Money Mella Goes Hollywood

"But-But how can you be so sure?" Ari asked, tempting fate by interrupting The Money Mistress seconds before claiming her latest piece of ass.

Mella sighed loudly, her cock in hand as she explained, "Because I'm fuckin' Carmella, bitch, that's why! I fuckin' said it, didn't I?! I know a bitch hole when I see one? Well?!"

"Y-Yeah, I guess," Ariana awkwardly agreed, but Mella was quick to jump back in.

"You guess? You fuckin' heard me say that shit, slut!" Carmella barked, leaving Ariana no choice but to quickly apologize in an attempt to diffuse the situation, something that her spoiled and inebriated brain hadn't allowed her to do all night.

"I'm sorry, okay?" Ari pleaded, but it was already too late.

Angrily wagging a finger on her free hand, Carmella gruffly insisted, "No, no, no, 'cause now you got me ALL fired up! You've been doubtin' me all night, Pop-Bitch, and I'm pissed about it! Let's get something aBUNdantly clear, bitch: I am THE premier butt-fucker this side of Hell. There ain't a single woman in my line of work OR Tinseltown that can turn a broad into a bitch like me, capiche?"

"Yeah, I...I got it," Ariana cautiously agreed.

"No, I don't think you do!" Carmella snapped back, bringing her cock to that tight little bootyhole and pressing the tip against it; notably, she didn't push forward. "You've been doubtin' me all night, you little fucking brat, and I asked you to cut it out! So I'm done asking now! And I'm fucking done playing nice! So now...I'm gonna fuck your ass now...and you're gonna sit there and take it like a good little cocksleeve. And I don't want to hear ONE peep! NOT ONE, until you're ready to admit how much you love it! And now...you say: yes, my Money Mistress."

Ariana swallowed hard and responded, "Y-Yes...my Money Mistress." For the first time all night, Ariana 100% believed the words coming out of Mella's mouth.

"Good. Good bitch. Gooooood little Pop-Bitch," Carmella complimented, somehow managing to fold up Ari's tiny body even further as she centered her cock again. "Okay. Now that we've both got the proper understanding of what I am...let's hear you say it. Right from that pretty little mouth of yours...tell me what I'm about to do to you, Ari."

Ariana knew the answer; thank God she knew the answer. Admitting it wasn't easy, though. Hell, she didn't even WANT to get fucked in the ass! Honestly, she didn't want anything to do with any of this topping and bottoming lesbian shit...mostly. There was that small part, that little section of Ariana's brain that was and had been loving every second of her trial run as Money Mella's newest pet. And that, mixed with the wine and the newfound fear and thus appreciation for The Staten Island Princess, helped push Miss Grande to respond exactly how her Money Mistress wanted.

"You're..." Ari gulped, half-ashamed and half-surprised to hear herself utter the words she was about to. "You're gonna fuck my ass."

Carmella smiled, but quickly fired back. "That's good. Again."

"You're gonna fuck my ass."

Ariana found the words a bit easier this time, something that didn't go unnoticed.

"Say it again."

"You're gonna fuck my ass," Ariana repeated for a third time, sounding even more confident in every syllable.

"Tell me again, Ari," Carmella re-ordered, continuing the trend, Ariana barely letting a second pass as cried out her latest response.

"You're gonna fuck my ass!" The Popstar proclaimed, passion seeping from her words. Like the truest of predators, Carmella made the idea of becoming her prey alluring. The closer the big cock came to plunging into her little asshole, the more Ariana actually wanted it to.

"Fucking right. Now be a good girl and beg for it." One last order, one that Ari never dreamed she'd find obeying so easy.

"Fuck my-" Ari began, fully swept up the heat of the moment, but not so swept that she couldn't realize that there was a better way to beg for Mella ram her bum. Of course, Mella's narrowing eyes helped matters, as well. "Will you...please fuck my ass?"

Carmella, after seeming to think over the response for a few seconds, issued a response of her own. "Needs work," She assessed, but ultimately softened, "But it's a start. And, in turn, so will I."

Ari, surprisingly, found herself grinning at this revelation which was...weird. This was all still very new for her. Nevertheless, Carmella continued.

