Elizabeth had spent years working on her start-up, years of hard work, long nights and pinching every penny. Like her tailor-made outfits, she was self-made, she’d started with just an online shop and a dream to show the world her art.
She’d grown this online store into four boutiques in three different cities, hired professional management and marketeers, and over a dozen seamstresses who created the clothes she designed.
Well, that was what was written in her biography anyway. In reality her first store had been bank-rolled by her father, the fashion designed by an old friend, and the hard work had been done by the people she hired. The only real truth, was that she indeed refused to spend a penny more than she needed to, except when it came to buying gifts for herself of course.
The hardest working person at Elizabeth’s company, was actually Bobby, her personal assistant. She worked tirelessly, seventy, eighty hours a week, though she was only paid a minimum wage, and she never got a day off. The business woman was harsh on her personal assistant, believing that if she wanted to be as successful as her, she’d need to prove herself through hard work and loyalty.
Even today, on the twenty-fourth of December, the day before Christmas, Elizabeth had denied the young woman a day off to prepare for the holidays. Instead, she required her to accompany her for the day, as she had several important meetings planned.
You see, Elizabeth had grown tired of running this company. She’d never been that interested in clothing or fashion, except for owning and wearing it of course. She’d been more interested in the money and just recently a large, global company had shown an interest into buying her brand.
She’d arranged showings, gifted samples, and sent countless of emails to push for this deal. There was a lot of money on the line, with which she could start something new, something that would make her even more successful and richer.
Well actually, Bobby had arranged those showings, chosen those gifts, and typed those emails; but Elizabeth had ordered her to do these things, so in the end it was her work, she thought.
The three important meetings that were planned for today, had been arranged by her personal assistant as well. The young woman had tried to point out how hard it had been to set this date, not only because it was the day before Christmas, but because they were very important people she’d be meeting with.
Elizabeth hadn’t paid the young woman’s whining any notice. She’d never really cared for Christmas herself – none of her seamstresses were getting a Christmas-bonus, no matter how much they begged – and didn’t think anyone important like her would care either.
Bobby had also prepared notes for these meetings: who they were meeting with, what their role was in the company, and what she should talk about to convince them to buy her brand.
Elizabeth hadn’t read any of it. She was already annoyed that her personal assistant had planned three meetings on a single day, that was already more work than she would normally do. She couldn’t possibly add all this reading to that, besides she’d just use her charms to convince them, that always worked.
The first meeting was at the center of town at a high-rise office building, where Elizabeth waited impatiently while her assistant parked the car.
“Why couldn’t we do just one meeting with all three of them?” she asked the young woman as they went up in the elevator.
“I’m sorry, miss,” Bobby repeated for the third or fourth time, “Their schedules were too busy, we couldn’t line anything up. This was the best I could do.”
“Hmpf, for your best, it isn’t very good, is it?” Elizabeth responded.
On the twenty-fourth floor, they were greeted by a clerk who guided them to a small meeting room where they were told to wait. Not much later, they were joined by a young man, not much older than Elizabeth herself.
She recognized him immediately, “Marley? What are you doing here?” she asked.
“I work here,” the man replied.
Marley was Elizabeth’s old business partner, though he’d been more interested in the fashion rather than the business part of things. He was the one who’d designed most of the clothing she sold even now.
Elizabeth crossed her arms, “Well, I’m not here for you,” she said, “I’m meeting someone important, over an important business deal.”
Marley chuckled and took a chair at the table across from them, “That’s the first time you’ve called me important,” he replied.
Elizabeth’s eyebrows raised in surprise, the business woman turned to look at her assistant who was reading through the meeting notes she’d prepared.
“Marley is the name I have written down here, miss,” she said.
Elizabeth rolled her eyes, there was no way that Marley, with as little business sense as he had, was important enough to have any say on this deal. “They’re letting you decide on business deals now?” she asked.
Marley shrugged, “The board of directors knows we used to work together, when the possible acquisition of your brand was brought up, they wanted to know my opinion of you, so I told them the truth.”
Elizabeth raised an eyebrow, “And what truth is that?” she asked.
“That you’re a miserable penny-pincher who stole my work,” Marley replied.
The business woman’s mouth dropped open in surprise, “You said what? I’m not a thief, I paid you for your work, and paid too much if you ask me.”
Marley shrugged, “Well you didn’t give me much of a choice, did you?”
Elizabeth shook her head in disbelief, after all the work she’d put in, he was going to ruin it for her. “So you sabotaged the deal, and arranged this meeting just so you could rub it in my face?” she asked.
Marley shook his head, “No, the deal is still on. I accepted this meeting to see whether you’d changed since the last time I’d seen you. If you have, I’ll let the directors know it’s all been worked out and the acquisition can go through.”
Elizabeth frowned, but held her silence, she really wanted this deal to go through.
“So, how can I convince you that I’m not a … what you said I am?” she finally asked.
“I want you to listen to what I have to tell you,” Marley said, “And apologize for what you’ve done.”
Elizabeth blushed slightly, he wanted her to apologize? Well… it’s not like she hadn’t told a small lie before, to get her business to grow so quickly.
“I know you however,” Marley continued, “And I know that you don’t mean half the words that come out of your mouth, so I’ve come up with another way you can apologize.”
Elizabeth raised her eyebrow again, “How?” she asked.
“You’re going to bend over this table here between us,” he said, “And take a firm spanking.”
The business woman’s eyes widened in shock, “What? You can’t be serious!” she exclaimed.
Her ex-business-partner crossed his arms, “I’ve worked with you,” he said, he looked at Bobby who had been silent this whole time as she sat beside her, “I’ve seen how you treated those beneath you, it’s about time you get a dose of your own medicine.”
Elizabeth looked at her assistant and then back at Marley. How did he know, she wondered, she’d never done that when he could’ve seen, had she? “She’s just my assistant,” she said, “You can’t do that to me,” by which she meant that she was too important, too rich to be treated like that.
Marley shrugged, “Do you want this deal to go through or not?”
Elizabeth bit her lower lip. This couldn’t be happening, she thought, he couldn’t ask this of her. Yet something inside her stirred, something seemed curious about what it would be like to be on the receiving end of such discipline.
