It had been two weeks since Sofie had signed the contract with her boss that allowed him to take advantage of her; to spank her when she was bad; to reward her when she was good.
Three times he’d put her across his lap since, and once she’d bend over his desk for a dose of his ruler. That last one really hurt, she could still feel the sting.
Sofie had given her boss a blowjob underneath his desk twice and once he had done the same for her, rewarding her for staying late to work on an important document.
This Monday Sofie was not expecting any special activities. She was sure all her work before the weekend had been satisfactory. She was not due another spanking and hadn’t had time yet to earn another reward.
When Jonathan arrived, she sat down in one of the sofa’s where they held their morning meetings.
“What were your plans today, Sofie?” Jonathan asked as he sat down opposite to her.
“There are just a few case-files I have to go over, Sir.” She replied.
“Nothing urgent, I imagine.” Jonathan replied. “Seeing as my agenda is nearly completely empty.”
“I could push them back if you need me to work on something more important.” Sofie agreed.
“In fact, I do.” Her boss replied. “Remember when we made our contact regarding discipline and rewards in the workplace?”
“Of course, how could I forget?”
“When we discussed discipline, you mentioned I could punish you for more than just work-related incidents.” Jonathan continued.
Sofie blushed slightly. “Yes Sir. I remember very well how you spanked me just last week for being late.” It hadn’t really been her fault either, an accident a few blocks from the office had blocked traffic where there usually was none.
That hadn’t stopped Jonathan from taking advantage however. Just like she had hoped for while sitting anxiously in her car.
“Exactly. Arriving late, unruly behavior, inappropriate outfits. Anything inappropriate for a notary’s assistant. Those where the words you used, I remember.” Jonathan said.
Sofie nodded, still blushing. “Yes, Sir.” Was she in trouble in a non-work related matter? She wondered.
“You specifically mentioned wearing inappropriate panties, do you remember?” He asked.
Sofie licked her lips. “Yes, Sir.” Of course she remembered, every other day for the past two weeks, he’d asked her to raise her skirt so he could verify that she was wearing appropriate panties. It was always a turn-on to start her day thus, with her boss taking that little bit of advantage to embarrass and expose her like that.
“Well, over the weekend I’ve been thinking. It would make things a lot easier for you, if we had dress-code at work, wouldn’t it? That way you wouldn’t have to wonder whether your chosen outfit was appropriate or not.” Her boss said.
Sofie raised an eyebrow and nodded. “I guess it would help.” She said.
“Of course it would.” Jonathan agreed. “So I took the time this weekend to pick out some outfits for you to try on. Including appropriate underwear of course. I want you to try them on, so I can exchange them if the size isn’t quite right.”
Sofie blushed again. “You bought clothes for me?”
“Work clothing, company owned.” Jonathan said with a grin. “You will be responsible for keeping them clean of course.”
Sofie smiled nervously. This could be fun or horrendous, it could go either way.
“After you try them on, I’ll buy a couple more sets so that you always have some spare to come to work. That way you can be sure you’re never dressed inappropriately.” Her boss said.
“Okay.” Sofie said. “So you want me to try them on now?”
“I’ve got them in my car.” Jonathan said. “Wait right here.”
Sofie waited nervously in the sofa, wondering what her boss could’ve gotten her. Nothing too bad, she assumed, she knew Jonathan well enough not to expect anything extreme.
He returned with a few bags under his arm, she even recognized some of the stores he had shopped at.
Jonathan placed the bags in the sofa opposite her. “Let’s start with the underwear.” He said, grabbing the smallest bag. “You’ll have to take off your clothes.
Sofie bit her lip. Her boss had seen her partially naked plenty of times now, her bottom bared across his lap, her skirt raised as she bent over his desk, his face between her legs when rewarding her; but never fully nude before.
A dress-code at work wasn’t that unusual actually, what was unusual was having your boss pick out your clothes and even more unusual, making you try them on in front of him. He was taking advantage of her again and she was loving it.
Sofie undressed until she stood stark-naked in front of him.
Jonathan looked her up and down, enjoying the view.
