Surrender to the Siren: A Sissy’s Oral Odyssey
In the dim glow of a rainy evening, Jake stumbled into the old Victorian hotel on the edge of the city, his heart pounding like a drum in some forbidden ritual. He’d come here chasing whispers from online forums, those shadowy corners where men like him confessed their deepest hungers. Jake wasn’t the burly construction worker everyone saw at the site; no, beneath the flannel and steel-toed boots, he was unraveling, thread by thread, into something softer, something aching to be claimed.
The lobby smelled of aged wood and faint lavender, a deceptive calm before the storm. He clutched the engraved invitation in his pocket, the one from Mistress Elara, a name that sent shivers down his spine. Elara wasn’t just any domme; she was a legend in the underground scene, her sessions rumored to break wills and rebuild them in lace and submission. Jake’s mind flashed back to that first tentative night alone in his cramped apartment, fingers fumbling with stolen panties, the silk against his skin igniting a fire he couldn’t extinguish. That was months ago. Now, at 32, with his broad shoulders and salt-and-pepper stubble hiding a secret shave, he was ready—or so he told himself.
A woman in a sleek black coat waited by the elevator, her emerald eyes locking onto him like a predator’s gaze. “Jake,” she purred, voice smooth as velvet over gravel. “You’re late. But I’ll forgive it this once. Follow me.”
Her name was Elara, taller than he’d imagined, with raven hair cascading like midnight waves and curves that screamed authority. She led him up creaking stairs to a suite that reeked of incense and leather, the air thick enough to taste. Jake’s cock—his “clitty,” as he’d started calling it in his private thoughts—twitched in his jeans, already betraying him.
Chapter 1: The Unveiling
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Stripped Bare
Elara shut the door with a click that echoed like a lock on his fate. The room was a cocoon of crimson walls and flickering candlelight, shadows dancing over a four-poster bed draped in silk sheets. A vanity mirror reflected Jake’s flushed face, and beside it lay an array of toys: plugs, dildos, vibrators, all gleaming under the low light. The scent of her perfume—musky rose and something darker, like earth after rain—filled his nostrils, making his head swim.
“Strip,” she commanded, her lips curving into a wicked smile. No please, no hesitation. Jake’s hands trembled as he peeled off his shirt, revealing the smooth chest he’d waxed that morning, skin prickling in the cool air. His pants followed, pooling at his ankles, and there he stood in nothing but boxers, his thickening arousal tenting the fabric.
“All of it, pet. Show me the sissy beneath the facade.” Her voice was a whip’s crack, soft yet unyielding. Jake hooked his thumbs in and let them drop, his clitty springing free, already leaking a pearl of precum. He felt exposed, vulnerable, the carpet’s rough weave under his feet grounding him as humiliation burned hot in his cheeks.
Elara circled him slowly, her heels clicking on the hardwood. She trailed a manicured nail down his back, from the nape of his neck to the cleft of his ass, sending jolts of electricity through him. “Mmm, you’ve prepared well. Shaved smooth, just like I instructed. But we’re not done. Kneel.”
He dropped to his knees, the impact jarring his bones, eyes level with her thigh-high boots. She opened a drawer and pulled out a pair of sheer pink panties, frilly and delicate. “Put these on. Feel how they hug your worthless little nub.”
Jake’s fingers fumbled with the lace, sliding them up his legs. The fabric whispered against his skin, cupping his clitty snugly, the elastic biting just enough to remind him of his place. He looked up at her, seeking approval, and she nodded, her eyes gleaming with dark delight. 🔥
Makeover Magic
“Now, the rest,” Elara said, guiding him to the vanity. She sat him down, her breasts brushing his shoulder as she leaned in, the warmth of her body intoxicating. Foundation first, cool cream smoothing over his stubble-shadowed jaw, then blush to pinken his cheeks like a doll’s. Eyeshadow in smoky purples, mascara lengthening his lashes until they fluttered like butterfly wings.