“If I do this, you will step aside and let me make this deal?” she asked.
Marley nodded, “Everything between us will be forgiven and forgotten.”
The business woman blushed and stood up. “Could you wait outside, please?” she asked her assistant.
Bobby stood up, but Marley stopped her from leaving, “I thought you insisted your assistant be present for this meeting?” he asked, “Besides, I think it might be good for her to see this.”
Elizabeth licked her lips nervously, she had indeed insisted, even refused to give the woman a day off. It wasn’t fair, she thought, she was Bobby’s boss, of course she should be allowed to discipline her. The truth is, she liked her, despite how much she wined about hard work, long hours and little pay. Bobby was loyal and obediently accepted her chastisements and punishments. She was the only one of her employees that got this special treatment. She told herself that it would help her grow and learn, so that she could someday be as successful as her. She wouldn’t admit that she did it mostly because she loved the feeling of being in control and it had never really occurred to her that the young woman liked it too, and even got a perverse feeling of pleasure out of her submissive relationship with her boss.
Blushing deeply, she now bent over the table in front of her, like she’d ordered her assistant to do on several occasions. She closed her eyes as she heard the chairs of the others being pushed back, Bobby moving to the side, whilst Marley stepped up to her side of the table.
When her ex-business-partner placed his hand on her backside, Elizabeth bit her lower lip. She was wearing a short dress, one of her own designs – well Marley’s actually – professional, fashionable and yet a bit daring as well. She’d always felt that her arguments were more easily accepted by the men she dealt with, when they were distracted by something else. Now however, in this precarious position, it meant that her bottom was barely covered, and as Marley’s big hand cupped her buttocks, the tips of his fingers caressed the bare skin below the hem of her dress.
“Do you know what I did, after you bought me out?” Marley asked her.
Elizabeth shook her head, “No,” she hadn’t really cared to follow up on his activities after she was rid of him.
“I used the little money you offered me to pay of my debts,” Marley continued, his hand gently squeezing her backside, “But it wasn’t even enough for that. In the end I didn’t even have enough left to pay my rent.”
Elizabeth rolled her eyes, she had never had to pay rent herself, her father owned the apartment building where she lived; though it couldn’t cost that much, she thought. “What does that have to do with this?” she asked, “Just get this over with.”
Marley threateningly squeezed her backside, “You were going to take this spanking,” he said, “And listen to what I have to say, that’s what we agreed upon.”
Elizabeth blushed, she’d forgotten that she was also supposed to listen to some sob-story he had planned for her. What a waste of time, she thought, she just wanted this over with. The intimate touch of his hand on her backside was making her uncomfortable, this vulnerable position, her assistant watching from the corner, she’d never felt this little in control.
“I lived on the street for a while,” Marley continued, finding work wherever I could. No-one would hire me though, you owned all my designs, they just thought I was stealing your work.”
Elizabeth was breathing heavily now, her ex-business-partner’s hand on her bottom was warm and firm, kneading, caressing. She had this strange feeling in her stomach, this gnawing sense that almost felt like excitement and reminded her of the times when she’d disciplined her assistant, though it didn’t make sense that she’d get the same pleasure she got from punishing her, when being subjected to this humiliating ordeal.
Marley now pulled up her dress, caressing her semi-bare bottom with the palm of his hand, his fingers playing with the lace edge of her panties, “Are you listening to what I’m saying?” he asked.
“Yes,” Elizabeth replied, she was listening, she had even emphasized with him for a moment, when he’d told her how people had accused him of stealing his own work. She imagined she’d be furious if people might accuse her of lying about all the hard work she did.
Suddenly Marley raised his hand and swung it down, connecting with her backside with a loud smack. Elizabeth grunted softly as a stinging sensation spread through her buttocks. It felt good, she thought, though she didn’t know why.
“I had to start over,” Marley said, “no money, no reputation, no daddy who can buy me my own store.” He raised his hand again and smacked her backside, sending another wave of stinging pain through her skin.
“I get it, I get it,” The business woman replied. She hated it when people reminded her she hadn’t paid for her own success, that she perhaps hadn’t worked as hard for it as she pretended. Perhaps she did deserve this, she thought for a moment, perhaps that’s why it felt so good.
Her ex-business-partner now hooked his fingers behind her panties and slowly pulled them down. Elizabeth blushed deeply, she couldn’t believe he dared expose her like this, yet she didn’t stop him. She felt like she couldn’t, she had no control, she’d never felt this helpless before. He’s doing this to me, she thought, it’s not my fault this is happening. Yet she made no effort to stop him either, perhaps she thought, because she deserved it, or perhaps because of that gnawing feeling of excitement in her belly, because she liked it.
“After a while and a whole lot of luck I got taken in by this company,” Marley continued, his hand now greedily fondling her bare bottom, “They believed me and gave me a chance. They admired my work and allowed me to grow. They did all the things an employer, or business partner is supposed to do,” he raised his hand, “unlike you,” and then smacked her bottom once more.
Elizabeth licked her lips, but did not reply, resigned to listening to what he had to say.
Marley however was done talking, he raised his hand and spanked the woman’s backside, again and again, her buttocks bouncing under the impact of his hand.
Elizabeth moaned and groaned as her bottom was slowly set on fire. The stinging pain in her backside built until her buttocks were sore and red. When it became too much to bear, she couldn’t help but yelp and squeal, kicking her legs, her high heels drumming against the floor.
Marley didn’t hold back, painting her bottom red with the full swing of his arm, his hand raining down on the greedy business woman’s backside.
Elizabeth whimpered and moaned. She wished he’d kept talking, wished to hear more about his story, even if it meant him scolding her. She wished to feel that gentle touch of his hand again, even if it made her feel funny, embarrassingly aroused. Yet instead she was the one talking, her squeals telling him that she was listening, her whimpers assuring him that she was learning a lesson, the trembling of her poor bottom testament to the pain she endured, just like she’d made him endure. And even through all that pain and embarrassment, that funny, arousing sensation in her belly and between her legs refused to go away.
