It had been six months since Emma had made the decision to start working for herself and she never wished to go back to the office. The ability to choose your own clients, set your own deadlines and manage your own schedule, no boss, no rules or company policies, no fixed working hours or working days, it all added up to one thing: freedom.
Working as a freelancer had freed up so much time for her, it was well worth the added responsibilities and administrative work. And that’s not mentioning the increase in income.
Yet, freedom did come at a price.
That self-appointed schedule and those loose working hours often meant working late at night, the day before those self-assigned deadlines. Emma did manage to get her work done on time usually, and when she didn’t she’d just have to invoice a couple of extra hours. Some deviation from the estimated time should be expected after all.
Emma was a User Interface designer, this means she’s makes sure that the app on your phone or interface on your smart-product doesn’t just look good, but works smoothly and intuitively as well.
Her current client is the company she left six months ago. She’d left on friendly terms, her boss Jake had even promised her regular work for his company if she was interested, he’d always been happy with her work.
Emma was meeting him today, to show him her finished designs. Well, her nearly finished designs, she’d only managed to finish sixteen pages out of twenty.
Jake would understand though, she knew, those four pages were not the most important part of his app. And when she still worked for him, he’d always shown an understanding that when she had to estimate the time needed for a project, that it was just that: an estimate.
They would be meeting at Emma’s home-office. Which was actually just her kitchen. She was having a spare bedroom remodeled into an office, but it wasn’t finished yet.
For other clients she’d insisted on meeting at their company office-building, but she knew Jake well enough to feel comfortable inviting him to her home.
Her old boss arrived perfectly on time as he always did and complimented her on her choice of home decorations.
Emma showed him to the kitchen and offered him a drink before they sat down at her kitchen table, where they could both look at her laptop screen.
She showed him her finished work – this wasn’t the first time he’d seen it of course, this was all work he’d seen before, but with the last feedback applied – until she reached the first of the last four pages.
“Now these are done as well, but as you can see I haven’t had time to edit the last details as per your feedback.” Emma explained.
Jake nodded. “Aha, okay, and when will those be finished?”
Emma licked her lips and looked at the screen of her laptop as if she had to think about her schedule. “I should have them done by end of day tomorrow.” She said.
Her old boss smiled. “All right, I think my developers can start to work on it then. If you can assure me they get the last few pages tomorrow?”
“Yes, of course.” Emma replied. “I’ll make sure of it.”
“Very good.” Jake said. “I assume you’re not going to bill me for those extra hours of course? The deadline was today after all.”
Emma blushed. “I…” She’d noticed a change in Jake’s voice. She’d heard it before, when she still worked for him and accompanied him to a client. His business voice. “I did go slightly over the estimate, but it’s just a few pages.”
Jake shook his head. “Four pages, that’s twenty percent.”
Emma licked her lips. Sure, four pages out of twenty, but these were the least important pages and they were all largely finished anyway. “Perhaps I could do them at half the rate?” She offered.
Jake shook his head again. Emma had never seen him this determined before, was this how he was while negotiating? It was almost a turn on. “I could just have some of our in-house designers finish those last pages if you don’t have the time.” He said.
Emma thought about it for a moment. They were just some last few details and she’d be able to start on one of her other projects. But no, she hated submitting unfinished work. “That won’t be necessary, I’m sure we can come to some kind of an agreement.” She said.
Jake leaned back in his chair, looking at her for a long, silent moment. “You know, I’m not your boss anymore, right?”
Emma raised one of her eyebrows, of course she knew. “Yes, why?”
Jake licked his lips and smiled. “Well, I do have a suggestion, but it would’ve been quite inappropriate if you were still working for me.”
Emma blushed. Did he want sex from her? “What?” She asked, slightly scared of the answer.
“If you were to let me spank you as punishment for missing your deadline, I’d happily agree to pay full price for the remaining work.” Jake said.
Emma blushed deeper. That was not what she’d expected, but just as inappropriate as he had predicted. “I’m not going to let you spank me for money.” She replied.
