The Work Trip Mix-Up

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Greg finds that his boss has more to offer than he expected.
4.5k words
4.7
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Part 1 of the 7 part series

Updated 08/15/2023
Created 10/23/2022
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niniku18
niniku18
248 Followers

Greg climbed out of his rental car. After nine hours of driving, he was eager to stretch his sore muscles. He had one foot on the ground before the first gust of icy wind hit him square in the face. His teeth were frozen by it. He sank back into the safety of the car and shook his head.

Fucking Wisconsin, he thought.

It was barely November, and already there were snowflakes accumulating on the windshield. He rushed to the trunk to grab his jacket, then dragged out his luggage, cursing his way through it all.

The hotel his boss had selected was in a town he'd never heard of, twenty miles north of where they wanted to be. The middle of nowhere had been all booked up, it seemed, and so had they settled for true wilderness.

Greg pulled the heavy wooden doors open and stepped inside. He flexed the cold numbness out of his hands, then lugged his bags over to a bench in the main hall.

It looked more like a house than a hotel. It was almost exactly what he pictured a lodge would look like. There was an empty fireplace along the wall. Deer watched him from up high. A poorly-stuffed black bear stood off in the corner beside a staircase leading upward.

The rack of pamphlets for nearby restaurants and attractions was the only thing that hinted this was a place of business.

"Hello?" Greg called out. He glanced between the doors along the far walls. Which one to check, he wondered.

Before he could move, a small elderly woman peeked her face from the balcony up above. "One moment!" she called down to him.

He waited as she descended each step with care, wishing that someone had lit the fireplace.

"Good evening, dear. Checking in?" Greg nodded. "Checking in under the Elwood account, right? Here for the meeting?"

"Right again," he said.

The conference was bringing in thousands of his kind from across the country. Last year, his employer had sent eight people. This year, with budget cuts, it was down to just Greg and his manager.

"I just had your other one in here," she grinned. "Just showed her to her room."

Greg gave her his first genuine smile. His boss, Riley Elwood, had a permanent, blood-curdling glare affixed to her face. It was as if the whole world had irritated her to just before the breaking point. Her only mood was 'barely-restrained contempt.'

And he had just missed running into her. If that wasn't a sign of good luck, he didn't know what was.

The elderly hotel manager wrote his information down by hand, then handed him a key -not a keycard, but an ancient, gold key. She asked him if he needed help getting to his room, and he politely declined.

He went up the stairs as silently as he could. The rooms on the second floor weren't numbered, but he found his quickly ("Bumblebee Estates") and slipped the key in softly. He stepped into the room and pulled his bags in after him.

"Gregory?"

He teeth snapped together painfully.

"Hello," he said, poking his head back out from the door. "Welcome to Wisconsin, ma'am."

"Didn't you read your email?" she asked, pulling her long coat tighter.

"I just got in," he said. There was nothing he could think of to add to that explanation.

"You don't have your phone?" she asked incredulously.

"I was driving."

"Well, don't bother with it now," she huffed, striding closer.

She was a tall woman, taller than he was. And when she loomed over him and glared, it was like he was ten years old again.

"I needed to know which of the restaurants to make a reservation at. It's nearly four already."

"Anywhere you want is fine, really," he told her.

He had hoped to appease her with that, but she seemed more frustrated that ever.

"Just read the list and then tell me as soon as possible, Gregory."

"I'll do it first thing," he promised. "I'll do it right now, in fact." He pulled his phone free from his pocket.

He didn't see it, but he felt her eyes rolling. She straightened her coat and disappeared back down the hallway.

He didn't breathe again until he was in his room with the door locked tight. Less than a minute of conversation, and already sweat was beaded across his forehead.

But at least he wasn't cold anymore, he thought.

He logged into his email and scrolled through her list. There were three pubs to pick from, and they all looked identical. He texted her the first option, and added again that any of them were fine.

She texted back ten minutes later. "They do not accept reservations. We can leave at 7."

"Sounds great!" he wrote back with a grimace.

He dug some thicker clothes out of his bags, then laid on the couch to watch TV. He had hoped to relax for a moment, but the dinner hung over him like a guillotine. The minutes vanished away, and soon he was showered and dressing again to face the cold.