The sound of a naughty, selfish woman getting disciplined could be heard loudly throughout the meeting room, the hallway outside, and other rooms around them. The sound of a firm hand connecting with her bottom, echoing against the far walls as her buttocks bounced. Her squeals and moans filling the short stretch between smacks. It was Christmas Eve however, so Elizabeth hoped, that unlike her, people here cared about the holidays, that those other offices would be empty and no-one could hear her embarrassing punishment.
“Please, you can’t do this to me,” she begged, but Marley was relentless.
“I’ll pay you,” the business woman promised, “I’ll pay for your designs,” but his hand kept coming down, kept inflicting that hot, stinging pain on her backside.
“I’ll apologize,” she finally whimpered, “I apologize.”
Then, the onslaught on her backside finally stopped. Her poor bottom was on fire, burning where Marley’s hand gently caressed her. “I almost believe you,” he said, and raised his hand.
“No, wait! Please!” the business woman begged, “I mean it, I’m sorry, I should’ve treated you better.”
Marley must’ve heard something in the tone of her voice, for he didn’t spank her again, but gently lowered his arm, reassuringly squeezing her backside before stepping aside. “Alright,” he said, “I believe you, you can get back up.”
Elizabeth immediately reached back as she got up, grasping her glowing bottom in both hands, whimpering as she rubbed and squeezed some of the pain away. She looked up at Marley, and then at Bobby who was looking at them from the far corner of the room. The young woman was blushing red, almost as red as her boss for having witnessed this punishment.
She decided to ignore her assistant for now, thinking she’d have to deal with her later. Instead she focused on Marley, licking her lips as she tried to get herself back under control, and get some control of the situation. She pulled up her panties and ironed out her dress over her hips.
Ignoring the pain in her bottom she tried to sit back down on her chair, as if to continue this meeting, wincing as her sore backside connected with the firm wooden surface.
Marley moved back to his chair as well, ignoring her squirming as he sat down.
“So, we’re even now?” Elizabeth asked.
Marley nodded, “The acquisition can go through as far as I’m concerned.”
Elizabeth nodded, and then quickly stood up again. “Thank you,” she said, then blushed, “For making this deal possible,” she explained, she wasn’t thanking him for spanking her.
“My pleasure,” Marley replied simply.
With the first meeting finished, Elizabeth and Bobby quickly left the office, taking the elevator back down.
“Not a word out of you,” the business woman told her assistant.
“I didn’t say anything, miss,” Bobby replied.
Elizabeth huffed, no-one could ever again tell her she didn’t work for what she had, not after what she’d had to endure just now.
“When is this next meeting anyway?” she asked.
“Little over an hour from now,” her assistant replied.
Elizabeth groaned and reached back to sooth her stinging backside. How was she supposed to go through another meeting, if she was hardly able to sit down?
***
On their way to the next meeting, Elizabeth sat in the back of the car. She preferred this because it made her feel like she had her own driver, chauffeuring her around. Today it had the added benefit that Bobby wouldn’t see her squirming in her seat as she tried to deal with her sore, sensitive backside.
They stopped along the way for a quick bite to eat, but the other meeting was a half-hour drive away across town, so the business woman spent most of her time sitting uncomfortably in the back seat of the car. Yet when they arrived, that hour seemed to have passed much too quickly, her bottom hadn’t yet fully recovered to endure the firmer seating arrangements in a meeting room.
This was a smaller building, her assistant told her these were mostly offices the company provided for their employees that came from out of town, it wasn’t often used to invite clients or conduct meetings.
When they arrived on the second floor, they were greeted by a man slightly older than Elizabeth herself. He guided them through the open office space to one of only two meeting rooms.
Beside them, no-one else seemed to be at work. Elizabeth scoffed at this lack of work ethic, all these people taking a day off for some silly holiday. It did give her some hope however, that if things had been the same in the other building, that her punishment had been more private than she’d feared.
The man introduced himself as Tim, greeting Bobby heartily, and Elizabeth with a questioning look. Unlike Marley, he was actually an important man, part of the board of Directors, who would help make the final decision in this business deal.
Elizabeth was delighted to find out this meeting room had a set of leather couches facing each-other with a small table between them, in one corner of the room. Instead of having to hide her discomfort when sitting on some hard chair, she could comfortably settle down on the soft cushions.
“Well, here we are,” Tim began, “To discuss the acquisition of your brand by our company, I believe.”
The business woman nodded. For a moment she wished she’d actually ready the notes her assistant had prepared for her, so she’d know what this man expected of her. “Yes, I’m here to hopefully ease all your doubts and show you why my brand would be a great asset for your company,” she began.
The man smiled, “Actually,” he said, “I’m already convinced, I’ve looked through the paperwork, I’ve crunched the numbers, it all looks very promising.”
Elizabeth smiled broadly, this was too easy, it must be karma rewarding her for what had happened during that first meeting, she thought. “Great,” she replied, “So… Was there something else you wished to discuss?”
Tim nodded, “To make this deal, and make you an even richer woman than you are now, I have one condition,” he said.
Elizabeth raised an eyebrow, curious to what he might want. “And that is?” she asked.
“I want to hire your assistant for our company,” the man replied.
Elizabeth was surprised, he wanted Bobby? “Why?” she asked.
“It will be good to have someone who knows about your brand, your stores, your employees, to help integrate them into our systems,” the man replied.
Elizabeth licked her lips. What he said made sense, yet she was oddly hesitant to give up her assistant. True, when she sold the company she wouldn’t need Bobby anymore, but she had other plans, plans she would need an assistant for and she didn’t want to train another one. Bobby was loyal, hard-working, submissive, exactly what she wanted. “I’m sure you have plenty of people working for you who could figure all that out,” she replied.
“True, but I’m sure that Bobby would be happier with us. We’ll give her a raise, better working hours, a better work-life balance…” the man countered, “Why don’t we ask her what she wants?”
Elizabeth crossed her arms, she didn’t like it when people tried to take something that she considered to be hers. “Why do you care so much?” she asked, she was getting a bit suspicious, with how familiar this man spoke about her assistant.
“Because I’m her uncle,” the man replied, “And she’s been living at my home for the past six months because you don’t pay her enough to rent a flat. And yet some days I hardly see her because she comes home from work when I’m already in bed, and she leaves in the morning before I get back up.”
