Cover of The Calendar of Surprises

The Calendar of Surprises

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Margot and Rupert are a married couple in their early 40s living in a picturesque English countryside village. Their sex life has been pretty quiet for a few years and Margo wants to give Rupert an invigorating and kinky Christmas gift - 12 months of sexual encounters with new ladies! Her gift is given in a cryptic way, she gifts Rupert a nude calendar from the local Women's Institute (she herself is a member). Each month of the calendar features a cheeky nude of one of the lady members. There is a gold star on a day in each month - which Margot reveals to be the day of the mystery sexual date with the lady in that month's photo.

Chapter 83: Eleven Pipers Piping

The cage, once a shocking imposition, now felt like a mundane, if uncomfortable, fact of his anatomy. The memory of the photoshoot played in Rupert’s mind in sharp, surreal flashes—the glare of lights, the scratch of tinsel, the cool assessment in Sylvia’s eyes. He found himself glancing at ordinary objects—the mantelpiece, the bedposts—and seeing them as props.

Margot was busy, humming as she organised WI meeting minutes and potted up forced bulbs. She was solicitous, affectionate even, but her touch was fleeting, her kisses chaste. The constant, low-grade ache between his legs was a backdrop to everything, a persistent question she refused to answer.

On the morning of the thirty-first, she laid his clothes out on the bed: simple grey sweats, a loose t-shirt. “Julia’s,” she said simply, catching his look.

The drive to Julia’s was quiet. Rupert watched the bare, winter-blasted hedgerows, his stomach a tight knot. The dungeon, when they entered, was exactly as he remembered: the opulent dimness, the scent of beeswax and leather, the silent, intimidating presence of the equipment. It felt both familiar and newly terrifying.

The trainee—a different young woman this time, with a stern mouth and efficient hands—met them in the antechamber. The ritual was the same. The silent, clinical stripping. The cool application of oil to the steel of the cage. The heavy leather hood settling over his head, cutting off the world with a creak and a click, reducing him to scent and sound and touch. He was led, sightless, into the main room.

The air was cooler here. He heard the soft rustle of Julia’s trousers as she approached.

“Kneel,” her voice commanded, no-nonsense.

He knelt on the hard floor. Hands—Julia’s, he thought, from their sure, strong grip—took his wrists, guiding them behind his back. He felt leather cuffs encircle them, then the pull and click as they were fastened not to each other, but to a strap attached to the back of his collar. The position forced his chest out, his shoulders back, arching him slightly. Vulnerable.

“Good,” Julia said. “Now, up.”

He was maneuvered backwards onto a low, wooden kneeling bench. His shins settled into carved grooves. A bar was lowered and locked across his thighs, pinning him securely to the device. Then, with a soft hydraulic whir, the entire platform began to rise. It tilted him forward just a degree, presenting him. He was utterly immobilized, a sculpture on a plinth.

Something soft and padded was secured over the eyeholes of the hood. Total blackness.

He heard Margot’s voice then, from somewhere to his left. “He looks so… contained, Julia.”

“He is,” Julia replied. Her footsteps circled the platform. “The position is about presentation and acceptance. There is no hiding, no fidgeting. Only exposure.” A hand, cold and slightly rough, cupped his caged genitals. “Margot has entrusted me with something, Rupert.”

A key slid into the tiny padlock at the base of the cage.

The click was obscenely loud in the quiet room. The constrictive pressure vanished as the device was carefully, slowly removed. The sudden, cool air on his freed flesh was a shock so profound it was almost painful. A wave of dizzying, illicit sensation washed through him. He shuddered involuntarily.

“There,” Julia said, a note of clinical satisfaction in her voice. “Now, listen carefully. You are to be brought to the very edge. To learn the precise shape of your own peak, and to hold yourself before it. This is the lesson.”

Something small, lightweight, and plastic was pressed into his right palm. His fingers were curled around it. A thumb rested on a single, prominent button.

“This is a beeper,” Julia explained, her voice close to his hooded ear. “When you feel the approach of ejaculation—the point of no return—you are to press it. A single, clear signal. Do you understand?”