He pulled open the door to his room, and jumped back a foot. Riley was standing just outside.

"Are you ready?"

He nodded silently, and then followed her down the stairs.

The snow fell harder now. Already, a dusting of it had coated the parking lot, and their cars. The air was much colder, as well.

"Should we walk?" Riley asked. "It's just around the corner."

Greg gripped at his thin jacket as a sharp wind blew through it. "Sure," he squeaked.

They marched in silence down the road, him following just behind her. His sneakers slid and squeaked against the wet, uneven ground. Her heels clacked onward readily, seeming not to notice.

The pub he'd selected was called The Modern Goat. It may have been modern when it was first built, a hundred years prior, but it looked like it hadn't been updated since.

An elderly man at the bar looked up at him in confusion when they stepped inside. There were only a few tables occupied, and each of the occupants was older than the last.

"Sit where ya like," the old man called over.

Riley glanced around the room. It was an unusual little place, full of small nooks and hallways. It seemed to have been expanded over time, and it stretched out in all directions. She found a small table down a hall in the back, and they sat down into uncomfortable silence.

Her eyes shot around the place rapidly. Her face was hard-set, revealing nothing of what she thought about it. Greg held his breath and waited for time to pass.

A girl half his age suddenly appeared from the corner and handed out menus.

"Something to drink?" she asked.

To Greg's surprise, Riley ordered a beer on draft. "I'll have one, too, I guess," Greg told the girl.

She disappeared back around the corner, leaving them alone again.

His mind reeled helplessly, trying to think of something to say. "What time should we leave in the morning?"

"Six-thirty," she shot back quickly, her eyes on the menu. He buried his face behind his own, and waited for rescue.

Thankfully, they didn't have to wait long before their drinks were set in front of them. And they were no small glasses, either, but full pints in heavy glass mugs. He was still taking in the size of it when Riley muscled it into the air and drank, like some kind of Viking princess.

He raised his mug in salute, and then he followed her example.

"Better get your orders in, dears," an old woman said as she slipped on an apron. She seemed like she might have been the owner. "It's starting to snow."

"Ah, yeah. We caught some of that coming in," Greg told her.

He ordered a sandwich, and Riley ordered a steak. She took out her phone and they drank in silence as they waited for their meal.

As the young girl returned to drop off their food, she asked if they wanted another round. Riley shook her head. "We've got an early day tomorrow."

Greg tore into his food in a hurry, eager to be done with it. In less than a minute, half of it was already in his mouth.

"Hm," Riley said, still watching her phone. He stopped, waiting for more.

"The conference has been cancelled. Because of the snow."

Greg's heart dropped. "What? It's hardly snowing. That can't be right," he said, straining to see her screen.

She quickly pulled it away to make a call. He strode off down the hall, beer in hand, to go see the weather.

It was a blizzard. The cars outside had their tires halfway buried already. You could hardly see a few hundred feet out the door.

"I told you it was snowing," the old woman chimed in behind him. He nodded vacantly, and the woman went to join the man behind the bar.

"Are... do we need to leave?" he asked.

She shook her head. "We live upstairs. It's no bother to us."

Greg went back to the table and collapsed beside his boss again. He relayed everything he'd seen, and she told him about the closed highways. Weather report called for worse snow in the morning, too.

"What should we do?" he asked.

"I'm ordering another drink," Riley said.

She waved the young girl back over and ordered them a second round. "It's going to take a lot more than a pint to get me back home in heels," she muttered.

They clacked their glasses together, sloshing beer across the table They grinned and then they drank deep.

"This miserable place," she groaned, shaking her head. "I swear it snowed the last time I was here, as well. It was June."

Greg laughed nervously.

It was like watching a miracle. Like some kind of strange, unnatural miracle. Riley had made a joke. She was almost smiling. Not one of coworkers were going to believe him when he came home with this. He didn't believe it himself, and she was sitting across from him. He could hardly look away.

"Do you drink whiskey?" he asked, feeling bolder with the second pint down.

Her laughter cut off, and she raised an eyebrow dramatically.

"Oh waitress," she sang out, still looking into his eyes. Greg gripped the table tighter.

The elderly owner shuffled over after a moment. "What's your best bottle of Scotch?" Riley asked.