Elizabeth’s eyes widened in surprise as she turned to her assistant. “He’s your uncle?” she asked.
Bobby nodded, “Yes miss,” she replied.
Elizabeth shook her head, if she’d known her assistant had connections in the company, she could’ve used that to her advantage for this deal, though perhaps that’s how she had managed to arrange this meeting in the first place.
“So, Bobby, what do you think about coming to work for us?” Tim asked her before Elizabeth could say anything else.
“I’m fine where I am now, sir,” she replied.
Elizabeth grinned broadly, loyal Bobby, “See?” she replied.
“So you don’t have any complaints about the work you have to do now?” her uncle asked.
Bobby blushed and looked from her uncle to her boss and back, she didn’t like lying, so replied honestly, hoping not to upset her boss, “Well, the hours are sometimes a bit long…”
Tim nodded, “What about holidays, or taking time off? I know you were hoping to be free today to prepare for tomorrow, but here you are…”
Bobby nodded, “I guess I could use a day off sometimes.”
“What about the money, do you feel like you earn enough for all the work you do?” the man asked.
“I guess I could use a bit more, to get my own place, to pay for food…” her assistant replied.
Bobby was blushing deeply as she answered these questions, and Elizabeth wanted to put a stop to this. It was obvious to her that her uncle was making her uncomfortable, but then she realized she was actually uncomfortable because she didn’t want to paint a bad picture of her boss, while still telling the truth. Loyal Bobby, hard working, honest, and yet overworked and under-payed. The business woman couldn’t help but feel guilty.
“Does she at least show you gratitude and appreciation for all the hard work you do?” Tim asked.
Bobby shook her head, “Not really, sir,” she replied.
“Then what does she do?” he asked.
There was a short silence as Bobby thought, then she picked up her purse, opening it slowly, hesitantly. She pulled out a small leather strap, folded in half. “She uses this when she’s disappointed in my work,” she replied.
Elizabeth blushed deeply when her assistant pulled that out of her purse. She wasn’t supposed to show that to anyone. She made her carry that with her, as a reminder that she needed to work hard and act professional, always.
Tim’s wide-eyed shock showed her that he was just as surprised by this sudden reveal as she was. “She uses that,” he asked, “To do what?”
Bobby licked her lips, “To spank me, sir.”
The director’s eyes now swiveled to Elizabeth, his mouth working quietly before he was able to say anything, “I think I’ve heard enough, Bobby stays with us, or the deal is off.”
Elizabeth rolled her eyes, “What, you’ve never had to discipline one of your employees before?”
Tim shook his head, “No, not like that, though I have someone in front of me right now who I wished was one of my employees.”
Elizabeth blushed, subconsciously shifting in the couch, its soft cushions had almost let her forget the previous meeting.
“You could use this,” Bobby suddenly said, holding up the strap.
Elizabeth and Tim both looked at the young woman in surprise. “What do you mean?” her uncle asked.
Her assistant licked her lips, “If miss Elizabeth allows you to spank her with this strap, will you sign the deal and allow me to keep working for her?” she asked.
Elizabeth’s eyes widened, had she really just suggested that? She couldn’t be serious.
Tim’s eyes were twinkling with excitement however. “Now that’s a good idea,” he replied, “Spanked with the very strap she used on you, that would be a fitting punishment,” he turned towards Elizabeth, “What do you think, do we have a deal?”
Elizabeth blushed deeply, this couldn’t be happening, she thought, not again. Her bottom hadn’t yet recovered from her previous punishment, and the strap would be so much worse. She’d heard Bobby squeal and beg, and watched her squirm when she applied that on her backside. She didn’t want the same to happen to her, but then again… If her assistant could take it, then surely, she could as well.
“You’ll sign the deal?” she asked.
Tim nodded.
“And Bobby stays with me?” she asked.
Tim nodded again.
Elizabeth licked her lips, what was she doing, she thought, she could easily get another assistant. Why would she take this punishment, just for her? Though part of her knew she deserved it, for how she’d treated the poor woman, how she still treated her.
She looked at her assistant suspiciously, first the meeting with Marley and now with her uncle. She’d arranged these meetings, she’d shown him the strap and made this suggestion. “Did you plan all this?” she asked her.
Her assistant blushed, “No, miss, of course not,” she replied.
Elizabeth frowned, but she knew Bobby never lied to her. “In that case,” she said, “I will accept this punishment, for you.”
Bobby blushed deeply, and smiled broadly, this was the first time her boss had done something noteworthy for her.
“Alright,” Tim then said, “Bobby can you get up and give your boss some room? Elizabeth, I want you face-down on that couch, on your belly.”
The business woman blushed as her assistant stood up, leaving her alone. She bit her lip as she turned around to lay down on the couch. Already that now slightly familiar feeling of arousal and anticipation was gnawing at her lower belly as a warm glow of excitement spread between her legs. She decided to ignore this, she didn’t like this, she was only doing it because she had no other choice.
“Raise your dress,” Tim commanded her.
Elizabeth blushed, but it wasn’t the first time today that she had to expose herself like this. Slowly, ignoring the excited butterflies in her stomach, she lifted up her dress.
A long silence followed, as the director stared in what must be surprise, at her already slightly red bottom.
“I was going to offer you a bit of a warm-up first,” he finally said, “But it seems like someone’s already done that for me.
Elizabeth’s blush deepened as she buried her face in the couch cushions.
“Our last meeting had a similar… subject,” her assistant replied.
Tim chuckled, “I see, it almost seems like you’re on a path of redemption, young lady,” he addressed Elizabeth, “Pull down those panties, let me have a better look.”
Elizabeth bit her lower lip, but she once again found herself unable, or unwilling to disobey. She could feel the director was now fully in control, even as he made her bare herself, rather than doing it himself. She slowly pushed down her panties, completely exposing herself and her glowing red backside. It was fair, she thought, she never let Bobby keep hers on either.
Then she felt the cold touch of the leather strap placed against her behind, menacingly, waiting for that first swat to land. No warm hand, no squeezing or fondling, no taking advantage of her vulnerable position like Marley had done. Elizabeth wondered whether the director was holding himself back in front of his niece, she could almost believe that she missed that intimate touch.