Sofie was deeply aroused.
“Let’s try these on first.” Jonathan said.
He handed her a pair of plain black lingerie, full-bottomed panties and a matching bra. When she pulled them over her bottom however, those panties turned out to be completely see-through. They fit perfectly. The bra was see-through as well, unable to conceal her erect nipples. It wasn’t a perfect fit, Sofie imagined she’d want either a larger cup-size, or a narrower band-size.
For displaying purposes it was good enough however. Jonathan was definitely enjoying the view.
“These look great.” He said. “They’ll definitely be part of the dress-code.”
Sofie smiled. She felt incredibly sexy. “The bra needs some adjusting.” She said.
Jonathan nodded. “I’ll give you the receipts, so you can have them fitted at the store.” He said.
Jonathan handed her another set. This one was white and the panties not more than a tiny triangle of fabric and a thong to pull up between her buttocks.
Sofie pulled them on and found out the bras was rather small as well, leaving the upper part of her breasts – including a large part of her nipples – bare. She almost felt more naked with them, than without.
“Perfect.” Her boss said. “Two out of three. Let’s try on the last pair.”
Sofie took them off, baring herself for the third time as her boss gave her another set. This one was red.
The panties of this set were all lace, with a broad band covering her hips, cut almost horizontally to leave the lower half of her buttocks exposed. The cups of the bra were lace as well, which made them see-through, though not as much as the first pair had been. They felt incredibly sexy as well.
“What do you think, Sofie?” Her boss asked. “I think all three are lovely.”
“They look amazing, Sir.” Sofie said. “Do you think they’re appropriate for a notary’s assistant?”
“Of course.” Jonathan said. “As my assistant you should feel confident and bold. You can’t do that while wearing boring or prudish underwear.”
“Now, let’s get you dressed.” Her boss said.
He handed her several packages of nylon stockings from the same small bag that contained her underwear.
Sofie rolled them out one by one. They were all thigh-highs. Two of them were plain, but of different opacity, one had a flowery pattern and one had a single stripe down the back.
She choose the latter to start with, thinking they represented the classic secretary fantasy the most. Jonathan looked on in admiration as she sat down in the sofa to pull them on.
They fit wonderfully well, but didn’t stay up by themselves. She was just about to comment on that, when Jonathan offered her a garter-belt from the same bag.
Sofie blushed. She didn’t even own anything like that at home. It wasn’t hard to put on however and the black belt contrasted wonderfully with the red underwear she was still wearing.
“Amazing.” Jonathan said. “You can leave these on, no need to try them all, they’re all the same size.”
Sofie nodded. She thought she’d never looked this sexy before in her life. Which included being tied up in rope by her friend.
Jonathan finally switched to one of the larger bags. This one seemed to contain a collection of skirts. They were black, blue or dark-grey.
The first pair he handed her fit tightly around her hips, accentuating her curves. It was also barely long enough to cover the bare skin above her stockings. Bending over would surely reveal most of her legs and perhaps even some of her bottom.
Sofie blushed as her boss handed her a white button-down blouse from the other bag and then made her parade around the office.
“Keep on the blouse. Let’s try out the skirts first.” Jonathan said.
He had her in and out of skirts, seven in total, parading in front him for every one. Some were tight like the first, others very loose and even more revealing. All of them were short.
Then he gave her two more blouses, all of them white and the last one nearly see-through. Not only did he make her put those on once, he made her take off her bra and wear them again.
“The first two you can wear with a bra.” Jonathan said. “But for the last one you’ll have to go bare-breasted. It’s too see-through and it wouldn’t be appropriate for your bra to show through.”
Sofie nodded, wondering excitedly how her boss would take advantage of her not wearing a bra.
“One last thing.” Jonathan said. “Then we’re done.”
He grabbed the last bag and revealed a box for shoes.
Inside was a lovely pair of black heels, with very high and narrow heel.
“These have a very appropriate, red bottom, Sofie.” Her boss said as he handed them over.
Sofie blushed and turned them over. “These are so expensive.” She exclaimed, wondering – not for the first time – how much her boss had spend on all this.
