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The Boss's Retreat

Mira Lockwood

Cuckold, Humiliation, Workplace Humiliation

Arrival and Pairings


The gravel popped under the tires as Finian pulled the car up in front of the lodge, the sound sharp and brittle, like bones snapping. Even with the windows up, the place reeked of pine sap and wet dirt, the kind of smell that stuck to your skin and hair for days. He cut the engine and just sat there, gripping the wheel, staring at the lodge with its fake-perfect porch and a lineup of rocking chairs that looked like they’d never been touched.

Isadora unbuckled her seatbelt with a soft click. “You’re gripping that thing like it owes you money.”

He forced a half-smile. “Just making sure we don’t roll backward into the lake.”

She let out that low, throaty laugh he used to chase like a dog in heat. Now it just hung there, awkward and distant. She shoved her door open and got out, stretching so her sweater rode up, flashing a strip of bare skin above her jeans. Finian stared, watching the way her back arched, her ass tight in the denim, her auburn hair catching the light and going copper. His cock twitched, the old hunger still there, but now it was tangled up with something heavier. Resignation, maybe. Or just the knowledge that he wasn’t the only one looking.

They grabbed their bags from the trunk. His was a battered black duffel he’d had since college; hers was a sleek leather weekend case that still smelled faintly of the boutique where she’d bought it two Christmases ago. As they started up the wide steps, the front door swung open and Lazare stepped out onto the porch.

Lazare was tall, broad-shouldered, the kind of man who looked like he could break you in half without trying. The charcoal Henley clung to his chest and arms, showing off muscle that didn’t need to brag. His hair was slicked back, still wet from a shower, and when he grinned it was all teeth, the kind of smile that said he could fuck your wife and make you thank him for it.

“Finian. Right on time.” The voice carried the same clipped authority he used in conference rooms. “And this must be the famous Isadora.”

She extended her hand. “Just Isadora works.”

Lazare took it, held it a beat longer than necessary, thumb brushing the inside of her wrist. “Pleasure. Heard a lot about you.”

Finian’s jaw clenched so hard it hurt. He’d never told Lazare a damn thing about Isadora. Not once. The bastard must have dug it up on his own.

Inside, the lobby smelled of cedar and woodsmoke. A massive stone fireplace dominated one wall, flames already crackling even though the day was still warm. A handful of other team members milled around—accountants, two marketing analysts, the new junior copywriter who kept looking at his phone like it might save him. Everyone wore variations of business casual: chinos, button-downs, the occasional fleece vest. Finian had chosen a navy polo and khakis; he felt like a kid playing dress-up next to Lazare’s effortless command.

Lazare clapped his hands once, sharp. “Alright, people. Gather up.”

They formed a loose semicircle. Lazare stood at the center like he’d been born there. “This weekend isn’t about quarterly targets or pipeline reviews. It’s about trust. Real trust. The kind you can’t fake with spreadsheets.” His gaze swept the group, lingering—deliberately—on Isadora. “We’re going to pair off for the exercises. Some will be blindfolded, some will be roped together, some will have to rely on nothing but voice and touch. No swapping. No trading. You get who you get.”

Finian’s gut twisted. He already knew what was coming, and it made his balls crawl.

Lazare pulled a small burlap sack from the side table. “Names in here. I’ll draw first for myself, then we go clockwise.”

He reached in, pulled a slip, unfolded it without looking. “Isadora.”

A ripple of murmurs. Someone—probably the junior copywriter—gave a soft whistle that died quickly under Lazare’s glance.

Finian felt his face go hot, a flush crawling up his neck. "That’s my—"

“Wife. I know.” Lazare’s smile didn’t reach his eyes. “Lucky me.”

Isadora’s mouth curved, amused. “Guess I’m in good hands.”

The words hit him like a punch to the gut. Finian bit back the urge to say something, swallowing it down with the rest of his pride.

The rest of the pairings were over in seconds. Finian got stuck with Greg from finance, a pudgy guy who reeked of menthol and wouldn’t shut up about his fantasy football stats. They were stuck with the blindfolded trust walk, same as everyone else, but on a different trail. Lucky him.

Lazare addressed the group again. “First exercise starts in twenty. Grab water, use the restroom, whatever you need. Meet at the trailhead behind the lodge. And remember—” He let the pause stretch. “This only works if you let go. Completely.”

The group dispersed. Finian caught Isadora’s elbow before she could follow the others toward the restrooms.

“You okay with this?” he asked, voice low.

She tilted her head. “It’s a trust walk, Fin. Not a blood oath.”

"He’s—" Finian cut himself off. "He’s a prick at work. I don’t trust him not to make this... fucked up."

Isadora looked him over, eyes sharp. Then she leaned in, her lips brushing his ear. "Maybe I want it to get weird."

She pulled away before he could say a word, leaving him with her breath hot on his skin and the smell of her shampoo—sweet, vanilla, the kind of scent that made his cock ache and his stomach twist.

Twenty minutes later, they were at the trailhead. Lazare was already tying a black silk blindfold over Isadora’s eyes, the kind of thing you’d find in a sex shop, not a team-building retreat. His fingers worked the knot slow, knuckles dragging over the back of her neck. Isadora’s lips parted, a little gasp slipping out, and Finian felt his cock twitch and his stomach drop at the same time.

“Too tight?” Lazare asked.