“Open,” she murmured, applying lipstick, the waxy cherry taste lingering on his lips. Jake stared at his reflection, transforming before his eyes—a stranger with full, painted mouth and rouged skin, feminine and fuckable. His clitty strained against the panties, the friction delicious torment.
Elara stepped back, admiring her work. “Look at you, my pretty slut. But prettiness is nothing without purpose. Today, we’re training that eager mouth of yours. Oral obedience for a sissy like you means surrender, means craving the taste of cock, the stretch of your throat.”
Jake’s pulse raced, mouth watering at her words. He’d fantasized about this, nights spent with fingers in his mouth while humping a pillow, but reality was sharper, more visceral. The room’s heat wrapped around them, candles sputtering softly, their wax scent mingling with her arousal—he could smell it now, faint and heady.
She handed him a bottle of lube, cold and slick. “Lube up, pet. We’re filling that greedy ass first. Discipline starts from behind.”
Chapter 2: Filling the Void
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The Plug’s Embrace
Jake’s hands shook as he squeezed lube onto the butt plug—a thick, black silicone beast, ridged and unyielding, bigger than anything he’d tried alone. Elara watched, arms crossed, her presence a weight that pressed him deeper into submission. “Bend over the bed, ass up. Spread those cheeks for me.”
He obeyed, face buried in the silk duvet, the fabric cool against his burning skin. The air kissed his exposed hole, puckered and waiting. Elara’s gloved hand—leather creaking—parted him, and he felt the plug’s tip nudge against his entrance, slippery and insistent.
“Relax, sissy. Breathe through it. This is your pussy now, made for plugging, for fucking.” Her voice was a soothing growl, and then she pushed. The stretch burned, a fiery bloom that made him gasp, fingers clawing the sheets. Inch by inch, it sank in, the ridges popping past his ring, filling him with a fullness that bordered on pain and promised ecstasy.
“Good boy,” she cooed, twisting it slightly, the motion sending sparks up his spine. Jake moaned, the sound muffled, his clitty throbbing untouched in its lacy prison. The plug settled, heavy and constant, every shift of his hips a reminder of his penetration.
Elara pulled him up by the hair, gentle but firm, and positioned him before a full-length mirror. “See? Filled like the slut you are. Now, panties back up. Keep that pussy plugged tight.”
He adjusted the fabric, the plug’s base pressing against the lace, a secret bulge. Looking at himself—made up, pantied, plugged—Jake felt a rush of shame-laced lust, his reflection a pornographic dream.
Tease and Denial
Before the main event, Elara had a new twist in mind, one she’d planned to break him slowly. She led him to a chaise lounge, the leather sticky-warm under his thighs. “Kneel here, hands behind your back. We’re playing a game: tease the sissy without mercy.”
She straddled his lap, her skirt hiking up to reveal garters and no panties, her shaved pussy glistening inches from his face. The musky scent hit him like a drug, sweet and salty, making his mouth water. “Lick the air, pet. Pretend it’s me, but don’t touch.”
Jake leaned forward, tongue darting out, tasting nothing but his own desperation. Elara ground against the air above him, her breaths quickening, nipples hard peaks under her blouse. “Beg for it. Tell me what a cock-hungry faggot you are.”
“Please, Mistress,” he whimpered, voice cracking, “I’m your cock-hungry faggot. I need to taste, to serve.” The words tumbled out, crude and raw, his clitty leaking steadily now, dampening the panties.
She laughed, low and throaty, then slapped his cheek lightly. “Not yet. Edge yourself with words. Describe how you’d worship my strap-on.”
As he babbled—tongue swirling imaginary shafts, throat opening for deep thrusts—the plug shifted, rubbing his prostate, building a pressure that had him humping the air. Elara’s fingers trailed her own body, pinching nipples, dipping into her wetness with a wet schlick that echoed in his ears. She came first, shuddering above him, her juices dripping onto his chest, warm and sticky. Jake nearly broke, but her glare held him fast. 💋
“Enough play. Time for the real training.”
