Punish Me, Please Me

by Ashley Zacharias

  “A prostitute? Hooker? Whore?”

  “Yes,” he said in a low voice and his blush deepened.

  “No. I’m a manger in a mid-sized manufacturing company. I’ve never had sex for money. I’m not having sex for money now. I’m doing this...” It was her turn to search for the right words.

  He waited patiently.

  Why was she doing this? The bottom line was that she would get money from this transaction. That made her a whore. But not really. She wanted the status of the corner office more than the bump in salary. But even that wasn’t accurate. She was more interested in the power of being a VP than anything. She liked power. She liked the power that she had right here, right now. She felt like she was holding this fat, sad, unattractive man in an iron fist. She knew instinctively that he would do anything she asked in return for her favors. She felt more powerful right now than she had ever felt in her office, rubbing elbows with senior executives or dressing down her subordinates.

  Tonight was an adventure. Something naughty that she would hold secret in her heart forever after.

  She started walking and, as she walked, she talked. “I’m a professional woman. After graduating from college, I had a few different jobs, starting as a copy editor. I became a manager quickly but after that I rose from one management position to the next fairly slowly. I had to learn a lot about management to succeed. I’ll be honest with you. More honest than I’ve been with any man before. I’m not a quick study. I’m smart enough but I’m not brilliant. I worked hard in college but I mostly got Cs and Bs. I never got many As. Never stood out in class. But I do work hard and I’ve learned what I need to know to be a good manager. That hasn’t left much time for my love life. I’m pretty enough and get my share of dates. I usually have a boyfriend hanging around but never anyone who is serious about me. I’ve been dating for a dozen years and have had about that many lovers. I’ve never had a one-night stand. Never had sex with a man on a first date. Or even on a second date. Tonight is a strange adventure for me. For me, taking a stranger to a hotel room and giving him a blowjob and then walking right back out and never seeing him again is an outrageous thing to do. I’m shocked to find myself here. I never could have done this if Eli hadn’t arranged it for me.” She stopped and looked at him. “You’re my walk on the wild side. That’s why I’m looking forward to blowing you more than you can possibly know.” She looked down and saw a pole tenting his pants. She grinned and stroked her hand against his crotch in a slow, deliberate movement, right there on the street. “So let’s find that room so that I can get to it.”

  He practically creamed his pants right there.

  She was lying. She was into the adventure in an intellectual sense, but she wasn’t looking forward to getting down on her knees in front of this man. He was too homely. Too sad. Too weak. She was lying to make sure that he understood the deal and would go along with it. He had reservations about being serviced by a prostitute so she told him what he needed to hear to understand that she was a real person and not a sex worker. Honesty was a tool that she was using to manage him. That’s what she did. She managed people. And if, sometimes, that required being honest, she could do that, too.

  The key to management was to project the right image at the right time.

  She was dressed in a conservative business suit to project one image but she had planned to change that image as soon as she entered the hotel room.

  She turned on all the lights. Then, when she removed her navy wool jacket, Dixie could see clearly that she was wearing a sheer white blouse and no bra. Her nipples were erect and pressed hard against the thin material. He could see every detail. Her tits flowed and heaved freely as she pulled a chair away from the wall.

  Dixie was standing stock-still in the middle of the room, watching her every move with eyes almost popping from his head.

  She unbuttoned his shirt and then his pants. After pulling his pants and underwear – clean white briefs, thankfully – to his ankles, she told him to take them off.

  His erection was monumental. She automatically expected fat men to have small cocks. Dixie did not. He was definitely bigger than average: not too big around, but as long as a telephone pole. His member stood far out from his fatty pubis.

  She doubted that she would be able to get the whole thing in her mouth. But she was certainly going to try. For a moment, she wondered what it would be like to have that whole length buried in her cunt. It looked like it would reach her naval. But she dismissed that thought in an instant. That was not the deal and it was not happening.

  She seated him in the chair.

  There was no reason for her to remove her clothing but she took pleasure in standing in front of him and slowly unbuttoning her blouse. She was not an exhibitionist and had never taken any special joy in undressing for a man before. But Dixie had a lustful look on his face that she found strangely delightful.

  When she slipped her skirt off her hips, she revealed wicked black stockings, a garter belt, and a G-string underneath the conservative shell.

  She stepped between the fat man’s legs and sank gracefully to her knees, lowering her head to begin slowly licking the smooth bulbous end of his cock with her soft, wet tongue.

  He was breathing hard and fast, rhythmically gasping for air. He was about to come and she could have ended it right there with a touch of her hand and a moan, not thirty seconds after she had begun.

  But she wanted the event to last a little longer. She wanted leave Dixie more satisfied than he had ever imagined in his best fantasies. She pulled her head back and looked up at him. “I love the feel of your cock against my tongue,” she said. “You have a wonderful texture.” Then she grabbed him gently at the base of his shaft and lowered her head again.

