MILF in Office Trouble Pt. 01

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MILF manager needs to find a way to motivate her team.
8.6k words
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Part 1 of the 8 part series

Updated 06/09/2023
Created 08/15/2019
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"Oh, Fuck, how am I going to get out of this one!" Mary thought as she sat at her desk in her private office.

Mary just finished reading the new project outlined by upper management. Her team of developers had to code a new section of their company's enterprise business software in less than six months! If she failed, she would be out of a job. She had been set up to fail by the new CEO, Markus Davies. He was going to make her pay for turning him down when he tried to hit her during the last corporate party. If she somehow was able to get this release of software out in time, she would be a hero, but she just could not see a way to make that happen.

The development team was made up of young millennials who all got paid way too much. They were not motivated to work hard because they all thought Mary was a controlling bitch.

Mary is a 45-year-old middle manager who had climbed the corporate ladder for years to lead a team of developers. She was quite good looking at 5' 10" tall, with long blonde hair that fell over her shoulders in curls and bright blues eyes with high cheekbones with full lips and a cute button nose. Her generous bust had just the beginning of sag, but for DD breasts, they looked great. She had to hide her nipples under a padded bra as they would stick out too much otherwise. She knew her looks could be distracting, so she dressed very conservatively to hide her assets from the team.

She could also be a real bitch, but she thinks her attitude is warranted.

"These kids just have no work ethic! I hound them to finish work on time and budget, but this new project will take a herculean effort to finish on time. Usually, it's not a problem when projects are late, but this project MUST be done on time. I am screwed! My asshole boss, who is also the CEO, has set me up to fail! Once the project looks to be behind, he will have the political will within the company to fire me outright. I should have fucked him when I had the chance!! No, no way, I made the right decision to tell him to fuck off!" Mary thought, feeling helpless.

The next day, Mary pondered what the hell to do, suddenly, it dawned on her.

"If bitching and complaining won't work, how about a more subtle approach. I know these kids find me attractive; maybe if I could influence the two team leaders by flirtation, just enough, then I could get them to perform." She thought excitedly.

Ever since entering the corporate world, Mary has concentrated on her career and put aside her promiscuity. The thought of showing off her body again sent chills down her spine after years of covering her body and pinning her hair up in a tight bun.

Mary got dressed the next morning differently, breaking out clothes she had not worn in years. She put on a lace shelf bra that lifted her breasts up and together and put on a slightly see-through white blouse. She unbuttoned the top three buttons, so her cleavage was very noticeable, especially when bent over. The round globes of her breasts were out on display like they haven't been in a long time. It was short of slutty, but definitely not the office look she was used to. Next came a short grey pencil skirt. She looked at herself in the mirror.

"Wow, what a difference!" She thought.

She buttoned her blouse back up and put on an overcoat. She did not want anyone else in the office, besides her team, to see how she was dressed.

Mary got to the office, walked inside, and took the elevator. She navigated her way through the maze of offices until she reached her area and went into her office. She had half of the 5th floor with 20 programmers and the only one with an office, which was in the far corner. Her office had a great view of downtown with windows on both walls.

Mary went through her usual morning emails and then set a meeting with the team leads just after lunch. No one from her team comes into her office with any frequency, so she decided to dress for the meeting early. Unbuttoning her blouse, Mary pushed her breasts up, arranging them for maximum effect. She removed the nipple pads, so her prominent nipples poked out nicely. The shirt was open to about mid breast level with deep cleavage visible. Mary put on bright red lipstick and arranged her hair, so it fell around her face and down her front, framing her perfect breasts in golden locks.

"Man, I look hot!" She thought.

She waited for the meeting with nervous apprehension.

"This had better work!" She thought.

Around 1pm, she heard a knock at the door. She got up and let them in. Dave and Mike did an almost comical double-take as they stared down at her cleavage then back up to her face.

"Hello Ms. Davis, you are looking different today!" Dave said, stuttering.

"I am glad you noticed, please come in and sit down," she said with a smile, as she turned toward her desk and sat down.

She went around her desk and began to sit down, then she pretended that she forgot her notebook and leaned over to get it, right near both of them. Her breasts shifted as she leaned, spilling forward just enough. They looked straight down her blouse and got an eye full of her full breasts. Her nipples were hard from the excitement and showed as they poked out of her bra. She slowly sat down and looked them in the eye.

"The current milestone deadlines will be hard to achieve with the team's current rate of production, wouldn't you agree?" She said, staring at them with a questioning look.

"Yes, almost impossible. I can't really understand what management was thinking, giving us such a short amount of time!" Mike said, smiling, while he continued to share right at her breasts.

