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HTTYB - Day 10, Part 3
🕑 Added 2021-01-26 11:05:41 +0000 UTCthis ones kinda a weird fuckin chapter LOL. lots of uhhhhh creative liberty sfhskfhsk
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Tuesday, May 25 (cont.)
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Despite the tumultuous start of having been sat on by his sister for the car ride, Reese actually ended up having a lot of fun initially. There were some other attendees who were between his and his sister’s grades, and he got to catch up with them. It wasn’t at any kind of official venue, so nobody cared that he was 18 or asked for his ID when he tried to get drinks. He even saw one of his friends there, and both of them had been surprised that the other one had been invited, but were glad they were nonetheless. At one point, Olivia ran into an old friend of hers who had been a junior when she was a senior. Her name was Kayla, and she was an effervescent, young girl who had been on some of the same sports teams as Olivia. She was half black and half white, resulting in her short hair being super curly, and was just under 5 feet tall herself. But her energetic spirit was so fun and infectious, she hardly seemed as small as she really was. Of course, she wasn’t as small as Reese though.
They ended up spending a solid 10 minutes catching up in the kitchen together, since neither of them had seen each other since Olivia’s final year despite being relatively good friends. Eventually, Olivia couldn’t help but mention that Reese had contracted DSD, and of course Kayla just had to see him for herself. She briefly knew of him, since he had been an incoming freshman during Kayla’s final year of high school, but being several grades apart, they had never had the chance to get to know each other like Kayla and Olivia. But seeing someone she had always known as being quite a bit taller than him, now looking up to her as much as she had to look up to Olivia, was an exciting idea to the tipsy 21 year old.
“Oh, there he is!” Olivia exclaimed, pointing out his body that was dwarfed by the sea of people surrounding him. “Reese!” she beckoned, and was glad that he had heard her over the noise, and started to come her way.
Kayla gasped as she saw the little man approach the two of them, before breaking out into a fit of bubbly giggles. “Oh my god, Reese! It’s me, Kayla, from like, your freshman year I think? How are you? Do you remember me?”
It’s refreshing to run into someone so small for once, he thought, although he was still at eye level with her stomach, which was immediately visible because of her crop top. It beats being so much shorter than someone that you fit between their fucking legs. “Actually yeah, I kinda do,” he chuckled, giving her a polite and quick hug. It was also refreshing to be able to hug someone’s torso, even if it meant pressing his head up against their belly, rather than having to hug their waist or even their legs. I forgot she was kinda cute, he realized as he pulled away from the hug and looked back up at her. If I couldn’t find another girl with DSD my own size, at least someone as short as her could work out well enough. When he was tall, it was easy to quickly sneak a peek up and down a person if they just glanced away. But for some reason, always having to look up to meet people’s eye lines, made it feel a lot riskier whenever he saw someone who was attractive. He was nervous to break that eye contact with her. “So how have you been?” he asked, more out of politeness than genuine interest.
“Oh I’m doing really good! I love college, I’m actually kinda sad that I only have a year left, but like, I’m also kinda ready to be done, you know? Kinda like with high school, I’m sure you feel the same way now.” He nodded; there were definitely more than a couple reasons why he was excited to be done with high school. There were a few seconds of silence, before Kayla turned to Olivia and back to Reese. “Well, hey, that’s kinda crazy, huh?” she said, looking Reese’s body up and down before tilting her head to the side to motion to Olivia. “The tallest girl I know and the shortest guy I know are siblings, what are the odds of that? I mean, you’re only a couple inches shorter compared to me than I am to your sister. Or wait… does that make sense?” She looked up, trying to calculate her wording in her head. “I mean like… you come up to… like I’m up…” She shook her head and giggled, “Nevermind, I don’t even know what I’m saying. I just meant it’s crazy cuz to me I don’t feel like you’re that short when I look at you, cuz how short you are to me is like almost how short I am to everyone else! Does that make sense?”
“Yeah, actually, I think I see what you’re saying,” he replied. He only half understood the half drunken girl, because he was more focused on what she had said. That she didn’t see him as being that short. Just her saying that seemed to double her attractiveness to Reese, and she was already pretty cute.
“It also helps that I got these super high heels on,” Olivia remarked, before swinging her long leg up onto her brother’s shoulder. If he was a normal height, it would’ve been impressive flexibility, but because of how small he was standing across from her, she didn’t even needed to bend 90 degrees. “They’re four inches, see?” she added, rolling her ankle around on Reese’s shoulder, the black plastic rubbing against the back of his head while he did his best to withstand the weight of her hefty calf and foot.