“Don’t worry about that. It’s all coming out of company funds, they’re work clothes after all.” Jonathan said.
Sofie giggled. “Did you really ask for an invoice for all this at the lingerie-store?” She asked while pulling them on.
Jonathan grinned. “I ordered them online.”
“They’re a size too large.” Sofie said. “But I love them.”
“I’ll get you the receipt as well so you can exchange them.” Jonathan said.
“Thank you, Sir.” Sofie replied.
Sofie sat at her desk in her new work-outfit. She wore the see-through blouse with no bra underneath and a short and tight dark-grey skirt that revealed the top of her stockings while she sat down.
Jonathan hadn’t asked anything else of her after the fitting session, instead he’d insisted she get the bit of work done she’d planned for today.
There was only an hour left before her lunch break. But it wasn’t a lot of work, she’d expected their morning meeting to bring on more. Instead, she was ready with todays work before lunch, even after spending most of that time taking off her clothes for her boss.
When she turned off her computer and grabbed her coat, Sofie hesitated.
The sexy stockings and short skirt were all well to show off to Jonathan, but she wasn’t sure she wanted to wear them outside.
She knocked at her boss’ office.
“Sir, is it okay if I wear my own clothes when going outside?” She asked.
“Of course.” Jonathan replied. “During your free time you can wear whatever you want.”
“Thank you.” Sofie replied. Returning to the main office area where her clothes still rested on the sofa.
Jonathan joined her just in time to see her mostly naked before she pulled on the dress in which she had arrived.
“It’s up to you whether you get dressed at home or at work, Sofie.” He said with a grin. “Unfortunately, there is no money in the budget to provide a dressing room, so you’ll have to do all your undressing right here in the office.”
Sofie giggled. “I don’t need a dressing room, Sir.”
“You will of course wear your work-outfit when we’re visiting clients…” Jonathan continued.
Sofie blushed, but then remembered how all this had happened in the first place. Her boss walking in on her when she was with her friend. The excitement she had felt back then was new. Perhaps she could explore that feeling a bit further by dressing overly sexy when accompanying Jonathan to his clients.
“Of course, Sir.” She replied.
“Are you going to the store?” Jonathan asked.
“Yes, doing some groceries while I pick up lunch.” Sofie replied.
“Can you pick up a few things for me as well?” He asked. “I made a list.”
“Of course.” Sofie replied
Sofie went through Jonathan’s list on her way to the store. It didn’t seem anything special at first: grapes, some bread and cheese – probably for his lunch – but hidden among the rest, as if it didn’t mean anything: condoms, whipped cream, zip-ties, … things that might not be as innocent as they might seen.
When she finally returned to work, Sofie returned to her boss’ office. She had no more work planned today.
“Come in, Sofie.” Her boss greeted her.
Sofie put the items she bought on her boss’ desk and watched curiously as he inspected them. The whipped cream joined the rest of the food into his own bag, but the condoms and zip-ties went into a drawer of his desk.
“I have another surprise for you today, Sofie.” Jonathan said. “But please, take off your clothes first and into your work-outfit.”
Sofie blushed. She’d nearly forgotten.
She undressed in front of her boss again. She still wore the red underwear, but took off the bra to wear the see-through blouse, followed by the same grey skirt as before.
“Wonderful.” Jonathan said. “Now you remember, last week I had to use my ruler to spank your bare bottom?”
“Yes, Sir.” Sofie replied. “I had made a few mistakes in a document that you’d already corrected three times before.”
“Exactly.” Jonathan said. “Now, I don’t think it is very appropriate to use the office equipment to discipline the work-force, so I bought something specifically for that purpose.”
Sofie blushed as Jonathan pulled a wide paddle out of the drawer where he’d placed the condoms before.
“Have you ever been paddled, Sofie?” Her boss asked.
Sofie licked her lips. “Yes, Sir.”
“How does that feel?” He asked.
“I love it.” Sofie admitted.