Chapter 3: Mouthful of Submission
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The Dildo’s Demand
Elara retrieved the dildo from the vanity—a veined monster of flesh-toned silicone, eight inches of girth that matched her favorite strap-on. She placed it on a low table, suctioned firm, standing proud like a sentinel. “On your knees before it, sissy. This is your master now. Worship.”
The carpet bit into Jake’s knees as he positioned himself, the plug a constant throb in his ass. The dildo’s rubbery scent, mixed with fresh lube, filled his nose. Elara stood behind him, one hand on his shoulder. “Take it in. Slow at first, then deep. Show me you’re ready for the real thing.”
Jake leaned forward, lips parting around the tip. It was cool at first, then warming with his breath, the texture bumpy against his tongue. He sucked, hollowing his cheeks, saliva pooling as he bobbed, the slurping sounds obscene in the quiet room. Gagging came quick—his throat rebelled at the depth—but Elara’s hand pushed his head down. “Breathe through your nose, pet. Gags build character.”
Tears pricked his eyes, mascara running in black streaks, but the humiliation fueled him. He imagined it was her, or a thick cock from one of her bulls, pounding his face. The plug amplified everything, each swallow clenching around it, sending pleasure-pain waves to his clitty.
“That’s it, slobber like the whore you are,” Elara growled, her free hand slipping under her skirt to touch herself again. The wet sounds of her fingers joined his, a symphony of depravity. Minutes stretched, his jaw aching, but he didn’t stop, lost in the rhythm.
Vibrations of Surrender
At what felt like an eternity, Elara introduced the vibrator—a buzzing wand, sleek and powerful. “Nipples first,” she ordered, pulling his panties down just enough to expose his chest. She pressed it to one flat nipple, the hum vibrating through him like an earthquake.
Jake yelped around the dildo, the sensation shooting straight to his core. His nipples hardened into peaks, sensitive and raw. She switched sides, then trailed it down his belly, teasing the waistband. “Now, your clitty. But only the head. No full relief.”
The vibrator kissed his tip, and oh god, it was too much. Intense buzz against the sensitive glans, his clitty jerking in the open air. Precum flowed freely, mixing with the vibe’s hum. He sucked harder on the dildo, desperate to please, his body a live wire.
“Cum for me, sissy. But catch every drop.” She thrust a glass bowl under him, the cool rim brushing his balls. Jake’s world narrowed to the buzz, the suck, the fullness in his ass. Orgasm hit like a freight train— not explosive, but a leaking, pathetic dribble, his sissy juice splattering into the bowl. He moaned around the silicone, body shaking.
Elara pulled the dildo from his mouth with a pop, strings of spit connecting them. “Pour it on. Lube your new friend with your shame.”
Trembling, Jake tipped the bowl, milky strands coating the dildo’s head. The sight was filthy, his own essence glistening. “Back in,” she commanded. “Suck it clean. No swallowing yet.”
The taste—salty, bitter, mixed with rubber—flooded his mouth. He swirled his tongue, gathering it all, the volume growing with his saliva. Time crawled; post-orgasm sensitivity made every lick a torment, but Elara’s praises—”Good slut, keep that load in”—kept him going. Spill? He scooped it back, fingers slick, pushing it past his lips.
Strangely, arousal built again, the degradation twisting into dark pleasure. His clitty stirred, the plug grinding deeper with each bob.
Chapter 4: Cycles of Craving
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Endless Oral Endurance
Fifteen minutes more, Elara timed it with a cruel smile, her phone’s glow casting eerie light. Jake’s mouth was a swamp of cum and spit, the dildo slipping in and out with lewd squelches. His knees screamed, jaw numb, but he persisted, eyes locked on hers for guidance.
“Feel it building again? That’s your sissy soul awakening. Cum from service, not stroking like some alpha prick.” Her words wove through the haze, and sure enough, the second edge approached, slower but insistent. The plug’s pressure, the vibe she’d reintroduced to his balls—everything conspired.