Then the strap was raised into the air, and there was no more time to think about such things.
It landed with a sharp crack across the business woman’s backside, and she squealed loudly.
Tim took his time with each stroke, raising his arm, aiming, striking her backside. Her earlier spanking had been fast and impassioned as her former business-partner got his revenge. This one was slow and methodical, each stroke aimed perfectly aligned with the previous, making sure she learned a lesson.
Elizabeth moaned and squirmed, digging her face into the couch cushions, drumming her feet against the arm-rest behind her. Yet she could also feel her back arching, her bottom curving upwards as if inviting more punishment, as if she wanted it, liked it.
The pain was different than before, perhaps not worse, for Marley’s hands had been strong and heavy while the strap was light and quick, but across her already sore backside it felt that much more painful.
She mewled and groaned as bright red stripes were painted across her poor bottom, across the already sore, red skin.
Again and again, the strap landed, and Elizabeth squealed.
I hope you’re watching, she thought, thinking about Bobby, I hope you can see what I’m doing for you. Though the fact that her assistant was watching this, brought its own level of embarrassment.
“Please,” she begged, as the strap kept coming, without mercy, “Please, I’ll treat her better,” she promised.
Tim aimed the strap at her poor bottom, pulling out more promises with each stroke.
“I’ll give her a raise,” Elizabeth promised.
Whack!
“She won’t have to work such long hours!”
Whack!
“She can take the holidays off…”
Whack!
“Please, I won’t even spank her again,” she promised.
Whack!
Elizabeth whimpered and moaned, as none of her promises could make up for her behavior up to this point. Until finally, when her legs were trembling and her bottom bruised and sore, her punishment ended.
“Alright,” Tim said, “I think that’s enough. You can get up and cover yourself.”
The business woman whimpered softly, reaching back to caress her poor bottom. She made not effort to get up yet.
“Are you alright, miss?” Bobby asked, she’d suddenly appeared, kneeling beside her.
This is all your fault, Elizabeth wanted to say, but it wasn’t, it was her own. “It’s alright,” she replied, “Just a bit sore,” she couldn’t let her employee know how much she was hurting of course.
“Here, take this,” Bobby said, “It should help.” She handed her a small round pot.
“What is it?” Elizabeth asked, not immediately accepting the item.
Her assistant blushed slightly, “It’s an ointment that should soothe the pain, I got it shortly after you started to use that strap whenever I misbehaved and always carry it with me just in case.”
Elizabeth licked her lips, it was probably something cheap, she thought, with how little she earned, but than blushed at that thought and accepted the pot. “Thank you Bobby,” she replied.
Clumsily, she opened it up and tried to spread some of the cool ointment over her poor bottom. Somewhere behind her, she knew Tim was watching, she wanted to cover herself up but couldn’t, not until her poor bottom wasn’t burning so badly.
“Let me help, miss,” her assistant said, taking the pot out of her hands and quickly, almost expertly placing her fingers against her trembling buttocks.
Bobby’s touch was gentle, barely noticeable, the polar opposite of Marley’s fondling, and yet that made it that much more intimate. Especially when the ointment did its work, soothing her pain and cooling down her backside, did it ignite the arousal inside of her. Elizabeth buried her face in the couch cushions, hiding her blush and the excitement on her face.
“I think that’s enough,” she said after a moment, as the most immediate pain had subsided and her arousal was getting so hot that she had to squeeze her legs closed to hide the wet excitement between her legs.
“I’m sorry, miss,” Bobby replied, “I wasn’t sure how long I should continue.”
Elizabeth blushed and carefully pulled up her panties, covering herself up, “You did well,” she replied, while she wished she could’ve let her continue a bit longer, “Perhaps we can add another layer later.”
Elizabeth got up, careful not to put any weight on her backside before she stood. She brushed back her hair and pulled down her dress before facing Tim, who’d been watching her closely all this time.
“You remember all those promises you made?” he asked.
The business woman nodded, “I do.”
“Good, then I will happily vote in favor of our business agreement.”
Elizabeth waited, impatiently, as her assistant said goodbye to her uncle, before finally leaving the meeting room.
They didn’t speak until they were in their car, Elizabeth in the back-seat, squirming and grumbling.
“Miss?” Bobby asked before they left.
“What is it?” Elizabeth asked, growing slightly irritated now that her punishment was done and she was reminding herself of who she was and how unfairly she’d been treated.
“You promised my uncle that you wouldn’t spank me anymore,” her assistant continued.
Elizabeth rolled her eyes, yeah she had, and she also had to give her a raise and all that other stuff. She was beginning to wonder why she’d agreed to any of this.
“I don’t really mind,” Bobby said, “So you don’t have to keep that promise if you don’t want to.”
The business woman’s eyes widened slightly in surprise, “You want me to keep doing it?” she asked.
“If you want to,” Bobby replied.
The business woman frowned, wondering why she would ever agree to that after she’d promised not to do it any more, but then again, she’d agreed to it in the past as well. Sitting sorely, uncomfortable on her own red bottom, she couldn’t help but think about that gnawing feeling of arousal, that excitement she’d felt, both times today as she’d been disciplined. Perhaps she and her assistant had more in common than she’d thought.
“Did your uncle at least give you back that strap?” she asked.
“He did,” Bobby replied.
Elizabeth grinned, “Then perhaps we should see that as a sign that it’s okay to break that one promise.”
Her assistant chuckled. “Are you ready for the last meeting, miss? We have to be there in little under an hour.”
The business woman groaned. “I’m not sure I’ll be able to sit through another meeting,” she said, “But I guess I don’t have a choice…”
“We have a bit of extra time before we get there,” her assistant replied, “I could apply another layer of that ointment, that might help.”
Elizabeth blushed slightly, “Thank you, that would help,” she replied, but she wondered how much. Part of her was very anxious for this last meeting. She was two out of two already when it came to suffering some harsh punishment in these events. She wondered whether it wasn’t some karmic justice that had come for her. She wanted to think that couldn’t be true, that she didn’t deserve all this, but part of her knew she did.