"Get ready, Pop-Bitch! You're about to find out that God is a woman, and her name is Carmella! Hahahahahahaha!!!!" Carmella's maniacal laughter, a result of the rush she felt from being mere seconds away from defiling one of the world's biggest stars, was what helped propel her into a mental state capable of handling such pressure. The fate of Ariana Grande's potential bottoming future rested on her shoulders, an enormous amount of responsibility for any top, but a responsibility only the greatest top could actually bear. Carmella was that top. The money-est of all mistresses, unironically, the only one capable of guiding Grande towards her new future as an anal bitch. And, without any further adieu, Mella put the training wheels on and began to teach her new bitch.

Quite literally, in fact. Even when Carmella finally pushed forward beginning the slow, torturous process of forcing that little booty to accept something it wasn't designed to, The Princess of Staten Island made sure to take things easy on The Princess of Pop, just as she'd promised. Sure, taking five inches of girth wasn't exactly the Webster definition of "easy", but with the prior preparations, a little more lube, and Carmella's guidance, Ariana was more than fit to handle it. At least, once she got past the worst of things.

Naturally, that worst included her virgin, or rather formerly virgin, butthole opening up at least five inches just to fit that massive cock-head up her cute chute. Which was painful, mostly because of her lack of experience. But also, Ariana couldn't help but notice that it wasn't as painful as she first thought it would be. And maybe that was because of the adrenaline rush she was currently experiencing, or attributed to the freshly supply of lube that, with a bit more elbow grease, finally helped that tip pop into her backdoor. Either way, her expectations had not been met; a welcomed surprise. What was not surprising, however, was Carmella's reaction to officially plugging Ariana's booty, something she just HAD to brag about.

"Ooh fuck, how's that feel, Pop-Bitch? Huh? How's it feel to lose your butt cherry? 'Cause, I know it feels pretty fucking great to take! Hahahahahahaha...yeah, there it is! Mine! All mine! I got Ariana Grande's asshole cherry! God, I can't wait to hear what my other bitches are gonna think! Some of them are really big fans of yours, Ari! Bet they'll love you even more after they find out you're a naughty little butt bitch, just like them!"

"W...Wait-fuuuuuck...y-you can't be serious...right? You can't tell a-anyone about...this," Ari insisted, but with a cock officially up her ass, just itching to add some inches, her argument has very little ground to stand on. Especially when Mella had gotten her to comply so naturally.

"Oh, don't worry, hoe. I won't tell anyone who matters that I own the cutest fucking little butt in the world...at least not until I'm ready, anyway. Because if I-oh God, if I do that, then every top in the WWE's gonna want to share this little booty, Ari! And I never, ever....EVER," Mella barked, emphasizing the last EVER by slowly pressing on, continuing her folded missionary-fueled trek inside of that uncharted tunnel as she finished, "Wanna share your butt with anyone!"

Ariana was primed to respond, but that sharp thrust immediately reworked any sort of calmness inside of her bum into pure chaos, to the point where Grande wasn't able to yap back several moments after the fact, while Mella was still filling her up. "D-Don't tell anyone...e-ever! N-Nobody can know a-about this," Ari cried back, feeling more and more full with each passing second, naturally because Mella was working with such a large strap-on cock, but also because that cute little poop chute was just so, SO tight.

In retrospect, five inches of girth was probably far too challenging for such a tiny girl; Mella understood that much. But, Ariana was taking it well, or at least as well as she probably could given the circumstances. It was definitely painful, the worst of which was etched all over that famously gorgeous face of hers, but Mella continued to give, only for Ariana to hunker down and hold her own. In reality, Ari was more worried about the prospect of these shady and vile happenings getting out than anything else, a fact that probably helped make the pain as unnoticeable as possible.

Not completely silent, but nothing a bit more lube couldn't fix, Mella reaching for the bottle as she got about halfway in, bringing her hip motions to a brief stop to apply another heaping helping to the area of action, replying, "Did you forget that I can and will do whatever the fuck I want?"

Ari quickly looked away, obviously blushing, and answered softly, "No."

"No...what?" Mella growled, tossing the lube bottle aside again, hoping that she wouldn't need it again. Several seconds passed for Ari realized that Mella was looking for a very specific response, and another several after the proper response actually worked its way into her diluted brain.

"No...my...Money Mistress," Grande expressed, remembering that Mella wanted to be addressed that way going forward after her last big blow-up.

"Aww, good bitch! See, doesn't it feel good to submit to a real woman? Mmmmm....yeah, it just feels right, huh, Ari? You, giving up your little butt, calling me your Money Mistress? They almost feel as right as this..." Carmella lingered as Ari looked on, dazed and confused by what she meant by "this". At least, until Money Mella elaborated.