  This time, she took him between her lips, opened her mouth wide enough to admit him and slid him inside. She began rocking her head, pushing him further into her mouth until he touched the back of her throat.

  She had no intention of trying to take him any deeper because she knew that she couldn’t suppress her gag reflex. Instead, she started pumping his shaft with her hand as she kept working around his head with her tongue and lips.

  After another minute, he came in her mouth.

  His volume surprised her. He had been excited all week and had been building a store of semen without releasing it himself.

  She didn’t have to wonder if she could make herself swallow, she had no choice. She couldn’t hold that much cream in her mouth without the bulk of it flowing down her throat.

  So she began swallowing with abandon.

  She had always imagined that a man pulsed a couple of times, shot out a load, and stopped. Dixie, though, kept pulsing, on and off, for a long time. His orgasm must have lasted thirty seconds, pausing and then starting again.

  She was determined to do it right. When he finally stopped and his cock began to soften, she gamely sucked him clean.

  She was a full-service cocksucker.

  She stood, told him, “That was wonderful. Thank-you,” dressed and left the room.

  He didn’t say a word, just slumped in the chair.

  She never saw Dixie again. Her last impression of him was the look of utter bliss on his face as she closed the door.

  She was extraordinarily proud to know that she had put that look there.

  * * *

  “You must have given Dixie one hell of a blowjob.”

  Keri shrugged and said nothing. This was a conversation that she wasn’t going to have.

  “He had the goofiest grin on his face when he handed over the root password to his servers. I don’t think he knew where he was or what he was doing. You didn’t just blow his prick. You blew his fucking mind. You should have seen him.”

  She had seen him. She remembered the look on his face when she closed the hotel door after herself. “Explain what you’re going to do with his servers now that you have the password.” Keri didn’t really want to know; she wanted to change the subject.
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  Eli was happy to spend the next twenty minutes spouting a continuous stream of technobabble.

  Keri didn’t understand a word but she was happy to watch him flap his gums about something other than her epic blowjob.

  When Eli finally wound down, she smiled, thanked him for his explanation, and told him that she had a meeting in a few minutes.

  “No problem,” he said. “It’s important that I had this chance to explain everything to you. If you’re going to be our vice president, you need to understand how this division operates.”

  “I know how the division operates,” she replied, archly. “I have been the manager of the entire division for almost five years.”

  “Oh,” he replied.

  She couldn’t mistake the disbelieving tone in his voice, it was so exaggerated, but she didn’t care. She was still his manager. She didn’t have to take shit from him. He had to take shit from her. That was the way a hierarchy worked.

  After lunch, she had to prepare her input for the monthly management meeting. That meant taking the highlights from her section heads’ reports and editing them together into a coherent document to pass upstairs. It was easy because she’d trained her section heads to deliver exactly the right information using exactly the right words. Mostly her job was cutting and pasting. Most of the time, most of her job was cutting and pasting to create various documents.

  She had barely begun when Eli walked into her office. He never knocked any more, just walked in whenever it suited him. He had a paper in his hand.

  “What?” she asked.

  “I have some questions for you to answer,” he said.

  “What are they?”

  “I’ve written them down.” He slid the paper across her desk.

  It was a list of questions, all right. A hundred multiple-choice questions on five pages. It looked like a test.

  She’d had her fill of tests in college and didn’t like them. She intended never to take another one. “What’s this?”

  “You said that you understood how your division worked, you being the manager and all,” he replied. “That’s good because we’ve made ourselves central to most of the other divisions. This is an assessment of your knowledge of our operations. If you want to me to help you get promoted, you’re going to have to demonstrate your knowledge to me. That’s the price of admission to a corner office.”

  “I don’t have to demonstrate anything to you,” she snapped back.

  “You don’t have to get promoted, either,” he replied. “It’s your choice. Either you take my test or you stay in your current position. I’ll be back to collect your answers in an hour.”

  She looked at the test again, then looked up at him. He still couldn’t meet her eyes.

  “I should warn you,” he said. “There is a consequence for every wrong answer.”

  “What kind of consequence?”

  “A painful consequence. So you better prove that you know as much as you claim.”

  She wasted a few minutes fuming over the arrogance of that self-righteous geek daring to demand that she justify her fitness to be a vice president. Then a couple of more minutes deciding that fuming wouldn’t accomplish anything. She needed him on her side, at least for now, so she would have to take his damned test, no matter how humiliating it was.

  And it might well be the most humiliating thing that he had asked her to do so far.

  The questions were straightforward but tough. How the hell should she know what proportion of the users’ complaints could be answered by quotations from the user manuals? Why should she care? If she needed to know, she could ask Pete, the line supervisor for the drones who fielded telephone queries. Or would he know? Oops. That was the next question: Who would know what proportion of complaints could be resolved by making the manuals more readable? That had to be Pete. Unless it was Patrice, the manger of the Communications Division. Or that guy who reported to Patrice who wrote the manuals.

