Cindy spun the bottle and it ended up pointing at Jim with the smaller end and Zuemy with the larger end. The usually confident self-proclaimed playboy gulped, it had been made evident a while ago that he was out of his depth here but he wasn't complaining entirely.
"We already know where this is going, it's gonna be a dare... am I gonna get buried under Lillian's ass too?" He asked with a bit of a chuckle that made Cindy, Zuemy and even Jen giggle while Lillian was a bit less amused at the joke, though she still found it funny but wouldn't show it.
"Give us a little bit of credit" Zuemy replied "Plus, you have to admit seeing Joel get squashed like that was pretty funny"
"At least he held Lillian up for like 2 seconds" Cindy reminded and giggled again.
"Yeah, that was hilarious" Jim chuckled again "So, what's it gonna be?"
"I think I got a good one in mind, here" Zuemy lowered her hand to the floor and Jim walked towards it, once he reached it he hopped on. Zuemy then scooted over and brought her hand close to Cindy's chest "I dare you to escape from Cindy's cleavage in less than 5 minutes" She said and promptly tilted her hand, tossing the blond lillie into the yawning chasm.
"Oh shit, with a time limit?!" Jim managed to say before he disappeared between the fleshy twin mountains as Cindy giggled. Feeling him slide down into the depths of her cleavage tickled her and she couldn't help herself.
"Somehow I feel I inspired that dare" Jen said, smiling in amusement but also because she was still feeling you get pressed into her nipple and by the lack of struggling she assumed you were quite comfortable in there.
"Perhaps" Zuemy replied with a smug grin "Cindy's not complaining" She added and indeed, the chubby nerd was just looking down at her chest, feeling how Jim was trying to move while getting engulfed by her own flesh. It felt like he was swimming and his limbs' strokes only tickled her more, making her giggle and causing her humongous chest to jiggle.
Seeing that, Jen felt a little curious and subtly made her chest bounce as well, just to feel how her chest's mass shifted and wobbled with you sinking even more into it. She was surprised that you were pressed into her nipple but hadn't gone crazy horny yet, as she'd seen some rumors about a possible sensory overload that could happen to male lillies.
'Either those aren't true or he's made of tougher stuff' She thought, realizing she couldn't even be too mad if the case was the latter because then that'd mean you wouldn't be easily tempted into cheating. The many jokes Zuemy and Lillian made about her boobs and even suggesting she'd like them sucked kept resonating on the inside of her head, awakening an itch she wasn't too aware of until now. Still, she knew she was already pushing things forward quite a lot and that trying to force things wasn't going to end up well.
Meanwhile, you were struggling a lot more than anyone outside would think but you were at least somewhat good at keeping quiet. You couldn't stop your heart from beating wildly nor your hands from feeling tingly all over on the inside, there was a scent in the air that was notably less subtle now and it was messing you up the more you breathed it in, you didn't even understand why it was making you react like this, you'd never experienced this before...
Hold on, really? Did you never experience this before? Somehow, these feelings ring faintly, somewhere down in the depths of your subconscious, enough for you to realize that there is something. You tried to dig deeper into your memories, losing yourself into your inner thoughts as you tuned out the world with the intoxicating scent acting more like some kind of incense or some aromatherapy thing, as it allowed you to take a dive into old, largely semi-forgotten memories, searching for the proverbial needle in the haystack... except that this time, the needle glowed and there was a trail that you could follow.
It didn't take nearly as long as you expected when you found your lead, you definitely had felt something akin to what you were experiencing right now and it was apparently way back, on the fringes of what you could ever recall: Your kindergarten days. Those memories were very blurry but the more you tried to get at them, the clearer they became.
Unfortunately, your thought process was cut short when your entire self-contained world shook and wobbled and you found yourself once more back in the real world, getting engulfed by Jen's nipple, which seemed to be growing stiffer than before along with a certain, annoying part of yourself. You couldn't get the exact moment but now you knew for sure that you once felt something similar to this back then, back when you were close with a brob girl that protected and cared for you. Once more, you wondered what became of her and whether or not you'd be able to recognize her now.
