Shy to Surrendered – Wild Sissy Penthouse 🔥

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Sissy’s Total Surrender to Bulls and Bliss 💋

Evenings like this one pulsed with electric hunger in Sophia’s sleek downtown penthouse, the city skyline glittering like shattered diamonds beyond the floor-to-ceiling windows. Jamie—once plain old Ethan, now her quivering sissy pet—fluttered around the kitchen, heart hammering as he plated the roasted lamb with rosemary crust. Tomorrow’s dinner party loomed massive, a ritual of ruin where he’d finally shatter his last virginity to Rocco, the burly bi beast, while Darius, that towering ebony god, claimed Sophia again. But tonight, alone with her, Jamie felt the week’s buildup churning inside him like molten lava.

Sophia lounged on the leather chaise, her crimson silk robe slipping open to bare one full, heavy breast, nipple stiff in the cool air scented with jasmine incense. “Jamie, darling,” she purred, voice husky from last night’s moans, “show me how the plugs have stretched that greedy little boycunt of yours. Crawl over here.”

He dropped to all fours, the click of his 4-inch stilettos echoing on marble tiles. The jeweled plugs—Sophia’s “graduation gifts”—had escalated from pinky-sized to a fat, glittering ruby monster by Thursday. Each insertion had been agony laced with bliss, her fingers probing deep, whispering filth while his caged clitlette dribbled uselessly. Last night, she’d swapped it for her strap-on, that veiny black silicone brute mimicking Darius’s wrecking tool, pounding him till he squealed like a bitch in heat.

Now, peeling down his satin boy-shorts, Jamie arched his back, presenting the winking, lubed rosebud. Sophia’s nails raked his pale cheeks, parting them wide. “Mmm, so puffy and ready. Rocco’s thick Italian sausage will slide right in tomorrow, won’t it? And you’ll thank him while Darius splits me open.”

Her tongue flicked out, hot and wet, circling his rim. Jamie whimpered, tasting salt on his lips from biting them. The memory flooded back—Tuesday’s shopping trip, new scene of public shame. She’d dragged him to that seedy adult boutique downtown, making him try on sheer babydoll lingerie in the dim fitting room. “Twirl for me, sissy,” she’d hissed, while the clerk—a smirking tattooed punk—watched through the curtain crack. Jamie’s face burned as she bought the sluttiest set: crotchless panties in electric blue, a garter belt framing his caged nub, and a choker screaming “BBC Slut Trainer.” Back home, she’d fucked his throat with the new vibrating plug remote in hand, buzzing him to the edge while he gagged on her spit-slick fingers.

“Enough teasing,” Sophia murmured, rising with feline grace. “Bedroom. I need your tongue worshipping my cum-dump before guests arrive.”

Jump to Chapter 2 | Jump to Chapter 3

Plugging the Path to Perversion 🔥

Flashback to Monday morning scorched Jamie’s mind as Sophia led him upstairs, her ass swaying hypnotically. He’d woken in the guest loft—frilly canopy bed, walls papered in pink lace—slipping into lavender thong and babydoll that hugged his smooth, shaved body. No more man mornings; Ethan was buried deep. Creeping to the master suite, he’d found Sophia tangled in sheets with empty wine glasses, the air thick with musk and her solo vibrator buzz still faint.

“Wake me proper, petal,” she’d mumbled, eyes cracking open. Jamie knelt, inhaling her tangy sleep-scent, and lapped delicately at her swollen folds, remnants of her midnight play coating his tongue like forbidden honey. She stretched, moaning low, then nodded to the nightstand. “Now Daddy’s cock. Gentle. Earn your breakfast.”

There was no Arno here—just memories of past lovers. But Jamie imagined Darius, that 6’6″ colossus with skin like polished obsidian, veined shaft thick as Jamie’s wrist. Crawling under sheets, he nursed the phantom, lips stretching around air, till Sophia yanked him up. Breakfast was avocado toast and her dripping snatch for seconds.

By Tuesday’s boutique humiliation, plugs began. Sophia unpacked the set in their sunlit living room—crystal gems graduating to fist-width. “Bend over the coffee table, sissy. Guests tomorrow expect a well-prepped hole.” Lube squelched cold, her gloved fingers scissoring wide. The first popped in easy, a delicious pressure. But the second? Jamie bucked, tears smearing mascara, as it locked behind his ring. “Breathe through it, whore. By Friday, you’ll beg for Rocco’s girth.”

Walk around plugged all day, her rule. Grocery run turned torture—each step jiggled the jewel against his prostate, clitlette weeping into panties. Evening brought reward: Sophia on the velvet ottoman, legs splayed, him slurping her to gushers while the plug vibed remotely. “Taste how wet big cocks make me? Yours never did.”

