The Work Trip Mix-Up Ch. 02

He heard the disappointed click of her tongue cutting through the rest. "That will not do, Gregory."

He gasped like the dead and, with a distant, detached effort of will, his body rose once more.

"It's too late," she told him. He felt her slip off of the bed. "You disobeyed me. And were you told to cum?"

He shook his head in a daze.

"Answer me."

"No, ma'am."

"So, you understood. And you could speak. Tell me you're sorry," Riley commanded.

"I'm sorry, ma'am."

He heard her pace around the bed. He pulled his back straighter still.

"Well, I'm sorry to have to do it," she muttered. "But I don't know what else to do with you."

A bag unzipped from the far side of the room. Her steps came faster as she dashed back toward the bed.

A hot flash of pain flashed up the side of his ass as a deafening clap rang out across the room. His hands sprang free of the post and his feet kicked aside the sheets in surprise.

Riley was standing beside the bed with a wide, leather riding crop in her hand. Her face was pure fury and hellfire. She pointed back at the mattress. He didn't need her to say it.

Position.

He settled himself back onto his knees and straightened his back.

CRACK

CRACK

CRACK

He thought he could weather it. It wasn't the pain that made him fall, in the end. The pain wasn't much of anything. But his legs were jelly from whatever she had done to him before.

She didn't stop swinging when his belly hit the mattress, though. She didn't stop when his head burrowed into the sheets, either. His hips sank last, and still she whipped the leather hard against his ass.

Now it stung. He turned to find her, to make her stop. But it was like being under water. Every limb felt like it weighed a thousand pounds. He blinked dully around the room, trying to find her, panting for air.

"Are you feeling sorry?" Riley asked standing over him, just out of sight.

He opened his mouth, but couldn't think of what to say, or what she might need to hear.

"No? Have I not punished you enough? Are you still disobedient?" she asked.

His mouth opened and shut silently.

She slipped the hem of her skirt down. She had nothing on beneath it. He had the start of a response forming in his mind. But it didn't get any further than that, and so she rammed the thick head of her cock down his tongue.

His body jerked as she hit the back of his throat and drove down deeper. She gripped him by the skull and held him still, pushing in harder, sinking down into his lungs. The rough hairs of her crotch scraped against cheeks as she ground in harder.

His body shook again and she held him in place. "Silence," she said.

His air was gone. The weight of his empty lungs were crushing.

But he willed his body to be still.

"Don't you move," she said.

He did as she commanded. She slid out slowly. Color returned to the world once more.

Then she began to fuck his mouth in earnest.

She was an animal. She seemed to hold nothing back. A terrible, howling cry was dragging out of her lips. It was a cry of victory.

She popped out of his throat like a cork, then rammed back in. With every stroke, she drove the air out of him. He barely had a chance to suck in more. The world went foggy. It was like being drugged. His lips were puffy and growing sore. Every time she smacked into him, spit and drool splashed across his face, leaving him soaked to the chin.

It might have lasted a minute or an hour. He laid there and shook until she gave him the order.

"Position."

He was there in an instant. She was inside him half a breath later.

His body crushed around the thick weight of her. It was like a battering ram. His hands turned white from the knuckles down to the elbow as she pushed further in.

He wasn't going to let go this time. Not ever again.

The head of her drove open the muscles of him, splitting him apart. And his body swallowed her in greedily.

"Please, ma'am. May I come?" he begged.

"No."

He grit his teeth and clenched at every muscle he could, trying to hold the feeling of it back. But it needed to break free. Only the thought of being whipped again held it at bay. And it wouldn't hold long.

She slipped back up the length of him. The head of her settled right inside the rim of his asshole, stretching it wide as she toyed with him.

He braced himself hard to hold her in. And, just when he thought she might pop free, she drove down the length of him.

It felt like being punched him in the diaphragm. He made a sound like a wet grunt.

"Now," she said, her voice suddenly shrill.

His body released, shaking violently as she stroked him over the edge.

He could feel her unloading into him. He could picture the white, frothing mess she was pouring inside. He gave a long, rumbling whine as his balls tightened painfully, emptying the last of their load in a puddle between his knees.

She wasn't done, though. As he collapsed, she continued to pound away. The wet, slapping sound of it rang through the room as she worked.

And, when she had emptied out every last drop, still she held there inside of him, waiting.

Her cock twitched, again and again, tugging at the muscles inside. Each time, she dragged the muscles of his insides up for one brief, blissful moment. After awhile, she slowed.

And then he found he could squeeze around the length of her, gripping her tight, and make her twitch. It didn't take long before her hips began to slide in and out again.

Soon, she was stroking against something tender inside of him. Something that made his mind go hazy. It was like with her fingers all over again. He realized his body was wet with sweat all over again. The room was far too hot.

His balls squeezed tight. He gave a long, whining cry as a weak dribble of cum spat out of him.

Except, this time, she didn't stop.

She dragged herself in and out, in and out -always against the same spot, hardly moving at all. His whine rose to something inaudible. He curled up against the sheets and let her take him.

It wasn't long before another warm, heavy blanket of pleasure dropped onto him. Again and again, until he was smothered beneath them.

He shot back to life as she slipped herself out of him. His ass hardly seemed to register her she was gone. The rim of him still gaped like a fish against the warm air of the room. It seemed permanently opened wide.

"You did well, Gregory. I'm very satisfied."

He rolled over the side of the bed and crawled to the bathroom on his belly. He awoke twice with his face against the tiles, then climbed into the bathtub and turned it to full blast. He wiped himself down in a half-crouch, feeling heavily drugged. He wasn't sure if he was clean by the end of it but, after a while, he didn't care.

Gingerly, he stepped back out into the room. She was waiting for him beside the bed, towering high in heels, her skirt firmly back in place. Some of his clothes from the suitcase were laid out on the bed for him.

Greg limped closer to look it over. She stroked the tender, pink skin of his ass when he was close enough. She had a gentle touch. He could see her frowning at the welts she'd left behind. A disappointed clucking sound came out of her lips.

Without a word, she handed him his dress socks and he slipped them on. His eyes drooped close as he eased them into place. Every muscle felt so terribly weak.

He blinked at the bed, waiting for her to hand him his boxers.

A pair of pink, silk panties dropped into his palm instead. He ran a thumb over a band of white lace, trying to process it.

"I want to see you in it," she told him. "I want you to wear it for me.

"We're going to go down to that tavern down the road, as a date. And, if the date goes well, I'm going to take you into the bathroom. You're going to strip down to just these. And then you're going to make me cum with your mouth."

He nodded along to every word. He swallowed instinctively as he pictured it. He couldn't take his eyes off of her now.

Even as he slipped the cold silk up his thighs, he couldn't look away from her. She was so perfect. So wonderfully beautiful.

"Then, when we return, I expect you to listen."

He rubbed at his bottom again. His balls still ached between his thighs. He could feel their painful emptiness. He could feel the heavy weight of exhaustion. Even making it down the road seemed an insurmountable task.

But what else could he say?

"Yes, ma'am."