Office Play Ch. 05

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Diane has to get work done to avoid punishment.
3.3k words
4.57
131.6k
13

Part 5 of the 8 part series

Updated 10/30/2022
Created 01/16/2005
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Goldeniangel
Goldeniangel
12,565 Followers

Monday morning, Michael's greeting included a caress of Diane's very sore breast, he smiled at her when she winced but didn't voice a complaint. "Come see me in my office in a few minutes." she nodded, finished what she was doing and came in.

More smiling at her obvious trepidation, "Don't worry beautiful, I knew you wouldn't be up to anything too strong today, I just want to start getting something ready for this weekend." His smile became a grin, "Come over and bend over the desk." Apparently the empty desk which she had been tied to last week was going to be a permanent fixture in his office, Diane bent over carefully, leaving her ass positioned high in the air. Deftly, experienced hands flipped her skirt up, a lubricated butt plug was slowly pushed into place. It hurt, but because her ass wasn't as sore as the rest of her, things definitely weren't as bad as they could have been… and after reflecting on things for a moment, she decided that the preparation before this weekend wouldn't be bad at all. Getting his dick into her pussy had been pretty difficult in and of itself, trying to work it into her much smaller hole without anything leading up to it wasn't an attractive thought. Once the butt plug was securely in place she was dismissed from her office to go back to work.

However, work wasn't exactly easy today. Everything distracted her, the soreness in muscles, the fullness (and discomfort from sitting on the butt plug) in her ass, the constant knowing looks she was getting from Juan, or Michael's occasional forays in and out of his office. Tuesday passed in pretty much the same way, both days she did much less work than she normally got done. At the end of the day on Tuesday Michael warned her that she needed to get her performance back together, and took her over his knee for 10 warning spanks (and say that next time it would be 20) just to make his words stick.

Wednesday morning she came in determined to do better… however, along with the butt plug, Michael slipped a dildo into her pussy as well during what had become almost a morning ritual. Apparently, he wasn't going to make it easy for her to bring her performance back up… after several days of almost no sexual activity she was feeling very horny, and not in the least bit sore. Still, she was determined not to give him an excuse to spank her at the end of the day. Despite the distractions, she worked much better all morning. After lunch time Diane was confident in her abilities to make up for the work that she hadn't gotten done the two previous days, unfortunately, she didn't know that Michael was planning on a rougher weekend for her. The work he'd given her for the week wasn't really all that important (not that she was aware of that) because he wanted her to fall behind. Last weekend had been an introduction to the pleasure, this weekend would be an introduction more to the punishments that she could expect whenever she couldn't meet standards. He'd become quite attached to her over the past weeks, but if she was going to become his only submissive - something he hadn't had in 8 years - she was going to have to be trained. So this weekend would introduce her to some of what she could expect when she failed him.

About 15 minutes after lunch, Diane was working harder than usual - determined to catch up - when the dildo in her pussy came alive. She jumped at the unexpected vibrations and then bit her lip in pleasure. About five minutes later the dildo abruptly stopped and she realized that she had been just sitting there, doing nothing while it buzzed. It occurred to her that this was a ploy of Michael's to see that she had not finished all her work at the end of the day. Furiously, she began working again, and when the plug in her ass started buzzing 10 minutes later she tried to work through it. When it went off again, she had to re-do a lot of the work that she had just tried to do. Gritting her teeth she worked through the afternoon, and through the buzzing.

Only one other time did she get distracted… about an hour before the end of the day Juan came into the main room and began working on something at his desk. It wasn't all that unusual, although he was only there about once every couple of weeks. A couple minutes after he sat down to work both her ass and pussy started buzzing, but it was on a much lower vibration that it had been all day. It wouldn't have been as distracting except that she was now worried that Juan would notice something was going on. Every couple of minutes the vibrations kicked up to a higher level, causing her to wiggle in her seat. Juan was looking at her out of the corner of his eye, she bit her lip and stopped wiggling. A few minutes later it was a short moan that caused him to look at her, when the vibrations finally kicked up to their highest level she stopped even noticing that he was watching, and clutched her seat and clenched her teeth to keep the noise level down while she came.

She panted as she came back down to earth, and moaned again as she realized she only had 15 minutes left to finish her work. Thankfully, no more interruptions came. The amount of work done was more than it had been either of the previous days, but still not as good as it should have been. Sighing with resignation, she entered Michael's office. Even though he'd engineered the reason she hadn't gotten all her work done, she was sure that he wouldn't care to hear that as an excuse. Twenty spanks that day, with the warning that if she didn't improve, not only would she get thirty tomorrow, but she'd have to finish all the work on Friday or else this weekend would be used as an example to her of why she needed to get her work done promptly.

On her way out the door he also reminded her that she was not to play with herself. That night was pure torture, finally totally recovered from the last weekend, she was dying to touch herself. Instead she took a cold shower and watched a Schindler's List. It definitely killed her sex drive for the night.

