My Taboo Harem!-Chapter 493: Cassiopeia’s First Anal (r-18)

A/N: Content Warning: This next Chapter contains explicit anal play and penetration. If that’s not your thing, feel free to skip ahead. The rest of the story continues after the scene.

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Phei’s fingers buried back knuckle-deep in her dripping cunt after the toy settled in her other hole... three thick digits curling and pumping in slow, relentless thrusts, pads dragging molten fire along her fluttering walls while his thumb rolled merciless, slick circles over her swollen clit.

The fat pearl throbbed visibly under the pad—dark-red, engorged, glistening with her own cream—pulsing in time with every brutal curl inside her.

Cassiopeia’s hips bucked wildly—ass clenching hard around the pink plug still seated deep, thighs quaking so violently her knees nearly gave.

Her cunt spasmed and gushed fresh slick down his knuckles in thick, viscous rivulets that dripped steadily onto the floor in warm, sticky puddles, pooling beneath them in a glossy mirror of her surrender.

He twisted the plug once more—slow, deliberate grind—making her virgin asshole stretch and flutter around the silicone, the tight pink ring clinging desperately to the flared base like it never wanted to let go.

Then he pulled it free with a wet, obscene pop—her asshole gaping open pink and empty for a long, aching heartbeat, the stretched rim winking shut and open again in helpless spasms, slick strings of her own cream stretching from the toy to her ruined hole before snapping wetly against her trembling cheeks.

At the exact same moment he shoved his pants and boxers down to mid-thigh—cock springing free, impossibly thick and veined, the fat crown flushed angry red and leaking thick ropes of pre-cum that slung in sticky arcs onto her ass cheeks, painting glossy white streaks across the plush, jiggling globes.

Cassiopeia felt it first... his cock for the first time on her bare private skin, the heavy, scalding slap of his monstrous girth against her cleft—heaviness hot like molten iron settling into the crease of her ass, hot and unyielding, veins pulsing thick against her sensitive rim.

Then the warmth bloomed—scorching skin-on-skin contact, the ridged underside dragging slow along her crack as he adjusted his stance, pre-cum smearing in glossy trails down her inner thighs to mix with the cream already leaking from her empty cunt. 𝒻𝑟ℯℯ𝑤𝑒𝑏𝑛𝘰𝓋𝑒𝓁.𝒸𝑜𝘮

"Fuck—Phei—your cock—" she gasped, voice cracking raw and wrecked, asshole clenching hard at the feel of him nestled there, the sheer size of him making her virgin ring flutter in panicked, greedy anticipation.

He squeezed her ass cheeks together—palms full of plush, trembling flesh—trapping his cock between them like a hot, veined vice.

The supple globes molded around his shaft, jiggling firmly with every shift, her slick from earlier coating him in glossy sheen that made every glide audible: wet schlick-schlick as he rocked forward, pre-cum bubbling and frothing at the base where his crown kissed her puckered hole.

Then he thrust.

Slow at first—hips rolling forward, cock gliding through the tight channel of her squeezed cheeks, the flared crown nudging her asshole on every upstroke, veins scraping fire along the sensitive cleft.

Her ass rippled in response, supple cheeks bouncing and wobbling wildly with each drag, slick schlicking audibly as his pre-cum mixed with her earlier cream, leaving sticky strings webbing between cheek and shaft every time he pulled back.

Cassiopeia lost her mind.

Her head thrown back, moans turning to sharp, broken cries—thighs trembling violently, cunt fluttering around his still-plunging fingers, clit throbbing under his thumb’s cruel rolls.

The very thought of him finally penetrating her pussy—stretching her wide, filling her deep—consumed her.

For the first time since arriving, the binding rune on her bracelet faded from her mind. Fuck the soul-bind.

Fuck the plan.

She just wanted him to fuck her—ruin her holes, claim her completely. The bind could come later—after he’d made her scream and squirt and break on his cock.

"Phei—please—your cock—fuck my pussy—need it—need you inside me—"

He thrust harder between her cheeks—faster now—ass flesh jiggling wildly, bouncing up and down with every snap of his hips, the wet slap-slap of his heavy balls against her thighs echoing obscene.

Wet mixture of he cream frothed along his shaft from the friction, bubbling white at the base where her slick leaked down from her cunt to coat everything in glossy white rings.

