Chapter 515: Eenie-Meenie-Miney-Mo

The room was a furnace of moans, wet slaps, and the creaking of the massive bed as Cassius rotated between the four bent-over women like a man possessed.

Isabelle’s back arched with every brutal thrust, Vivi’s tiny frame shuddered on loving strokes, Portia’s stern facade crumbled under savage pounding, and Diana melted into gentle, reverent worship.

On the sidelines, Nala, Aisha, Julie, and Skadi stood frozen, faces flushed crimson, thighs pressed so tightly together it hurt. They were sweating through their clothes, hearts hammering, eyes wide as saucers.

Julie was the first to break the stunned silence, letting out an awkward, breathless chuckle.

"Okay...I-I thought this was going to be awful. Like, painful. But look at them. They’re...they’re loving it."

She swallowed hard, eyes locked on Diana’s blissful expression.

"I’ve also known Lady Diana since I was a child. She used to visit my family, always so graceful, so gentle—like a literal saint. And now she’s moaning like an animal in heat, begging for more."

"...Who would’ve thought?"

Aisha nodded slowly, one hand unconsciously rubbing between her own legs through her skirt.

"Her daughter too...all the reports painted Vivi as the sweetest, most innocent angel in the estate. Everyone adored her. And now Cassius is wrecking that angel’s tiny little ass and she’s screaming for it."

She bit her lip, voice trembling.

"Why is this so hard to watch...and why am I so wet?"

Nala’s tail twitched nervously, her gaze flicking to Portia, whose strict, terrifying head-maid persona had completely dissolved into desperate, filthy pleas.

"I was honestly scared of Portia at first." Nala whispered. "Those sharp eyes, that glare—she looked like she’d scold you into the next life if you stepped out of line."

"And now she’s spreading her own ass, begging Cassius to ruin it. He really does have a way with women...I thought I was easy for letting him do whatever he wants, but...everyone here is the same."

But just then, Skadi, tail swishing, suddenly blurted out the question that had clearly been bothering her for a while.

"That’s all super hot and everything, but...how do they poop?"

Dead silence.

"Skadi, you absolute beast—shut up!" Aisha groaned, slapping a palm to her forehead. "You’re ruining the mood!"

"I swear I’m signing you up for etiquette lessons tomorrow." Julie pinched the bridge of her nose. "There are things you do not say out loud in company."

"But I’m serious!" Skadi blinked, genuinely confused. "They had those crystals jammed up there for so many days! You can’t just...poop around a butt plug, right?"

"I just want to know if they take it out every time? Put it back in? Or do the women in this mansion just not poop at all? I need answers!"

Nala opened her mouth, closed it, then whispered.

"...I kinda want to know too."

Aisha and Julie both rolled their eyes so hard it was audible, even though the curiosity was clearly gnawing at them as well.

Before anyone could pursue the logistics further, Cassius let out a deep groan and yanked his glistening cock free from Vivi’s tiny, wrecked hole to which she slumped forward with a delirious whimper, barely able to stay on her knees.

Meanwhile, Cassius stood there, cock throbbing, veins pulsing, precum dripping in thick strands from the tip. He was right on the edge of releasing it all.

But he wasn’t looking at the four exhausted women who had been taking him all night.

He was looking straight at Nala, Aisha, Julie, and Skadi.

And in response, four sets of eyes widened in pure, unfiltered panic.

"W-Why are you looking at us like that?!" Nala squeaked, tail curling around her.

"Yeah!" Julie waved her hands frantically. "Focus on them! They’re the ones who waited weeks for this! Finish them off!"

Skadi, ever helpful and slightly too eager, dropped to her knees instantly.

"If you need to cum, I can take it in my mouth! I’m ready to serve, Master!"

Cassius’s grin turned absolutely feral.

"Sorry, pup." He purred, voice dark and dripping with hunger. "This load isn’t for your mouth."

