The Work Trip Mix-Up Ch. 02

"Up," Riley commanded in a sharp voice.

Even in the depths of exhaustion, his sleeping body obeyed. He sprang upright, pulling the bed sheets aside, and blinking into the blinding white light of the morning.

He regretted it instantly. Aches cried out from across his body. The rim of his asshole still pulsated and gaped. A cold puddle had formed beneath him; a slippery combination of God knows what fluids.

But, she had spoken. And he didn't need her to say it twice.

He slipped his feet from the mattress and burrowed them into the warm, shag rug. He managed to stand without wincing, but he limped as he went to collect the robe she held out for him.

It was white, and warm, and plush. Not something he would have ever considered putting on before, She watched him tie the lash, then pulled open the door to the room and stepped back, waiting for him to go first.

Greg stammered something, and then stopped as she snapped her head in his direction. He regretted it already. "I'm... going out there like this?"

He was wearing nothing underneath the white robe. For God's sake, he was still dribbling something down his leg.

"You'll be fine," she said, hardly even seeming to hear him.

She strode out down the hall. He couldn't help but notice she was still wearing high heels. Even in bed, she hadn't taken them off. Breakfast apparently wasn't an exception either.

The elderly innkeeper poured them each a coffee as they sat down at the dining hall on the first floor. Greg held down a gasp as he settled down into the chair. Thankfully, it was a well-padded.

A cold breeze blew through the cotton folds and up his naked thighs, making his belly curdle with shame.

"Did you make it in alright?" Riley asked the old woman. The snow had buried the world outside their windows in two feet of snow.

"Oh, I..." she stammered, "We live on the bottom floor here." She cleared her throat delicately. "I slept right through it, though." She drifted quickly back toward the kitchen.

Greg shut his eyes, his breath growing shallow.

Of course the old woman lived here. And, in this pleasant, snow-muffled house, she heard every creak of the bed as Riley pounded his asshole and made him moan like a dying animal. Jesus fucking Christ.

"What's wrong?" Riley asked sharply.

His cheeks burned hotter. "She heard us," he mouthed. His eyes flickered over to the kitchen, making sure the old woman was still out of sight.

"Heard what?" Riley demanded.

He flicked his head upward this time, gesturing toward their rooms.

"And?" she asked, sounding more exasperated than ever.

She drank down a long pull from her coffee. He tried to follow her example, but the boiling hot liquid melted the tip of his tongue and he had to spit it back out.

"Regardless, that does bring me to what I wanted to discuss."

She spoke rapidly, then paused, and seemed to take in a calming breath before pushing on. Just as he began to feel a touch of sympathy for her forming, her eyes flashed at him again and his insides froze all over again.

"Why are you looking at me like that?" she asked, her eyebrows narrowing hard again.

He shook his head, and waited for her to go on.

"What we did last night, and our drinking, it obviously crosses beyond a line of professionalism," she began. "I am your manager and I would..." She stopped and exhaled carefully, sounding frustrated. "I would ask that you please do not share any of the details of our time together with the others. I would hope to keep this matter private. I would," she said, audibly gritting her teeth, "consider that a favor."

Greg nodded his head, but she waited, apparently wanting a real response.

"Oh, of course. I would never tell anyone."

Jesus, he thought. What would I say to people?

Did she expect him to gather everyone around the Keurig? To tell them all about how the boss had cleaned out his pipes with her hairy, eight inch cock? It wasn't exactly high on the agenda.

"Thank you," she said crisply. "Now, with that said..."

The elderly woman came back with a basket of toast as Riley set a heavy napkin over her leg. "I've got biscuits and sausages started," the woman told them. "We have eggs, or I can make an omelet if you like. We also have waffles, if you'd rather have something sweeter."

The woman didn't quite make eye contact with either of them as she spoke.

"I'll have all of it," Riley said. "Do you have mushrooms, spinach, onions, and sausage for the omelet?"

The old woman seemed caught off guard by the request. "Oh, I suppose I could see if Freddy could run some over..."

"Thanks," Riley said, cutting her off.

"Just some eggs for me," Greg told her. "Over-easy or scrambled. I don't care."

"Nonsense," Riley said, as she grabbed a piece of toast from the basket. "He'll have a bit of everything, as well.

