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Taylor trembled while her picture-perfect blue eyes fluttered shut and her cotton candy pink lips twisted into a nice wide O shape, the gorgeous blonde like a ticking time bomb about to be set off at any given moment. Wanting to cement herself as a worthy top, Olivia did what she could to keep Taylor on the edge for a few minutes longer, soaking in the power she mined from getting the 31 year old to approach orgasm but not letting her achieve it. However, all good things must end, and Olivia really did intend to hold true to her words. Thus, all it took was a couple of rough thrusts and Swift was struck with a cavalcade of climaxes, screaming at the top of her lungs as she rode the series of peaks that flew her way.
That full throttle frenzy caused Oliva to flash a bashful smile that then developed into a goofy toothy grin the longer this very visible pleasure took hold of Taylor's psyche.
"Mmmm, yesss Taylor!!!" Olivia howled. "Cum! Cum with my big dick in your ass! Yeaaaaahhhh!!!! Mmmnhhh, oh my God...I...I actually just said that! And...and it's actually happening too! Like what?! So crazy! I've never, neeeeverrr, seen someone cum that hard, Tay. I didn't even think that was possible. I mean, I...I wouldn't think it was possible if you weren't squirting all over right now. Ohhhh Gooooood, just look at you, Tay! Making a total mess as you cum like a little bitch! My bitch!! Oh God, can...can I say that?"
Swift didn't answer back with anything coherent, but her wild whinnies of pleasure were answer enough. Her juices absolutely cascaded out of her hot cunt, her girl cum spilling out onto the floor beneath her while her slim hips bucked wilder than a bronco. Swift's breaths grew more and more shallow, feeling as if she was on the verge of losing consciousness as orgasm after orgasm struck her prone quaking body.
Her garbled up gratitude became ever so slightly more comprehensible, a jumbled mess of 'thank yous' aimed towards her most recent mistress flurriedly and hurriedly racing out of her mouth in a mad dash. Finally, she collapsed onto the soft soaked carpet beneath her, her body left in a heaving heap as she slowly came down from her otherworldly mental high.
Giving a gleeful gasp, Olivia doted on her own handiwork, licking her lips as she looked into Taylor's gaping crater. Running over to her stuff, Rodrigo grabbed her phone from inside her heels and snapped a quick pic of Swift's cavernous cavity, even going so far as to pose with that loosened anal tunnel, taking a couple of cute little selfies with her cherished prize. However, she knew in the back of her mind that there were more important matters to tend to, namely prepping and prodding her next pet.
"So... Billie..." The "All I Want" singer hummed, slowly sauntering away from her idol, who was freshly unconscious on the floor.
"Fuckin' save it." Eilish growled. "You really think you've done something, huh? You think you're hot shit because you've laid claim to the biggest bottom in the game?"
Growing increasingly bashful, the brunette reeled back, "What? No...no...I don't think...I mean..."
"Uh-uh." Eilish eye rolled. "You don't get to backtrack now, bitch. You think you're a top like me? You're not even in the same league. I could bend you over right the fuck now and expose you as the poser you are!"
"You could?" Olivia questioned with a frown.
"Damn straight." Billie boldly nodded.
"Then...if you don't mind me asking...why haven't you?" Olivia pointedly inquired, her lips curling up into a slight smirk.
"I--" Billie froze, searching for an answer and coming up empty. "Mmmnh, I am now! That's right, bitch! You had all your little fun but it's time you get put the fuck back in your place!"
In a curious move, Billie, after delivering that diatribe about asserting her dominance, didn't put her strap-on back on. Instead, the spunky blonde backed her own phat ass up, going so far as to twerk that meaty backside in front of Olivia's face.
"So, you an ass girl, huh?" Billie shifted her tone, almost purring those words while flaunting her big booty, already knowing the answer.
"Ye...Yes." Olivia softly squeaked, hypnotized by that enormous behind.
"Well..." Billie trailed off before growling, "Then kiss mine, bitch! Mmm, yeahh, show me exactly who you are! Fuckin' pucker up and become a good ass kissing little ho! Seriously, bitch! Get on your goddamn knees right the fuck now and worship my booty? Aight? Aight? Are you even listening to me?! Ugh, come on! Why don't you just make this easy on your pretty little self and do as you're told?!? I said do as you're told!!! What the fuck? Come onnnn, bitch. Pl-Please? Pleaaassseee? Please just--AAAAHHHHAAAHHHH FUCKING FINALLYYYYY!!!"