'Weird that I've never felt this with mom, Ariadne, Dolores, Arianna or anyone else so far, why now?' You thought and then extended one of your arms, touching the rough yet soft flesh. That feeling against your hand was pretty unique and shortly after it felt like fireworks were going off inside of it, you couldn't take your hand away from it.
'Wait, holy shit!' You almost screamed and abruptly withdrew your hand as it finally sank in that you'd been feeling up a girl's nipple.
'I really shouldn't have been doing that' You told yourself, trying to go against your own inner feelings because if you were sincere, it felt good. Even now that you weren't using your hands you were still largely engulfed from behind by Jen's nipple and the rest by her areola.
'Then again this whole thing was her idea, what is she getting at?' You thought.
'Maybe... just maybe I could have a shot. She wouldn't have put me here if I disgusted her, right?' You wondered, slightly lamenting the lack of anyone wise enough to give you some confirmation or valid input. Maybe you should talk to your dad about this when you get a chance.
You felt a slight increase in pressure: Jen's nipple grew larger, having become more engorged with blood, whose added warmth you also noticed but in spite of its apparent stiffness the whole thing remained pretty soft and squishy. You turned your head to get a glimpse at it and contemplated your choices. Albeit put up to it by Zuemy, you were bold enough to at least actually go and commit to the dare, climbing up Jen's back and unclasping her bra.
Something deep down told you that if there was a time where it was fit to use that boldness it was now. 'What's the worst that could happen?' You tried to reassure yourself and then extended one of your hands, grazing the middle of the nipple, taking in the whole feeling in your hand. With some slight hesitation you began to caress it as it felt good but your hear raced, wondering if she'd feel it.
Jen suddenly blushed and felt a surge of intense ticklish tingles on the inside of her boob, she could distinctly feel your tiny hand rubbing her nipple, which made her feel like her own face was getting hot like a furnace while her groin matched said heat. Even her other boob grew aroused and its nipple became just as stiff as the one you were pressed against. She kept looking down at her chest, blinking a few times in disbelief. So far she thought you were gonna be too shy to try anything but the fact that you went and unclasped her bra already intrigued her and this only further piqued her curiosity, proving that you could respond to her affections at least with enough prompting. Right now all she did was silently wish that you kept touching her and even hoping you used both hands but she was aware that you were already quite cramped inside her bra cup, a thought that made her giggle quietly.
In the meantime, once Jim slid down as far as he'd go into Cindy's cavernous chasm of a cleavage he began his climb back up. Despite his reputation with lillie girls he didn't really have much experience with gullie or brob ladies with just one exception: Miriam, your mom, who unofficially acted as his sole remaining mother figure knowing that he didn't have much of a relationship with his stepmother.
Getting stuffed down her massive cleavage was among the many things that came with the territory of getting the 'mom treatment' from her and so, at the very least he knew what being trapped between huge, mountain-sized boobs felt like. Cindy's flesh was softer and squishier than Miriam's but his climbing technique largely worked the same, all he had to do was grab on harder and to put some extra effort into climbing itself
"Ooh, that tickles!" Cindy giggled and tried her best at staying still, seeing that even with just that little bit of laughter her chest bounced and jiggled quite a bit and as fun as it was to feel someone tiny stuffed down there, she didn't want to make Jim's challenge any harder.
'And you're not the only one' Zuemy thought, noting Jen's reaction and even noticing that her nipples were slightly poking through her shirt in spite of her bra. She was amused and intrigued, figuring that you must be doing something to arouse her.
As for Joel, he remained pinned immobile beneath Lillian's enormous ass, feeling the weight of the entire world resting upon his back although in a much squishier, gelatinous form that he honestly didn't mind as much. The lingering smell from her earlier farts made the already stale atmosphere a tad harsher to breathe in but he was in no position to complain. His fingers and toes tried to twitch simply to avoid letting the limbs fall asleep.
Right now, the only lillie not under any active dares was Pete, who looked at Zuemy and her gleaming eyes along with her smug grin with some concern. Then again, nothing had been too bad anf they'd been getting quite the close up with these gigantic, thicc beauties. Maybe a bit too up close and personal but what can you do. For the time being, Zuemy was keeping an eye on her phone's stopwatch function to see if Jim would succeed or fail at escaping Cindy's cleavage before running out of time...