“No.” Her voice was steady, but there was a thread of something else underneath. Curiosity. Maybe more.

Finian watched Lazare’s hand linger, then slide down to the small of Isadora’s back, fingers splayed wide, steering her toward the trail. It looked professional if you squinted, but Finian knew exactly what it was—a claim, right in front of everyone.

Greg tugged at Finian’s sleeve. “Our loop’s this way, man.”

Finian followed Greg, but kept looking back over his shoulder. Isadora was walking blind, shoulders loose, head cocked like she was listening for something. Lazare was right behind her, too close, his hand flat on her back, fingers spread like he was marking his territory. Finian’s fists clenched. He hated how much it turned him on.

The trail Finian and Greg took was wider, less intimate, bordered by ferns and the occasional birch. Greg chattered about his league standings. Finian answered in monosyllables. Every few minutes he caught snatches of laughter drifting from the other path—Isadora’s laugh, bright and unguarded, followed by Lazare’s deeper rumble.

They reached the first checkpoint: a fallen log Lazare had marked with orange flagging tape. Greg was supposed to guide Finian over it blindfolded. Finian tied the cloth around his own eyes, the world going soft black. Greg’s hand on his elbow was damp, hesitant.

“Step up, big step… okay, now down… whoa, easy.”

Finian tripped anyway, grabbing Greg’s shoulder to keep from eating dirt. He fucking hated this—being blind, helpless, every sound in the woods too loud, every laugh or voice in the distance making his skin crawl. He wondered what Lazare was doing to Isadora right now, and the thought made his cock twitch and his stomach churn.

When the blindfold finally came off, Finian blinked against the light. Greg was grinning like he’d just closed a deal.

“Good job, right?”

Finian didn’t answer. His gaze was already searching the trees, looking for the other pair.

They finished their loop and came back to the trailhead. Lazare and Isadora were already there. She was laughing, head thrown back, her hand gripping Lazare’s forearm like she needed him to stay upright. The blindfold dangled from Lazare’s hand, swinging like a prize he’d just won.

Isadora’s cheeks were flushed, her hair a mess, strands stuck to her sweaty skin. Lazare’s shirt was half-untucked, sleeves rolled up, his forearms thick and hairy. They looked like they’d just finished fucking, not a trust walk.

Finian’s throat tightened.

Lazare spotted him first. “How’d it go, Fin?”

“Fine.”

Isadora turned, her pupils blown wide, either from the blindfold or something else. "It was... intense," she said, voice a little shaky. "You have to really listen. Really feel everything."

Lazare’s mouth curved. “She’s a natural.”

Finian forced his hands to stay loose at his sides.

Dinner was served family-style in the lodge dining room: roasted chicken, garlic mashed potatoes, grilled asparagus, red wine poured generously. The long table was lit by low pendant lamps and the fire. Conversation flowed—work stories, weekend plans, the usual surface chatter.

Under the table, Isadora’s knee pressed against his. He looked at her, and she gave him a small, secret smile, the kind she used to give him before everything got complicated. For a second, he let himself believe she was still his.

Then he caught Lazare’s arm moving. Just a little. Just enough for his hand to vanish under the tablecloth, out of sight but not out of mind.

Isadora’s smile faltered. Her breath hitched, just loud enough for Finian to hear. Her thigh went stiff against his, and he knew exactly whose hand was on her under the table.

Lazare didn’t even look at them. He laughed at Greg’s dumb story, voice smooth, while his foot—Finian was sure it was his—slid up the inside of Isadora’s leg, slow and deliberate.

She didn’t move away.

Finian stared down at his plate, appetite gone. The chicken looked like something dead and cold.

After dinner Lazare stood, glass in hand. “Tonight we’re doing cabin assignments. Two to a cabin. Same pairing as the exercises. Builds continuity. Deepens trust.”

A few groans, a few nervous laughs.

Finian spoke before he could stop himself. “I’d prefer to stay with my wife.”

Lazare’s gaze settled on him, calm, almost kind. “I get it. But the point of this weekend is to step outside comfort zones. You’ll be fine, Fin. Everyone will.”

Isadora touched Finian’s wrist under the table. Her fingers were cool. “It’s just sleeping, babe.”

He studied her face. Her eyes were bright, pupils still blown wide, lips swollen like she’d been sucking on something. His cock twitched, shame burning in his gut.

Lazare handed out keys.

When he reached Isadora, he pressed the brass key into her palm slowly, letting their fingers brush. “Cabin six. Best view of the lake.”

She closed her hand around it. “Thank you.”

Finian got cabin eight. Alone.

Later, after everyone split off to their cabins, Finian stood on the porch of number eight, staring across the dark grass at cabin six. It was maybe forty yards away, windows glowing gold behind curtains that hid everything he didn’t want to imagine but couldn’t stop picturing.

He could make out two shapes moving inside. One big, broad-shouldered. The other smaller, with curves he knew too well. His fists clenched, cock aching and stomach twisted up tight.

A breeze moved through the pines. Somewhere in the trees, a red light blinked once—then again.

Trail cam.

Finian’s gut knotted, a sick mix of jealousy and something darker.

He went inside his own cabin, shut the door, and slumped against it, letting the silence close in around him like a fist.

Across the lawn, the light in cabin six dimmed.

The door clicked shut behind them.

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