Adam and Jon left shortly thereafter, so Olivia and Elle returned to where Reese was laying. He had fallen asleep, and Olivia was about to tap his ankle to wake him up, but a better idea took ahold of her imagination and she looked at Elle with a grin. “Hey, I wanna pull a prank on Reese,” she told her friend, quietly kneeling down onto the sand next to her brother. “He had a loooong night last night; I don’t even think he went to bed. So I don’t really blame him for trying to catch a nap.” She figured he probably fell asleep in her suitcase too during the drive to the beach, but considering the sensory overload she’d subjected him to last night inside her hamper, the single hour of shut-eye he got in the car only took a small bite out of his exhaustion. “But having to sleep on the ground probably isn’t very comfortable,” Olivia added, and quickly explained her plan to Elle with a twinkle in her eye.

Getting on her hands and knees, she scooped several large handfuls of sand out of the ground, making a pit for her boobs so she could lie on her stomach more comfortably. Once she laid down, she stuck her legs straight out behind her, and Jordan helped pack some surrounding sand both in between her friend’s legs and on either side of them. Once Olivia felt that it was good enough, she indicated for Elle to bring Reese over. “Bring him over here, but slowly. So he doesn’t wake up. I mean he’s not a light sleeper so you should be good, just be careful.” Elle still wasn’t sure that she liked being a pawn in Olivia’s ploys to humiliate her brother, but she’d already stuck her sweat-laden feet on his face back at the Smiths’ house; if she could inflict that kind of olfactory torture on someone, then what Olivia had in mind next would be a cakewalk.

Kneeling down at his side, Elle gradually worked her hands underneath Reese’s neck and thighs and slowly lifted him up. With a sort of crouch-walk, she carried him to where Olivia was laying, and laid his body down on top of Olivia’s generously-sized legs. And then as a final adjustment, she positioned his head so that it was right on top of Olivia’s butt, allowing his sister’s ass to act as a sort of pillow as he slept. Having him sleep on her legs was a narrow ordeal, but her butt was so huge—especially compared to Reese—that his head just wouldn’t have been able to lay properly on Olivia’s rear if the rest of his body had been on the ground instead. On her legs though, the difference between her thighs’ and her butt’s heights was just enough to simulate the experience of a real mattress and pillow.

“Take a picture, take a picture,” Olivia giggled, biting her lip as she tried to remain as still as possible. She posed with several different expression’s for the camera—a natural one of her looking back at him and laughing, one where she was pretending to sleep too, and a third where she was reacting to him with disgust and anger. 

“Mmmm…” Reese moaned softly amidst his slumber, and then readjusted himself so his head was more comfortable on top of Olivia’s right ass cheek. Now both the girls reacted with stifled giggles, and Elle didn’t even need Olivia to tell her to switch to video so she could record the shrunken boy’s sleepy antics. With what sounded like a discontented sigh, Reese turned his body over (almost falling off Olivia’s legs, but not quite, thanks to how much skinner he was compared to them), and laid his head to rest on his sister’s other cheek. But this time he tried to cuddle closer to his pillow, and via a sequence of movements that lasted a couple minutes, he ended up wrapping his left arm underneath the bottom of her butt, and snaked his right arm between her cheeks to rest on the top, effectively hugging his face against his sister’s ass cheek as if it really was a pillow. Now the girls really started laughing, watching Reese cuddle with his nap-time pillow in blissful ignorance to what it really was. It was easily the closest his head had ever been to her butt (besides when she sat on his face), and the clear view to compare the two made for some great contributions to Elle’s camera roll. His head wasn’t even half the size of her gargantuan cheek, but that just made it that much better of a pillow, with Olivia’s soft skin caressing his face and warming it up, and the bountiful amounts of her fatty flesh jiggling from every his every movement. The longer he slept with it, the harder they laughed, until eventually they became loud enough to finally stir Reese from his nap.

It took him a few seconds to fully wake up and comprehend what was going on, but as soon as he realized he was cuddling with an ass so monstrously thick that it had to belong to his sister, he cried out in surprise and tried scrambling away. But Olivia had been ready for his escape attempt, and she quickly pulled her legs apart, causing him to drop onto the sand, right before she deftly crossed her knees and trapped his fragile body between her thighs. “Where you going in such a hurry?” she asked, clenching her muscles tighter to quell his meager attempts at struggling. “You seemed to be having such a nice nap. Don’t let me stop you!”