"Oh, I don't know..." the old woman said. "I'd have to go look. We don't have many. Would you like a glass of what we have?"

"I'd like a bottle of what you have," Riley corrected her, flashing a pearly white smile.

The owner returned with a bottle of Talisker and two glasses. Riley gave them each a generous pour, and they clacked their drinks together again.

"To the first snow day I've had in..." She thought about it for a moment. "I don't know. In too long."

Greg could see her cheeks shining red now. They were nearly as red as her lipstick, and looking warm. She shrugged out of her floor-length coat, revealing a tight black dress beneath it.

It was cut low, unveiling a deep stretch of cleavage. Her small shoulders were bare and smooth. It was so utterly unlike anything he had seen her in before. His brain faltered. He sipped at his drink and forced his gaze away.

He was feeling a lot warmer himself.

"Have you ever taken a day off?" he asked. Now that she had mentioned it, he couldn't remember a time when she had.

"I've been away at meetings before"

Greg laughed. "That's not a day off."

She thought about it for a moment longer. "Does a funeral count?" She grinned at him wickedly again.

"Well, perhaps it's something to look into when we get back," he said, and they tapped their glasses together. "You're fun when you're off the clock."

She was draining her Scotch when he said it. Her eyes fluttered back at him, with her red lips still on the glass. "Hm?"

Greg swallowed, quickly losing his nerve. "Oh, nothing. Just... it's fun getting to see you like this."

"Really?" she said, looking serious again. She poured them both another measure of Scotch and set her arms over the top of the seats. "What makes me fun?"

He eyed the arm that stretched out toward him, and the tone of muscle that ran up it. Her fingers were almost near enough to brush against him. He saw the smooth skin of her chest, and the heavy curve of her breasts. She sipped at her drink and waited.

"I don't know," he said, grinning sheepishly, flushing under her hard gaze.

She nodded at him slowly, studying him curiously. "Finish your drink, Gregory. It's nearly eleven. And I'll need your help getting home."

She paid at the bar. The old man at the register offered to try and start his truck, but Riley waved him off. "It'll take more than cold to kill me," she told him, pointing a finger at the man's face like a threat. Greg wasn't sure if she meant it as a joke or not.

Whatever she had meant, though, her bluster was gone from the moment they stepped back outside. Someone had plowed out the entrance, but the sidewalk was over two feet deep with snow.

"I am going to need you to do something for me now, and then never speak of it again," she told him.

He looked over at her through the wind. She watched him back.

Her dark eyeliner made her look like some kind of powerful goddess. He shook his head. He wasn't sure where the thought had come from.

"I will require a piggyback," Riley said. He desperately held back a laugh, and she circled around him without waiting for his response.

He felt the weight of her wrapping around him. He gripped at her thighs, but he couldn't hold onto her well. The slick fabric of her coat made it impossible.

Each time he tried to hold her still, she slipped until his hands were on her ass. He began to move, trying to block it from his mind. He pulled his knees high to stay out of the snow, and they made slow progress.

Riley nestled her face comfortably against his shoulder. Her breath was on his neck, and her soft lips brushed against his ear. Despite the cold, and the snow, and the weight of her, something stirred to life between his legs. It jutted against the cold fabric of his pants. He slowed down as they got closer, hoping to wait it out. He had nothing to hide himself with.

"Getting tired already? My my..." she said.

"Not at all," he replied, readjusting her again. His hands ran up her thighs as she sank back down, until they cupped against her round backside. "I just think it feels nice out here. I'm enjoying the night."

"You're enjoying your hands on my ass," she said, laughing.

Greg went quiet, and his face flushed warmly.

"Maybe I should set you down."

"No! It's too cold!" she cried in mock panic. Her voice echoed down the snowy street as she laughed.

He carried her the last few steps to the door, then sank down to let her climb off. He reached for the handle, and she kissed him on the cheek.

He turned back, looking into her face, unsure of what had happened.

Should I kiss her back?

It would have been an unimaginable thought even a few hours earlier. But after that dress, and her smile, and her soft lips... Does she want me to kiss her?

He'd barely thought the words and then she was pressing him against the door, her mouth over his. Her small tongue stroked against his own. He slipped his arms around her, and pulled her closer. He could taste the whiskey on her lips, and smell the perfume on her neck.