Billie rejoiced as Liv at long last listened to her attempt at a command, Eilish ashamed that she devolved into pleading towards the end there. But she couldn't get too hung up on that, not when she was being worshipped by these picture perfect pink lips. As badly as she wanted to seem more put together than this, Billie pretty much instantly moaned once the "All I Want" singer began planting a parade of passionate pecks to the "everything i wanted" singer's plump posterior, the "Happier Than Ever" musician always ecstatic to have another woman giving her the respect she deserved.
Unfortunately, that had the unintended side effect of the seven time Grammy winner letting her guard down, meaning she barely registered when Liv spread her pudgy cheeks apart and licked that pink starfish up and down, going so far as to pump her moist muscle in and out of that rosy sphincter. Billie's tush was tight enough that the tip of Liv's tongue didn't make it very far but a message had been sent nevertheless.
And it wasn't even a message that Billie could respond to, as she was admittedly enraptured by this first class rimming from her contemporary, loudly howling as this anilingus persisted. Fuck! This was supposed to be her chance to re-establish her dominance and now it felt like Olivia was closer than ever to making her her bitch.
But no, she HAD to stay strong! She hadn't built herself up as one of the most dominant forces in the industry just to get overtaken by some Disney Channel dropout in desperate search of some edge.
A fresh sense of panic surging through her, Eilish's mind flashed back to all of her triumphant conquests in an urgent attempt to regain the blustering lustful luster she had possessed then.
Annihilating Ariana's jiggly and juicy tanned booty and yanking back on her high ponytail hard enough to make the former Nickelodeon star let out her famous whistle notes while on all fours. Slamming Selena's tiny tunnel until the Waverly Place Wizard wept for the kind of shameful orgasm only anal could provide her. Decimating Demi's derriere by making the ex-Disney product bounce their ridiculously fat ass back on a 14 inch strap-on, since that was the only length that had half a chance of being felt by the butt sex obsessed submissive. Conquering Camila Cabello's caboose with such vigorous viciousness that the petite yet thicc Latina was left yearning for the days she palled around with a group of four far gentler, albeit inferior, tops.
And of course, topping Taylor Swift better than this bright eyed raven haired beauty ever could.
Yet, reveling in those heavenly memories didn't produce the desired result for Billie. Rather than remembering and tapping into the incredible mental high mined from claiming some of the hottest pop stars on the planet as her trampy little trophies, the 'My Strange Addiction' singer pictured herself in those subs' place, wondering what it would be like to be on all fours, to be getting an ass full of cock, to be truly helpless against the will of a superior woman...FUCK!
No, this couldn't be happening! This total poser behind her, this, this 'COPYCAT' was kissing her ass. Billie was in control here! It was NOT -- N-O-T --the other way around. Billie hadn't worked so hard to have such a rapid and meteoric rise just to be outdone and undone by some half-assed Mickey Mouse replacement. So why did it feel like that was exactly what was happening?!
No sooner had that last thought entered Billie's brain than had she let out an embarrassingly loud and whorish moan in response to this Fillipina beauty vigorously and eagerly thrusting her tongue in and out of the 'Don't Smile At Me' songstress's pink crinkled starfish. Humiliated by a reaction so unbecoming of a dom like her, Billie covered her mouth with clasped hands, which would turn out to be a major mistake by Eilish, one she'd fixate on everytime she replayed this fateful night in her head. What she should have done in that moment was take those hands and push Olivia's head away before turning the tables on the 'good 4 u' singer, but the thought never even crossed her mind.
Instead, Billie was falling faster and harder into a world of sordid pleasure, feeling a rush of emotions tops were never supposed to feel. It was bad enough Billie was actually enjoying that moist muscle moving through her rosy sphincter--the last thing she needed was to yearn for something more, something bigger. But, much to her chagrin, the newly minted blonde was left wondering what something longer and larger would feel like knocking at her backdoor, mortifyingly crying out at the very thought of Olivia's big dick entering her anus.
Infuriatingly, these unwanted wanton howls from the Academy Award winner caused Liv to chuckle into Eilish's pillowy cheeks, which in turn further frustrated the youngest Coachella headliner in history, who longed to break away from her pop contemporary's tongue yet found herself rooted to the spot. Getting expertly rimmed by this doe-eyed Disney runaway was already proving to have a surprising outcome for poor Billie, but now Olivia was enthusiastically squeezing the plump and pudgy cheeks she was currently pulling apart, giving an undeniable dominant flair to an act that could be seen as submissive.
