked.

Olivia shrugged, “I never said you had to close them.”

He paused, absorbing what she’d said; his guess was that she still didn’t have a top on, especially since he hadn’t heard her even move. “OK, well I don’t wanna see you without a shirt on,” he insisted. “It’s fucking crazy to me that I even have to say that out loud, as if that makes me like, a prude or something.”

“I mean considering we just took a shower together,” she chuckled, “I guess ‘prude’ wouldn’t be very accurate, you’re right. But you’re definitely not progressive or anything. Which I can’t really blame you for entirely, you’re still young and haven’t really experienced that many other cultures, on top of how conservative America is already.” If his eyes weren’t closed, he wouldn’t rolled them. Just cuz I don’t wanna see my own sister’s tits doesn’t mean I’m not a progressive guy. “Studying abroad that one semester was honestly so eye-opening to other cultures. Like a lot of places in Europe just aren’t as fussy about nudity or anything, you see it on TV during the day even. So many more nude beaches and stuff. And I’m not even actually naked, like I still put my panties on so you won’t have to see my genitals. But boobs aren’t inherently sexual or anything, my nipples look pretty much the same as everyone else’s. So if someone wants to sexualize that part of my body, I shouldn’t be shamed for it.

“I don’t expect to change the culture where we live or anything,” she continued, “at least not anytime soon. But I’m in my own home. In my room. If I wanna be comfortable and not wear any clothes, this is literally the best place in the world to do something like that.”

Reese took a deep breath, thinking over his words slowly. “You’re right. You should be able to be comfortable in your room whenever you want. I may not have boobs, but I still have… you know, like… a dick. And it’s not comfortable wearing some clothes with that either and having it get squished and stuff, so it’s nice to just kinda hang free in my room sometimes or when nobody’s home. BUT, that’s not the same. Because I only do that stuff when I’m alone, and you’re not alone, cuz I’m here, I’m literally your brother.”

She groaned again, shifting her weight as she crossed her arms, still looking down at him even though his eyes remained closed and he was staring ahead at her hips. “You keep saying that, like mentioning how we’re siblings and stuff. But like… I’m not trying to get you to be comfortable with me being topless because I’m your sister. I think you should try to be more comfortable with that stuff in general, and I just happen to be the one trying to help you.”

“OK, well…” he paused for a moment. “I guess I don’t know how to respond to that.”

“Good!” she exclaimed, a glimmer of hope on her face.

“But I still haven’t changed my mind.”

She put her head in her hands, beginning to feel impatient with her brother. “Oh my God,” she muttered quietly to herself, going over to sit on the edge of her bed. “You know what makes it even more confusing, is like how close we’ve been over the past few weeks. I mean, on more than one occasion your head’s been literally stuck in between my boobs. And like even today you helped washed them and literally stuck your arm into my cleavage. But even with all that, you’re still acting like this?”

“Yeah, but those were never things that I wanted to do,” Reese replied. “Like I know that I complained about that stuff a few times before, I definitely never went into any of that enthusiastically or anything. Like at best I guess I just became kinda fine with it?”

“And that’s OK!” Olivia insisted. “I mean honestly if you were too enthusiastic then yeah, it’d be weird. Like if you busted in my room and were like ‘oh my gosh Olivia I wanna see your boobs!’ But just being fine with it is literally all that I’m asking you to do. I just wanna be comfortable in my own room, that’s all this is, and I’m just saying you should be fine with that. It’s only weird if you make it weird, basically.”

Reese could tell he wouldn’t convince her of his point of view. But he also wasn’t being swayed to her side either. So he just stood there awkwardly, biting his lip while keeping his eyes closed, wondering if he should just turn to leave.

“Seriously though, what’s so scary to you about a nipple,” she laughed, getting off her bed to stand on her knees and walk up behind him. He froze, suddenly feeling her boobs pressing up against the back of his head. She lifted them up and then scooted forward so she was just inches behind him, and then dropped her tits back down so they landed on his head and bounced down to the sides. “Oooooh, so scary,” she sarcastically teased, cupping them in her hands and bouncing them against the side of her brother’s head. Reese was more still than he’d ever been before, feeling the gentle warmth of her body against his back, while getting his head knocked around by boobs that felt unfathomably huge. But then she took it a step further, grabbing his shoulders as she stood up and lifting his body up before bopping the underside of her tits with the top of his head. Reese was wincing but didn’t move a muscle as his sister played around with him like he was just a toy. “Bing bong bing bong,” she laughed, alternately bouncing his head against the bottom of both her boobs, letting them fly up momentarily before plopping back down on his head.

“Jeez, you really are no fun,” she sighed, setting him back down on the ground. “I’ve had boobs ever since I became a teenager, and I still think they’re fun to play with.” She looked down at her breasts and poked them a few times, and then wobbled them around with admiration. “I get to play with these huge-ass titties any time I want,” she laughed, “but you can’t, cuz you’re a guy and you don’t have any. And yet you don’t care, you don’t even wanna try.”