"You'll need your energy later, as I was trying to say," she said, seeing his startled look, "Or, I suppose it is what I meant to ask. We're going to be here for awhile. I'd rather my time not be wasted."

Greg watched the old woman back away at record speed.

"She. Heard. You," he hissed across the table His eyes were frozen on the kitchen door.

Riley shot a look backward, to see who he was referring to. "The innkeeper?" she asked. He nodded frantically. "And?"

"She..." He was so confused by her confusion that he was lost for words.

"Are you not interested?" Riley asked, the barest trace of emotion creeping into her voice.

"You were the one that wanted to keep this private!" he hissed. He gestured wildly in the direction the woman had fled in.

"From your coworkers," Riley explained. "And I hardly think she's going to tell them."

His chest heaved as he tried to find the words. "I don't want that grandmother hearing us fuck," he said finally.

"What does she care?" Riley asked, seeming genuinely baffled. "Do you think we're the first?"

"She cares," he assured her.

"Well, I don't, Gregory." She shook her head to clear it. "I'm trying to say, I have certain expectations. That is what I wanted to speak to you about -if you would like to pass the time with me. And if you don't want to hear about them, tell me now. I have other things I could be doing."

It had all come down to this, he thought. An entire evening spent having my worldview fucked in the ass, and now I only have an instant to decide what to do next.

Her eyes burrowed into him. A trickle of sweat ran down the length of his back. His lungs were too heavy to breathe.

"Of course," he choked out. "I like spending time with you."

She had been an entirely different woman, back in the restaurant. He wanted that side of her again.

And the woman she had become when her dress slipped off.... That strange merging of fearsome boss and knockout sex god. Jesus Christ, he thought again.

The memory of her taking him into her mouth played back through his mind, and his cock swelled back to life.

He needed that side of her again, too.

"Well, I would be happy to discuss these expectations. But if you're uncomfortable here..." she said, trailing off and sighing.

"I-" An older man had backed out of the kitchen holding a wide tray, and Greg went silent.

"The wife's had to run out for a spell," he told them as he loaded the table with dishes. "Anything else I can get for you?"

They waved him off. Greg knew it in his bones that the old woman had refused to walk out here again. It was no use bringing that up with Riley, though.

The old man vanished out of sight again. "Well, let's hear it," he prompted.

The fork twirled around her finger and then she began slicing into her waffles. "There isn't much to say. I will expect you to follow orders. That is the beginning and the end of it."

Greg shuffled his eggs around the plate. "I thought... Isn't that what we did last night?"

"It is not," she told him. "There was hesitation. There was consideration. You thrusted back at me, trying to bring about your own orgasm," she said, pointing an accusatory finger in his direction.

"If I hadn't brought the handcuffs, we would both have spent the evening unhappy and minimally satisfied. I am quite certain, in fact, that you would be upstairs right at this moment," she said, gesturing at the ceiling with her eggs, "listening at the door, starving, and waiting for me to clear the dining hall. Do you agree?"

He gave the smallest trace of a nod.

"I am not interested in humiliating you," Riley went on. She jabbed her fork into a small, pan-fried sausage with unnecessary vigor. Her chin lifted and she slid the length of the meat down her tongue. Her eyelids fluttered briefly in satisfaction.

Greg's mind went hazy again.

"But," Riley continued on as she chewed, "if you're going to whisper and creep about, because some old woman you'll never meet again might hear us, then I will not be satisfied. You would not be satisfied. Is that what you want?"

He shook his head.

"Precisely. When there is hard work to be done at the office, I do not debate the merits of every assignment with each employee. Do we discuss every tangential link? No," she answered for him. "I have a larger plan. I give the small assignments. The goal is met. You are satisfied. I am satisfied. Everyone has done well." She gave a small round of mock applause.

"I just need you to place that very same trust in me during our personal time together," she said.

Greg picked up his biscuit and set it back down again for the third time.

"Uh huh," he offered.

"You were well-pleased last night? And earlier this morning, yes?" she asked.

It was like a fever dream, he thought. Like a drug trip out of a movie. God knows where all that cum had been stored away inside of him. He had soaked the place down. He had pulled muscles he didn't even know his body had.

"Very pleased," he told her.