“Oh yeah, I didn’t even see those before!” Kayla marveled, tracing her finger along them and momentarily ignoring the person whose shoulder was being used as a display shelf. “Where’d you get them?”
“PrettyLittleThing,” Olivia answered, finally taking her leg off her brother’s shoulder now as Kayla took a step back again.
“So, do you always let your sister just use you to show off her shoes now?” Kayla asked with a giggle to Olivia’s brother, who was looking plenty over it.
“Yeah, totally. She pretty much does that every day for her leg stretches after she comes back from her runs,” Reese answered sarcastically, and Kayla laughed.
“That’s actually not a bad idea,” Olivia added, causing Kayla to laugh again, although Reese wasn’t smirking as much this time, knowing she might actually want to try that one day. “I’m joking, obviously, but we have been doing some like… tests? If you wanna call them that?”
Reese’s heart dropped upon her bringing up the subject. “You’re not gonna make me do one again, are you? Really, here?”
Olivia shrugged and looked around, before looking down to her little brother. “Why, because of all the people? That’s fine, I guess.” Kayla looked back and forth between the two of them, hungrily curious what ‘tests’ they were talking about, as Olivia looked back up and spotted a hallway with some closed doors. “Come on, we can show her in there,” she said, and before he could protest, she’d stooped down to grab Reese’s hand, pulling him along beside her towards the hallway while Kayla followed behind.
Olivia knocked on the door a few times, but nobody answered, so she cracked it open and saw that the lights were off. “Ooooh, perfect, we’ll just be real quick,” she said, ushering her brother and her old friend from high school into the room as she turned on the lights, revealing someone’s little office space with a desk and some chairs. “OK so, basically,” she started, closing the door and turning to Kayla, “we tried to see if he could fit into any of my clothing, since clothing is normally like, you know, half a person’s height or so, and he’s roughly half my height.”
Kayla’s interest was piqued now, and she leaned against the desk, setting her drink down and crossing her arms. “OK now I’m even more confused and even more interested, show me show me show me!” she exclaimed in a hushed whisper, biting her lip in anticipation.
“Alright, so first I tried to see if he could fit in my yoga pants. As in like, just one of the legs. So he got all wrapped up like he was in a cocoon,” Olivia said with a giggle, reminiscing in the experience while Reese rolled his eyes but smirked at how goofy the moment had been. And then we did it in one of my rompers, so like I lifted him up and deposited him downwards through the top,” she explained, using her hands to indicate the motions. “And then his legs rested against the crotch section so he couldn’t fall down, and I was able to barely button the top up too. So all that you could really see of him were his little legs sticking out in front of mine.” Kayla laughed at the image in her head, looking to Reese and back to Olivia as she imagined him stuck inside his sister’s clothing.
“I feel like you could sneak into a movie or something like that,” Kayla said, her mouth widening with her idea as her eyes widened. Aw, fuck, Reese thought. Just when I was starting to like you Kayla, don’t give Olivia any more ideas! “I mean I’m sure people with DSD who are even smaller than Reese have done it before too,” Kayla continued. “I saw some people on YouTube do it once, a guy just like wrapped himself like a monkey around his friend’s waist and then stuffed some clothing in so it looked like he was super fat, but it worked! They were never caught. And Reese is several feet smaller than him, I bet he could do it no problem. You should try it!”
“What, like, here?” Reese asked nervously. He didn’t want to set the stage for Olivia to try and pull off a stunt like that in the future.
“I mean, you guys came into this room so no one else would see us, right?” Kayla said, looking around and motioning to the fact that they were alone.
Reese glanced at Olivia with a tired, unamused glance that basically told her he didn’t want to, but she didn’t say anything. “Doesn’t mean we still have to,” he quietly continued, looking to Kayla again.
Kayla tilted her head to the side and bit her lip, “C’mon Reese, pleeeeease?” Fuck, I kinda wanna be on her good side, I don’t wanna disappoint her. I mean, I dunno if I necessarily wanna ask her out, but like… I might? And I’ve already done this stupid ‘being worn’ thing a few times before, I guess one more isn’t that bad. Kayla’s hands were clasped together while she wore a puppy-eyed smile on her face.
Reese looked downwards and shook his head, chuckling at how easily he was letting himself get persuaded. “Fine.” He looked up to Olivia, who was silently looking to him for confirmation, “Let’s just do it and get it over with.” But now she beamed, having been given permission to pretty much play around with him again.
“Well, I’m wearing a dress now instead of a romper like last time, so how are we gonna get you to not just fall out?” Olivia asked, walking over to her little brother and examining his body for clues and ideas.