***
The third meeting was planned at yet another building across town where the company had some offices. Elizabeth wondered for a moment whether these three separate meetings in three separate locations had been planned this way to impress her.
She didn’t think too long about this however, she was too preoccupied with what her assistant was doing.
They’d arrived early and decided to just wait in the car, on the parking lot right outside the building. Bobby had joined her in the back and Elizabeth now knelt on the back-seat, facing backwards, as her assistant had raised her dress and cared for her poor bottom with another layer of soothing ointment.
It was embarrassing, having to be cared for like this by her assistant, and she could only hope no-one saw them out there. The lot was mostly empty luckily, here as well everyone seemed to have taken the day off for the holidays.. Yet it was also enjoyable, her assistant’s soft hands, her gentle touch, the cool soothing creme. She couldn’t help but enjoy this pleasant feeling, whilst trying to ignore the arousal building in her body.
“I think we should go inside about now,” her assistant suddenly said.
Elizabeth licked her lips and then looked at her watch. She was surprised by how much time had passed. “You’re right,” she replied as she pulled up her panties and lowered her dress, “I think I should be able to sit through a short meeting now.”
Her assistant giggled, and the business women wanted to tell her off for laughing at her, before she realized she’d made a joke. She usually never joked around with her employees.
Together with Bobby she entered the also nearly-empty office building, until they reached yet one more meeting room. The older man that greeted them looked vaguely familiar, though she couldn’t quite place him.
They sat down around a large table and Elizabeth was able to sit without grimacing, thanks to her assistant’s skilled hands and soothing lotion. Yet she was still nervous, still worried that this meeting would turn out like the others, like some kind of grand coincidence of fate. The fact that she seemed to recognize the man in front of her, but not remember him, made her anxious.
“Elizabeth,” the man greeted her, “And Bobby, I assume?”
Her assistant nodded, and the business woman licked her lips as she felt like he was expecting her to know his name and greet him accordingly. Perhaps that information had been in Bobby’s notes as well.
“You don’t remember me, do you?” the man replied, “That’s alright, it has been many years.”
Elizabeth nodded, “I’m sorry, sir,” she might not work as hard as she claimed, but she knew how to act tactful in a situation like this, “I seem to recognize your face, but I can’t remember from where.”
The man smiled, “It’s Charles, your father and I used to be close friends,” he reminded her, “It’s been what, fifteen years now? You’ve grown a lot.”
Elizabeth smiled in turn. She remembered now, one of her father’s close friends. She’d been but a teenager at the time when he was a regular visitor at their home. “Quite a while indeed,” she replied, “You and father were business partners, were you not?”
She blushed, being suddenly reminded of her own partner Marley and how their business had ended. If she remembered correctly, her father and Charles hadn’t separated as friends either. She was suddenly very nervous about where this meeting was headed.
“Once upon a time,” Charles replied, “It’s interesting that I now might do business once again with your family.”
Elizabeth licked her lips, “I am not my father though,” she replied, wanting to separate herself as much as possible from any bad blood that was between the two of them.
The older man nodded. “Maybe not,” he said, “Though I’ve heard rumors that you have quite a lot in common with your old man.”
The business woman raised an eyebrow, “Like what?” she asked.
“Certain business practices,” Charles replied, “A love for money over people, putting yourself above others…”
Elizabeth blushed, for she knew there was truth to these accusations. “Would it help our deal, if I told you I’ve only recently been made aware of some of these… minor issues?”
Charles laughed, “Oh don’t worry, I’m not here to sabotage our business deal,” he said, “I just wanted to talk to you, and see that you do not end up like your father.”
The business woman’s eyebrows raised in surprise. “My father is rich, and successful, who wouldn’t want to end up like him?” she asked.
Charles shook his head, “Your father is miserable, and lonely,” he said.
Elizabeth frowned, “He has many friends,” she replied, “He’s never alone.”
“Not alone no,” Charles replied, “But lonely. The people that surround him want his money or his favor, but no-one is there for him. He has no friends, except for his money… I think that I was his last true friend and he’s been alone for many years now.”
Elizabeth blushed, she couldn’t listen to him saying these things about her father, but part of her recognized it as the truth.
“If you go on the same path as your father,” Charles continued, “If you care for nothing, not the company you’ve built, not the people you employ, then you will end up like him, miserable and alone.”
The business women bit her lower lip, she didn’t want to believe what he was saying. She didn’t want to believe in this grim version of her future. “So what then?” she asked, “How do you think you can save me from myself, from the way I’ve been raised?” she thought back on what had happened to her that day, to the lessons she’d learned and how she’d learned them, “Do you think some punishment, some spanking is going to magically fix all of it?”
Charles laughed loudly, surprised, his face slightly shocked by her choice of words. “I merely wanted to warn you,” he said, “Though that certainly is quite an idea. I did use to think, at times when I was a visitor in your home, that your father would’ve done better to put you across his knee, instead of buying your happiness with gold.”
Elizabeth licked her lips, she couldn’t believe she’d just said that out loud, she’d been so sure that this meeting would go like the others that she’d blurted it out before he could’ve even threatened her with it. It was happening again, she thought, and this time she instigated it herself and yet her whole body was tingling with anticipation.
The silence between them stretched for what seemed like an eternity.
“Is that what you want?” Charles finally asked.
Elizabeth blushed. No, of course not, she was rich, important, leader of her own company. She didn’t need anyone to discipline her, she wasn’t going to end up miserable and alone… “I think so,” she replied.
Charles smiled, slightly confused, but interested as well. “I will vote in favor of our deal regardless,” he said, “You don’t have to do this if you don’t want to.”
Elizabeth’s blush deepened, she didn’t want this, did she? “Like you said,” she replied, “This isn’t about the deal, it’s about the future.”
The older man nodded, his smile widening. “Alright then,” he said, “Do you want some privacy?” he asked as he looked at Bobby.
Elizabeth had almost forgotten her assistant was still there, “She can stay,” she said, Bobby had already seen it all, and she felt a bit better knowing she was there, knowing she knew what it was like and was there to help her get through this.