"Yeah...that's every inch up your fucking asshole, Pop-Bitch! Every goddamn inch! Nothing feels as right as that! Hahahaha!!"

"H-Huh? E-Every inch?" Ariana croaked, her entire body weak and lifeless. "No way! No way!" Despite Mella's insistence, the shock and awe of experiencing first-hand how skillful The Staten Island Princess is with a strap-on left quite the effect on little Ari.

"Oh, yes way, bitch! Yes, mother-fucking way, all the way, right up your butt!" Mella gloaded, taking a victory lap of sorts as she soaked in the surreal sight of the immense mass of her cock buried into the deepest depths of Ariana Grande's esteemed bowels. "See, bitch? I told you this hot lil' booty of yours was made to be fucked!"

Grande whined and cried, and her face was a wincing mess despite its natural gorgeousness. But in reality, the ease at which her butthole welcomed that dick shouldn't have been a surprise. Noted several times throughout the night, both by Mella and herself, Ariana had found enjoyment every step of the way. Every new, vile act, each completely different with an unique set of reservations for Ariana to overcome, all conquered in the name of pleasure. And while having a ten-by-five monster jammed up her pooper wasn't on the "OHMIGOD" end of the pleasure spectrum quite yet, Ariana's pussy was still as wet as ever.

Grande was still leaking, still spewing sex like a garden hose because, truth was, she didn't hate it. The feeling was certainly new and strange, much like the previous ass-play, and definitely far from painless. But the smallest of pleasure seeds had already been planted, and based on Carmella's previous assessments, Ariana couldn't argue that the watering and growing of said seeds was inevitable. Now...admit that even the smallest part of her could possibly enjoy something as dirty as getting her asshole pounded? Hell-to-the-no!

Hell, if ever asked once all of the debauchery was over, Grande would still probably deny even admitting that she ACTUALLY begged Carmella to fuck her ass. You know, despite the fact that she literally begged Carmella to fuck her ass? But of course, what choice did she have, right? Money Mella was still fully in control and absolutely not taking no for an answer, right? It didn't matter that, in that moment, with that moon-walkin', trash-talkin' goddess's body on top of her's, keeping her folded like an accordion, Ariana was completely spellbound by the woman she so easily referred to as her "Money Mistress". But again, if pressed, little Ari would deny the plausibility and genuineness of that, as well.

However all of her bratty attitude and childish delusions were bound to wash away eventually, especially when Carmella finally began to fulfill her destiny, slowly extracting that massive shaft and beginning the process of properly pounding Pop-Bitch's pooper. Immediately, Ariana's trademark tune, or whatever was still left of it, became even harder to maintain as that stunning rod began to slither around a bit more consistently, pumping in and out of that delicious little butthole. Of course, Carmella was long-dick stroking from the jump; no, that would've been a rookie mistake.

For all of the talk about breaking bitches and making them fall in love with getting their asses wrecked, Carmella understood that taking care of an inexperienced butt was so incredibly important, partly because of etiquette but also, and especially, because an anal bitch prospect could quickly turn sour if things ever became too much. Mella was a generational top, no doubt, with all of stats in every category maxed to the gord. But it took more than just big talk and a big cock to make bitches swoon the way she has in the past. Usually.

Sure, Mella's broken a number of bitches with ruthless ass-fuckings, and even broken one of her most loyal bitches, Brie Bella, without even fucking her once! But, a skilled top would never expect such an inconsistent phenomena to become the norm, nor would they even risk attempting such a ridiculously incredible feat with a peach as prestigious as the one Carmella's hips were currently smacking into every few seconds.

This ass? That pair of beautiful, tanned cheeks, equal parts plump and perky on such a petite package? Absolute heaven on the eyes and heaven to fuck as well; Miss Grande's as sexy as she is vocally talented. The clout alone that Mella could potentially receive from owning Ari's sweet Italian cheeks was worth all of the money and effort to get here, not to mention the high of turning such a famous babe into her personal sex doll, a high that already was working its way into Carmella's favorite topping moments ever.

And how could it not? Had Charlotte Flair ever fucked Ariana Grande? Had Ronda Rousey? Maybe a bit more likely for the latter, but according to Ari herself, the answer was still no. Truly, Carmella was the one and only woman to fuck Ariana Grande's perfect little bubble booty. Nobody, not one of her co-workers or any potential undercover tops in Hollywood could lay claim to such an incredible distinction. And thus, getting overzealous and pummeling that cute peach from the start wasn't on Mella's cards.