Thursday exploded it all. Home from her gallery job—curvy brunette locks tousled, paint-splattered blouse—she stripped him raw. “No cage tonight. Dinner naked, then ass up.” Jamie stirred pasta in the buff, cocklette twitching free but ignored. Post-meal, blindfolded on the king bed, lube drizzled endless. First, Mich’s mimic: 9 inches girthy white, her hips snapping brutal. “Feel that, future slut? Rocco’s waiting.”

He groaned, prostate milking dry spurts—no full cum, just waves crashing. Then the swap: black behemoth, 11 inches, 3 thick. “Darius preview.” It breached slow, burning bloom to ecstasy. Sophia railed merciless, sweat-slick bodies slapping, her tits bouncing wild. “Cum for Mommy’s monster!” Jamie shattered, prostate orgasm ripping screams, ass clenching vise-like.

She collapsed atop him, panting. “Good girl. Now eat me out—earn a pity pump.” His tongue delved her flooded gash, clit throbbing under assault. She bucked, squirting tart nectar down his chin. “Fuck me, Jamie. Prove you’re still my man.” On elbows, ass high, he mounted sloppy seconds. Two thrusts: boom, spent. Shame flooded as she sneered, “Clean your mess, loser. Cage time.”

Friday’s finale: largest plug sealed the deal, ass gaping hungry. New scene—video tease to Rocco and Darius. Sophia propped phone: “Boys, check Jamie’s progress.” Naked on knees, he demonstrated, plunging fingers in prepped hole while they jerked on cam, voices gravelly promising ruin. “Saturday, sissy. We’ll wreck you both.”

Back to Chapter 1 | Jump to Chapter 4

Dinner with Devils in Disguise

Saturday dusk bathed the penthouse in amber glows, jazz crooning soft from hidden speakers. Jamie primped in the guest bath—smoky eyes, ruby lips, blonde wig cascading waves. Outfit: sapphire cocktail dress hugging his padded curves, sheer stockings whispering up thighs. Underneath, the new “sissy specials”—hot pink lace, backless for easy access, front pouch tucking his nub downward like a girl’s slit.

“Practice peeing, slut,” Sophia had coached earlier, watching him squat over a glass, stream hissing through the flap. Perfect humiliation prep. Dinner simmered: oysters aphrodisiac-slippery, filet mignon oozing juices, chocolate torte for sinful close.

Doorbell chimed like fate’s gong. Jamie minced to answer, curtseying deep. Rocco loomed first—5’11” brick wall, inked arms bulging from tight tee, buzzcut and goatee framing a wolfish grin. Darius eclipsed him, mountain of muscle in crisp shirt straining buttons, dark eyes devouring. “Who’s the fresh pussy?” Rocco chuckled, palming Jamie’s ass.

Sophia swept in behind, bombshell in emerald micro-dress, tits spilling cleavage, hem barely grazing ass. “Meet Jamie, boys. My sissy bloom. Pour drinks—start with champagne fizz.”

Dining under chandelier sparkle, aromas of garlic butter and lust mingling. Jamie served starters, oysters gleaming on shells. “Suck ’em down like you’ll suck cocks later,” Sophia winked. He sat wedged between Rocco and Darius, thighs pressed hot.

Main course devoured with crude banter. “This lamb’s tender—bet Jamie’s hole is too,” Darius rumbled, voice like thunder rolling. Foot under table: Rocco’s toe probed Jamie’s crotchless panties, circling the tucked clit. Jamie squirmed, serving dessert with shaky hands, tiramisu cream mirroring his dripping bud.

Plates cleared, heat ignited. Darius yanked Sophia onto his lap, mashing lips bruising, hands mauling tits till dress ripped open. Rocco’s fingers invaded Jamie’s dress, pinching nipples through lace bra. “Bedtime, bitches,” Sophia gasped, leading the charge upstairs, heels stabbing carpet.

New beat: balcony tease en route. Pausing mid-stairs, Sophia bent over railing, city winds whipping her skirt up. “Appetizer, bulls?” Darius unzipped, unleashing the python—12 ebony inches, flared head weeping pearl. Rocco matched with 10 veiny white ropes. Jamie dropped, throats offered. Gagging symphony: slurps, chokes, balls slapping chins. Sophia ground on Darius’s face, juices pattering balcony floor.

Stripping the Shame

Master suite reeked of promise—saffron candles flickering, silk sheets turned down, restraints dangling coy. “Undress show, Jamie,” Sophia commanded. Dress pooled at heels, revealing slutwear. Guests howled approval.

He unzipped Sophia first, peel revealing thong biting her shaved mound. Then Rocco: tee peeled pecs etched like marble, pants dropped to free the bi-batterer, shaft curving wicked up. Darius last—trousers tented obscene. Briefs tugged: monstrosity sprang, slapping Jamie’s cheek with salty thwack. Both hands stroked, velvet steel pulsing, pre-cum glazing palms.