Jake raised his hands defensively. “Is it really about the money?” He asked. “I’ve already paid you much more than when you still worked for me, I’m sure you don’t need that tiny bit of extra income.”
Emma bit her lip, he was right. “Okay, it’s not, I’m not doing it for the money.”
“Then what are you doing it for?” Her old boss asked. “I did offer to let my people finish it for you.”
“It’s out of principle. I don’t want to submit unfinished work” Emma explained.
Jake smiled. “Well then, it is my principle that missing a deadline should have consequences.” He said.
Emma blushed. “I don’t remember those consequences when I still worked for you.” She said.
Jake laughed. “Oh trust me, I thought about it often. But like I said, I was your boss back then and that would’ve been very inappropriate.”
Emma blushed even deeper. Her boss had thought about spanking her when she still worked for him? The thought was quite unnerving, but also, somewhat exciting.
“I’m not going to make you do anything.” Jake said. “It’s your own principles demanding you finish the job. But if you want it, you’ll have to accept the consequences of not finishing it on time.”
Emma bit her lips, weighing letting others finish her work, to getting spanked. In all this she’d completely forgotten the first option, finishing the work for free.
“All right.” She said. “I don’t have a choice do I, I’ll accept my punishment.”
Jake smiled. “You do have a choice, remember, I’m not forcing you.”
Emma blushed and nodded. “Yes, sir.” She hadn’t called him that since she worked for him.
“Let’s get this done right away then.” Jake said. “So you can get back to work.”
He stood up from his chair, so Emma followed suit, unsure of what to do.
Jake picked up her laptop and set it aside. “Bend over the table, please.” He said.
Emma blushed deeply and bent down over her kitchen table. Was this really happening? She wondered.
Her old boss placed a hand on her lower back and pushed her down until she lay flat against the table’s surface.
Emma wondered for a moment whether she should be happy that she’d invited him to the privacy of her own home for this meeting, here she should feel safe and comfortable; rather than having met him at the office-building where he might have spanked her in his private office where her ex-colleagues might’ve heard them down the hall, though perhaps then he wouldn’t have suggested it at all.
Jake placed his other hand on her bottom and slowly raised her dress to bare her thighs and then her bottom, chasing away all such thoughts until all she could think of was the here and now.
Emma was nervous and afraid, but she could also not shake this feeling of excitement and how sexy this felt.
Her old boss traced the edge of her panties with his finger and remembering the black, lace panties she put on that morning, the scene grew more and more sensual in Emma’s mind.
Then, his hand came down with a loud smack across her buttocks and Emma moaned deeply. It didn’t really hurt and a few more smacks made her bottom tingle allover.
This is what you get for procrastinating all your deadlines she told herself. Emma immediately blushed at the thought, the idea that she somehow did deserve this.
The thought didn’t last long however, for the next few smacks did hurt. Not a lot, but enough to make her feel the sting in her backside.
Emma moaned as smack after smack landed across her barely-covered bottom.
Every half a dozen smacks or so, Jake placed his hand gently on her bottom, rubbing away the sting he’d just created. His large hand squeezing and caressing her buttocks. And then he’d raise it again, bringing back the sting with the palm of his hand, swat after swat.
Half a dozen became a dozen, two dozen, each of them harder and sharper, while Emma moaned and squealed, longing for the gentle massage offered at the end.
The gentle touch of his hand felt intimate, perhaps too much, but Emma welcomed it as it eased away the pain and she welcomed the arousal that had made her blush at first, but made her wet and horny now.
Emma’s bottom was already red and sore when her old boss grabbed her panties and pulled them in one swift motion down to her knees.
“Wait, no, stop!” Emma gasped as she reached back, trying to pull up her panties, trying to cover her now bare bottom and exposed, wet pussy.
Jake took her arm and pinned it on her lower back whilst also giving her a few well-aimed swats on her bare buttocks. “Unlike you Emma, I don’t stop until my work is finished.”