Thursday was torture. It was just her and Michael in the office, which meant much less embarrassment from being watched by Juan, but it also meant that she was craving even more attention from Michael. Especially because Michael had added something new today, rather than just putting in her butt plug and dildo, he'd undressed her completely, and tied a soft silken rope around her, with knots going straight down her back and front and several encircling her body. One loosely around her neck, one above and below her breasts, and one across her hips. The end of the rope went through her pussy lips and ass cheeks, knotted above her clit and pressing it tightly. Her clothes were back on over all of it, but she was acutely aware of what was hidden beneath. All day, whenever she sat or moved, there was rough pressure on her clit from the knot, it rubbed her… it barely mattered if one of the vibrators went off, she was distracted already.

Three orgasms that day. Three orgasms, thirty spanks, and the announcement that Friday night she would be punished for her poor performance… of course she still had the opportunity to keep Saturday pleasant if she finished her work tomorrow. Right, she gritted her teeth, the vast opportunity. Not only would Juan be working tomorrow, she was sure that Michael would find some reason for Juan to stay in the office. And although she certainly couldn't think of anything else Michael could possibly put on her body to distract her, that was no reason to feel assured that he wouldn't be able to think of anything to do to her.

That night was torture, wanting to touch herself. On the other hand, she wasn't totally sure that somehow Michael wouldn't be able to tell. Constantly reminding herself that the orgasms she'd had while playing with herself had just made things worse helped her a little bit. Wondering what kind of punishment he had in mind for this weekend didn't. To take her mind off things she began touching her ass with her own fingers, wondering how she was ever going to fit something as big as his dick into that small hole, even though she'd adjusted to the butt plugs, he had kept all of them thinner at the base than his dick was, and they weren't nearly as long. Two of her fingers fit in easily though, which was encouraging. Maybe it wouldn't hurt so bad…

She ended up being up for half the night perusing porn sights online. Looking at girls pushing impossibly sized dildos and "monster cocks" up their asses meant that she should probably be able to get Michael's dick in hers. After all, he was big, but he wasn't that big compared to what she was looking at right now, it might hurt, but at least she know that he wasn't trying something impossible. Then came the bondage and bdsm sights. There were definitely things she had never considered - although she did see some pictures of the kind of rope bondage Michael had put her in. It apparently came from Japan. The rows and rows of toys she found for sale made her a little nervous, both about Friday and the upcoming weekend. Who knew what kind of stock Michael had, just the toys she had already become acquainted with put her collection to shame - all she had was a dildo, a vibrator and some massage oils.

At 2am she realized that she needed to get sleep, especially if she was going to make up for the work lost. Being in bed didn't necessarily help though, she tossed and turned for at least an hour. Imagination could be such a dangerous thing.

Friday was torture. Juan was in the office, and took plenty of opportunities to look her over and smirk. Michael had taken her jacket in the morning, and all she had was her very sheer (and unfortunately one of her tighter) blouses, underneath which was the rope, tied in the same way. The rope at least wasn't clearly visible, but Michael had also removed her bra and attached two nipple clamps, which meant that her nipples were poking through. He did tell her that she needed to take rotate having them on or off every 20 minutes (jokingly, "I don't want any real damage done of course, not with such the kind of weekend that I anticipate."), but she wasn't allowed to go to the bathroom to do it. Instead, every twenty minutes Juan got a free view of her reaching into her blouse to clip or unclip her own nipples. The clamps weren't tight at all, really just a steady pressure, but by the afternoon it also meant that she was rubbing her breasts every time she took them off, because even with the light pressure her nipples were getting sore. Gritting her teeth, she hoped Juan enjoyed the show.

Surprisingly, Michael hadn't turned the vibrators on too often. Maybe he was just busy. Or maybe he knew that he didn't really need to, she was having to waste time moving the clamps, plus the fact that her nipples became more and more distracting every minute. In the afternoon, that changed some. The vibrators turned on for a couple very long periods of time, but in very low settings. Always enough that she could at least hide her arousal from Juan, even if it distracted her mentally.

By four o'clock the situation was hopeless. There was only an hour left, and there was no way she was going to finish in time. The vibrators had been on for 45 minutes and she was starting to sweat with her need for release.

Michael walked into the room, circled her desk and began looking over the work that had been done and the work that still needed to be done. Slow smile at her pleading face.

"You can't finish this in time," he stated. She shook her head. "Then this weekend, you're going to have to be punished." Startled look at Michael, surprised that he would speak so freely in front of Juan… who apparently didn't see anything out of the ordinary. He was watching them with an almost expressionless face. Diane looked back at Michael, unsettled. Michael grinned.

"Kneel."

Slowly, mortified humiliation, she knelt. Hands were tied behind her back, and the sheer blouse pushed down her shoulders, leaving her breasts exposed - they didn't have the clamps on but her nipples were still hard from her arousal. Diane closed her eyes to Juan's hot stare.

"Open your eyes." Pleading filled them as she stared up at Michael. He had unzipped his pants and his semi-hard dick was in front of her. Resignation… and submission. Diane opened her mouth and engulfed his dick, sucking slowly, teasing with her tongue as it grew. Feeling Juan's eyes watch her every move. As his dick filled her mouth he began moving back and forth, hands deftly releasing her hair so his fingers could entangle themselves in her curls. Everything was moving much more quickly than she was used to, he was already starting to pump in and out of her throat.