“Suck circle, sissy,” Rocco growled. Jamie alternated: Darius’s crown stretched jaws to ache, impossible depth; Rocco’s girth choked throat raw. Sophia orchestrated, fingering herself to squelch. “Watch how real men feed throats.”

Jump to Chapter 5

Impaled in Ecstasy’s Grip

Bed became battlefield. Sophia first victim: on knees, worshipping Darius’s obsidian pillar. Lips stretched translucent, throat bulging as she swallowed inch by impossible inch—practice paying off, nose burying in wiry pubes. “Fucking legend,” Darius grunted, tits freed and mauled, nipples twisted crimson.

Flip: ass-high, Darius mounted missionary-style, cunt swallowing half his length in one slick plunge. “God, stretch me—ruin this married hole!” she screamed, walls fluttering. Jamie and Rocco ringside—sissy perched ass-back on Rocco’s lap, shaft nestling thigh-gap, grinding slow.

“Your turn, princess,” Rocco lubed fingers, circling Jamie’s trained pucker. Bed-kneeling face-to-Sophia’s blissed mug, knees splayed. Breach: blunt head kissed ring, pop—half-buried. “Fuck, tight as virgin ass!” Rocco hilted, balls smacking. Jamie wailed, “Master! Deeper—breed my sissy gash!”

Synchro-fuck: Darius hammered Sophia’s cervix, her tits heaving hypnotic; Rocco reamed Jamie doggy, prostate pummeling sparks. Mirrors reflected debauch—sweat rivers, grunts animal, pussy farts lewd on withdrawals. Sophia crested first: “Cumming—flood my womb!” Body convulsing, but Darius edged, pulling to throat-fuck her gush-smeared maw.

Jamie shattered next—prostate sissygasm, no-touch waves ripping, ass milking Rocco’s load. Hot jets painted bowels, overflow bubbling. Collapse in tangle, but revival quick. Sophia eyed Rocco: “Ass next? Stretch my backdoor while Jamie cleans.”

Oral duty: Jamie tongued Rocco’s creampied cock, ass-tang and cum bitter-salt cocktail. Then Sophia’s turn—bent double, Rocco’s spit-lubed angling in. Inch-grind till seated balls-deep, her rosebud gripping white-hot. Darius remounted her mouth, spitroast symphony.

Jealousy flicker—new conflict: Jamie whimpered sidelines, clitlette raging caged. Sophia beckoned: “Stroke Darius while he throbs in my lips.” Touching the bull’s base, veins jumping, ignited bi-fire. Darius grinned dark: “Bi-curious sissy? Mount up.”

Sissy’s Shattering Completion 🔥

Total surrender crested on sweat-drenched satin. Jamie straddled Darius prone—blindfolded still, heart thundering. Rocco’s seed lubed the way, but Darius? Apocalypse. Head nudged, ring protesting vicious… then yield. Inch by burning inch, impossible girth split him asunder. “Too big—oh fuck, YES! Daddy’s destroying my guts!” Pain bloomed pleasure, prostate crushed ecstasy-overload.

Darius rutted slow then savage, hips slamming, balls battering taint. Jamie’s world narrowed: stretch-fire, pre-cum fountaining ignored, screams raw-throated. Sophia orchestrated beside: riding Rocco reverse-cowgirl, ass gobbling his renewed steel, tits bouncing frenzy.

Climax cascade. Sophia first again—double-stuffed illusion as fingers plunged her snatch. “Sissy’s watching—cum with your slut-wife!” Gush exploded, soaking Rocco’s sack. He followed, painting her bowels pearly ropes.

Darius swelled cataclysmic in Jamie: “Take seed, bitch-boy!” Torrents erupted, bloating belly, excess rivulets painting thighs. Sissygasm supernova—vision whiting, body seizing endless, prostate milked supernova-dry.

New peak scene: all-four heap. Recovery breaths mingled, but Sophia craved more. “DP me, bulls. Jamie directs.” On back, legs hoisted: Rocco anal, Darius vaginal—double penetration sandwich, thin wall smashed. She thrashed demonic, orgasms chaining, “Wrecked—forever yours!”

Jamie nursed spent sacks, tongue bathing until revivals. Bi-chain finale: Rocco fucked Jamie missionary while Darius plowed Sophia beside, hands crossing to jerk partners. Cum symphony: loads swapped mouth-to-mouth, Sophia snowballing Jamie’s mouthfuls, sealing completion.

Dawn crept, bodies strewn limp. Sophia cradled Jamie’s tear-streaked face, kiss tender amid ruin. “You’re complete now, my perfect sissy cuck. No turning back.” He nodded, ass throbbing fulfillment, heart chained eternal. City hummed below, oblivious to the transformed soul perched in paradise’s wreckage. 💋

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