Emma struggled slightly in his grasp. She thought her position had been embarrassing before, bent over her kitchen table for a spanking, her panties revealed to her old boss. It was nothing compared to being fully bared, not just her bottom, but her pussy also, she knew well enough with how hot and aroused she felt that it would be unmistakably wet, her excitement visible for him to see.
“Are you going to let me finish this, Emma?” Jake asked, focussing on keeping her in place rather than spanking her.
Emma’s struggle slowly ceased. She’d chosen this she reminded herself, she should see it through until the end, she had enough unfinished business as is.
Jake let go of the arm pinned on her back then, letting her put it back in the more comfortable position on her kitchen table. Then, he raised his hand and spanked her now unprotected bottom.
Emma moaned deeply and squealed when the palm of his hand made her buttocks bounce. The smacks on her bare bottom hurt more than they did before, but also felt even more intimate without that thin layer of protection.
When her old boss paused, gently caressing her now bare bottom like he had before, Emma forgot her embarrassment and could only feel arousal. The closer Jake’s hand came to the most private area between her legs, the louder she moaned.
Yet he always raised his hand before he reached it, spanking her poor, sore bottom until she squealed.
“You know, I’ve always wanted to do this.” Jake said during one of the longer, gentle squeezing moments. “I sometimes fantasized about it when you still worked for me.”
Emma blushed deeply. He’d said that before, but she’d almost forgotten. Forgotten that her boss used to think about spanking her. Back then she wouldn’t have let him do such a thing though, right?
“Can you imagine?” Her old boss asked. “I would’ve asked you to come to my office after work. Bend you across my desk and teach you a lesson about coming to work on time, on sloppy work and a tidy work environment or finishing your work on time like today. I had plenty of reasons back then.”
Emma moaned deeply. Jake hadn’t smacked her bottom in a while and his fingers had now reached the sensitive spot between her butthole and pussy.
“Perhaps I wouldn’t even have waited until after hours.” Jake continued. “Let your coworkers hear what happens to employees who displease the boss.”
His fingers now caressed her wet lips and Emma dared not interrupt him for he might continue to spank her instead.
“Do you like that thought, Emma? Being spanked in your boss’ office?”
Emma moaned deeply as his fingers slipped between her lips.
“Perhaps I wouldn’t even need my office. I could spank you at your own work-station. Right there where everyone could see.” He pushed two fingers deep inside of her.
Emma gasped, unable to speak or think. She’d agreed to this spanking, not knowing how aroused she’d be. Now, she didn’t know how far she was willing to let things go.
“I asked you a question, Emma.” Her old boss said. He pulled back his hand and smacked her bottom.
Emma moaned in disappointment. She realized she’d been silent too long.
“Do you like that thought?” Jake asked again. But he did not give her time to answer this time. He spanked her bottom, hard and fast.
“Yes, sir.” Emma gasped. She didn’t want him to spank her more, she wanted him to continue what he’d stopped just now.
Her old boss wasn’t having it however. His hand came down again and again, spanking her hard and fast. Emma moaned and squealed, her bottom turning red and sore.
“Please sir.” She begged when it seemed he wasn’t going to stop to squeeze and caress her bottom this time. “Please, I’ll be a better employee.” She begged as his hand came down unrelentingly.
“You’re not my employee, Emma.” Jake said, not even slowing down the onslaught on her bottom to speak. “I am just an unhappy customer.”
“Please, I’ll get the work done.” Emma promised. “I won’t miss any more deadlines.”
A few more swats landed across her sore backside, each of them making poor Emma squeal. Then, her old boss placed his hand on the soft, red skin.
He rubbed it gently, squeezing and caressing. “Can you promise me no more missed deadlines if I choose to work with you again in the future?” He asked.
“Yes, sir.” Emma replied, sighing softly as he rubbed away some of the sting.
“I don’t know.” Her old boss replied. “This project and the work you did when you were still my employee give me little confidence in your ability to keep that promise.”
Emma blushed but did not reply.
“I will need some sort of warranty if you want us to work together in the future.” Jake continued.
Emma licked her lips. “What kind of warranty?” She asked.
