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 42: Tools of the Trade

The chalk scratched against the board, a final, definitive sound that sealed his small victory. Five points. Rupert’s breath shuddered out of him, the tension in his shoulders easing just a fraction. He could still smell Margot on the inside of the hood, a ghost of fig and vanilla that was now a talisman.

“Do not become complacent,” Julia’s voice cut through his momentary relief. She paced before them once more, a panther in leather. “Intimacy is more than mere recognition. It is about performance. Connection. Even when the connection is… synthetic.”

She clapped her hands twice, sharp reports that echoed in the rafters. The waiters moved with renewed purpose, rolling out three large, padded mats and placing them side-by-side on the floor before the fire. Then, from a shadowed alcove, they carried out the contestants for the next round: three life-sized, anatomically correct female sex dolls. They were placed on the mats with a soft, unsettling thud, their vacant vinyl faces and rigid, outstretched limbs a grotesque parody of anticipation.

A ripple of laughter and excited chatter moved through the women. “Oh, I say!” Agnes chirped. “They’ve got more life in them than my Arthur had in his last decade!”

“Contestants, on your knees before your partners,” Julia commanded.

Rupert lowered himself, the cold of the floor seeping through the latex suit. The doll lay before him, a blank canvas of pliable plastic. Its garish red lips were parted in a perpetual, empty smile.

“You will be blindfolded,” Julia continued. “The music will start. You are still confined, so use your hands, your mouths, your entire bodies to put on a show. Demonstrate passion. Technique. Creativity. We,” she gestured to the roaring crowd of women, “will be the judges. The score will be out of ten.”

Thick, black cloths were tied tightly over their existing hoods, plunging Rupert’s world into utter blackness. The loss of sight was profound, disorienting. The rustle of clothing, the clink of glasses, the low murmur of the women—it all became magnified, a symphony of anticipation.

Then, the music started. A deep, thrumming bassline filled the barn, followed by the smooth, velvety baritone of Barry White. “I can’t get enough of your love, babe…”

“Go on, Number Three! Show her what you’ve got!” Margot’s voice, laced with laughter and something else—pride?—cut through the music.

His cheeks burned under the layers of hood and blindfold. This was absurd. Degrading. And yet, the five points on the board glowed in his mind. Freedom. The plug within him seemed to pulse in time with the music, a constant, humiliating reminder of the stakes.

He heard a slapping sound and a grunt from his left—Paolo, already enthusiastically engaged. To his right, there was a timid, fumbling rustle. Henry.

Rupert reached out, his gloved hands meeting cool, unnervingly smooth vinyl. He traced a curve of a hip, the unnatural firmness of a thigh. How did one perform? He thought of Margot, not as she was now, watching him, but as she had been in the early days, on a rainy afternoon in a cheap hotel, all eager hands and hungry mouth. He leaned down, finding the doll’s neck with his lips, kissing and nibbling at the plastic as if he could find her pulse there. He moved his hands over the torso, kneading the stiff breasts, tracing the ribs.

“Use your tongue, Number Three! She won’t break!” Felicity shouted from the crowd.

He complied, running his tongue along the collarbone, the taste of plastic and dust filling his senses. He shifted, moving down the body, his movements becoming less stiff, more fluid as the ridiculousness of it all was burned away by a desperate, competitive fire. He was an accountant performing cunnilingus on a sex doll in a barn full of his wife’s friends while Barry White crooned about eternal love. The sheer surreal horror of it unlocked something. He stopped thinking and let his body act, pouring every bit of remembered passion, every flicker of rekindled desire for his wife into the performance for this inert object.

The crowd was roaring. He could hear specific voices now, egging them on.

“Look at Number One go! He’s a natural!”

“Oh, for heaven’s sake, Henry, put some back into it!” Elizabeth’s voice was sharp with frustration.

Rupert found the doll’s inner thigh, biting gently through the latex of his hood, then lavishing the spot with open-mouthed kisses he hadn’t given Margot in years. He rolled, pulling the doll partly on top of him, one hand tangled in its synthetic hair, the other gripping its hip, grinding himself against its leg despite the cruel barrier of the chastity cage. It was a pantomime of lust, but the effort was real. Sweat dripped down his back inside the suit.

The song swelled to its climax and faded. Another began, but Julia’s voice cut it off. “Time!”

The blindfolds were ripped away. Rupert lay panting on the mat, the doll splayed across him. He pushed it off, his body trembling with adrenaline and exertion. He dared a glance towards the tables. Margot was watching him, her bottom lip caught between her teeth, her eyes dark and unreadable.

Julia conferred quietly with a few of the other women—Agnes, Dolores, Elizabeth. They whispered, pointed, and nodded.

“The scores for performance,” Julia announced, turning back to the room. “Contestant Number One. Flamboyant, energetic, if a little theatrical. Seven points.”

Paolo gave a slight, bowing nod, his chest heaving.

“Contestant Number Two.” Julia’s tone flattened. “Tentative. Uninspired. Two points.”

A groan of sympathy mixed with derision echoed around Henry. He seemed to shrink into the floor.

“Contestant Number Three.” Julia’s eyes locked onto Rupert. “A surprisingly… committed performance. Authentic passion. Eight points.”

The chalk hit the board. Eight. Combined with his five from before, he was in the lead. A wild, disbelieving hope surged through him.

“Well done, darling!” Margot called out, her voice thick with emotion.

Julia let the moment hang, then gestured to the waiters. “Prepare the third game. It’s time to test their… strength.”

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