Diana's anus throbbed, the lingering sensation of Cassius's finger still pulsing through her, intensified by the wet, smacking sounds of his passionate kiss with Vivi behind her. Bound and gagged with Vivi's underwear, the musky taste of her daughter's pussy flooding her mouth, she was lost in a haze of arousal.

"Squelch!♡~"

But her focus shattered when Cassius's finger suddenly withdrew, leaving her anus quivering, only to be replaced by the cool, round edge of a pill pressing against her slick rim.

She gasped into the gag, her eyes widening as she craned her neck to look back, meeting Cassius's sneaky, knowing gaze.

Without a word, he was pushing the suppository into her anus, the lubricated entrance offering little resistance after Vivi's spit had made it so slippery.

"Plop!♡~ Thwap!♡~"

The pill hesitated at her rim for a fleeting moment, caught by the tight ring of muscle, before sliding inside with a soft, wet pop, her anus closing around it.

"Hmmm!♡~ Nnn!♡~ Haughh!♡~"

Diana moaned, the sensation bizarre yet thrilling, the small, hard object nestling deep within her spacious anal cavity. Unlike her pussy, her anus felt roomier, allowing the pill to shift slightly as she clenched her muscles, a strange, playful feeling, like a toy she could manipulate at will.

"Mmmph!♡~ Nnn!♡~" She whimpered into the gag, her ass lifting instinctively, expecting Cassius to follow with his finger, to push it deeper as he had with her pussy, her body eager for more of his touch.

But to her shock, while Vivi remained oblivious, lost in their heated kiss, Cassius reached for the box again, pulling out another pill and without warning, he pressed it against her anus, pushing it in with a thrust.

"Slosh!♡~ Glug!♡~"

Her hole resisted briefly, then yielded with another soft pop, the second pill joining the first inside her, the two small spheres bumping against each other.

Diana's eyes widened, her muffled gasp lost in the gag, her anus quivering as she felt the added weight, the strange fullness growing. Cassius's knowing look told her this was no accident, he was teasing her, playing with her body in a way that drove her wild, all while kissing her daughter, who had no idea of the audacious act unfolding.

"Cassius...Don't please." She tried to mumble through the gag, her voice a garbled plea, her ass shivering as he reached for yet another pill.

This time, he shoved it in without hesitation, his finger following to push it deeper, the intrusion making her anus pulse, the three pills now sliding against each other inside her.

"Schlurp!♡~ Splish!♡~"

Diana's body trembled, the sensation overwhelming, her pussy squirting a little onto the sheets as the fullness in her anus sent waves of pleasure through her.

She thought he'd stop there, her ass already feeling so packed, so strangely alive with the movement of the pills, but Cassius was relentless.

While Vivi's tongue danced with his, he grabbed two more pills, spreading her anus wide with two fingers, stretching her rim until it gaped, then pushed both pills inside together, like dropping parcels into a delivery box.

"Splat!♡~ Squish!♡~"

Diana's muffled scream vibrated against the gag, her anus stretching to accommodate the double intrusion, the pills slipping in with a wet squelch, joining the others in a crowded, sliding dance within her.

"Gloop!♡~ Drip!♡~ Splurt!♡~ Plop!♡~"

Five pills now filled her, their smooth surfaces rubbing against each other, lubricated by Vivi's spit and her own natural slickness, creating a sensation so intense she could barely process it.

"Thwap!♡~ Schlurp!♡~ Squish!♡~ Sploosh!♡~"

Every slight movement made them squirm, rolling against her inner walls, a perverse, pleasurable torment that felt so good yet so dirty she fought the urge to writhe, knowing each shift would only amplify the sensation.

Her bound hands flexed uselessly, her body arching, her pussy dripping as she surrendered to the overwhelming fullness, her butt a playground for Cassius's teasing.

Vivi, finally pulling back from the kiss, her lips swollen and glistening, caught the exhausted, flushed look on her mother's face. Her breath hitched, concern flashing in her eyes as she turned to Cassius.

"Young Master, what's wrong with Mother?" She asked, her voice trembling with worry. "Why does she look like that? What...What happened?"

Cassius's smile was sly, his hand stroking Diana's ass like he was petting a prized animal.

