"You know what, I think we should help you" Zuemy then said, interrupting your thoughts.
"How about we show you more clearly so you can make an informed choice?" She added in a soft, whisper-like voice while giving you a smug grin.
The other girls only half-deduced what Zuemy was getting at but then they saw that she stood up, unbuckled her shorts and lowered them, then she sat down and turned around, giving you a pretty clear of her massive ass and the deeply wedged panties within, hers seemed to be plain black but most of them had been swallowed already.
Cindy was the second but Jen followed closely, the two did similarly, lowering their pants and then sitting again and turning around to show off their pantied behinds. Jen even gave you a flirty wink as she wiggled her hips a little and her tiny red thong did get swallowed deeper. Cindy seemed to be wearing a more conventional pair of panties but just like the other girls, the sheer size of her ass was what forced the garment to cosplay as a thong. Lastly, Lillian only had to turn around since she was already in her underwear, staring at you quite intently, as if trying to call you without words.
'Wow, these girls are going hard for him, lucky bastard' Jim thought with an amused grin, enjoying some of the spectacle himself, stealing glances at Cindy, Lillian and Zuemy but not Jen. Similarly, Pete and Joel enjoyed the free eye candy but they knew better than to look at Jen as they knew to a lesser extent that she was interested in you.
"Take your sweet time, just get a gooooood look and then make your choice, you get to pick 2 girls" Zuemy said, leaving you to look at the 4 gigantic asses with badly wedged underwear. None of them would be a very easy task but by the look of it Cindy's might be less difficult, her panties were the least skimpy so there was more cloth to work with, the other 3 were pretty much makeshift or actual thongs... Come to think of it, how were you even supposed to pick out a wedgie from a thong? Aren't they supposed to be a wedgie by default?
You were briefly hit by the realization that you had a suspicious amount of knowledge on women's underwear but then again how could you not? Growing up with your mom, your big sister and their many friends, you had spent a lot of time in, on and under their bodacious asses and with that, the underwear they had on. Thankfully you had enough self-awareness of this to not give yourself away when talking casually, though your friends got a lot of info from you as they knew of your recurrent shenanigans.
In a way, your decision was already made but Zuemy making you look still got you flustered. You definitely wanted to go with Jen once more, feeling a strange mix of feelings as your own determination clashed with your embarrassment. This was the first time you willingly went into a girl's butt, not counting family members like Arianna. Plus, this is a girl you actually like in a romantic way, making this a first in your life but then again, something in the back of your mind nagged you, as if trying to remind you of something you forgot, something important from the past.
Something about Lillian called you for sure, even against your better judgement given that her was the biggest, heaviest ass and by the sound and smell from recently, the most dangerous as well. Plus, somehow you sensed that without words she still said "I know you're not gonna pick me" and that hit you way harder than you thought, you legit felt bad with her. Maybe because of your previous experiences with people like Arianna and Dolores you were a bit more understanding that it wasn't her fault that she was so big and that you shouldn't make her feel bad for it.
"Alright, I've made my decision" You said, taking a deep breath to muster up as much courage as you could, Zuemy's smug amused look made it all the harder to maintain your composure. In some ways you felt like you wish you could get out of this situation and recluse yourself but you knew that wasn't the way, if you never tried anything you'd never get anywhere and right now, you might as well and try to have some fun.
"I choose Jen and Lillian"
"Ooh! How ambitious! I didn't take you to be the voracious type" Zuemy giggled.
"Huh?!" You took a step back, not expecting that sort of answer but even you could understand what she meant. Jen and Lillian were the sexiest of the group but that was not to say that Zuemy or Cindy weren't quite beautiful in their own right.
"Hope you don't choke on so much meat~" Cindy teased you further. She didn't seem to be mad or even disappointed that you didn't choose her, almost as if... she understood your reasoning? No, there's no way. But why did she wink at you so confidently then?
You shook your head and slapped yourself to snap back into the real world, laughing awkwardly and nodding in response to her. You then looked at Jen who was staring at you pretty intently though her expression seemed cryptic and then, compelled by the sense of being watched you turned and looked at Lillian who seemed pretty happy with your choice, blushing a little even.
'Man, I hope Veronica looks at me that way one day' Joel thought, also seeing the way Lillian and Jen were looking at you.
