HTTYB - Day 19, Part 9a (Patreon)

The four of them made their way to the water, finally able to let loose and have fun in the ocean’s waves. For the most part, Olivia acted as if Reese wasn’t there, and would mess around with her friends, ride on the skim board, or splash amongst the waves as if there wasn’t a three-foot-tall boy trapped in her swimsuit and holding up her tits. On several occasions, the shrunken boy was unfortunate enough to get a face-full of ocean spray to his face whenever the waves would crash against Olivia’s torso. But she was at least considerate enough not to go diving beneath the water; pushing his breath-holding abilities to their limits would’ve been a bridge too far, apparently.

But that wasn’t to say that Reese wasn’t uncomfortable. Being forced into the giant girl's swimsuit wasn’t a statement to be taken lightly—he truly did feel forced and constricted. Having the tight garment compress against his meager frame, like it was trying to mold him into Olivia’s stomach, discouraged him from taking deep breaths. Every once in awhile, he’d catch a glimpse of his legs, dangling awkwardly on top of Olivia’s, and he’d feel embarrassed by how much skinnier and smaller he was compared to someone so brawny and fit. The speedo he was wearing still felt unnecessarily tight. If he ever got a boner—which he really hoped he wouldn’t, considering whose body he was attached to right now—he was sure it wouldn’t even be able to form a noticeable bulge, since his dick was so tightly squished in against itself.

Mentally, his head was giving him the most stress though. Somehow, for some reason, by some means, it was more clear than ever that God had gifted Olivia with the largest pair of breasts that Reese had ever seen, let alone felt. Every day was a reminder of just how small he now was, but when his head was trapped within her cleavage, he easily felt smaller than ever before. Even at his reduced size, a lot of boobs weren’t big enough for him to really bury his head into—he might be able to put his head between them, but to actually become engulfed wasn’t as easy. And yet Olivia’s tits were so massive that they were easily able to exert a tight grip on the small boy's small head just by nature of existing. Even if she was completely naked, with nothing to hold them back, they were so massive on her figure that it was like they were bursting forth, even if there was nothing for them to burst from in the first place. Which meant that even if she hadn’t been wearing a bathing suit, there would still be a deep canyon of cleavage between them. And now that Olivia had had Reese make himself at home inside, his head was destined to reside within her boobs until she granted him freedom. Even he hadn’t been perched inside her tight and skimpy swimwear, he was sure that her tits were gripping him enough that he’d be able to hang from between them anyways. All of that would’ve been annoying on its own, but for it to be coming from her just made it even more embarrassing. Which, of course, Olivia was aware of. That was part of why she was doing it. It was tough love; she wanted to put Reese in his place. And she knew that spending such a considerable amount of time between her tits would do just that. Especially now that they were both wet—his head kept sliding all around within her slick, bouncing tits, and yet somehow managed to never escape them at the same time.

After a while, Olivia finally retreated a bit in the sand and sat down, watching Jordan and Elle play while she took a break. Reese took it as an opportunity to beg for freedom; it wasn’t the most painful or most smelly or even most uncomfortable she’d made him do, but for some reason it ticked all the boxes for him of being the most embarrassing. “Are you going to leave me in here the whole time we’re at the beach?” he asked, writing around for the hundredth time.

“What was that?” she replied, reaching her hands in and pulling her titanic-sized breasts apart from his face. “Your voice was kinda muffled.” It wasn’t, and she’d understood him perfectly fine, but she just felt like teasing him anyways.

“I said are you gonna leave me here the whole time we’re at the beach?”

Olivia was silent for a few seconds, seemingly mulling over the question as Reese waited impatiently to see if she’d be merciful. “Wait, didn’t I tell you back at the house that you had to call me master for the rest of the day?”

Reese sighed, but made an effort not to grumble to noticeably or sound as moody as he felt. “Sorry. I was wondering… Master… if you wmmph—” He was cut off as Olivia withdrew her hands from pulling her breasts away from Reese’s head, allowing her tits to crash against his head again and forcibly muffle his request before he had to chance to ask what he wanted.