By greedily groping those pasty globes of ass meat, Rodrigo was making it known she wasn't kissing that ass, she was owning it, which honestly was somewhat impressive. Olivia was pretty effortlessly dominating this supposed top with nothing more than her tongue, using that tiny muscle to make her fellow young colleague let out a litany of loud howls that in turn only made the HSMTMTS actress tongue that shit slit with further fervor.
And the only time Olivia's beaming face was away from Billie's ample ass was when the 'drivers license' singer herself pulled back from those beautiful big butt cheeks with a shit-eating grin (which, given the context, was a bit too apropos). However, removing her face from in between those meaty globes didn't prevent the rising star from continuing to grope that round rump to her heart's content. In fact, the slightly younger brunette seemed to end up fondling that phat ass even more frequently once she had stopped rimming Eilish's anus, happily handsy with this pert posterior for what felt like an eternity.
Billie easily could've swatted those hands down, but she didn't, instead oddly opting to allow Olivia to continue to assert her authority over that voluptuous booty. With every passing second, Billie felt less and less like her rotund rear was her own. Though that thicc caboose was obviously attached to her curvy figure, it seemed like the longer this night went on, the more it seemed like that dump truck belonged to...Olivia. To...Mistress Liv.
AAAAHH, fuck NO! Those thoughts, that dreadful nickname--none of it should be crossing her mind. So, why was submission more and more the only thing she could think about? And why did she feel her knees going weak just hearing this slightly younger stunner's chipper squeaky voice?
"Mmm, sooo yummyyy. Thanks...'Mistress Billie'." Olivia softly cooed, her use of that title dripping with insincerity. "Is...Is that what we're going with here? Just wanted to make sure because...a couple of those moans--they, uh, they didn't seem very mistress-like."
"Yo, shut the fuck up." Billie snapped though notably had no other comeback or counter, instead simply letting Olivia continue to eagerly squeeze her meaty backside.
"Awww, come on, don't be like that." Olivia playfully pouted even as she made Billie yelp with a vicious double smack to that pasty plump posterior, which in turn produced a glorious sight that distracted the 'good 4 u' singer for a couple moments. "Heheh, whoa. I, S-Sorry, I, I was gonna say more but...like...Omigod! That, that might have been THE greatest jiggle I've seen from a pair of big fat ass cheeks... ever. Seriously, just...mmm...just, ah, no words, no notes, those cheeks, they're just...perfect, hahahahaaa. And with an ass that perfect...it honestly seems like you deserve more than just a tongue up there."
Unmistakable mischief evident in her voice, Olivia then ploddingly circled her index finger around Billie's recently rimmed puckered hole, as if she was simply waiting for, no, daring her pop colleague to protest. And, as mildly upsetting as it was for poor Liv, Billie wound up taking that dare, albeit barely as she weakly squeaked out what sounded like apprehensive pleading,
"O...Oliviaaa..." Eilish anxiously grunted out, begging the doe-eyed brunette to show her some mercy as she felt her confidence slipping more by the minute.
"Yes?" Olivia asked in an infuriating faux innocent tone, as if she couldn't possibly know why this recently dyed blonde bombshell was frantically squealing out her name.
Worse yet, Billie was rendered speechless, as just croaking out her tormentor's name had taken a lot out of her. At this point, Eilish was so far gone that even merely saying Olivia had her growing weak at the knees, which obviously proved to be a sobering reality for the 'bad guy' singer.
Ugh, everything had been right before! Olivia had been seconds away from getting in position and taking Billie's cock like the bottom she was. So why was the desire to submit to this obvious poser so irrepressible at present?
"Hmm, cat got your tongue?" Olivia cheeked, sounding more and more like a mocking mean girl and less and less like the stammering newbie she had come across as at the start of the night. "Then let me see if I can give you something to talk about..."
Without warning, Olivia slipped her digit into Billie's delectable derriere, triggering another ridiculously loud gasp from the 'wish you were gay' singer. Truth be told, despite a slightly hardened exterior, Rodrigo was deep down terrified that doing this would incite Eilish to lash out, as she was in all honesty taking a risk making such a bold move without receiving explicit permission from her budding conquest.
Thankfully, however, Olivia's hair-brained scheme to lure this newfound golden haired hottie into submission had worked like a charm, and all she got in response from this soon-to-be former dom was a near endless series of wails and whimpers. And given Billie was seemingly and surprisingly an anal virgin, said shrieks were mostly out of sharp pain, but Olivia swore she could hear pleasure in those shrill howls even then, though maybe that was wishful thinking on her end.