She walked around to the front of him and sat criss cross before him so they were eye level with each other (even though his eyes were still closed, of course). But then she reached forward, grabbed both of his arms…

And placed his hands directly on her boobs.

As soon as he felt his sister’s nipples against his palms, he tried jerking his arms away, but Olivia had obviously expected his reaction and firmly held onto his wrists to make sure he wouldn’t go anywhere. “See? They’re just nipples. Just like yours.” He was squirming from discomfort, unable to believe that his sister had forced him to practically grope her. But even beyond that though, his hands felt so dwarfed compared to the rest of Olivia’s boobs. His fingers were splayed out and his hand fully flattened, yet they were still only touching the front. Too massive for his hand to reach the sides or the tops or bottoms. She wiggled his wrists around, forcing Reese’s hands to rub even more of his sister’s tits. Making him squeeze her boobs together, lightly slapping them so he could feel their jiggling response. “Like how do you honestly not wanna play with these, it’d just be so fun if you lightened up.”

She let go of his arms, and wasn’t surprised to see him immediately lurch them back to his sides, holding his clenched fists behind him. “Well whatever, I’m not gonna waste all morning trying to make you not to sensitive about shit.” He sighed with relief, glad that they could move on. “But you still have to do my nails. And I’m not gonna cater to you. So how do you wanna do this.”

Reese pursed his lips, not wanting to back away from his duties and trying to think of a solution. “I mean, I could still do your nails. I just wouldn’t look up.” She raised an eyebrow. “Like you can lay in your bed or sit on the edge or wherever you wanna be, and I’ll just make sure to only look at your feet.”

“You have to do my fingernails too,” she reminded him.

He shrugged, “I’ll probably still be able to do them too.”

Olivia sighed, standing up and fetching her nail kit. “Alright, as long as you get them done I guess.” Knowing the general layout of his sister’s rooms, he reached out with his arms and blindly walked into the general direction of where her bed was. Once he felt himself reach it, he climbed onto it and sat down, his head faced directly downwards, and then finally opened his eyes. Sure enough, all he could see—including in his peripheral vision—was Olivia’s bed. She scoffed at how awkward he looked, partially hunched over to keep from looking anywhere else, and came back over to her bed to sit down near her pillows. Reese had seated himself around the middle of the bed, so she set the nail kit off to the side of where she was looking before placing her giant bare foot against the top of his head, using it as leverage to push his body several inches back to a more fitting position. Once she was content with where he was, she bent her leg and set the foot directly in his field of view with the sole facing down. Then she swung her other leg over, which was straightened, and rested her other foot on his shoulder, fondly rubbing the back of his neck with her heel. Her ankle was barely able to fit where she’d perched it, but it worked.

Over the next 20 or so minutes, Reese worked away at both of Olivia’s feet; clipping his sister’s toenails, filing them, and then painting them a bright white to cover up the fading red underneath. And all the while, she just lounged around with nothing but her underwear on. The whole time, Reese never broke eye contact with her feet, since he knew that looking up would have to mean seeing his sister topless. It might all end up being a waste of time, he thought as he dipped the brush back into the nail polish before continuing to delicately and carefully paint her toes. Maybe she’s gonna be topless the whole time at the beach house. I don’t think I’d be able to spend the entire day with my eyes closed. But at least for now, I’m not gonna let her win. I love her, obviously, but telling me that I should try playing with her boobs because of how fun they are is probably one of the most insane things I think I’ve ever heard her say.

“I think I’m done,” he announced, screwing the brush back into the jar of polish. He felt the weight of her foot lifted off his back as she set it side by side with the one he’d just finished painting, so they could both check his work together.

She wiggled her toes with a smile, admiring how cute the white nail polish looked against her tan skin. “Yep, looks great to me, thanks! Now for my hands.” He assumed he’d probably have to scoot closer to Olivia, and that she’d just rest her fingers on her leg or something. But apparently she’d already thought of how she wanted to do things. “C’mere,” she cooed, reaching forward and grabbing his shoulders again. He squeezed his eyes shut again, just in case, as he felt her bring his little body forward and spin him around. She opened up her legs and set him down so he was sitting right up against her, his back against her tummy and her thighs bordering his own. “Legs out,” she instructed, so he straightened them in front of him, and then finished pulling him all the way back until his head got squeezed between her boobs again. Initially, because of how small the 3-foot boy’s head was, his head sunk so deeply in between her breasts that the front of her boobs started to mold around his face since they were larger than his head. It was one thing for someone to rest their head against a pair of boobs, or even to squish their head in between, but Reese was so small and his sister was so large that she was almost able to completely submerge her brother’s head between the gigantic pair of tits. “Oh my God…” she snickered, and grabbed her phone to take a selfie. Since his eyes were still closed, he wasn’t even aware that she’d taken a picture of him snuggled within her. Maybe she’d send it to him later as a joke; it’d be funny if after all the freaking out he’d done over seeing her bare boobs, he ended up seeing them anyways from a random Snapchat. I could text him something like ‘Check out this pic of you I took the other day’ so he thinks it’s just a random photo, she imagined, and then it will be a picture of him, but one where he accidentally gets shown my boobs too. And maybe after he finally sees them he’ll stop freaking out so much since it will have already happened.