Twisting her back to look behind her, she reached back and grabbed a tuft of his hair, causing him to yelp in pain, “OW, that hurts!”

“That’s cuz of how much you’re trying to move,” she calmly explained, and once Reese realized she was right, he stopped trying to get away. Sure enough, it no longer felt like she was trying to rip his scalp off. It didn’t even hurt at all, other than a mild sense of discomfort.

Now that he wasn’t fighting back, Olivia pulled his hair—although a lot gentler this time—back towards the center of her butt. He grunted from the slightly painful feeling of having his hair pulled again, but it wasn’t as bad as before, and only lasted a few seconds. Once his head was where she wanted it, Olivia let go of Reese’s hair and grabbed the entire top of his head instead, twisting it until he was face-up. She eased her legs apart, freeing him from her clutches, but he was smart enough not to try and escape. “Now straighten out your body,” she told him. “…unless lying down like that is more comfortable for you?” Reese sighed, deciding that if she was going to make him use her ass as a pillow, he might as well get comfy at least.

Once his body was straightened out again, with his head nestled snugly between his sister’s butt cheeks, she swung one of her legs up, and Reese watched as one of her feet flew in an arc towards his head, her achilles tendon stopping just shy. “Boop!” she remarked, tapping against his forehead with the back of her heel, and then repeated herself several more times, “Boop, boop, boop!” With each one, Olivia used the back of her foot to gently hammer his head even deeper between her cheeks, continuing until Reese was finally wedged into her rump so tightly that the insides of her ass cheeks were rubbing against his face cheeks.

“OK there, now I’m done,” she decided with a giggle. “Now you can go back to napping,” she told him, as if that was even a possibility anymore.

“I doubt I’ll be able to fall asleep like this,” he grumbled, since his neck was bent at an awkward angle—not to mention the sheer humiliation, of course.

“Mmmmm… alright,” Olivia sighed, and there was a few moments of silence until she decided what to do next. “Let’s go see what Jordan’s up to!” To Reese’s surprise, he felt Olivia proceed to tense her glutes, squeezing Reese’s head as she carefully stood up so that it’d stay in place. And just like that, she was fully standing up, but Reese’s head was still stuck in her ass, since it was just large enough and he was just small enough that her butt muscles could hold him in place. “Ooooh, I really thought you were gonna fall out; guess my ass is deeper than I realized,” she laughed, and tried to look behind her at Reese’s dangling body. He hung limply behind her legs, just millimeters from being able to touch the ground when he straightened his toes.  Then she started walking.

Making her way to the water, Olivia did have to waddle a bit instead of walk normally—I mean, there was a shrunken little brother whose head was trapped in her ass, it didn’t exactly make walking very comfortable. But she obviously wasn’t leaving him there for comfort. And Reese wasn’t very comfortable either, since the insides of her powerful glutes began rubbing against the sides of his face in sync with her legs moving back and forward. He was glad that there weren’t a crowd of people around, but the squad wasn’t completely alone. It was a public beach, and there were a handful of people that could see Reese’s body hanging from Olivia’s butt. And since his face, though squished, was peeking through beyond his sister’s crack, he could see some of the people watching them, making him wish Olivia could’ve buried him even deeper (ironically) so that he could hide his embarrassment.

“Has she been skim boarding this whole time?” Olivia asked aloud, coming to a stop and waving for Jordan’s attention. “Hey, anybody home?” she asked, reaching her hand behind her and knocking on her brother’s forehead a few times. “You gonna answer me?”

“How the fuck should I know!?” Reese exclaimed. “I was taking a nap til 5 minutes ago.”

“Oh yeah,” she chuckled, waving for Jordan’s attention again until she caught her friend’s eye. “Come take a break!” she yelled, and then put her hands on her hips while waiting for Jordan to walk up the beach.

“Have you been skim boarding since we got here?” Olivia asked her friend once Jordan reached her.

“Yeah,” her friend nodded, “cuz I’m not the one with a family beach house, so it’s been a while. But you kinda had good timing, I think I need a break.”

Olivia turned around, and like a rag doll, Reese’s body swung with her. “By the way, Reese says hi,” she giggled, causing Jordan to gasp before breaking out into laughter.

