HTTYB - Day 10, Part 2 (Patreon)

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Tuesday, May 25 (cont.)

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Reese was dressed in skinny jeans with white sneakers and a white, long-sleeve shirt that had the sleeves rolled up, sitting on the armrest of the sofa, as he watched his sister come down the stairs after getting ready. She was wearing the dress she had picked up from the mall right before checkout; it was a kind of teal and gold skater dress, that ended around the middle of her thighs and had a neckline that was narrow but deep, coming down to her midriff. Obviously her breasts were prominently displayed because of this, her boobs tightly pressed together from how slimming the gown was trying to be. And on her feet were a pair of black, open-toed stilettos with laces on the front, and such a high heel that Reese wondered how she was able to walk down the carpeted stairs without falling over.

“Oh by the way, I forgot to email you the homework files earlier, so I just sent them just now,” she casually mentioned as she reached the bottom of the stairs, her laid back attitude contrasting how stunningly she was dressed. Her hair was bouncy and wavy too, and she had simple hoop earrings in as well. He nodded in reply as he hopped off the armrest and came to join her in the foyer. “What, not even a thanks?” she joked, having not seen his slight acknowledgement of appreciation.

He looked up to her with an open mouth to argue, “I... sorry, yeah, thank you,” he just said instead. I guess a head nod isn’t much of a ‘thanks,’ is it? He then went to hug her leg as he usually did, wrapping his arms around her thick, golden thighs like he was hugging a tree. Her skin was silky smooth from when he shaved her earlier, plus she had put on some lotion for some extra shine. “How tall are those heels?” he asked, looking to her feet.

“Uh… 4 inches, I think?” Fuck, she’s almost 7 feet tall now. “Actually, you look…” she began to say, before lifting the hem of her dress up a little bit. Reese could see her panties, but they suddenly came closer as she swung her other leg around and stationed it behind his back, essentially trapping him between her sturdy legs. The bottom of her crotch, covered only by her dark blue underwear, was only half an inch over his head. If her legs were any further apart, it’d be touching her brother’s head, but if her legs were any closer, he wouldn’t be able to fit between them. Which he was; he was just small enough to stand up straight right between her powerful calves and meaty thighs. “You fit perfectly!” she laughed, and for a brief moment, Reese was scared of what he would see if he looked up. He couldn’t face his sister to ask ‘what the fuck,’ only stare straight ahead while the warmth of her body surrounded him.

But then she was done, and continued walking forward, letting the back of her dress flap against the back of his head as she passed by overhead. “Anyways, you ready to go?” she asked, slipping her phone into her bra as she grabbed a glass of water from the kitchen and glanced between him and the front door with an arched eyebrow.

Just forget it, he told himself. “Yeah,” he confirmed, and Olivia nodded and headed out the front door with her brother in tow. “I guess we’re taking your car, right?” he asked, and she nodded. He didn’t expect them to take his car, of course, since it was her party. But at least their dad’s SUV would’ve had his booster seat. It looked like he’d have no such luck tonight though, which probably meant another humiliating session to keep him “secure” without one.

“Yeah, I don’t know when we’ll get back tonight,” she told him. She opened up the front door but stood back to let him get in first. “You remember what we did the other day?” He sighed, and reluctantly climbed into the car, sitting down with his head held back against the seat, waiting for his sister to sit on his undersized lap. She giggled, “Close, but not quite. I mean yeah, that’s what we did the other day, so I guess that’s actually correct, I just meant…” She bent over and grabbed his sides, before spinning him around 180 degrees and tilting him over slightly.

“Wait, wha— Olivia, what are you doing?” he asked abruptly, confused why their method needed changing so much. His body was in the same position, but flipped reverse, so instead of his legs sitting on the bottom of seat and his torso resting against the back, his legs were propped up against the back of the seat, while his back was laying on the cushion with his head facing up.

“It didn’t feel comfortable to have your head against my back,” she explained, standing up straight again and biting her lip to quickly assess how he looked and if he needed any final adjustments. “So we’re gonna try turning you around this time.” Satisfied with how he looked from where she stood, she took her heels off, throwing them into the passenger seat, and slowly stuck her leg into the car. It had been nerve wracking the last time to watch his sister get into the car with him already sitting down and realize she was about to sit on him, but now that he was practically laying down? Her smooth, bare thigh passed by over his head, and from his vantage point below her, it was impossible not to see her huge, bubbly butt underneath her dress as her body quickly approached his. But before she could finish seating herself on her brother, she paused: “Let me know it becomes too hard to breathe,” she said, and then unceremoniously dropped her massive ass onto his stomach, knocking the wind out of him. The front of her dress that covered the top of her legs was cutting off his ability to see all of his sister, but he could still see her as she gazed down at her little head between her legs, curiously wondering if he would recover his breath. He had plenty of access to air, but the sudden weight of his Amazonian sister had surprised him, even with the prior notice she had given. His lungs seemed to be restarting themselves as they only allowed him to gasp for oxygen every couple seconds, but she just watched patiently as his face reddened from the air cutoff. He couldn’t even get mad at her, because his body’s first priority was to make sure it get breathe before it could talk, and just being able to breathe again in itself was difficult enough when he was unable to escape the several hundred pounds of thick, weighty sister perched on his chest.

But eventually his face began to pale again, and the gasps lasted longer and came less frequently, as his body adjusted and he started to acclimate to his new position beneath her. “Oh good,” she sighed with relief, “I was beginning to worry you wouldn’t be able to breathe under me.” She laughed at the idea, but then went about lifting her bum a little so she could readjust her brother’s body so it would be more comfortable—ironically, completely ignoring any of his comfort in the process without even realizing it. Then she turned on the car and grabbed her phone out of her bra to plug in the aux cord and pick a playlist, then backed out of the driveway. But just as she pulled out onto the street, she glanced down to her brother. With his head trapped between her legs, he had nowhere else to look but up at her, and the sight of his head between her legs, constantly watching him, wasn’t one she wanted to enjoy for the drive. “Uhhh, that’s kinda unnerving me,” she awkwardly laughed with a grimace on her face, and pulled her dress down a little bit further so it covered up the rest of his face. Wiith a satisfied smile, she shifted to drive, and the two siblings began their journey towards the party.