  The more questions she answered, the more uncertain she became about who was responsible for what in her own division and how they interacted with the other divisions.

  When she had first seen the test, she had expected Eli to question her about technology. That was his thing, after all. But most of these asked about responsibilities and information flows between the divisions.

  When Eli came back in an hour, he was carrying the answer key. “Let’s see,” he said and began marking her answers with a red felt pen.

  “Not good,” he tutted when he was finished. “Not good at all.”

  “So what?” she snapped. “Those aren’t the kind of things that a vice president needs to know.”

  “Half of these questions could be answered from the logic chart that I created a few months ago. You remember the chart? It’s the one that you claimed that you made. Surely you should be able to answer questions about a chart that has your name on it. If you’re going to plagiarize something, you better learn what it says. The other half of the questions was background information that you’d have to know to make up the chart in the first place.”

  “Okay,” she said. “You’ve made your point. I shouldn’t have put my name on your chart.”

  “No. That’s not the point at all. I gave you the chart because it’s information that you need to know. You passed it on to William because it was information that the VP needs to know. And he passed it up to Chuck because even the CEO needs to know what was in that chart. In the larger scheme, it doesn’t matter that I created it. It matters that you never learned it. Look at this. You got fifty-three of these questions wrong. Fifty three!”

  “So what?”

  “The minimum that I expected was eighty percent. You fell below that threshold by thirty-three questions so you’re going to be punished with thirty-three strokes of a paddle on your bare ass.”

  “What?” she shrieked.

  “I told you that there would be a painful consequence for wrong answers. You’ll work late tomorrow evening. Everyone else will have gone home by eight. I’m going to come back here at nine with a wooden paddle. You’re going to bend over your desk and raise your skirt. Then I’m going to give you thirty-three strokes. It’s going to be painful and humiliating but you’re going to do it if you want to inherit that corner office.”

  “I’m not a child to be spanked by anybody. Who the hell do you think you are?”

  “I think that I’m a man who’s going to enjoy spanking you immensely,” he grinned at her. “When you’re working late tomorrow, I’d advise you to spend some of that time studying that logic chart. You never know when there’s going to be another test.”

  * * *

  “This is childish. You’re acting like a thirteen-year-old.”

  “Either you drop your drawers, raise your skirt to your waist, and bend over that desk or you can kiss your promotion goodbye.”

  “I won’t do it. It’s humiliating.”

  He turned to leave.

  “Wait,” she said before he got to the office door. “Wait. I’ll do it.”

  “Then you’re smarter than you look,” he said. “I know this is humiliating. It’s supposed to be. It’s also going to be painful. But you’ll survive.” He hefted the paddle. “It’s going to sting and bruise but this isn’t a baseball bat. It’s not going to break anything or do any lasting damage.”

  She turned to face her desk, bunched her skirt up to her waist, and bent down until her breasts were pressed against the cold surface.

  Eli smirked at the sight. She might feel obligated to protest but, as soon as he’d entered, he’d noticed that she’d cleared her desk off in preparation for this moment.

  Now he saw that her preparations had been better thought out than he’d expected. She didn’t have to drop her panties or pantyhose because she was wearing stay-up stockings and a black thong that left her buttocks naked.

  He wondered if she had changed her underwear just before the appointed hour or if she’d been wearing them all day.

&nbs
p; He bet it was all day.

  He’d made the paddle yesterday from a piece of two-inch-wide whitewood from Home Depot. It was about a quarter inch thick and light. He’d drilled a half a dozen large holes in it to make certain that it wouldn’t be slowed down too much by air resistance. He’d sanded it smooth and varnished it because he didn’t want to drive any splinters into the woman.

  He’d never paddled a woman before so he made the first stroke brisk but not too hard. Her soft, round ass bounced nicely and she gasped just a little at the shock.

  “Count them off,” he ordered.

  “One,” she replied.

  He hit her again but a little harder and she gasped more loudly. “Two.”

  And so it went.

  By the twelfth stroke, her ass was bright red and she was beginning to howl when he struck her.

  He worried that thirty-three was too many strokes. Originally he’d planned to give her one stroke for every wrong answer but, when he’d seen how many she had missed, he made an excuse for reducing the number by twenty. When he thought about how little she actually knew about the operation of her own division, he felt a surge of anger and struck her hard.

  She shrieked and her red ass bounced. It took a long moment before she was able to gasp, “Thirteen.”

  He struck her again at the same strength and she shrieked again. “Fourteen.”

  He eased up a little for the next dozen strokes. He was angry with her but he didn’t want to cause serious injury. A woman’s ass can take a fair beating but it’s not invulnerable. Eventually it’s going to sustain real damage.

  When he got to twenty-seven, she was sobbing as she counted. Her skin was so red that it looked like it was glowing but it didn’t seem to be damaged. She could take a lot more. He paused and said, “Now you’re going to feel six of my best. I’ll count them. Steel yourself.”

  She howled continuously as he laid into her with his full strength six more times.