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 55: Synced Humiliation

The groan that came from the speakers was low, masculine, and utterly visceral. On screen, Margot’s head moved with a slow, deliberate rhythm between the young man’s thighs. Her red curls bobbed. One of his hands was tangled in her hair, not forcing, but guiding, his knuckles white with the intensity of his hold.

Rupert’s own breath hitched. He was trapped in a vortex of sensation: the searing image before him, the warm, woody scent of the barn, the soft murmur of the women around him. Then came a new sensation—the distinct, chemical smell of latex, and a cool, slick touch at the very tip of his erection.

His eyes, wide and helpless, snapped away from the projection to Julia. She stood beside his chair, a small bottle in one hand, the other now sheathed in gleaming black surgical gloves. She gave him a clinical smile. “Can’t have you feeling left out, can we, Rupert?” she said, her voice a low purr that cut through the other noise. “We’ll just keep pace with the action.”

Her gloved fingers, slick with lube, closed around him. The touch was expert, firm, and utterly detached. She began to stroke him in a slow, matching tempo to the movement of Margot’s head on screen.

“Oh, look at her go!” Felicity’s voice rang out, delighted and loud. “She’s a natural. Always said she had hidden talents, didn’t I?”

“A proper little goer,” chimed in another voice from the shadows. “Putting on a right show for us, isn’t she?”

The comments were like little barbs, hooking into Rupert’s skin. Each one tightened the coil of humiliation in his gut, yet each one, perversely, made Julia’s stroking hand feel more intense. His hips gave an involuntary jerk, but the velvet restraints held him fast.

On the screen, the masked man threw his head back against the headboard, his throat working. Margot pulled away, leaving him glistening. She looked up at him, her lips swollen, and wiped the back of her hand across her mouth with a boldness Rupert had never seen. “Not yet,” she commanded softly, her voice husky. “I’m not nearly done with you.”

She rose to her feet, a queen ascending. With a fluid motion, she pushed him back until he was lying flat. Then she climbed onto the bed, straddling his hips, but facing away from him—and directly towards the camera. Her back was to his chest. She looked over her shoulder at him, then turned her gaze to the lens, her eyes locking with Rupert’s once more. It was a look of devastating conquest.

Reaching behind her, she guided him into her. Rupert saw the moment of penetration, saw the sharp, pleasurable arch of her spine, heard her gasp echo in the barn, mingling with a collective sigh from the audience.

“There she is,” Julia whispered, her hand tightening on Rupert in perfect synchronisation. Her strokes became a fraction quicker, a mirror of Margot’s initial slow grind. “That’s your wife. Taking exactly what she wants. Look at her.”

He had no choice. Margot began to move, rising and falling with a growing hunger. Her hands braced on the young man’s thighs, her head dropped forward, her curls cascading. The sounds were obscenely clear: the wet slap of skin, Margot’s escalating whimpers that built into full-throated cries, the man’s guttural encouragements. She was abandoning herself completely, a display of raw appetite that was both shocking and mesmerizing.

“Goodness, she’s insatiable tonight!”

“Rupert, you must never have filled the tank properly, love. She’s making up for lost time!”

“That’s it, Margot! Ride him!”

The voices of the WI women swirled around him, cheerful, ribald, degrading. They were cheering for his wife’s infidelity. They were pitying his inadequacy. The heat in his face was a furnace. Sweat beaded on his collarbone, dripped down his temple.

Julia’s hand was a relentless engine. She watched the screen, adjusting her rhythm to match Margot’s pace. When Margot shuddered through a particularly intense peak, crying out, Julia’s fingers became a blur, pushing Rupert to the very brink.

“She’s close again, I can tell,” Julia murmured, her breath hot near his ear. “You’re going to wait for her. You don’t get to finish until she does. Do you understand?”

Rupert nodded, a frantic, helpless motion. His entire world had narrowed to the conflicting fire in his groin and the devastating spectacle on the wall. Margot was astride another man, fucking him with a joyous, desperate energy, her body a landscape of pleasure he felt he was witnessing for the first time.

She suddenly changed position, rolling off the man and pulling him on top of her. She wrapped her legs high around his waist, pulling him deeper. The camera had a perfect, unflinching view. Her face was a portrait of ecstatic surrender. She was chanting “yes,” and “right there,” and “don’t stop,” words Rupert realised he hadn’t heard from her in years.

“That’s my girl,” Dolores said approvingly, sipping her gin.

The masked man was pounding into her now, the bedframe adding a rhythmic creak to the soundtrack. Margot’s cries were continuous, building towards a crescendo. Julia’s hand was a cruel, perfect instrument, mimicking every thrust, every gasp, bringing Rupert to an unbearable peak and holding him there, suspended on a razor’s edge.

“She’s going to break him,” someone chuckled.

Rupert strained, every muscle corded, tears of frustration and overwhelming sensation prickling at his eyes. He was a instrument being played by Julia, by Margot, by the entire, watching room.

On screen, Margot’s eyes flew open. She looked directly into the camera, through the miles, into the very core of him. Her expression was one of furious, beautiful release. “Now, Rupert,” she moaned, the command clear as a bell. “Watch me now.”

The masked man’s rhythm became frantic, final. He was on the edge.

Julia’s hand stopped dead.

The sudden absence of touch was a shock worse than any slap. Rupert made a choked, agonized sound, his body bowing against the restraints. He was dangling, throbbing, utterly denied.

On the screen, Margot’s climax overtook her. Her back arched clear off the bed, a silent scream on her lips before sound rushed back in—a long, shuddering wail of pleasure that filled the barn.

The masked man above her froze, poised at the very point of no return.

The chapter ended with Rupert howling silently into the warm, approving darkness, his wife’s ecstasy ringing in his ears, and his own release held hostage, just out of reach.

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