He let go finally—palms spreading her wide again—cock still nestled hot and heavy in her crack, the crown kissing her asshole with every throb.

He reached for the oil on the nightstand—poured a thick, warm stream straight onto her ass crack.

It traveled slow—glossy rivers sliding down the cleft, pooling around her stretched rim, trickling over the puckered ring until it shone slick and ready, dripping down to mix with the cream already coating her inner thighs in shiny sheets.

Phei lined up.

Just the crown tip—impossibly fat, flared head—pressing to her oiled asshole.

Cassiopeia screamed—pain and pleasure ripping through her like lightning, louder and sharper than ever before.

The massive crown threatened to split her—stretching the tight ring thin and angry-red around the very edge, veins pulsing against her rim, heat blooming unbearable as it nudged for entry.

"Phei—fuck—too big—hurts—oh gods—it burns—"

He pushed further—slow, relentless pressure—the crown breaching her with a wet, stretching pop as the rim surrendered, clamping tight around the ridge.

Pain bloomed hot and fierce—tearing, burning, her asshole stretched impossibly wide around the first thick inch, the ring clinging desperately, fluttering and spasming as untouched walls yielded to the invasion.

Cassiopeia’s knees buckled—body collapsing forward toward the bed—but Phei caught her for support and gentleness she did not expect him to show to her, arm banding around her waist, holding her up, ass impaled on that first devastating inch.

"Breathe for me, aunt," he said softly against her ear, his thumb still rolling her clit in tight circles, pinching the swollen pearl hard enough to make her cry out. "Let it burn. Let it stretch. You’re taking me so fucking beautifully—look how your virgin hole clings, how it flutters around my cock like it was made for this."

He pushed deeper—two inches now—her asshole stretching thinner, redder, the ring dragging along every pulsing vein as he sank inside.

Pain lanced sharp and hot—stinging fire that made her eyes water, thighs quake—but pleasure chased it, nerves exploding as his girth filled her completely, the heat blooming unbearable in her core.

Her cunt spasmed on nothing—squirting a forceful jet straight down her thighs, soaking the floor in hot arcs.

"Phei—fuck—it hurts—burns—but don’t stop—please—stretch my ass—make it yours—"

He kept pushing—slow, inch by inch—until half his monstrous length was buried in her virgin asshole.

The stretch was obscene—her rim stretched paper-thin and angry-red around his girth, clinging desperately, fluttering in helpless spasms as he held still, letting her feel every throbbing vein pulsing inside her.

He pulled back slowly—only two inches—watching her asshole gape pink and empty for a heartbeat, the stretched ring quivering and trying to close before he thrust forward again—three inches deep this time—making her scream raw and shattered.

"Too deep—fuck—too thick—hurts so good—please—more—fill my ass—claim it—"

He reached around—thumb finding her clit again—rolling, pinching, tugging the swollen pearl in cruel little twists that made her hips buck and grind back, forcing him deeper despite the burn.

Her cunt gushed in sympathy—slick squirting in messy jets every time he thrust, coating his balls, dripping down her thighs in thick, glossy rivers.

He fucked her ass slow and deep—long, deliberate strokes—each pull-out dragging her clinging rim outward in glossy, stretched rings, each thrust pushing deeper until the flared crown kissed her deepest walls, the burn melting into throbbing, overwhelming pleasure.

Her asshole fluttered and milked him greedily—clenching in rhythmic waves—pain and ecstasy twisting together until she couldn’t tell where one ended and the other began.

"Look at you taking me," he growled, voice rough with possession. "Virgin ass stretched wide and red around my cock—squirting just from having your hole filled. Such a good little slut for your nephew."

Cassiopeia sobbed—loud, broken—hips rocking back to meet every thrust, ass cheeks jiggling and bouncing wildly with each hilt-deep plunge, the wet slap-slap of his balls against her cunt echoing obscene.

Her clit throbbed under his thumb’s relentless pinching—fresh squirt jetting out in hot, forceful arcs every time he bottomed out, soaking his thighs, the bed, the floor in a wide, reflective lake.

He fucked her through it—slow, deep, owning every inch of her stretched asshole—until her screams dissolved into continuous, shattered wails, body convulsing, cunt gushing, ass clenching in helpless surrender around the cock that had finally claimed what no one else ever had.