“Y-yessir,” she squeaked.
“So I leave it to you. If you’d like to be trained to be a better secretary, fine. But if you find this too demeaning or objectionable, then you may get up right now and go. I’ll let Mrs. Dowd know.”
Emily’s mind raced. How could this be happening to her? This was the twenty-first century! A voice in her head declared:
Bosses can’t treat their employees this way!
But another part of her, deep down inside, told her something quite different—something startling and naughty.
This is extremely arousing.
She squeezed her legs together and realized it was true. It had been true when her father had spanked her and it was still true today. That strange feeling began to bubble up inside her.
“Sir,” she finally said, not sure which voice was about to speak, the modern woman or that other voice, the dark one. She felt she could’ve gone either way. “Sir, please teach me to be a better secretary.”
Emily’s knees grew weak when she realized what she’d just said—and why she had said it. She needed it. It wasn’t as much for Mr. Caudry as it was for her.
“Very well. You made two mistakes today and one yesterday. That’s three swats with this ruler. It would be best if you didn’t make any noise.” He went to a cabinet and turned on a radio. Jazz music filled the air. Emily braced herself. She didn’t dare look back. Instead, she kept her eyes on her mistakes.
Whack!
The first blow was a shock, but it was tolerable. Only afterward did she feel the burn of the mark on her flesh, through her clothes. She couldn’t help herself, she wiggled her behind, trying to cool the fire. He made no comment.
Whack!
This blow was harder. She bit her lip to keep from crying out. Emily had a sudden image of herself, hunched over his desk, her brown hair in disarray, her ass wiggling at him. She felt embarrassment mix in with arousal in her stomach and loins.
Whack!
The pain was sharp, but she immediately felt better now that it was over. She shook her bottom from side to side, not caring that he was staring at it. She just had to cool it off! The pain softened and spread and Emily realized with great embarrassment it was making her wetter! She pressed her thighs together and hoped he wouldn’t notice.
He came around the desk and put the ruler away. “Very well. You accepted your punishment with grace. You may pick up the letter and go make your corrections.”
Emily straightened up at once, grabbed the letter and fled. Closing the door behind her, she looked out over the cubicles, certain that everyone would be staring at her. But the office seemed to hum along normally. No one paid her any attention. She ducked down behind her partition and sat gingerly in her chair, wincing at the slight sting. Yet she could not deny the feeling it had given her. Her clit seemed to be buzzing. She wanted to press her fingers against it and come. Debating whether she should correct the letter or make a quick trip to the bathroom, she paused. What would Mr. Caudry want? She made the corrections instead.
She took the freshly printed letter into his office and placed it on the desk. Her insides churned and she hoped she hadn’t missed any more errors! At long last, Mr. Caudry nodded and gave her a thin smile.
“See how quickly you learned?”
“Thank you, Mr. Caudry,” she said and began to back out of the room.
“But you forgot one thing,” he said, freezing her in her tracks.
“W-w-what, sir?”
He held up the letter. “How am I supposed to get this to the recipient?”
She felt a sudden pang of fear. She had forgotten to type up the envelope! How stupid! “Oh! I’m sorry! I’ll get you the envelope at once!”
He nodded. She fled.
Emily fed an envelope into the printer and typed out the address, not bothering to sit down. Her body seemed to be on fire, wondering if he would spank her again. It felt strange— part of her was terrified by the idea and another part of her was secretly thrilled by it. Why? Shaking her head, she took the envelope into Mr. Caudry’s office.
“Here you go, sir. I’m sorr—”
“Assume the position.”
She stared at him, stricken. “Sir?”
“Did you not want to keep your job?”
“Uh, no sir, I mean, yes, sir,” she said and quickly moved up against the desk, bracing herself with her elbows. Her heart pounded and her pussy throbbed.
“That’s going to be two strokes this time,” he informed her, sliding open the drawer and taking out that damned ruler.
He did not waste time. Whack! Whack! It was suddenly over. Emily stayed in position until he gave her permission to rise. When she did, her face red and her body trembling, he gave her another smile. It made her shiver with fear or desire, she couldn’t tell which.
“I’m glad to see that you are learning so quickly. There’s hope for you yet, Miss Robinson.”
“Yes, sir. Thank you, sir.” She retreated.
Outside, she paused long enough to grab her purse and headed for the bathroom. Safely inside a stall, she pulled her pantyhose down and flipped up her skirt, twisting back to examine her bottom. Each mark with the ruler was clearly outlined—five in all. Three on her left cheek, two on her right.
Now that she was alone, Emily couldn’t stop herself. She sat on the toilet and her hand went between her legs without even thinking about it. Her pussy was dripping wet, as if she had undergone an hour of foreplay instead of a painful spanking. Touching her clit made her shudder with pleasure. Biting her lip to keep from moaning aloud, Emily rubbed herself to a quick climax, right there in the bathroom. It was something she had never done before in the workplace.
What is wrong with me? she wondered.
When she returned to her desk, she realized a precedent had been established. Is that what she wanted? Or should she quit despite her shaky financial situation? Something besides her need for money made her decide to stick it out a while longer. Just to see where this all would lead. Maybe, just maybe, she’d learn so quickly the spankings would stop and she and Mr. Caudry would be able to achieve some kind of détente.
But her pussy told her a different story.
That night, after a half-bottle of wine, Emily was relaxing on the couch in her sweatpants and T-shirt, glad to have ditched her confining work clothes. She recalled her embarrassing punishment and tried to understand her feelings about it. Everything she had learned told her that this was wrong. She shouldn’t be allowing this behavior. No job was worth it!
Why, I’m going to march right into Mrs. Dowd’s office tomorrow and let her know what’s going on! I won’t put up with this kind of treatment! What kind a man is this Mr. Caudry?
Her clit throbbed and Emily’s internal diatribe faded away. Her hand stole to the vee of her legs and rubbed her pussy through the soft material. Her eyes closed and her head tipped back.
“Ohhhhh,” she breathed.
Her fingers wiggled their way underneath the waistband and into her panties. Her pussy was once again wet and she shook her head. Stop this! She scolded herself. You’re not supposed to be turned on by that kind of behavior! But her fingers ignored her. They drew up the moisture to her clit, which seemed swollen with desire.
“Oh, god,” she moaned, rubbing herself. Her climax was right there, hovering and she brought it crashing over her in less than a minute. Her fingers kept moving.
“Jesus!” She muttered when she had recovered and felt another one coming along. “What is happening to me?”
3
For the rest of the week, Emily double- and triple-checked her work, handing over perfect letters, complete with envelopes, for Mr. Caudry’s approval. She even remembered to run them through the meter for him. She never gave him a reason to punish her and, in return, she received his thin smile, which she had come to learn was his only sign of appreciation. But it was clear he did appreciate her efforts. Emily felt a breakthrough had been achieved and she was certain she would succeed where the others had failed.