Charles got up out of his chair and joined her on her side of the table. There he grabbed another chair, turned it around and sat down. “Well then, across my knee, young lady.”
Elizabeth bit her lips. Why was she doing this? She wondered. Her bottom was already so sore, Bobby’s ointment had helped, but not that much. Would she even be able to take another spanking so soon after the others?
Yet while her mind hesitated, her body acted on its own. She got up off her chair, her whole skin, head to toe, tingling with excitement. She lowered herself across the man’s lap. This position, with her body draped over his felt much more intimate than those before, when she’d bent over the table or lain down on the couch. She could feel his lap underneath her, his muscles moving as he pulled her up further onto his lap until her bottom was right in the middle, her hands touching the floor as her feet dangled in the air. She could feel a faint heartbeat coming from him, it was fast, like her own.
Then she felt his hand, warm and strong, gliding up her leg, her thighs, pushing up her dress until it cupped her buttocks.
“It seems this is not your first punishment today,” Charles noticed, his voice sounding shocked as he discovered that her bottom was already red.
Elizabeth blushed, “Those are in the past,” she replied, “This one is for the future.”
Charles chuckled, “Well you asked for it,” he said, and then raised his arm.
Elizabeth moaned and groaned as the older man spanked her behind. Her bottom was sore and tender, sensitive after so much attention in one day, and whilst he didn’t spank her hard, the pain from before quickly returned, the fire that had been subdued by her assistant’s gentle touch brought back to life.
Again and again, his hand connected with her backside, her buttocks bouncing, her mouth wide open as she moaned.
Yet she knew he was holding back, she knew now how hard and painful a spanking could be. Perhaps he was being lenient because she already looked so sore and bruised, or perhaps he didn’t think she deserved it.
“Harder, please,” Elizabeth asked.
Charles paused for a moment, perhaps surprised by her request. Then he hooked his fingers behind her panties and pulled them down, baring them completely. The next swat across her now bare bottom was hard, almost rocking her off his lap.
Elizabeth squealed but then next swat already landed, just as hard, sending torturous pain through her poor, throbbing bottom. She wailed and moaned, wondering why she’d asked for this, wondering why she’d needed him to go harder.
She kicked her feet but found no purchase in the air as she dangled across his lap. There was no couch pillow this time to bury her face in as she squealed and moaned.
Her bottom was on fire, and still her punishment continued, his hand mercilessly raining down on her backside.
Charles was relentless, either eager to save her from the future he foresaw for her, or perhaps just taking advantage of what she had asked of him, taking pleasure in disciplining her. Again and again, the sound of his hand connecting with her behind echoed in the room. Whatever his motivation was, he was in full control, all Elizabeth could do was moan and shriek, and accept his discipline.
She didn’t beg this time, didn’t make promises, not to him, but as she whimpered and moaned, she promised herself that she would not end up like her father.
Then finally, her punishment was over. Charles stopped, his hand heavy and hot on her trembling buttocks. She could feel her own heartbeat against the palm of his hand and could feel his coming from underneath her, from an embarrassingly firm bulge in his lap that had formed while she’d lain there struggling, moaning and squirming.
“Is this what you wanted?” Charles asked her.
Elizabeth whimpered softly, “I don’t know,” she replied honestly.
Charles helped her back up on her feet. She stood unsteadily, her legs trembling whilst he held her by her elbow, “Come with me,” he said.
Confused, a bit dazed, she let him take her to the corner of the room, her panties still dangling around her legs, almost making her trip.
“I’ll give you some time to think,” Charles said, “So that you can figure out what you want.”
Elizabeth blushed when she realized he was making her stand in the corner, like some naughty girl.
“Put your hands on your head,” Charles told her.
Blushing even deeper, the business woman placed her hands on her head, standing in the corner, nose against the wall, bare red bottom exposed.
She listened as the man returned to his seat and then started a quiet conversation with her assistant, though she couldn’t hear what they were saying.
Beside her was a Christmas tree that someone had placed there to decorate the meeting room for the holidays. Elizabeth found herself distracted by its lights. She examined its ornaments and began counting them so that she would stop thinking about what had happened to her and to distract herself from the pain in her poor backside.
When she’d counted them all twice, she pulled up her panties, pushed down her dress and turned around to join Charles and Bobby.
The older man smiled at her, “Have you had time to think?” he asked.
Elizabeth nodded, waiting for him to ask her more. When he didn’t, she replied, ‘I know what I want now.”
Charles smiled, “Good,” he replied, still not asking her what it was she wanted, somehow respecting her privacy, after having just spanked her bare bottom.
“I think we’ve said all that needs to be said,” her assistant suddenly said, interrupting the awkward conversation.
The older man smiled slightly, “Yes, I think this meeting, whilst short, has already been more productive than I’d anticipated.”
Elizabeth nodded, “I agree.”
“Well, we’ll see each-other again when the paperwork gets signed,” Charles replied, “I have a feeling it will all work out in your favor.”
Elizabeth couldn’t help but smile, even with the burning, stinging pain covering her bottom. She’d done it, she thought, had it been worth the price?
After they left the offices, she asked her assistant to drive her home, but not before asking her to join her in the back-seat once more to soothe her poor bottom, she’d need it to deal with the ride home, and even after Bobby’s gentle hands and cool ointment, she sat squirming the whole ride.
***
Elizabeth had gone to bed early that night. After all that had happened that day, her mind couldn’t stand being awake, reliving it again and again in her head.
It was over now, she’d thought, the deal would go through, she’d be rich, powerful, no-one would ever do that to her again. Except that they did, in her dreams, it happened over and over again, Marley spanking her for her misdeeds in the past, Bobby’s uncle punishing her for her current behavior towards his niece and others, and Charles disciplining her as a warning for her future.
She’d slept naked, with no sheets, laying face-down on her bed because her bottom could not endure being touched, and yet she woke up sweating and hot, early in the morning.
It was Christmas day, no-one would be working, not even Bobby.
Elizabeth had plans however, she went to her home office. She’d built this to show people how much she worked, that even at home, she was always busy. In reality however, the office saw little use. Right now it felt empty, like something was missing. She couldn’t fathom what it was, until she thought about those offices and meeting rooms she’d visited the day before, all decorated with Christmas ornaments and lights. Hers had none of that of course, though at the moment she thought that perhaps a small Christmas tree would fit nicely in here.