Jake gently rubbed her bottom, his fingers slowly moving up and down as if he was taking his time to think. “A punishment-clause, like what happened today, in case you fail to deliver on time.”
Emma blushed deeply, but with her old boss’ hand on her sore, throbbing bottom, his fingers inching closer to her wet, aroused pussy, she didn’t have to think long about it. “I guess that’s fair.” She replied.
“For all future contracts.” Jake said.
“Yes, sir.” Emma replied.
“I was very pleased with the work you did deliver, Emma.” He then said.
“Thank you, sir.” Emma replied.
“I don’t want you to think that because I had to spank you, that the work you did do was unsatisfactory.” His fingers slipped between her lips again.
Emma moaned softly.
“I would like to reward you extra for the work you’ve done so far.” Jake said. “If you want.”
Emma blushed deeply. “Yes, please.”
Her old boss’ fingers pushed into her pussy. This time he did not pull them out to spank her again, but thrusted them in and out, harder and faster while Emma moaned louder and louder. Finally, she came with a long, shuddering moan, before Jake pulled back his hand.
Emma stood up. Her bottom was sore and throbbing, her hair a mess and she was blushing scarlet while looking her old boss in the eye for the first time since bending over her kitchen table.
“So, I will be getting those last four pages from you tomorrow?” He asked matter-of-factly.
“Yes, sir.” Emma replied. “I will get to work on them straight away.
Jake smiled. “Good, I’ve always thought a sore red bottom on a firm kitchen chair made for excellent workers motivation.”
Emma bit her lip. She had a perfectly fine, soft-cushioned office chair, but something inside her already urged her to follow Jake’s advice.
“I’ll be in contact later then, I have some more projects I think would be perfect for you.” Jake paused for a moment. “You are still interested, right?”
Emma nodded. “Yes, I still have room in my schedule.”
“Good, I will talk to you later then.”
Emma walked her old boss to the front door and after she closed it behind him she stood there staring. What had just happened? Had she really just…? She should probably get to work on those last four pages before it happened again.
Two weeks later, Emma arrived at the office-building where she used to work. She still knew everyone who worked there and greeted them amiably as she passed the working-floor to Jake’s private office.
The previous project she’d worked on finished without further issue and she hadn’t seen him since their meeting in her kitchen. She felt quite nervous to talk to him again.
“Emma, how have you been?” Her old boss asked as she entered his office.
“Very good, you?” Emma asked.
“Good as well. I’m sure you found your way back easily? It hasn’t been that long since you worked here after all.” Jake continued.
“Of course.” She replied.
“I’m just asking, because our meeting was supposed to start twenty minutes ago.” Jake said.
Emma smiled. “I’m sorry, I guess I got a bit caught up in greeting all the old colleagues.”
Jake nodded. “I understand, but in our last meeting we did discuss some expectations I’d have if we were to work together again.
Emma blushed. “What do you mean?”
“Some sort of punishment-clause in any and all new contracts, I believe.” Jake said with a smile.
Emma licked her lips nervously. “That was just in case of missed deadlines.” She protested.
Jake nodded. “I guess it was. Though perhaps we shouldn’t view things so narrowly.”
Emma bit her lower lip, not knowing what to say. These past two weeks she’d often fantasized about the spanking her old boss had given her.
“There were plenty more things I wished I could’ve spanked you for when you still worked here.” Her old boss continued. “I remember tardiness being one I specifically mentioned when I had you bent over your kitchen table.”
Emma blushed. “I remember.” She said.
“If you remember, then why did you not make sue to arrive here on time, young lady?” He said.
Emma’s heart was bouncing. She didn’t know what to say. Part of her didn’t want to say anything and just submit to the spanking she knew her old boss was itching to hand out.
“So, do you agree the punishment-clause can encompass a broader range of misbehavior?” Jake asked.
Her bottom tingled, Emma could already feel the spanking she was about the receive. “Yes, sir.” She replied.
“Well then, before we discuss this new project, I want you to come over here and bend over my desk, Emma.” Jake said.