"I'll start our weekend now." Pumping, "You see, I used to have girls in and out of the office all the time. Wives or girlfriends of friends and their acquaintances who needed a little discipline, and Juan here was very helpful with that. I'm sure you noticed the women who used to come in here… since you've proved to be so willing to replace them for me, I haven't had them coming in. You've been such a good girl, except for this week, but that's to be expected. I just have some questions which you need to answer."

Big eyes stared up at him, full of her own questions.

"Do you want to continue to replace them? Continue on as we've begun?" Frantic nodding, although she would have shouted her yes if her mouth hadn't been full. There was nothing that she wanted more. Everything she had been through with him had been more wonderful then she would have ever thought, and it filled something in her that had always been empty. Some part of her desires which he had touched and filled. In some way, she needed it, everything he could give her.

"We'll go over the details at home, but for now, will you obey me absolutely? Be mine in every way? Let me be your guidance and train you to be the submissive I want?" After all her research the night before there was no way she could have misunderstood his meaning. More nodding. The images she had seen and words she had read the night before had filled her with a kind of yearning.

"Good girl."

Last plunge down her throat, holding her head tight against his crotch as he spilled his load. Gulping eagerly, she again became aware of Juan's intense gaze. It made her uncomfortable, but after all, she had just agreed to do whatever Michael wanted, and apparently he wanted Juan to be able to watch. The hold on her head lessened and she gently tongued the softening dick in her mouth… and froze in shock at Michael's next words.

"Now it's Juan's turn darling. After all, he misses helping me out in the office, and he got all of his work done today." Reluctantly, not wanting to believe what she had just heard, she looked up at Michael as he pulled away. He just stared back at her as Juan got into position in front of her. "Treat him as you would me, he deserves it." A pat on Juan's back as he released his already hard dick. It wasn't as long as Michael's, only about 7 inches, but it was the thickest she'd ever seen. Easily as thick as the monster ones she'd seen on her computer the night before.

Tentatively she flicked out her tongue, and began running it over his head while he moaned. Lubricating it with her spit, tonguing as much of the shaft as she could, she finally started working it into her mouth. Her jaw ached with the effort of being held so wide, and it wasn't helped by the fact that she couldn't use her hands. Slowly, his dick slid in and out of her mouth, as she got more accustomed to the girth of it. Michael watched as she did her best to follow his order, wanting to please him by sucking the dick of a man she worked with but didn't really know that well.

Juan was enjoying finally having the beauty on her knees before him. Michael had promised, after that first day with Diane, that if she turned out to be everything he hoped for, that Juan would be able to help him just as he had with the other women. He reached down to finally feel her creamy breasts, playing with the bright cherry nipples. As he pushed more of his dick down her throat he could feel her muscles playing over it. He knew he was thick, but that just meant that everything felt tighter… he couldn't wait until Michael let him at her ass. The feeling of his dick finally being lodged in her mouth, and the thought of pushing it into her tight ass caused him to cum more quickly that he had wanted to. Gripping her boobs firmly in his hands he pumped his cum into her mouth.

He smiled at Michael and left, as agreed upon before, content with the day's work.

Diane remained on her knees, slightly nauseous. It wasn't that she didn't have some attraction to Juan, but she barely knew him… and she'd just swallowed his cum, just because Michael had told her to. And not only that, but just following the order, doing something that she hadn't wanted to do… had made her wet. But looking at Michael, she felt content again. He was smiling at her, pleased.

That didn't diminish her punishment though. They went down to his car, her as she was: hair undone, blouse around her waist and wrists, breasts hanging free on either side of the bondage rope, and wrists tied together behind her back.

On the way home they passed by an 18-wheeler, and Michael slowed to its speed so that the trucker could get a good look at her exposed state. She blushed and held her head down - until Michael turned on both her vibrators at full blast, causing her to orgasm after a day of being teased. The trucker got quite a show of her spasming and heaving in the seat until her orgasm quieted. As they pulled away he appreciatively pulled the horn.

______________________

i have understood from previous submissions that people like to have a climatic ending to each part of the story, I like how this one ends with a little bit of suspense, waiting for the weekend, but I am submitting part 6 at the same time as I am this one for those who are less patient =) I hope you enjoyed, and please, don't hesitate to leave comments or suggestions for me! Thanks!

Goldeniangel
Goldeniangel
12,565 Followers
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3 Comments
notusuallyshynotusuallyshyabout 10 years ago
That's more like it!

Just as I hoped. Darker and even sexier, written just for me!

AnonymousAnonymousabout 12 years ago
Wow!

A-m-a-z-i-n-g!!!!! Well, all of them are, but i'm too busy reading them to comment on all of them!!!

AnonymousAnonymousabout 19 years ago
I would give it more than a "5" if I could.

Bringing Juan into the dynamic was a stroke of genius. Michael dominating Diane while Juan watched was hot enough, but actually giving her to Juan, even temporarily, was incredibly hot. It shows the degree to which Michael owns Diane. I look forward to more.

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