When she sat down at her desk, her bottom was still sensitive and sore, not red, but pink and tender. The pain did not distract however, but encouraged her to work and focus. She spent hours by herself at her desk, squirming in her seat as she did more work in half-a-day than she’d usually do in a month.
Finally, when she was done, she had a stack of papers thicker than her fist, which she then separated in several folders that could fill an entire suitcase.
Now she needed her assistant.
She called Bobby, knowing she had the day off, celebrating the holidays. She had in fact invited her to celebrate with her family. She did so every year, and every year Elizabeth declined.
“Hey Bobby,” she said when the young woman picked up her phone.
“Hello miss,” her assistant replied, slightly worried that her boss was calling her on her one day off, “Is everything all right?”
“Is that invitation for Christmas still open?” Elizabeth asked.
A short stunned silence followed, “Of course!” Bobby replied delightedly, “We were about to start. Do you know where it is? Do you want me to come pick you up?”
“That’s alright, I know where it is,” Elizabeth replied, she’d looked up the address earlier, “I can drive myself, I will be there in about fifteen minutes.”
The business woman was a bit nervous, she’d never been to a party like this before. Her father didn’t approve of parties, claimed they were a waste of money.
There was light coming from the windows of the house she’d arrived had, laughter and music coming from inside.
Bobby let her in and showed her around, introducing her to her many family members whilst they offered her drinks and food. One of those family members was her uncle, the same one they’d met before. Elizabeth blushed meeting him again, now remembering he’d said Bobby lived with him. Yet he was friendly and welcoming.
Their home was comfy and cozy, the Christmas decorations made everything bright and cheerful. The food was good and they talked about the things that made them happy. Elizabeth enjoyed herself more than she’d anticipated, loosening up more with each glass of wine she drank.
At the end of the night, gifts were passed among each-other.
“I’m sorry, if I knew you’d be coming, I’d have gotten you a gift as well,” Bobby told her.
Elizabeth smiled, “Actually,” she said, “I brought you something.”
She picked up her suitcase that she’d left by the door and handed it to the young woman. There was a silence in the room, as the others looked. They had all watched with polite interest as the other gifts had been opened, but this one seemed to truly grab their attention, so much so, that Elizabeth wondered how much these people knew about her and how rare it was that she gifted someone with anything.
Excitedly, her assistant opened the suitcase, though the smile on her face turned sour when she noticed the big stack of folders and files. “Is this… work?” she asked.
“I needed your help,” Elizabeth explained, “I’ve been working on it all day.”
She saw that Bobby didn’t know how to react, that this might be too much, to be gifted with more work on Christmas day, even for her; so Elizabeth quickly continued her explanation.
“Those are all the contracts, of everyone in our company, from the managers to the delivery boys and seamstresses,” she said, “I compared their wages to those in other companies, and raised them all to be higher… But I don’t know what to do next, how to get these filed and make sure they all get their money.”
Bobby licked her lips, her eyes wide in surprise, “You’re giving everyone a raise?” she asked.
Elizabeth nodded, “And Christmas bonuses as well,” she said, “It’s all in there.”
Her assistant now smiled broadly, “I will sort it all out for you miss,” she said, “As soon as I can.” She was now quickly sorting through all the folders, looking at all the names.
“If you’re looking for yours,” the business woman said, “It doesn’t have your name on it.”
Bobby looked back up at her, surprised once more, “Why not?” she asked.
“Yours is a bit special,” Elizabeth replied, taking the bottom folder out of the case, one that had no name on it.
Her assistant opened it quickly, but then looked back up at her in surprise, “What is this?” she asked.
“If you sign that,” Elizabeth replied, “You’ll become my partner, no longer an assistant, you’ll have an equal say in our company.”
Bobby was now blushing deeply, tears forming in her eyes. “Our company?” she asked, “I thought…”
“I’ve decided I’m not selling after all,” Elizabeth replied, she smiled sheepishly, that had been the hardest decision to make, it almost felt like that meant everything she’d had to endure the day before had been for nothing, but she felt it was the right decision.
“Thank you,” Bobby stammered.
“You’ll decide your own wages,” Elizabeth continued, “Choose your own hours and even hire your own assistant… Though I do expect your help picking a new one for me as well.”
Her new partner giggled, “Of course I’ll help, miss,” a few tears rolling down her cheeks.
The others who’d been very quiet this entire time, now joined in on their conversation, congratulating Bobby on her promotion, expressing their surprise and gratitude.
As Bobby received hugs and congratulations, Elizabeth noticed her uncle standing beside her. She blushed slightly, wondering what he thought about her sudden change of heart and how much he might’ve had to do with it. “A true Christmas miracle,” he said.
Elizabeth chuckled, “Happy Christmas,” she replied.
Later that evening, when most of the guests had left, while Bobby’s uncle was cleaning up the dishes, Elizabeth found herself alone for the first time with her new partner.
“I guess things will change now,” her old assistant said.
Elizabeth nodded, “For the better, I hope,” she replied.
“Being your partner,” Bobby began, blushing slightly, “Does that mean I won’t be having to carry that strap with me anymore?”
The business woman chuckled and then licked her lips, slightly nervous. “Actually,”she said, “I was hoping you’d be willing to hold onto that for a little longer.”
Bobby raised an eyebrow, not in surprise, but in hope.
“You see, at the top, there is no-one to hold you accountable for your actions, so I was hoping we could do that, for each-other,” Elizabeth explained.
Her new partner licked her lips, “For each-other?” She asked.
Elizabeth blushed slightly, “I can make sure you keep working hard and fair and learn your new responsibilities,” she said, “And Is was hoping that you in return, could make sure I don’t fall back into old habits.”
Bobby giggled, “I’d love that, miss.”
Elizabeth raised the half-empty glass of wine she’d been holding, “To the future she said.”
Bobby raised her as well, “To the future… and many sore, red bottoms to come.”
Elizabeth drank her wine, and giggled, she couldn’t remember the last time she’d laughed this much.
***
The end
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