“Well, this obviously wouldn’t be a really great way for you to work,” Olivia said, allowing him to pull his head back out and open his eyes. But she still wanted to keep him sitting against her like they’d done yesterday in the bath, so she sat criss cross over his legs, ensuring he wouldn’t be able to go anywhere. “Hold your arm out in front of you, so it’s parallel with your body,” she told him, and then once his arm was raised in front of his chest she set her hand down on it. Her hand was so large she was able to cover his entire forearm and most of his hand with it, so she relaxed her muscles and allowed him to support its weight with his arm, so she could have her fingernails close to his face without having to tire her own arm out.

As he grabbed the clippers and got ready to trim his sister’s nails, she grabbed her laptop from her bedside table and set it open in front of them so she could watch Selling Sunset while her brother worked. He sat up straight so as not to feel her boobs against his head, and was glad that she didn’t care enough to make him use them as a headrest or any other excuse to make Reese get overly acquainted with his sister’s humongous, monstrously huge set of tits. Although there were a few times when she wanted to turn the volume up or rewind a scene, which gave her a chance to tease him. She’d have to lean over him to reach the laptop, and every time she’d squish her boobs around his head in the process.

Before long, he’d finished painting her nails too, so she held them up in front of her face to inspect them. “Great job,” she congratulated him, “these look great too!” She ruffled his head playfully and got up from her bed to head over to her dresser. Glancing back at the bed to see that he’d closed his eyes again, she rolled her eyes as she grabbed a loose-fitting t-shirt from one of the drawers. “I’m putting a shirt on, ya weirdo,” she told him, walking back over to the bed after getting half-dressed. He tensed up as she grabbed his arm and pressed it against her boobs again, but sure enough he could actually feel the cotton shirt that covered them now, so he peeked his eyes open and sighed with relief to see that she was at least somewhat more modest.

“I’ll figure out how to fix your paranoia later,” she explained, “but for now I didn’t wanna deal with your bitching.” She dropped his arms and picked him up to turn him around again so he was facing her headboard, and then sat back down and leaned against her pillows. “Cuz there’s still something I told you this morning you were gonna have to do,” she smirked, reaching out with her foot and placing her sole against his chest before sliding him further down the bed. “Remember?” Reese sighed reluctantly, recalling from earlier when he’d been freshly rescued from her hamper prison, and told her he wouldn’t complain about whatever else she wanted him to do for the rest of the day. He cringed as he recalled when she asked him to lick her feet, and how he’d almost gone through with it despite how sweaty and filthy they were. At least she had let him clean them off in the shower before making him taste them, although he still wasn’t very enthusiastic about the whole thing.

“Yeah, I remember…” he groaned, grabbing the ankle of her left foot with both his hands and raising it up in front of his face. It was easily twice as tall as his head was, a daunting task to think about as he took in the sight of the tanned, 2-foot-tall sole before him, her toes wiggling in anticipation of his tongue. He sighed one last time, and then leaned in with his tongue out and slowly licked up the soft surface of her arch. He wasn’t sure how exactly she wanted him to go about the task, so he moved on to another area after a few licks, just in case she wanted to feel some variety out of his tongue service.

“There you go, you’re getting the hang of it,” she giggled, laying back and watching him. Although she couldn’t even see his face since her foot was covering it; she just saw his chest vaguely bobbing up and down below her heel, in line with the tongue strokes that gradually covered more and more of her foot. “Let me know if you have any questions!” He rolled his eyes but continued licking away, as Olivia pulled out her phone and opened up FaceTime so she could call Jordan.

“What’s up?” her friend asked, causing Olivia to grin in response. “Just finished packing so I was about to head over in a minute.”

“Oh, nothing much,” Reese’s sister replied, shrugging with fake boredom, and then switched to the outer camera so she could show her friend what her brother was up to. “Just hanging out with Reese!” She quickly whipped her foot out of his hands, catching him off guard with his tongue sticking out, saliva about to drip down from it.

“Holy shit, are you serious?!” Jordan exclaimed, laughing hysterically as she closely inspected her screen. Reese blushed, grabbing his sister’s ankles again and yanking it back down in front of him as if to hide himself from the embarrassment. “Was he just doing what I think he was doing?”

Olivia chuckled as she switched back to the selfie camera and nodded, glad to feel her brother’s tongue get back to work on giving her foot a tongue bath. “Yeah, so you better get over here quick if you don’t wanna miss out,” she quietly told her friend, although Reese was still able to overhear and got anxious as he imagined how much his childhood crush might mock him once Olivia inevitably ordered him to lick her friend’s feet just like he was doing with hers. But then he reminded himself that it still wasn’t even noon; they hadn’t even left the house to head for the beach yet. And considering that he’d agreed to be his sister’s servant for the rest of the day (which in turn meant also being a servant for whichever friends she invited with them), he knew that licking his sister’s foot as a show of obedience would just be the tip of the iceberg for all the weird, uncomfortable, or downright humiliating things he was about to do for them throughout the rest of the very long day.