He managed a hoarse, “Yes.”

“There is a penalty for failure,” she continued, matter-of-fact. “If you go over without signalling, the session ends immediately. You will be cleaned up, re-locked, and sent home. No release. No pleasure. Only failure. And the next session will be… corrective.” Her hand returned, now slick with something cool and slippery. She took him in a firm, practised grip.

It began.

After weeks of denial, of frustrating pressure and confined ache, the direct stimulation was seismic. It wasn’t tender or loving; it was efficient, rhythmic, relentless. Julia’s hand worked him with the precision of a mechanic, varying speed and pressure in a way that was ruthlessly effective. The sensations built with terrifying speed, a scorching tide rising from his core.

His world narrowed to the slick, tight motion of her hand and the terrifying mandate of the plastic device in his own. His thumb trembled against the button. The need to press it, to just let go and be done with this exquisite torment, was a physical scream in his nerves.

He thought of the photoshoot—the flashing lights, the feeling of being an ornament. He thought of the dance studio, the women’s laughter, the sweat and the press of bodies. He thought of Margot’s bell, jingling. The sensations coiled tighter, a spring wound to its absolute limit. The peak was a cliff edge, visible, rushing toward him.

His breath came in ragged grunts against the leather of the hood. His body strained against the cuffs, against the bar, every muscle locked in a furious battle between obedience and biological imperative.

Now, his body shrieked. Now, press it!

But pressing it meant stopping. It meant denying the crest. He hovered, agonisingly, in that razor-thin space before.

Julia’s other hand gently squeezed his testicles. The added, complex sensation tipped the balance. The fall was inevitable. He slammed his thumb down on the button.

A sharp, electronic BEEP-BEEP-BEEP shattered the room’s tension.

Julia’s hand stopped instantly. The ruthless motion ceased, replaced by a still, firm hold at the very base of him. He was suspended, trembling violently on the precipice, the orgasm a monstrous, living thing trapped inside him, clawing to get out. A whimper escaped him.

“Good,” Julia said, her voice devoid of praise, simply acknowledging a fact. She held him there for ten eternal seconds, letting him feel the full, desperate tension of denial. Then her hand began again, slower now, a cruel, teasing reprieve.

The cycle repeated. She would build him up, expertly, mercilessly, to that same screaming edge. Each time, the beeper’s shrill cry was a lifeline and a defeat. Each time, she stopped, held him in that hellish limbo, before beginning anew. He lost count. Time dissolved into a liquid state of unbearable, thwarted pleasure.

Sweat dripped down his chest under the hood. His cries were muffled by leather. He was a machine of need, his entire being focused on the single point of contact between her hand and his flesh, and the plastic button under his thumb.

Finally, after what felt like hours, she slowed to a halt. He was panting, slick with sweat, trembling from head to toe. The urge to climax was a constant, pounding throb.

He heard the soft clink of metal. The cage, cool from the air, was guided back into place. The click of the lock was a profound, final punctuation.

The bar across his thighs was released. The platform lowered. His wrists were freed from the strap. He slumped forward, almost collapsing off the kneeling bench, but strong hands—Julia’s, and the trainee’s—steadied him. They helped him stand, his legs shaky and weak.

The blindfold was removed from the hood, then the hood itself was unbuckled and lifted away. The dim light of the dungeon felt blinding. He blinked, his eyes wet.

Julia stood before him, wiping her hands on a towel. Her expression was one of professional assessment. Margot stood to the side, her eyes wide and dark, her lips slightly parted. She looked enthralled.

“He did well,” Julia said to Margot, as if Rupert wasn’t there. “Excellent control under significant duress. The foundation is solid.” She turned her gaze to Rupert. “You may get dressed"

Rupert fumbled into his soft clothes, the fabric feeling alien against his oversensitive skin. The cage was a familiar, heavy presence again, a regained secret.

In the car, Margot was quiet for a long while. Then she reached over, not touching him, just resting her hand on the seat between them. “You sounded…” she began, then hesitated. “It was very compelling, Rupert. The beeper. The strain in your voice.” She glanced at him, that mischievous glint returning to her eye.

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