Jonathan grinned. “Great. Now, I have a policy that all new office equipment must be thoroughly tested, to make sure we don’t have any problems with it later. So I’m going to have to ask you to bend over my desk, Sofie.”
Sofie blushed. She’d been yearning for some intimacy all day with how her boss had made her expose herself to him.
A paddling might be rough, especially one she hadn’t earned, but she wasn’t going to complain. Others might think it would be unfair to get spanked for no real reason. But for Sofie this was just another way in which her boss could take advantage of her.
She bent willingly across his desk and gasped slightly when her boss bared her bottom. Jonathan needed both hands to pull up that tight-fitting grey skirt, her bottom nearly popped out at the end.
“What a lovely target.” Jonathan said, commenting on how the black garter-belt and stockings framed her bottom, covered only partly by the red panties.
The latter he pulled down as well, baring her completely.
Jonathan warmed her up with a few well-aimed smacks of his hand. Sending a gentle sting through her bottom, painting a soft-pink target for his paddle.
Then, he placed the paddle against her backside.
Sofie bit her lip.
With a loud thwack, the paddle landed across her bottom.
Sofie jumped up and squealed, followed by a low, deep moan.
Her boss spanked her again and again, slowly and methodically, the paddle landing firm and hard.
Sofie moaned and squealed, her bottom swaying from side to side.
“This seems to be working.” Jonathan said. “Now let’s see how well it holds up if I put some effort behind it.”
Sofie held her breath, but the paddle didn’t land as hard as she thought it would. Instead, it skipped across her bottom fast and firm. Not a hard smack, but half a dozen in the time that it had previously taken to land one.
Sofie squealed as het boss paddled her bottom. This hurt even more than before and with the smacks coming this fast she had no time to recuperate or dodge them. She could not sway her bottom to the side, but instead held on tightly to the edge of the desk.
“Not bad.” Jonathan said. “There’s a bit of air-resistance,but I can see from your bottom that it’s doing its job.”
Sofie moaned. “Are we done, Sir?” Her bottom was on fire.
“Just one more thing, Sofie.” Jonathan said. “One day I might have to teach you a really hard lesson, and we have to make sure this thing doesn’t break when I do.”
Sofia blushed. “Oh no…”
“Six swats should do.” Her boss said. “That’s a whole lot less than you’ll get if you really do get in trouble.”
“Yes, Sir.” Sofie said licking her lips. She could take six of the best.
The paddle landed with a loud crack across her backside.
Sofie jumped up with a squeal. “One, Sir.” She cried out.
Jonathan didn’t say anything, but prepared the second.
“Two!” Sofie moaned as it landed. Jonathan hadn’t asked her to count. She’d just begun doing it naturally, when sh’d been spanked like this in the past, it had been asked of her.
“Three!” She whimpered as another set her bottom on fire.
“Four!” She moaned.
“Five!” She could barely stand, her bottom trembling as the desk supported most of her weight.
“Six!” She squealed as the last one landed.
Her bottom was on fire, her legs trembling. But a tiny part of her said: You could take more, if you’d earned it.
“Very good.” Jonathan said. “The paddle held up well, and so did you, I must say.”
“Thank you, Sir.” Sofie said with a blush.
Jonathan stood behind her. His hands felt like hot pokers on her skin, but they eased the pain away as he squeezed and massaged her tortured bottom.
“I have one more thing for you today, Sofie.” Jonathan said. “But first I’m going to fuck you.”
Sofie blushed deeply. He gave no reason for wanting to fuck her. It was no reward or punishment. He didn’t say why, nor was he asking permission. He was just taking advantage of his assistant, laying half-naked across his desk. Just like she wanted him to.
She looked up as he approached the other side of the desk, grabbing the condoms she had bought for him from the drawer. He let her watch as he pulled down his trousers and freed his large, erect cock to put one on.
Sofie had seen her boss’ dick before. She’d sucked it more than once. Yet this was the first time he’d fuck her with it. She licked her lips in anticipation as he walked around the desk again.
She could feel his hands on her hips, the tip of his cock at her pussy. She moaned when he pushed it inside, filling her up until his hips pressed against her sore red bottom.
