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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 32: The Marathon is Just Beginning

The black plastic cage had become a part of him, a constant, maddening presence. For two weeks, it had redefined his existence. Sleeping was a battle, his body straining against the unyielding device, waking him with jolts of futile arousal. Showering was a lesson in torment, his hands washing over a part of him he could no longer truly touch.

Each morning, Margot would retrieve her phone, her expression a blend of wifely affection and cunning strategist. “Photo time, darling.”

The sessions had evolved. The first few days had been simple, clinical shots of his confined state against their neutral bedroom wall. Then came the props. Yesterday, it had been a pair of her silk panties, a delicate lilac, stretched taut over the cage, the fabric doing nothing to hide the rigid outline of the plastic beneath. The day before, suspenders clipped to his own socks, pulling them high up his thighs, making him feel absurd and exposed.

This morning was different. She came into the living room holding a tube of lipstick. A vibrant, shocking red.

“Come here, Rupert. Stand by the fireplace.”

He obeyed, the familiar dread and excitement coiling in his gut. The fire crackled, casting dancing shadows across the bare skin of his legs.

“I want you to put this on,” she said, handing him the lipstick.

He stared at it. “On… my lips?”

Margot let out a rich, warm laugh. “Don’t be silly. On your nipples. I want them pretty for the girls.”

The ‘girls’. The WhatsApp group. He could picture them—Georgina with her analytical gaze, Henrietta with her hungry smile, Dolores, Felicity, all the others—looking at these images, commenting, laughing. The humiliation was a live wire, sparking directly into the pool of heat gathering low in his abdomen. He was hard, a painful, persistent pressure against the confines of the cage.

His hands trembled as he uncapped the lipstick. The waxy, floral scent filled his nostrils. He looked down at his own chest, at the pale, flat nipples. It felt profoundly wrong. He touched the tip of the stick to one, circling it, staining the skin a garish, clownish red. He did the same to the other, the color standing out violently against his flesh.

“Good,” Margot purred, her phone already raised. “Now, hands on your head. Let’s see how desperate you look.”

He complied, feeling the stretch in his shoulders, his entire body on display. The cage felt tighter than ever. She clicked the photo, the artificial shutter sound freezing this moment of debasement.

“The ladies are going to love this,” she murmured, her thumbs already tapping on the screen. “Julia especially. She has a keen eye for detail.”

A moment later, the phone began to chime with a rapid succession of pings. Margot grinned, reading the responses aloud.

“Georgina says, ‘The shade really brings out the frustration in his eyes.’ Oh, and Henrietta… my, my. She says, ‘I’d love to smear that lipstick all over his chest with my teeth.’” Margot looked up, her eyes gleaming. “They’re really enjoying your journey, Rupert. You’re the talk of the Institute.”

Later that day, he was sent to the village shop for milk. The simple errand felt like a gauntlet. Mrs. Abernathy, the octogenarian postmistress, gave him a knowing wink from behind her counter. As he browsed the shelves, he felt a presence beside him.

It was Julia, the former police officer. She was a tall, imposing woman with a stern jaw and sharp eyes that missed nothing.

“Rupert,” she said, her voice low and direct. “Margot shared that delightful picture this morning. Very… creative.”

He felt a hot flush creep up his neck. “Julia. Hello.”

She reached out and, with a casualness that stole his breath, flicked a piece of lint from the front of his trousers. Her knuckles brushed deliberately against the hard plastic of the cage through the fabric. A jolt, equal parts shock and electric stimulation, shot through him. He gasped.

“It suits you,” she said, her voice dropping to a conspiratorial whisper. “Confinement. It brings a clarity of purpose, doesn’t it? I had a suspect in the cells once, back in the city. He had that same look in his eyes. The look of a man who knows he’s not in control anymore.” She smiled, a thin, sharp line. “I’ll be seeing you soon.”

She walked away, leaving him rooted to the spot, his heart hammering against his ribs. The casual, public intimacy of her touch was more violating than anything Henrietta had done in the privacy of the barn. It was a reminder that his condition was public knowledge among a select, terrifying group.

That evening, as Margot was cooking, she said offhandedly, “You know, it’s not just you. Makes it easier, doesn’t it? Knowing you’re not alone in your… predicament.”

Rupert looked up from the table where he was trying to read the paper. “What do you mean?”

“Oh, just that there are two other husbands in the village enjoying the same kind of attention from their wives. The WI is full of innovative thinkers.” She stirred the sauce. “It’s become quite the friendly competition. Whose husband can be the most obedient. Who can devise the most creative… challenges.”

The revelation landed like a physical blow. He wasn’t a unique experiment. He was one of three. A participant in a secret, village-wide game. His mind raced, scanning the faces of men he knew at the pub, at the farmer’s market. Was it Henry, with his vast mansion and quiet demeanor? Or perhaps the butcher, a jovial man with a thick beard? The mystery was its own form of torture.

“Who?” he breathed.

Margot just smiled, tapping the side of her nose. “Now, now, that would spoil the fun. But I will say, their wives are very impressed with your progress. Especially after the lipstick. Elizabeth said her man nearly came in his cage just from the description.”

The crude language, the shared intimacy, the knowledge that his shame was a source of entertainment and comparison—it was all too much. He felt a surge of anger, of rebellion. He stood up, the chair scraping loudly against the floor.

“Margot, this is… this is insane!”

She turned from the stove, her expression calm. “Is it? You’ve never been more alive, Rupert. I’ve never wanted you more. Look at you.” Her gaze traveled down his body, lingering on his groin. “You’re straining so hard against that plastic I’m surprised it doesn’t crack. That’s real. That’s feeling. That’s what you said you wanted to rekindle.”

He had no retort. She was right. The anger was just another shade of the all-consuming arousal that had been his constant companion for weeks. He was a live wire of need, and every tease, every photo, every whispered comment from Julia was another turn of the screw.

He sank back into the chair, defeated, exhilarated.

Margot came over, wiping her hands on a tea towel. She stood behind him, wrapping her arms around his shoulders, her breasts pressing against his back. She nuzzled his ear.

“Only two more weeks until Halloween,” she whispered, her voice husky with promise. “And your date with Julia. She’s been planning something very special for you. She showed me her playroom.” Margot’s hand slid down his chest, over his stomach, and cupped him firmly through his trousers, her palm applying direct, unrelenting pressure on the locked device.

Rupert cried out, his back arching, his entire world narrowing to that point of contact—the friction, the pressure, the impossible, agonizing barrier.

“Two more weeks,” she repeated, squeezing harder, making him whimper. “I wonder if you’ll even be able to speak

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