“Oh my God, I can’t believe he fits,” Jordan commented, slapping Olivia’s ass and watching as Reese blushed, his head shaking slightly from the impact. After Jordan quickly pushed Reese’s head into Olivia’s butt a little but, to make sure his sister’s cheek still had a firm grip on him, the three of them headed back up to their things, where Elle was sitting in some shade and eating a snack she’d brought.

Reese caught sight of Elle’s food for a brief moment when Olivia’s back was turned to her, but then his sister got back down on the ground to continue laying on her stomach, enjoying the sun warming her up. In doing so, Reese’s arms got trapped under Olivia’s thighs, making him even more stuck than he already was with just his head. He gritted his teeth and tried pulling his arms out, but they wouldn’t seem to budge. “What do you need your arms for?” Olivia asked with a chuckle.

“Cuz I’m hungry,” he huffed. “I wanna eat something.”

“Yeah, Elle’s onto something,” Olivia agreed. “What other kind of food did we pack? There should be a couple sandwiches in there.”

“Oooh, yeah there are,” Jordan said, somewhere off to the side that Reese couldn’t see. “Here,” she said, tossing a ziplock bag to Olivia and grabbing a second one for herself. “Reese, you want a sandwich?” she asked, pulling it out of the bag and walking around to where Reese was laying.

His eyes started devouring the food before his mouth even got a taste, and he felt his stomach grumble in anticipation. “Yes please,” he replied politely.

“Alright, here ya go!” But instead of bending over to hand it to him, she turned around, and he watched as she slowly started squatting over his body, backing up until her own butt cast a shadow over Reese’s face.

“Wait, what are—!” Before letting him finish his sentence, Jordan dropped the rest of the way down, her butt crash landing on both the boy’s face and his sister’s ass.

Olivia yelped in surprise, looking behind her to see what was going on. Her friend was wiggling her butt triumphantly on top of Olivia’s own, trapping Reese’s face between the two and kickstarting a fresh round of squirming from him. “What are you doing?” Olivia asked with confusion, not exactly liking how it felt.

Jordan shrugged, “He said he wanted a sandwich, but he didn’t have any free hands, so I gave him one of my own!” With Jordan’s butt crack pressing down on his face, sealing him tightly between the two girls’ asses, Reese tried shaking his head to announce his discomfort—and for once, his struggling actually had an effect on Olivia.

“Well stop,” his sister grumbled, “you made him start squirming again, and it feels annoying.”

“Oh, my bad,” Jordan apologized. “I think I can make him stop for you though.” With a mischievous grin, she hopped a few inches to the side, so that instead of her crack being on top of Reese, the left side of her butt was instead. 153 pounds (which felt like nearly a thousand to Reese) suddenly slammed onto his face, driving his head as deep into Olivia’s crack as was physically possible. Jordan was right; buried in between a trio of three cheeks, Reese didn’t have the ability to move anymore. But Jordan’s little stunt had been too much for Olivia.

“Ow!” she exclaimed. “Shit Jordan, he feels like he’s splitting my ass apart.” Evidently, Reese’s head had been sent too deep, and to Olivia it felt like someone was trying to pry her butt apart. “Get him out!”

Jordan apologized with a grimace and climbed off Olivia, quickly putting her sandwich on the towel and hurrying down to Reese’s feet to try and pull him out. But with his arms stuck under Olivia’s legs, he still wasn’t budging. “His arms are stuck, roll over.”

Starting to get upset now—partially at herself, since this had all stemmed from her idea—Olivia rolled onto her back, and Reese suddenly found his face getting pressed into the sand. But now his arms were on top of her, so Jordan grabbed onto his ankles again to try a second time. It took a bit of heaving, but on her third tug she was able to finally yank Reese’s body out from under Olivia’s ass.

The three of them sat there for a couple seconds while Elle watched in amusement; Reese panting for air, Jordan sighing with relief, and Olivia hoping the sore feeling would go away soon. Reese was the first of them to get up, and he marched over to the towel and snatched Jordan’s sandwich, taking a big bite out of the real thing while glaring at her. She rolled her eyes but figured it was fair enough to let him eat her food, and went to see if there was anything else to eat in the beach bag.

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If you wanna read ahead, the next 3 chapters (~12,500 words) are available on my Patreon at patreon.com/jessajess99

Thanks for reading!