“Oop, sorry,” she giggled. “I had an itch on my back.” She quietly scratched herself, letting him linger for few seconds, and then pulled apart her boobs again. “OK, you can continue.”

“I was wondering if you were going to leave me in your swimsuit for awhile, Master?” he asked, feeling irritated now but managing to keep his cool.

“Why do you ask? Is it comfy?” she cooed, scratching his head like he was her pet. “I’d imagine it feels pretty cramped since my boobs are so big, but maybe I underestimated how small you were. If all you were going to ask is if I’m leaving you in there all day though, then the answer is no, I’m planning on letting you out eventually.”

“Wait, that’s nmpph…!” She pulled back her hands again, trapping his head once more, and then spontaneously decided to start stretching her arms and humming a song. For the moment, shoulder stretches seemed to be her favorite, but unfortunately for Reese the exercise squished her boobs together even more than normal, to the point that they folded around him so much that he couldn’t even see in front of him anymore. Only titty flesh seemed to surround the poor boy, as Olivia sent him back into a state of being ignored while she stretched herself.

Elle, who had been playing with the skim board, passed it to Jordan and walked up to Olivia and Reese. “You already bored or something?” the blonde girl asked.

Olivia not only shook her head, but shook her whole body in the process, sending her boobs flapping back and forth so that they’d slap against Reese's head over and over. “No, I’m not,” she laughed, smirking down at Reese’s predicament. “Just taking a break.”

“OK, well I’m gonna go grab one of the water bottles—you want one?”

Again, Olivia shook her head, this time even faster and more aggressively since it thrilled her to feel Reese’s wiggles of discomfort.

But for the first time in the several hours that they’d been hanging out, Elle started to finally loosen up to Olivia’s ploys, and she grinned down at Reese, thinking of a question this time that she knew would prompt another “no” response from Olivia. “Do… you think Reese is enjoying himself?”

Olivia glanced down at him. “What do you think, Reese. Yes or no?” His instinct was to say no, since that was the honest answer, but he realized the trap that Olivia had set up for him. Because if he did answer no, he’d cause her to shake her torso again; he’d be the cause of his own discomfort. But obviously he couldn’t answer yes. Even if it wouldn’t be an honest answer, he knew Olivia and her friends would just use it to humiliate and tease him even further. It was a lose-lose scenario. So he figured he might as well try to just answer honestly—although neither of the girls could even tell what he said anyways. “I think that’s a… no!” Olivia laughed, shaking Reese's head between her slippery tits for a third time. Elle giggled and blushed, feeling naughty for participating, and ran back to their things to get some water.

Even more miserable now than when Olivia had sat down, Reese was pretty sure he was starting to get a headache, and groaned in discomfort. He still had his arms underneath her boobs, although he’d long since given up on trying to carry their immense and unbelievable weight. “Were you trying to say something?” Olivia asked, pulling apart her boobs to grant him permission to speak to her again.

“Please!” he cried out. “Your boobs are so heavy O… Master, and I’m starting to get a headache. I’m begging you, please give me a break Master. Please show me mercy.” He winced as soon as he heard it come out of his mouth; it came off a lot more desperate than he was planning, but he didn’t have much room (literally) to care about his ego at this point.

“Mmmmm… alright,” Olivia sighed, not wanting to be too mean to him. He almost didn’t believe she’d free him at first, but she reluctantly stood up and then unceremoniously grabbed his head and unsheathed his body from her swimsuit, setting him on the ground in front of her. “Feels kinda like, weirdly loose now,” she mumbled, readjusting the straps as Reese smiled and took a deep breath, enjoying the feeling of freedom.

“Thank you, Master,” he told her, and she faintly smiled back at him, not too thrilled about having to let him go but knowing it was the right thing to do nonetheless.