He stroked himself once, slowly, eyes raking over the four of them as he said,

"You see, fucking the same four trained, experienced asses and dumping my load inside is...predictable. Boring." His voice dropped to a dark purr. "What I want is a fresh, virgin asshole that’s never had a cock inside it before."

"One that’s going to fight me, clench around me, scream for me while I force it open and paint it white from the inside. That’s exciting."

He glanced back at the bed where Isabelle, Portia, Diana, and Vivi lay in a trembling, cum-drunk heap.

"You ladies don’t mind if I break in some new territory tonight, do you?"

Four weak, blissed-out nods and a chorus of slurred "No, Young Master..." was all the permission he needed.

"You heard them." Cassius turned back to the four frozen women, cock bobbing heavily with every heartbeat. "Strip. Bend over. Asses out. Now."

The command hit like a thunderclap.

Nala squeaked. Aisha’s knees buckled. Julie’s aura flickered like a dying candle. Skadi’s tail actually tucked between her legs.

"B-But—" Julie stammered. "We didn’t—we haven’t—"

"I wasn’t asking." Cassius’s eyes narrowed.

Hearing this, they knew they had no choice.

One by one, like they were moving through molasses, clothes hit the floor and revealed all of their asses.

Julie first—her proud, round, athletic ass the biggest and firmest of the four, muscles flexing as she tried and failed to hide her trembling.

Skadi next—her bouncy, plush wolf-tailed rear jiggling with every nervous shift, pale skin already flushed pink.

Nala third—half blue skin, half shimmering white scales forming the most exotic, breathtaking butt any of them had ever seen, the transition from soft flesh to scaled perfection making it look like a work of art.

And finally Aisha—tiny, soft, and impossibly tender, almost as petite as Vivi’s, looking far too delicate for what was coming.

They climbed onto the edge of the bed beside the four exhausted women, bent over in a perfect line of virgin asses presented to their master, cheeks spread by shaking hands.

And just like that—

Eight trembling holes in total—four experienced and dripping, four terrified and untouched—all waiting for Cassius to decide whose innocence he would claim first.

Eight pairs of eyes also looked back at him over shoulders: four blissed-out and encouraging, four wide, pleading, silently begging for mercy they knew they wouldn’t get.

Julie was the first to try to wriggle away, as she looked back over her shoulder.

"C-Cassius, wait! Can we not do this today?" She pleaded, voice trembling. "It’s literally our first official day as part of the family! I don’t want my very first memory to be...losing my anal virginity!"

"Can’t we schedule this for, I don’t know, next week? Next month? Next year?"

Nala, Skadi, and Aisha all nodded frantically in perfect unison, tails and ears twitching in desperate agreement.

Cassius just tilted his head...and shook his head.

"Sorry, ladies. This isn’t just because it’s fun. Though, let’s be honest—fucking gorgeous virgin asses is incredible."

They squirmed.

"But..." He continued, voice turning serious. "It’s actually a necessity. Next time I leave the estate, I might not be able to take any of you with me. And when that happens, every single one of you will be wearing a plug just like these four did, so you never forget who you belong to."

He gestured to the exhausted, smiling women beside them before going on to say,

"Problem is, those plugs have to be custom-fitted. Too small and they fall out. Too big and they hurt. So..."

He picked up his throbbing, slick cock like it was a measuring stick and gave it a lazy stroke.

"...I need accurate measurements. And the most precise tool I have is right here."

Four sets of eyes widened in horror.

"Y-You’re going to measure our assholes...with your dick?!" Nala squeaked.

"Deep, thorough, and repeated measurements." Cassius confirmed cheerfully. "One full thrust per subject should give me everything I need. Totally necessary. No way around it."

Before anyone could protest further, he stepped forward, running warm palms over each presented rear like he was browsing fruit at the market.

"But who should I choose...Julie’s big, firm, masterpiece...Skadi’s bouncy, jiggly special...Nala’s exotic half-scaled work of art...and Aisha’s tiny, tender little thing that looks like it’s never been touched..."

He slid a teasing finger around each rim in turn, making them all shiver and push back instinctively.