"Nothing's wrong, Vivi." He said, his voice smooth and confident. "It's just that I've already pushed the suppositories in and not just one, mind you...five."

"I wanted Diana to really feel it, to understand every sensation of having her asshole stuffed with pills...It's all for her education, so she knows exactly how it works." His words were casual, but his gaze was teasing, daring Vivi to react.

Vivi gasped, her eyes widening as she looked at her mother, whose body trembled, her anus clenching around the hidden pills, her face a mask of overwhelmed pleasure and shame.

"F-Five pills?" She whispered, her voice filled with shock. "Mother, is...is she okay? Is it safe to have so many inside of her? What if...what if it hurts her, or...or has bad effects?" Her concern was genuine, her hands hovering as if unsure whether to touch her mother or pull back.

Cassius chuckled, his hand gliding over Diana's plump cheeks, giving them a gentle squeeze.

"She's fine, Vivi." He said, his tone reassuring. "Her asshole took those pills like it was made for it. I snuck them in while you were...distracted, and it went so smooth, she didn't even fight it."

"...Her greedy little hole just ate them up, no resistance at all."

He leaned closer, his fingers brushing Diana's anus, making her whimper into the gag.

"Want to see them?...I can spread her open right now, show you those pills nestled in her pink, wet insides. It's a hell of a sight."

Vivi's cheeks burned, her eyes darting to her mother's trembling ass, then away, her embarrassment overwhelming.

"No, no, Young Master!" She said quickly, shaking her head, her voice high with panic. "There's....there's no need, really! I believe you, I just...I'm worried about Mother. Five pills...it's so much. What if it's bad for her health?" Her concern deepened, her gaze softening as she looked at Diana, her mother's bound, gagged form tugging at her heart.

"Don't worry, Vivi." He said, his voice calm and confident. "The effects of these pills don't stack up like that. No matter how many she takes, it's perfectly safe. Think of it like...candy, slipping into her body, dissolving nice and slow, giving her what she needs...She's fine, I promise."

His words were meant to ease her fears, and Vivi's shoulders relaxed slightly, a flicker of relief crossing her face, though a trace of doubt lingered in her eyes.

The reassurance about the pills calmed her racing heart, but before she could fully settle, Cassius's tone shifted, a knowing glint in his eyes that sent a chill through both mother and daughter.

"There is one problem, though..." He said, his voice low and ominous, making them both shudder.

Diana's tearful eyes met his, her bound hands flexing as Vivi's breath hitched, her voice hesitant.

"What...what's wrong, Young Master?" She asked, her gaze darting between him and her mother's trembling form.

Cassius looked at Diana, his expression teasing yet intense.

"When I pushed the pill into her pussy, it was easy." He said, his hand brushing her ass, making her anus clench around the pills. "That hole's nice and roomy, took my fingers deep without a fight...But this tight little asshole?"

He pressed a finger against her slick rim, drawing a muffled whimper from her gag.

"It's so fucking tight, I could only push the pills so far. They need to go deeper, all the way to the core, or they won't work right. And for that..."

His gaze flicked between them, a bright smile curling his lips.

"I might need an apparatus...Something long, rod-shaped, thick enough to stir those pills up, push them where they belong."

Diana's eyes widened in panic, her body jerking as she realized exactly what he meant.

She knew that 'apparatus' all too well his massive, throbbing cock, and the thought of it plunging into her already stuffed anus sent a surge of fear and arousal through her.

She struggled against the restraints, wiggling her ass in a desperate attempt to roll off the bed, her muffled pleas garbled through the gag.

"Mmmph! No, Cassius!" She tried to cry, her tears welling as she shook her head.

But Cassius was unrelenting, his hands swiftly grabbing her hips, pinning her ass down with ease, her struggles futile against his strength. He ignored her pleas, his middle finger even plunging deep into her anus, hooking inside her tight, slick walls, pulling down to anchor her in place.

"Squelch!♡~"

The intrusion made her gasp, her anus clenching around his finger, her body trembling in submission, her pussy squirting onto the sheets as the sensation overwhelmed her.

"Stay still, Diana." He said, his voice firm but teasing. "You're not going anywhere...This asshole needs a proper stuffing and you know it."

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