He came again, weaker, a few spurts into his hand that he smeared onto the dildo mid-suck. Elara moaned approval, fingering herself to the sight, her climax syncing with his whimpers. “Swallow now, pet. Earn your reward.”
Jake gulped it down, the thick mess coating his throat, tasting of defeat and desire. He licked the dildo pristine, tongue tracing every vein, then the floor where drops had fallen, gritty with carpet fibers.
“Up,” she said, helping him stand on wobbly legs. The plug’s removal was a void, his hole clenching emptily, lube trickling down his thigh, cool and sticky.
Ass to Mouth Ritual
Elara wasn’t done; this was the pinnacle, the interchangeable holes lesson. She lubed the dildo anew—now flavored with his ass juices from the plug’s residue—and bent him over the bed. “Pussy time. Take it deep.”
The dildo breached him, slick and forgiving after the plug’s stretch. Elara fucked him slow at first, her hips snapping the base against his cheeks, the slap of skin filling the room. Jake gripped the sheets, moaning, the fullness hitting his prostate like lightning.
“Feel that? Your pussy milking it. Beg for more, you anal whore.”
“Fuck me harder, Mistress! Make my pussy gape!” His voice was hoarse, broken, but the words poured out, crude and needy.
She pounded relentlessly, the dildo pistoning, his clitty flopping uselessly. Sweat beaded on his skin, tasting salty when he licked his lips. The room reeked of sex—lube, cum, her arousal—a heady fog.
Pulling out suddenly, Elara spun him around. “Taste your pussy, sissy. Clean it.”
The dildo, slick with his ass’s tang—earthy, musky—pushed into his mouth. Jake sucked eagerly, the flavors mingling: his cum’s remnants, lube’s chemical bite, his own forbidden essence. It was vile, intoxicating, pushing him over a third edge, dry orgasm rippling through him as he deep-throated.
Elara watched, eyes hungry. “This is you now. Holes for using, mouth for savoring. No limits.”
A New Craving Awakens
In a twist Jake hadn’t expected, Elara revealed a hidden door to an adjoining room, where soft music played—sultry jazz—and a tray of fruits waited. This was her aftercare innovation, blending tenderness with tease. She fed him strawberries, juice bursting sweet on his tongue, contrasting the saltiness still lingering.
“You’ve done well, my oral slut,” she whispered, wiping his face with a warm cloth, the touch gentle. But her eyes promised more. “Next session, we’ll invite a friend. Real cock for that trained mouth.”
Jake shivered, the idea terrifying and thrilling. As she helped him redress—panties staying on as a reminder—the plug’s absence echoed, his body humming with aftershocks.
Chapter 5: Echoes of Ecstasy
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Reflections in the Mirror
Hours later, back in the lobby, rain pattering against the windows like applause, Jake caught his reflection again. Makeup smudged but spirit alight, panties chafing sweetly under his jeans. Elara had slipped him a card: “Return soon, sissy. Your training deepens.”
He stepped into the night, the cool drizzle washing his face, carrying the phantom tastes—cum, ass, her command. No going back now. The sissy in him purred, hungry for the next filling, the next swallow.
The Lingering Pull
Days blurred into a haze of work and secret touches, Jake’s fingers tracing the card in his pocket. Flashbacks haunted him: the dildo’s girth, Elara’s moans, the vibrator’s relentless buzz. At night, alone, he knelt before his mirror, practicing without toys, just lips and longing.
But it wasn’t enough. The real pull was her, the sessions that remade him. Oral training had cracked him open, revealing a void only submission could fill. He texted her one evening, fingers flying: “Mistress, I’m ready for more. Please.”
Her reply was swift: “Good girl. Tomorrow. Bring your hunger.”
In that moment, Jake surrendered fully, the sissy’s odyssey just beginning, a path of plugged asses and cum-kissed lips stretching into the unknown.
The hotel’s echo faded, but the craving? It burned eternal. 🔥