"I genuinely don’t know where to start."

Then his face lit up.

"Oh! I know the fairest way."

He grabbed his cock by the base and began a singsong chant, slapping the heavy, slick length against each ass in rhythm.

"Eenie—" Smack on Julie’s round ass.

"Meenie—" Smack on Skadi’s bouncy one.

"Miney—" Smack on Nala’s scaled perfection.

"Mo—" Smack on Aisha’s tiny, tender cheeks.

He went through the entire rhyme, cock bouncing from ass to ass, the wet thwacks echoing obscenely.

"...if he hollers, let him go—eenie meenie miney MO!"

The final slap landed squarely on Aisha’s petite rear.

And instantly, Aisha’s head snapped up, eyes wide with dread.

"N-no, wait—!"

Aisha’s eyes went huge. But Cassius grinned like a cat who found a helpless mouse.

"Destiny has spoken. Aisha, remember that bet you lost earlier? And how you kept saying when I took your first time ’not the ass, anything but the ass’?"

"Looks like the goddess herself is delivering your cute little hole to me on our very first night."

"C-Cassius, please!" Aisha tried to scramble forward. "It’s too small! You’ll split me in half! Pick Skadi—she’s bouncier! Or Captain—she’s bigger! Anyone but—"

"Hey! Don’t volunteer my ass!" Skadi immediately yelped.

But Cassius just ignored her, before sliding one strong hand around Aisha’s slender neck and pressing her chest gently but firmly into the mattress, pinning her in place.

"Sorry, little one. Rules of eenie-meenie-miney-mo are sacred."

He then dropped to his knees behind her, spread her soft cheeks wide, and dragged his tongue in one slow, wet stripe over her virgin-pink ring.

"Ah—Ahhh—Ahhhhh!"

Aisha let out a shocked, high-pitched moan, legs kicking helplessly.

"Fuck, you taste sweet." He groaned against her skin, licking again, deeper, swirling around the fluttering hole until she was shaking. "Been waiting for this tiny ass for a while."

The other three watched in horrified fascination, equal parts relieved it wasn’t them yet and guiltily aroused.

Finally Cassius rose, lined the fat, glistening crown of his cock against Aisha’s impossibly small entrance, and locked eyes with her over her shoulder.

"Ready, Aisha? Ready to lose your anal virginity to the man who owns you?"

She could only manage a whimper, face buried in the sheets, tiny hands clutching the fabric.

Cassius pushed.

Slowly, relentlessly, the thick head forced past her trembling ring, stretching her open in a way that looked almost obscene.

"Nyaaaaa—!" Aisha’s back bowed, a strangled cry tearing from her throat as inch after inch disappeared inside her untouched ass.

And the second he bottomed out, hips flush against her soft cheeks, Cassius’s control snapped.

He roared, cock pulsing violently, and unleashed everything he’d been holding back from the last four women.

"Schlurp!♡~ Splish!♡~ Splat!♡~ Squish!♡~"

Thick, hot streams of cum flooded Aisha’s tiny, virgin passage in powerful spurts, painting her insides white, marking her in the deepest way possible.

"Ahhh!♡~ I-It’s inside!♡~ I can feel it filing me up!♡~ So hot!♡~"

Her eyes rolled back, a broken wail escaping her as her whole body shook with the force of it, while Cassius stayed buried to the hilt, grinding slowly, making sure every drop stayed inside.

When he finally pulled out with a wet, obscene sound, a river of cum immediately began to leak from her gaping, twitching hole.

"Measurement taken...I’ll make you a special plug tomorrow with your favourite colour."

He patted her ass affectionately, voice husky before looking at Julie, Skadi, and Nala.

They were currently staring in open-mouthed horror as Aisha slumped forward, delirious, a dazed little smile on her lips and Cassius’s seed dripping steadily down her thighs.

And seeing this, he got excited and wiped his cock on her cheek, then turned to the remaining three with a evil grin.

"Now, for the next round of measurements...Who’s next?"