“Like the video I mentioned,” Kayla chimed in. “He can just like, grab onto your torso. I mean that guy like just grabbed on like this—“ She paused outstretch her arms and legs. “Like if you had to grab onto a pole or tree or something.”
“Yeah, that could work,” Olivia laughed. “Here, I can’t really take my whole dress off so I’ll just have to lift it,” she said, and then reached down to the bottom of the garment at the sides and pulled it all the way up to her chin, instantly showing off the toned abs of her tan stomach, along with her black panties he had seen before and her gigantic boobs stored within her black bra.
“Holy shit, your stomach looks fucking great!” Kayla commented.
Olivia blushed, “Thanks, I majored in exercise physiology for college, I’m trying to be a fitness trainer.”
“Shit, I’d hire you with results like that!” Kayla remarked with an amazed smile. But then she turned back to her friend’s little brother. “So dude, whatcha waitin’ for?”
I was waiting because I wasn’t fully expecting my sister to suddenly lift up her dress and pretty much flash me wearing just her underwear… he begrudgingly thought, but climbed onto the chair next to his sister anyways, knowing he was still gonna go through with the dare. Because that’s what it pretty much was, a dare, even if Kayla didn’t say as much. He opened his arms up first, and slowly leaned in towards his sister, his head held towards the side, facing Kayla’s eager face. He couldn’t fit his arms all the way around her, but he still managed to get a solid enough grip, halfway around her chest, and then jumped up with his legs and quickly wrapped them against her waist. Her body was warm, but her skin was still soft against his arms. His head was tilted away from her body though, because he was dangerously close to her breasts, and didn’t want his head squished against them again. But besides that, he was just big enough that he could fit his limbs halfway around her, so that it was like he was squeezing her from the sides as he held on. “There…” he managed, his voice a bit strained as his muscles worked to keep himself latched to his big sister. “Kinda like this, right, yeah?”
“Well, except we’ve gotta hide you,” Olivia laughed, and let go of one of the sides of her dress so she could gently but forcefully guide his head closer to her body. Closer to her breasts. Against his will, but not to his surprise, his face got mashed against his sister’s giant boobs, with only her bra to keep them from fully exploding around his meager head. Although there was still so much bare flesh exposed, it hardly made a difference anyways. And with his body now fully pressed up against her, she was able to release the rest of the dress, and pull it down snugly over Reese. And it wasn’t a very loose dress either, so even though his body was small and relatively lean, it still pressed up against his back and made sure to keep him firmly poised against Olivia’s front torso. His limbs kept his body from sagging, but it was really her dress that was keeping him close. Uncomfortably close. “Can you look up at me too?” she asked, and Reese managed to scrape his head sideways, directly into the center of her deeply valleyed cleavage, before raising it up to look at her. And from Olivia’s point of view, she was able to look down into her dress, to see her little brother’s head staring up at her, mashed between her volumous boobs, each one bigger than his dome. Even Kayla came over now, standing on her tippy toes to be able to just barely see her friend’s brother, trapped within his sister’s dress.
“OH MY GOD, that’s perfect!” she shrieked happily, jumping up and down excitedly. “I mean it’s obvious there’s someone in your dress from like his body shape, and the little bit of his head popping up, but if you wore like a baggie sweatshirt or something it’d be perfect!” Alright, that’s enough, he inwardly grumbled, and let go with his limbs, quickly sagging down within his sister’s dress before spilling out the bottom like some kind of oversized baby being born.
“Fuck, Reese, you could’ve ruined my dress!” Olivia gasped, flattening out her attire and making sure it didn’t rip as he came falling out from within.
“And you could’ve ruined my dignity,” he mumbled. He turned to Kayla with a tired expression on his face. “Ta da.” He wasn’t very enthusiastic, but that didn’t dampen Kayla’s spirit.
“Well, I think that was pretty cool, I kinda wanna try it myself one day, although I don’t think I’m small enough to squeeze under your dress Olivia,” she laughed, lightening her mood a little with her endlessly exuberant spirit. “But I think it’d be fun to do with someone!” She hopped over to Reese and gave him a friendly side hug for a few cherished seconds, “Thanks for showing me you guys.” She smiled at him, and between her charming grin and upbeat, nonchalant attitude about the whole thing, he started to recover over the humiliation too.
“Glad you thought it was cool,” he stammered, scratching his forehead nervously. “Uh, anyways, I think I’m gonna head back out there now.” As much as he liked running into Kayla again, he didn’t want either of them to get any more bright ideas while they were still all alone.
“Yeah, I think that’s a good idea,” she said, and the three of them slipped back out into the party, with nobody any the wiser about what had just gone down.