"You should come to my room," she whispered against his lips.

He pulled her mouth to his again. And then he nodded.

They saw no sign of the hotel manager as they pushed through the front door. They bounded up the stairs like teenagers, and Riley pulled him by the hand until they reached her door. She flashed him another grin as she worked the key into it. Then she pushed him inside.

"Get on the bed, Gregory," she told him.

It was her boss voice again. The stern glare had returned to her face.

He stumbled over toward it, taken by surprise, and he sat down on the edge. She watched him silently from the doorway as she undid the buttons of her long coat. She tossed it across a chair and looked back at him again, standing tall and utterly confident.

She really is beautiful, he thought.

Slowly, she ran her thumbs up the neckline of her dress, until she found the clasp behind her neck. With a flick of her fingers, the dress spilled down to her waist, revealing her heavy, naked breasts. With a twist of her hips, the last of the dress spilled to the floor.

Rily wore sheer red stockings underneath, that ran up to her knees. They were held tight by bright red garters. There was a little pink bow across her matching panties. He could see the dark tangle of hair behind it.

She stepped out of her dress and strode toward him on long, lustrous legs. The muscles of her ass dimpled as she moved closer. In tall heels, she towered over him once more.

Riley pressed him back to the bed with the palm of her hand, and he laid flat obediently. Then she strode over to the night stand and bent at the hips to look inside.

The curve of her nearly drove him mad. He tore his coat and shirt off and tossed them to the ground. He heard a metallic clack as she stood back up. He looked down at her hands.

There were handcuffs dangling from her fingertips.

She ran her fingertips up his arms until she found his wrist. She stroked it for a moment, then pulled it taut against the rods of the bedframe. She clasped the handcuff around him and then waited for his other arm. He gave it to her silently and she clasped it tight.

Riley took her time undoing his fly. She seemed to take in every inch of him, savoring his body as she revealed it. She traced the length of his cock through his briefs with her fingernail. She pulled them down with clinical efficiency and tossed them toward the front door without looking.

Greg strained against his handcuffs, arching his naked back across the bed. She moved too slowly. She still wasn't even on the bed. He wanted her now.

She tossed her long black hair over her shoulder and bound it into a high ponytail. Then she found her lipstick and re-applied it slowly, watching his distress with mild interest.

She stepped around to the foot of the bed. He watched her bend over slowly between his feet. She squeezed her breasts together for him, then sucked at her pinkie finger.

With a devious grin, she climbed onto the mattress.

She crawled toward him, her ass held high in the air. He strained harder against the fur-lined cuffs until the metal cut into his skin. He tried to snatch at her with his legs, but she batted him away easily.

Her eyes dragged over his body with apparent hunger. Finally, her eyes found his, and she crawled between his legs.

He howled as her bright red lips slid down the shaft of his cock. His every muscle bulged as he tried to thrust himself deeper down her soft tongue.

Her lips churned beneath the head of his cock. Pre-cum spilled into the wetness of her mouth. She pressed him back flat against the bed, and he howled harder.

Every stroke of her mouth drowned his brain in pleasure. He couldn't think. Tears welled in his eyes. He moaned, and he screamed, and he shook. He was so close. She seemed to know just how to keep him at the very edge of it. No matter how hard he tried, she held him still, keeping him from going too far.

When he couldn't take any more, she pulled her lips free of him. With a disinterested face, she pressed his cock softly against his belly and she stroked at his sack with her tongue.

He watch the steady stream of pre-cum running down the side of his hip. He pulled hard with both hands, gasping with shallow breaths, hoping to pull the bedpost free. It only made the metal cut into him deeper.

He laid back down onto sheets already damp from sweat, and he waited for it to end.

She pulled her mouth away again, and watched him with seductive eyes. She stroked this insides of his legs as she leaned back up. She pressed her tits together and stroked them slowly with her tongue as he thrashed and howled again.

Riley leaned on her side, and hooked her thumbs into her panties. He went utterly still and silent.

She bit her lip as she slid the thin, red fabric down her silken legs. He thought his heart might stop from the sight of it.

She had a bush as black as her hair, but trimmed short. He held his breath as she shifted back onto her knees.

niniku18
niniku18
248 Followers
12