"Well then, go ahead! These wedgies can get pretty uncomfy, don't keep them waiting" Zuemy chuckled. You slowly nodded again and began wondering who to go for first. Your first impulse was to go for Jen first and then Lillian but what if she gets the wrong message? Then again if you go for Lillian first Jen might also get the wrong idea, but you could at least try to argue that you were leaving the best for last... but that probably would sound a lot worse outside your head.
'Goddammit, there's no winning here, is it? Maybe I made the wrong choice' You thought but you decided to still stick to your guns, even if it was screwup you might as well go all the way with it. With that, you decided to start walking in Lillian's direction, much to her surprise.
'Maybe Lillian's onto something picking this guy. He sure is brave if he's still daring to go into such a big ass after hearing it explode' Zuemy thought with a smirk of amusement and intrigue 'Then again, he doesn't know what Jen's is capable of' She giggled quietly.
'Welp, at least he's not afraid of big butts' Cindy thought, lightly caressing her own, knowing that getting you to cuddle with it wouldn't be as difficult as she first thought.
'Wait, he's going for Lillian first?!' Jen frowned, hoping that you'd go to her.
'Hmm, then again he did choose me along with her. Maybe he's saving best for last? Feels like it... but I'm worried Lillian's fat ass is already charming him. Dammit, I can't match her sheer size yet!'
In a matter of minutes you found yourself once more before the gigantic behemoth that was Lillian's humongous ass. Its immense size made the sight both alluring and ominous, the slight jiggling that ensued across those vast globes of fatty meat only further intensified the notion.
'The only ones I know to be this fat are Arianna's and Dolores', goddamn' You thought, gulping hard but unsure if it was from fear or simply shyness. As massive as it was, there was beauty to it, those massive jiggling globes were near perfectly round and smooth, with no apparent blemish on them save for a few scarce beauty marks.
Her yellow thong was practically nowhere to be seen, most of it was definitely swallowed hungrily between these gargantuan cheeks with only the puny triangle of cloth above them serving as proof that she had any underwear at all. The waistband was largely hidden as it cut into Lillian's pudgy waist and got swallowed into those slight rolls.
"Ready?" Lillian asked with a cheerful voice, snapping you out of an incoming train of thoughts of self-doubt.
"Y-Yeah, if you don't mind" You said, almost choking on those words. Uttering them had suddenly felt like the heaviest burden in the world yet you managed to pull yourself through and kept looking at where you'd be climbing into, making your task all the more daunting.
"Ready when you are" Lillian said, trying her best to ease you into it, already feeling like she was going to explode with happiness on the inside. It looked like her flirty teasing earlier was paying off quite handily, now all she had to do was to maintain the momentum she gained and keep the scales tipped in her favor. She knew she still needed to show herself as someone who could keep you safe to stop you from solely relying on Jen.
"Okay... here I go" You said quietly. 'May whoever is up above and watching protect me' You thought, directing that as a sort of semi prayer to whatever deity cared enough about your pitiful little soul. Maybe the ancient Quetzalcóatl, patron goddess of the Mexican people or perhaps Lustrog, the man-turned-god-like prophet of the Lillies as a whole.
You began walking towards the canyon-esque chasm that separated those colossal, mountainous cheeks, feeling like you were entering a forbidden cave. The atmosphere immediately got warmer as the air there didn't escape so easily from between such enormous, voluptuous meaty masses. The air felt heavier and thicker too, with the lingering stench of her previous fart still present but nothing that fazed you. Slowly but steadily you kept walking in a straight line, trying to calculate when you'd reach about the middle of her crack.
"Damn, he disappeared already!" Zuemy lightly teased "Well, he'd disappear in any of ours but still, it looked like you ate him" She looked at Lillian in the eyes, making her blush for a split second.
"H-He went in there willingly! I didn't force him or anything" Lillian replied, feeling more defensive than she thought herself.
A few minutes later you decided to pull your phone out and activated the lantern function. Thankfully lillie phones had a much more powerful light, which came in handy. You then looked up and your heart skipped 3 beats because you could see in the distance above something you didn't fully expect to see so easily: Lillian's asshole, and it looked like it was chewing on the thong as it flossed the cramped space in her crack...