Either way, Olivia persisted, pumping her slender finger inside Billie's rectum and shamefully reveling in the agonized cries of her unsuspecting sub, as hearing those resounding reactions ignited the sadistic side Olivia often tried to hide. But the longer she moved her finger inside that tight tunnel, the louder the screams from Billie were, in turn creating a vicious cycle in which Olivia was constantly encouraged to continue sliding her finger within that shitpipe.
And oh God, if just a finger was having this much difficulty penetrating the 'Your Power' singer's pert posterior, imagine how hard it would be for Olivia to get her hard girl cock up there. Not that she wouldn't still be trying to regardless.
However, if she wanted to get Billie prepped for that point, then she really needed to ease the 7 time Grammy winner's current nervous state. Sighing and rolling her eyes at this unrelenting tightness, Olivia did her best to mask her frustration with a soothing coo of her voice.
"Awww, it's gonna be okay, Billie. Believe me, you're phenomenal. If, if anyone can take this, it's you." Olivia hummed, her voice sounding almost musical as she lowly murmured into Eilish's ear and her compliment sounding backhanded as ever given exactly what she was doing to her pop colleague in this moment.
"You...You can't...I'm..."
Billie's feeble attempt at a reply was nothing more than an unintelligible stammering mess, the once proud top having trouble processing any of her thoughts when Olivia's finger was stuck up her big booty. She absolutely hated the fact that Rodrigo was doing this to her, but at the same time didn't want it to stop--her emotions greatly at odds with each other in the worst possible way.
While she was absolutely devastated her virgin rectum was being violated in this way, she also almost respected the hustle from this industry newcomer. God knows Billie had to pull a couple of strings here and there to claim a few of her conquests. It didn't happen often, as this industry was crawling with butt sluts just begging to be claimed, but every once in a blue moon, Billie had to resort to tactics such as this, and thus, game recognized game.
Plus, in addition to appreciating Olivia's cunning prowess, Billie did find herself mining the slightest bit of jubilee from that finger finagling its way inside her compact caboose. Olivia was correct in believing every minute of this finger pumping was hurting Billie like hell, but even now, hints of bliss were flowing through her.
Though Rodrigo seemed to recognize that too, and consequently elected to ramp up her fingerfucking by inserting another digit within Billie's portly rear. With two fingers rapidly thrusting within her tunnel, the 'Happier Than Ever' singer left out THE most ego and eardrum shattering screeches of her life, and the tomboyish nonconformist turned curvy bombshell finally grew fed up with the frisky Fillipina.
"Ffffuuuccckkkk...y-youuuu..." Billie barely managed to grunt out amidst her wretched screeches.
"Awww, but we already tried things that way." Olivia quipped, her voice remaining sickeningly saccharinely singsong. "Aaaanndd, it didn't quite work out, did it?"
Furiously, Billie spat out what seemed to be more of an attempt to convince herself rather than Olivia,
"It...No...I....I'm a top, dude!"
"Oh, I, I mean, I never said you weren't." Olivia shrugged, unable to conceal her ear to ear grin. "And, I mean, you know, no, I mean, I'm sure you're a top. A top who just so happens to, um, like getting her fat ass fingered. Which, I think is totally fine. Who am I to judge? 'You do you' and everything, right? Heheh."
"W-Watch it with that 'fat ass' shit." Billie seethed in between screams, not needing this ditzy Disney ho to be among her bodyshaming detractors.
"Oops, I, I guess that was kinda cringe, wasn't it?" Olivia apologetically murmured before assuring, "I'm sorry. But honestly...I meant it as a compliment. Like, I'm, you know, a top too, and I could only ever dream of having an ass this fat. Seriously, I don't know how you do it. You must be like magic or something, because how else can you have an ass this big and fat and f-fuckable?"
"OliviaaaAAAHH!!" Billie's attempt at a stern warning was instantly undercut by Olivia increasing the speed of her finger tenfold, making the poor incoming conquesting in denial wail so blaringly loud that both Billie and Liv were half convinced the entire party could hear them.
"Wowww." Olivia gleefully squealed before further teasing her prey. "Guess I should've figured you'd be a screamer, huh?"
In response, Eilish did her best to stifle her emphatic echoing cries, not wanting to give Olivia the satisfaction of hearing her bombastic reactions. Unfortunately, such suppression of her loud shrill howls was easier said than done, as Olivia's fast and furious fingering of Billie's pink crinkled starfish continued for several minutes more.