She folded her arms and studied him over. "Well, then, imagine if you had listened. If you could take instructions. If you could be trusted to keep your hands and your hips still. Don't you want to see what we could accomplish? Eat your breakfast."

He scooped a forkful of eggs into his mouth and started to chew.

"Excellent. Just like that," she purred. "You just need to listen."

"I... Well, first, I agree," he said, "To everything. You don't need to worry about that. But, I think there is something I want in return. Afterward," he added.

She sat frozen, raising only an eyebrow. "Continue."

He ate his biscuit in two bites, chewing slowly to bide time. "When we've, you know, done all that -afterward, I want you to go to dinner with me again."

Her brow furrowed. "What do you mean?" she asked. "How else would we eat?"

He chewed on a link of a sausage for a moment. "Like a date," he said, his voice a bit squeakier than desired. "Like last night. I liked being with you like that. I mean, I liked that, too."

She eyed him carefully, and took a slow drink of her coffee.

"Three drink minimum," he added, in the silence.

"Agreed," she said. Her eyes still burrowed into him suspiciously. "But I may require another piggyback." She said with a quick wink.

Fifteen minutes later, Greg turned the key to his room with a shaking hand, stepped in alone, and shut the door behind him.

He left it unlocked, as instructed.

Riley had told him to wait while she made her phone calls and 'took care of business.' It could mean twenty minutes, or it could have meant ten hours. Either way, he was going to make the most of it.

He turned the shower up to a furious heat, until steam poured from the head. Then he scrubbed his skin raw and worked his way through the bar of soap.

Only one part remained untouched, and he saved it for last. With his face against the cold tile, he positioned his ass under the spray of water and gingerly peeled the cheeks apart.

He sucked in a quick breath as droplets rained across him. He could feel the muscles of his rim trembling at the touch. It still felt like it was gaping. And it was sore, but in a dull, pleasurable kind of way he didn't quite get. It made his cock hard all the same, though.

The poor guy, he thought, looking down at the meat between his legs. It was still dark red and rubbed raw. It seeped out pre-cum in a never-ending stream. It had spent the last twelve hours caught somewhere between half-mast and full strength. If it didn't get some rest, it was likely to fall off.

He stumbled out of the shower, pulled an eye mask from his bag, and collapsed onto the bed. He was asleep on top of the sheets a minute later, the mask still clutched tightly in his fist.

He gasped, and jerked awake in a panic.

The shadows had shifted, and someone else was in the room. Riley was towering over him, he could smell her. She flashed one sharp fingernail in front of his eyes. She had been dragging it down his back to wake him up.

He glanced around the place again. The blinding white light of the snow outside had nearly vanished, and there was a desk lamp on instead, bathing the room in a soft glow.

"What time is it?" he asked, dragging a palm against his eyes.

"Just after four," she replied.

"PM?" he asked, glancing around more frantically.

"I've been checking on you. You seemed quite tired. I managed to get quite a bit more done than I expected."

He ran to the bathroom and flopped against the wall as he unleashed an endless stream of urine into the bowl. His eyes drifted back shut.

Nearly nine extra hours of sleep, he thought. My God.

She wasn't wrong, though. He had needed it.

"You would be very proud of me," she said, as he stumbled back into the room. "I was so very patient."

"I'm sorry, I-"

"Silence," she said. His throat closed up on her command. "Remove your robe."

With a flick of his hand, the heavy white fabric slipped from his shoulders and collapsed onto the rug.

"Get onto the bed on your knees. And grip the rail of the headboard with both hands."

His heart beat wildly in his chest. He could feel the pressure of it in his jaw. But his legs carried him forward quickly all the same.

"I was patient. I woke you up when that ran out."

The mattress hit his thighs and he pulled himself up and onto it. A thick, wooden bar ran along a gap in the headboard, just above the mattress. His hands wrapped around it until his knuckles went white. Only then did he wonder what she had planned.

"Stay like that," she called out, as he moved to lay down on his belly. He shifted back onto his knees, feeling more exposed than ever.

"Just like that," she cooed.

The mattress rocked as she climbed up after him, just out of view behind him. The furnace burred louder as more heat pumped into the room. He could feel the breeze of it pass against his hole.

She ran a set of fingernails up the back of his thighs, and his cock sprang to life, eager as ever.