She moaned again when he began to thrust, not slowly, but hard and fast. His hips smacking into her poor, spanked bottom.
It was pain and pleasure at the same time. Arousal mixed in with excitement as her boss fucked her on top of his desk.
Her body trembled and convulsed, reaching its climax as the orgasm took over her thoughts and actions.
And still he fucked her, hard and fast, taking no notice of her helpless quivering.
She couldn’t stop him, she couldn’t stop herself. The trembling continued, a second orgasm, following on the heels of her first. And then, Jonathan froze as well, reaching his own climax, cumming inside of her, protected by the condoms she’d brought him.
“You can get up now.” Jonathan said.
He’d pulled his trousers back on and was about to place the paddle in its drawer.
“Thank you, Sir.” Sofie said. She hesitated for a moment, she wasn’t sure whether she could handle any more excitement that day. “You had something else for me?”
“Yes.” Her boss replied.
“It’s not another spanking implement, is it?” Sofie asked with a nervous laugh.
Jonathan laughed. “No, don’t you think the paddle is enough?”
Sofie giggled. “You can never have enough office equipment, can you?”
Jonathan grinned. “I guess we can expand. Though you know that everything I buy, has to be tried out first.”
Sofie smiled. “Of course.”
“But that’s not what I have now.” Her boss said. “When buying the paddle, I thought it would be fair to not just have things to punish you with, but have something to reward you with as well.”
Sofie licked her lips as her boss took a small box from his bag. Inside was a smooth white egg.
“I’l keep this in my desk.” Jonathan said. “When I feel you’ve earned a reward, you may take it with you to your own desk and put it in. It even has three different vibrating settings, depending on how well you’re being rewarded.”
Sofie licked her lips again. A vibrating egg she could wear while working. That was… Well it certainly fit the description of a reward at work. It was also extremely hot.
“I will keep the remote control, of course.” Her boss said.
Sofie blushed, she only now noticed the control that had been hidden underneath the egg.
“How about you go to your desk and try it out now, Sofie.” Jonathan said. “You’ve barely spent any time behind your computer today. I’m sure you have some emails to answer before you go home.”
“Yes, Sir.” Sofie replied, accepting the egg before leaving his office.
She was surprised that Jonathan didn’t follow her to watch her slide the egg up her pussy.
As soon as it was in however, it started purring. He must’ve been watching from somewhere.
When she turned on the computer to read her mails, the vibrating increased. It was almost enough to distract her from her poor, sore bottom pressed down on her chair.
She moaned deeply as it reached the third, highest vibration setting. It was going to be hard to focus on her work…
“Ready to go home?” Jonathan asked as he left his office.
Sofie still sat in her chair, trembling, the egg still vibrating inside her, making it impossible for her to concentrate. She’d even cum once while trying to type an answering email.
“Just a bit more, it’s hard to concentrate.” She said.
Jonathan laughed. “If it’s hard now, imagine how it will be when we’re visiting clients.”
Sofie blushed deeply.
He wouldn’t, would he?
Of course he would… Yet somehow, that excited her greatly.
“Almost done, Sir.” She said.
Jonathan waited for her to finish her work, even lowering the intensity of the vibrations to make it easier for her.
“Go put this in the box alongside the egg.” He said as he handed her the remote control. “There is some washing gel in my drawer to clean it with first.”
Jonathan was still waiting when Sofie returned from his office.
Of course. He was waiting to watch her undress and put on her own clothes again.
“Take all the clothes with you, Sofie. I put the receipts in the bags. I’ll give you one week to get them in the correct size, after that I’m expecting you to follow the new dress-code.” Her boss said.
Sofie nodded. “Yes, Sir.”
“I’l see you tomorrow then.” Jonathan said.
“If you’re going to buy more, ehm … office supplies for punishment. Are you also going to get more for rewards?” Sofie asked.
Her boss grinned. “I guess that would be fair.”
Sofie smiled. “I’m really lucky to work for you, Sir.”
Jonathan smiled. “And I’m lucky to have such a dedicated employee.”