No, if there's one thing Carmella is besides arrogant, it's money. So, so money in every aspect of her luxurious life. So pump she did with small, manageable strokes for that tight, unpracticed hole until the time was right. Seconds, minutes, several of both passed and it didn't matter. Mella didn't adjust her speed and she never gave Ariana more than half of her huge cock until she deemed the "Side to Side" singer ready for more. Until The Money Mistress received her verbal cue to proceed in the form of a single, soft, solitary moan slipping from that petite goddess's plump, red lips.

Such a small sign was immediately gobbled up by the mighty Money Mistress, proof that her theory regarding Ari's inevitable and permanent transformation from pop-star to Pop-Bitch was already taking shape. That lone moan, barely audible by itself, wouldn't even have been heard by a lesser top. Lesser tops would've needed more to follow, and luckily for them, if place-swapped with Mella, those moans did come shortly after. But, they acted independently and unnecessarily. Because Carmella wasn't a lesser top, she was THE top, THE best butt-fucker and bitch-maker the world over, and her well-trained ears found that small cry, that desperate plea for more like an expert detective finds a lead.

Ariana wanted more, she wanted every inch pumped into her perky peach pronto. Maybe she was too stupid, or proud, or drunk to admit it. To admit that someone who she deemed less famous, rich, and talented than her was fucking her asshole and she was absolutely loving it, but also knew that she needed more. A bitter pill to swallow for the diminutive diva but, thankfully, a bill she got to swallow in solitude, as Mella took the cues and began plunging more of that rubber rod into Ariana's backdoor. And naturally, she couldn't help but gloat.

"Theeeeeeere you go, Ari. There you fucking go, bitch! How's that, huh?" Mella pushed, hoping to hear a bit of enthusiasm beyond some uncontrollable moans, but Ari still wasn't budging. Which, of course, didn't stop Mella from trying again. "Oooh, you feel your Money Mistress, don't you, Ariana? All deep in your little butt? You take it SOOOOOO good for me, is this really your first time?"

That last line managed to get the type of response Mella was looking for.

"Y-Yes," Ariana whimpered in between lustful groans, her big, brown eyes hazy, practically glazed over. "It's my...my...first...I swear."

"You're first cock up your butt?" Mella purred rhetorically, dicking that perfect booty down the way only she could, with a stamina and vigor that plunged every inch deep into Ari's heavenly bowels in one fluid thrust, and removed them just as quickly, only to repeat the process again and again.

"Y-Yes," Ari weakly agreed, hanging on every motion, completely and utterly putty, lost in Carmella's hungry, predatory gaze. And, surprisingly, the acclaimed pop and R&B superstar found that gaze coming closer and closer, Mella's pretty face drawing in until it sat mere inches away from Ari's. An easy feat thanks to how foldable and fuckable Ariana Grande actually was; a true sex doll come-to-life. And just as easy was what came next, Mella proving that every action she performs, every step she takes, has a purpose, The Money Mistress pressing her full lips down on Ariana's as she rammed her rod up that cute chute. And unsurprisingly, the Grammy award-winning artist immediately melted into the kiss.

No bratty attitude, no complaining or whining. Ariana welcomed those lips with open arms, the perfect distraction from all of the damage that Mella was causing her hip movements. Though, the damage wasn't on a physical level; it was purely mental. The mental toll that Carmella's expert ass-buggery was inflicting...it was incredible that Ariana had managed to endure as much as she has. But, the ease at which she welcomed Carmella's lips and offered her own in equal measures was proof that some cracks had already begun to form.

The kiss, a surprisingly passionate embrace from a pair of women who've spent their entire short, shared history at odds with one another. Passionate, until broken out of necessity, their lips briefly parting ways so Ariana could continue to moan as her asshole was stuffed. Before long, the process of kissing and breaking around Ari's lustful purrs became a recurring hit, a less-sordid sight to accompany the vulgarity on display as Carmella had her way with the chart-topper's forbidden passage. They'd kiss, pressing their plump lips together and even allowing their tongues to mingle every now and again until a particularly sharp thrust into that tiny tush sent the little sex bomb reeling, before she'd undergo a brief recovery period and repeat the process all over again. Poetry in motion, the most comfortable either woman had felt all night, unironically in the roles they were both meant to play: Carmella on top, and Ariana at the very bottom. And honestly, that dynamic in and of itself was absolutely perfect.