"The innkeeper and her husband will be out until exactly 8 p.m. this evening," she said. "I told them we would behave ourselves. Do not let go of that rail," she snapped, seeing his grip loosen by the barest degree.

Her nails dragged down his other thigh, and he trembled -half in nerves and half in pleasure.

"We're going to test to see if you still need the handcuffs. Do you still need the handcuffs?" she asked.

He shook his head, keeping his eyes locked onto the bed sheets.

"Answer me."

"No, ma'am."

"We shall see."

She ran her nails up his inner thigh. He moaned, despite himself. Her hand gripped him by the belly, and lifted him back up, keeping his back flat.

"Just like that," she instructed.

The soft pad of her finger brushed across his asshole. He gasped loudly.

Her hand traveled further down, then she trailed her fingers over his sack as she moved back up. The pad of her finger trailed over his hole again.

He felt himself sagging and he pulled his back straight again.

The strokes came faster, brushing between his cheeks again and again with her soft, warm finger. It was all he could feel. It was all he could focus on. She pressed into him for the briefest moment with every stroke.

His eyes closed. He tried to put all of his focus onto holding the rail, but every touch drove the air right out of his lungs. And then it stopped.

He heard the crack of a lid popping open. It was the lubricant. He could smell the sweet, vanilla scent of it as she sprayed it out against her palm.

He looked around for something on the bed frame to bite onto. There was nothing but the bar, and it was too low to grab without changing positions. And changing positions wasn't allowed.

Something slid into his body. "Ugh," he grunted.

Her finger pulled against the muscles inside of him. He had to press back against her to stay upright. He hissed out steady breaths through his clenched teeth as she worked her finger in and out. Then she added another. The wet, squelching sound of it drifted around the room.

"Position," she shouted sharply.

His eyes flew open and he pulled his shoulders back, propping himself upright once more. Her fingers dug in deeper, until his toes curled and it was hard to draw breath.

Riley re-positioned herself behind him carefully. He ground his teeth together harder and shut his eyes tightly, waiting for her to mount him, to use him up.

But it never came.

Her fingers continued to slip back and forth against the length of his insides, hooking and dragging hard against the muscles, never speeding up or slowing down. He waited and waited for something new to happen. He squeezed the rim of his ass around her fingers. But, other than slowing her pace down for a moment, she plowed on all the same.

I'm disappointed, he realized. He had wanted her to mount him. To be her little toy. A bit of fingering seemed so tame, in comparison. So unsatisfying. Maybe he was building it all up too much in his head, he thought. It had all been so raw and taboo last night.

He shut his eyes again, and let her play. A feeling of embarrassed for her crept into his mind.

But something else was off.

For one, his cock was swollen near to bursting. It felt like an overblown balloon animal. And, for another, sweat was dripping from his forehead like a fountain. And his skin had a strangely warm, buzzing feeling. Tiny muscles were spasming at random across his body. Was it lack of sleep? It was so very str-

Every muscle in his body seemed to lose control at once, all failing in unison. The wiring was scrambled. An odd, heavy feeling of pleasure was sinking onto him like a blanket.

His eyelids fluttered open and closed at random. It wasn't just his forehead -his entire body was wet with sweat. The rim of his hole gripped at her tightly, crushing against her. He couldn't make it let go. He saw movement and looked further down. His cock was spraying hard jets of cum down the length of one thigh. It didn't feel like an orgasm, though. It felt like waking up into a wet dream.

"Position."

He heard the words, but they meant nothing. Tears streamed down his cheeks. He tried to blink them away, but they kept pouring out, boiling hot and reeking of salt. He wanted to move, but the only thing he seemed to have control over was his crushing hold on the bed rail.

Position, he reminded himself. That's what she had said.

It was like watching his body from across the room. Like moving a puppet on a string. Little by little, he eased himself upright and flattened his back.

Her fingers still hooked inside of him hard. He could feel her. The wet sound of it washed over him again. He could-

Every muscle and tendon pulled taut. A hard streak of white cream splashed against his knee.

The battle was lost. His eyes rolled. He crumbled and hit the bed on one shoulder, spasming hard against the damp sheets like lighting was channeling through him. His hands were still locked tight, but his legs beat feebly, kicking their way off the bed.