Rubbing her hands together to give her strength, she returned to his cock. She stroked him, up and down, up and down, for another ten minutes but it seemed as if she was doing it wrong. He just smiled down at her and watched.
Finally, her strength gave out and she felt tears come to her eyes. “I’m sorry, sir. My hands are just too tired.”
“Well, that’s unfortunate. You’d better return to work.”
Disappointed in not being able to help him, but more saddened by her own unmet needs, Emily rose and straightened out her clothes. She found her thong and slipped it on. She headed for the door and Mr. Caudry stopped her before she could put her hand on the knob.
“I figure that’s worth about twenty swats, don’t you?”
She turned, her mouth agape. “What?”
“For failing to do your duty. You’ve gotten to come many times and yet I couldn’t come once. Please return here at five for your punishment.”
She knew the building emptied quickly and they would be alone. She started to say something, anything that would make him realize how unfair he was being. There was that word again. Fair. She could imagine, to him, she was being unfair to not allow him release. He was a man, after all. She found herself nodding and opened the door.
“Oh, and Miss Robinson?”
She turned.
“Don’t sneak off to masturbate. If I can’t come, you can’t come.”
Emily looked up quickly toward the cubicles, afraid his words might’ve carried. But other than a few glances, no one seemed to care what was happening in his office. She left quickly and closed the door gently behind her.
The afternoon dragged on. Her mound itched and she had to reach down often to scratch it, but she dared not go further. She had to pee and she worried that Mr. Caudry would assume she was masturbating, so she sat at her desk and squirmed.
Finally, just before five she couldn’t take it anymore. She jumped up and ran to the bathroom and peed quickly. She washed her hands and made it back just in time to hear her intercom buzz.
“Yes, Mr. Caudry?”
“It’s time.”
She slipped inside and closed the door, ready for her punishment.
“Remove your clothes first.”
She stopped halfway to his desk. “M-my clothes, sir?”
“Yes.”
“But, sir!”
“That’s twenty-five swats. Fifteen on your ass, ten on your pussy.”
Her body was shaking as she stripped off her clothes. Everything was moving too fast, she thought. Was it less than two weeks ago that she had arrived here, full of hope and promise? And now look at her! Being ordered to strip naked in her boss’s office and prepare herself to be spanked like a little girl.
And yet, she was doing it, just as he had demanded. What did that make her? She tossed her clothes onto a chair and stood before him naked, showing every part of her for the first time. She didn’t have anything he hadn’t seen, she told herself.
“Assume the position.”
Emily hunched over the desk, her ass an inviting target. He removed the ruler and moved around behind her. She heard the radio go on and her pussy immediately flooded with fluids. She groaned before he even touched her.
“What was that?”
“Nothing, sir.”
Whack! Whack! Her ass exploded in pain. He was not holding anything back this time. She bit her lip and tried not to scream. Was there anyone left in the office? Surely they could hear the sound they were making!
Whack! Whack!
“Please, sir! It hurts so much!”
“Then you’d better figure out a way to make me come. Otherwise, I’ll have to take my frustrations out on your ass.”
Whack! Whack!
“Let me try again! Please, sir!” Her ass danced and weaved as the pain flooded her senses.
He paused and she looked back at him, tears in her eyes, her expression hopeful.
“Very well. If you do a good job, I’ll forgo the rest of the spankings to your bottom.”
“Oh, thank you sir!” she babbled and followed him to his chair, her hands already unzipping him even as he sat down. She freed his cock and saw how her whipping had made him hard. She started in again with her hands, trying to coax his seed from him. But as she stroked, his dick seemed to soften slightly in her grip. Emily felt her panic rising. She couldn’t face any more swats like those.
Without thinking about it, she plunged her mouth over his cock and began to suck. She was rewarded when she felt it swell again and she made love to that cock, teasing it with her tongue, playing it like a fine instrument. She kept one hand below to stroke the base, building his sensations, trying desperately to make him come.
“Yes,” he whispered and she redoubled her efforts. Pushing the cock as far as she could down her throat and working at it with her tongue. She remembered every trick she had learned from her boyfriends.
Soon, she could hear him panting. Then a hoarse cry and suddenly, her mouth filled with his semen. Emily choked and coughed, pulling away so she could swallow some and spit out the rest into his waste basket.
Her happiness was short-lived. When she looked up, his expression was dark.
“What, sir?”
“You spit out my seed like it was vile? That will never do!”
“I’m sorry, sir! I was caught off guard!”
He nodded. “Very well. We’ll call it first time jitters. I’m sure you’ll do better next time.”
Next time? she thought. Of course there will be a next time.
“Now get into position.”
Emily stared at him, confused. “But sir! You said if I got you to come, you’d forgo the rest of my spanking!”
“I said I’d forgo the rest on your bottom. I still owe you ten on that beautiful bare pussy of yours.”
She felt her breath catch in her throat and the world seemed to stop for a moment. Then her body began to move as if she had no control over it. She slowly climbed up onto the desk and lay on her back. He moved between her legs and pressed her knees down to the sides.
“You know the drill by now.”
She nodded, trying not to cry.
The ruler struck her naked mound and she cried out, her body shaking. It was so much harsher now that she had no hair to cushion the blows!
Whack!
“Oh god, sir! It hurts!”
“As long as you obey the rules, you won’t have to be punished at all,” he said and she knew it was a lie. He liked it. He would always find a way to punish her.
With each blow, despite the pain, her orgasm rose up within her. She fought it, for certainly it made her look like a real slut. Who in their right mind would come when being slapped?
She couldn’t help it, her legs closed and she shook with a small orgasm. “Ow! Ow! Oh god!” Pain and pleasure were all mixed up in her mind.
“That was disappointing,” he said. “You only made it through four blows.”
“Please, sir, my pussy is still sore from the waxing! Please! I can’t take it!”
He relented. He seemed to be in a much better mood now that he had come. “Very well. I’ll strike your tits for the last six. Three each.”
She nodded, happy to sacrifice her breasts instead of her incredibly sore pussy. She scrambled up and sat on the edge of the desk.
“Present your breasts for punishment.”
Emily lifted them up from underneath and grimaced as he prepared the ruler.
Whack! First the left one, right across the top. She winced and more tears flew from her eyes.
Now the right, leaving a red welt.
Back to the left, further down.
Same place on her right tit. She knew what was coming next and tried to brace herself.
Her left nipple exploded in pain and she squealed and shook.
Now the right nipple and she nearly fainted, jerking back out of the way and holding both hands over her breasts.
“Oh god, sir! Oh my god that hurts!”
“You may get dressed,” was all he said. He was done with her.
She climbed back into her clothes, wincing every time her sore skin came in contact with them. He sat at his desk and watched.