Chapter 33: Teasing Intensifies
The two-week countdown to Halloween became a study in exquisite torment. The black cage was a given, a second skin of frustration. But Margot, in her relentless creativity, had introduced new variables.
It began on a Tuesday evening. The fire was lit, casting the living room in a warm, flickering glow. Rupert stood naked, as had become his evening uniform, the chill air raising goosebumps on his skin despite the heat from the hearth.
“I have a new accessory for you,” Margot announced, her voice light, as if discussing a new tie. She held up a small, sleek silicone object. It was a butt plug, its base adorned with a large, fake ruby that caught the firelight. “It’s to help you… focus. To remember your place even when you’re sitting down.”
He stared at it, a cold knot tightening in his stomach. “Margot, I don’t…”
“It’s non-negotiable, darling. The ladies are very keen on the idea. Georgina, especially. She says it’s foundational for proper control.” She held out a bottle of lubricant. “Now, be a good boy and get yourself ready for it.”
His hands trembled as he took the bottle. The act of preparing himself, of slicking his own finger and pressing it against that most private pucker, felt like the ultimate surrender. He was clumsy, his breath hitching as he worked himself open, the shame a hot flush across his chest. Margot watched, her phone already in her hand, documenting his awkward, vulnerable efforts.
“Good. Now, the plug.”
He took the cold, silicone object. It was heavier than he expected. He pressed the tip against himself, his body resisting for a moment before yielding with a soft, shocking pop. The fullness was immediate and strange, a constant, invasive pressure that made him acutely aware of every slight shift of his muscles. The jeweled base sat snug against his skin, a garish, weighted claim.
“Oh, that’s perfect,” Margot breathed, clicking several photos. “The red is so festive. It really complements the cage.” She typed a quick message. The subsequent ping from her phone was almost instantaneous. She read it aloud, a smirk playing on her lips. “Georgina says, ‘A fine start. Tell him a well-stocked man is a happy man.’”
The plug became a permanent feature of his evenings. He would watch television, read a book, or try to eat his dinner, all while feeling the persistent, humiliating intrusion. Every movement was a reminder.
The blindfolds started two nights later.
“I want your other senses heightened,” Margot explained, tying a strip of black silk over his eyes. The world vanished into a muffled darkness. The crackle of the fire became louder, the scent of her perfume more potent. “Your only job tonight is to please me. No hands. Just that clever mouth of yours.”
He was led to the rug before the fire. The heat washed over his front. He heard the soft rustle of clothing, then her hands guiding his head down, between her thighs. Her scent, musky and familiar, filled his nostrils. He began to lick and suck, his world narrowing to the taste and feel of her, the soft folds and the hard nub of her clit. He worked diligently, desperate for any approval, any scrap of physical contact. Her moans were his only guide, and he followed them hungrily, losing himself in the rhythm of it. She came with a sharp cry, her thighs clamping around his ears, her hands fisting in his hair.
It was the same the next night. The blindfold, the descent to the rug, the intense, focused worship. But on the third night, something felt different.
The scent was subtly altered. Less of Margot’s usual jasmine, and something earthier, more pungent. The texture under his tongue felt different too; the skin was looser, the folds more pronounced. The moans were higher, tighter, less a low growl and more of a reedy gasp. He dismissed it as his imagination, a trick of the sensory deprivation. He serviced her until she shuddered and went still.
Afterward, as she led him to bed, her hand felt bonier in his. He was almost sure of it.
“You were very good tonight,” Margot’s voice said from beside him in the dark. But had it come from the direction he’d just been led from? The silence that followed was thick with unspoken questions he was too afraid to ask.
The photos continued daily. Margot seemed to find endless, creative ways to showcase his predicament. A close-up of the ruby plug nestled between his cheeks, with the black cage visible in the foreground. A shot of him blindfolded, on his knees, his mouth poised expectantly. The WhatsApp group, he knew, was a frenzy of commentary and scoring. He was their collective project, their shared secret.
The tension was a live wire inside him. The constant arousal, the humiliation, the paranoid uncertainty about the blindfolded sessions—it all fused into a single, unbearable charge. He was wound so tight he felt he might scream.
The night before the Halloween party, Margot decided he needed release. A different kind.
“You’re too strung up, darling. You need to be clear-headed for Julia tomorrow.” She led him, blindfolded again, to the living room rug. The plug was already in place, a familiar burden. “Tonight, you don’t get to use your mouth. You’re going to watch. And you’re going to stay silent.”
She removed his blindfold. He blinked in the firelight. And froze.
Margot was there, naked and smiling. But so was Henrietta. The older woman stood by the fireplace, her heavy breasts bare, her gaze hungry and possessive. She held a sleek, black remote control in her hand.
“Hello, Rupert,” Henrietta purred. “We thought we’d give you a proper send-off.”
Margot lay back on the rug, spreading her legs. “Come here, Henrietta. Show him what he’s missing.”
Rupert could only watch, his cock straining against the plastic until it hurt. Henrietta knelt between Margot’s thighs, her head diving down with an expertise that made Margot cry out almost immediately. The sounds were wet, obscene, and utterly captivating. Margot’s back arched, her hands clawing at the rug as Henrietta’s tongue worked her over with brutal efficiency.
“Oh, god, yes! Right there, you filthy woman!” Margot gasped.
Henrietta looked up, her chin glistening, and locked eyes with Rupert. She grinned, a predator’s smile. Then she held up the remote and pressed a button.
A deep, buzzing vibration erupted inside Rupert. The plug came to life, a sudden, intense tremor that massaged his prostate, sending shocks of pleasure so sharp they bordered on pain. He cried out, his hips bucking involuntarily.
“Ah, ah, ah,” Henrietta chided, pulling her mouth away from Margot. “Silence. Or it goes off.”
She returned to her feast, and the vibration continued, a relentless, internal assault. Rupert bit his lip until he tasted blood, his knuckles white as he gripped his own knees. He was trapped, forced to watch the two women together, while the device inside him mocked his confinement, stimulating the very organ he was forbidden to use.
Margot’s climax was a violent, shaking thing. She screamed Henrietta’s name, her body convulsing. As she peaked, Henrietta turned the vibrator to its highest setting.
The world exploded behind Rupert’s eyes. It was too much. The sight, the sounds, the brutal, internal vibration. A hot, shameful tear leaked from the corner of his eye. He wasn’t coming—he couldn’t—but his body was wracked with a dry, agonizing orgasm, a seizure of pleasure that had no release, leaving him trembling and hollowed out.
Henrietta stood, wiping her mouth with the back of her hand. She walked over to him, looked down at his pathetic, shuddering form, and smiled.
“There now,” she said softly, patting his cheek. “All ready for the big night. Julia does so love a broken-in boy.”
She left, and Margot, spent and smiling, came to cradle his head in her lap. “See?” she whispered, stroking his hair as he trembled. “Everything is going to be perfect.”