Emma stepped further into the office and froze for a moment when she heard laughter coming from the hallway. The shared office-space where her ex-coworkers worked was just down the hall. There was a non-negligible chance that they’d hear anything louder than a gentle smack or soft moan and she was sure Jake wasn’t going to be gentle, which meant her moans wouldn’t be soft, let alone her squeals.
She blushed when she stepped forward despite that realization. She’d known that when she came here, she’d been aroused by the idea ever since Jake had mentioned the possibility during her last punishment. At least he wasn’t spanking her at her own old work-station, she thought.
Emma bent over her boss’ desk and moaned softly as he raised her dress, already aroused by his touch.
“You won’t believe how much I’ve wanted to do this, Emma.” He said, before firmly smacking her backside.
Emma moaned deeply, and the smacks kept coming.
“I remember how often you’d saunter in late for work.” Jake said as he peppered her bottom. “Sure, we have sliding hours, but too often you were the last to arrive.” He smacked her bottom again and again. “Sliding hours doesn’t mean arriving past ten in the morning letting your colleagues wait when they needed you.” His hand made her bottom bounce, without pause. “And the meetings at which you arrived last, just quickly grabbing a coffee, making everyone else wait.”
Emma moaned deeply as the sting in her bottom quickly built. Her old boss didn’t stop to caress her bottom as he had last time and she quickly realized this spanking wasn’t just for arriving late today, it was for all the times he wished he’d spanked her but couldn’t.”
“I’m sorry, I’m sorry.” She moaned.
Jake did stop then. He rubbed her bottom, squeezing it intimately. “At least from now on you will feel the consequences of your behavior.” He said.
Emma moaned deeply, already deeply aroused, by the spanking as well as his caressing hand. She felt exposed here in his office, unlike at her own home. There were other people down the hall and she didn’t remember locking the door after coming in. The way she’d bent over her old boss’ desk, her bottom was pointed directly at the door for anyone arriving to see.
Thus when Jake pulled down her panties to bare her bottom, Emma gasped and grasped the sides of the desk with both hands to stop them from interfering. She bit her lip and prayed that no-one came to see what all that noise was about.
Now, as Jake spanked her bare bottom, with firm and hard smacks, he did so like before, with short pauses to rub away the sting he’d built up, yet each session was longer and harder. Emma’s moans became squeals while her pinkish bottom became red and sore.
During the intimate, gentle caressing of her bottom, Jake’s fingers often stroked her pussy, softly teasing her lips. Now that he knew she enjoyed this, he hadn’t waited until the end to play with her most intimate parts. Yet he did not go further than that, just a teasing caress or cupping motion before he raised his hand again and rained down the smacks on her poor, sore bottom. She hadn’t done anything yet to be rewarded for after all.
As her bottom bounced beneath the onslaught of her old boss’ hand, Emma moaned and promised she would not be late again.
“You will be punctual and on time.” Jake said as he continued to spank her.
“Yes, please, I promise.” Emma begged.
When he finally stopped, Emma’s bottom was red and trembling.
“You can get up now.” Jake said
Emma turned around as she heard him dragging a chair across the room. She blushed as she pulled up her panties while Jake then moved to sit behind his desk.
“Have a seat.” He said.
Emma blushed. He had replaced the chair normally reserved for visitors by a fancy designer chair that was usually placed as decoration in the corner of his room. It looked beautiful, but was also made of hard, unyielding plastic. Emma whimpered softly as she lowered her sore, red bottom onto it.
“Let’s get you introduced to your next project.” Jake said with a smile.
Emma smiled too. She still didn’t know why – the spanking had hurt, her bottom was on fire, her friends had likely heard her squeals – but she had really enjoyed submitting for her punishment.
“Now this one has quite a strict deadline, it’s a bit of a last minute project and I don’t have anyone here to do it, which is why I want to hire you to do it.” Jake explained.
Emma blushed and licked her lips. “I can handle a strict deadline, sir.”
Jake grinned. “I know you can.”