"He is really acting blazingly, not even trying to pretend to look away. He is just locked on my breasts!" She thought as she stared back at both of them.

"Mike, my eyes are up here." She said as she shifted in her seat, feeling nervous.

He moved his eyes up and looked her in the face then slowly shifted his eyes back down, her deep cleavage showing the large globes sitting in her lace bra.

"I called this meeting to see if there is a way to motivate the team to perform better, so we can all get out of this jam we are in," she said while shifting her position in her seat to give them a better view.

"Ms. Davis, or may I call you Mary?" Mike said, with a glance up from her breasts.

"Mary will be fine, Mike," she said.

"Well, Mary, we are both very aware of the position you are in with this project. If it does not get done, you get canned. Is that about, right?" Mike said with a wicked smile.

"Well, no Mike, we all go down if we cannot deliver,'' She said nervously.

"Is there something they know that I don't?" She thought as she looked at them, trying to figure out where they were going with this.

"That is not what I understand, and I think you know that. Now Dave and I can get your project finished, but we need to agree on a few things first." Mike said.

Surprised and shocked by Mike's response, she answered, "What would it take to guarantee the completion of the project."

"A 20% raise upon project completion and personal cooperation from you, Mary,'' Mike said with a huge smile that sent shivers down her spine.

"That amount of raise may be possible, but what do you mean by personal cooperation," she said, dreading the answer.

Dave got up and looked down Mary's cleavage and said, "you've already started, without knowing it, with your new look. We all knew you were hot under those conservative clothes you wear. You don't fool us, Mary! You need this project finished, or your career is over. A career that you have worked on for 20 years. Also, we all dislike you and think you are a stuck up bitch. You have no more power over us. You can't fire us, as we can all get transfers to other departments that don't have a bitch for a boss, so Dave and I will get to take advantage of you until this project is finished. Then when the project is finished, and you are a superstar, it will all have been worth it. What do you say, Mary?"

Dave sat back down in his seat, feeling very satisfied.

"What the hell are you talking about, I should fire you right now!" Mary screamed.

"Go ahead, fire us, and see if you can pull together another team in time. You are fucked without us, Mary, and you know it. Besides, it looks to me, by the size of your nipples, that you like my abuse." Mike said, laughing.

Mary looked down and saw that indeed her nipples were straining against her bra, and she was excited. Still, she did not want to show Mike that she was at all happy with this situation.

"What do you want, Mike?" She said in a defeated but defiant voice.

"For each project milestone completed, you will be required to do certain things and dress a certain way. Only Dave and I will be involved for the most part, but in the end, you may have to do things for the whole team. I will put together a list for you to follow. We will all agree to it, and then you will obey, or we will leave," Mike said.

"Present your list, and I will let you know if I am willing," Mary said, looking angry but feeling excited.

"I really want this project done. If I had to give these little shits a show, it'd be worth it," Mary thought.

"Agreed, but first, we want a down payment, just a gesture to show us you are for real," Mike said with an evil smile.

"What kind of downpayment," Mary said, feeling butterflies in her stomach and a light sweat forming on her forehead.

"Stand up, and let us see your glorious breasts!" Mike said, salivating.

"What! No fucking way, asshole!" Mary said.

"Your choice Mary. Have fun in the unemployment line!" Mike said as they both got up and started to walk toward the door.

Just as they were about to open the door, Mary said, " Wait, wait ...ok, but no pictures ever, and no one else can ever know.''

Dave and Mike returned to their seat. Mike looked up at Mary, who was now standing and said: "Agreed, no pics, and no one gets to know, now show us, Mary, show us your beautiful tits."

Mike was amazed that she was going through with this. She must really want this project finished!!

She looked up at the ceiling as she unbuttoned her blouse. Tears streamed down her cheeks and ran down between her breasts. The humiliation was terrible, but she pressed on knowing she had to do this. She removed her blouse and reached behind her back to unfasten her bra. She then looked down at Mike and Dave as she removed the bra cups from each breast and dropped the lace bra on the floor. Her DD breasts tumbled out of the bra and bounced a little as they settled back on her chest. Her tits had the perfect sag. They filled her chest area from side to side, and the air conditioning was making her long nipples erect, standing in the middle of her wide pink areoles.

She was trying very hard not to cry as these two assholes took in her body. Waves of excitement and humiliation streamed through her. It was a strange mix that made it at least bearable.

Mike and Dave stared in awe as they beheld the most perfect set of tits they had ever seen.

They both became rock hard in an instant.

Mary noticed quite a large bulge in Mike's pants from the palpable excitement.

She unconsciously covered her breasts with her arms as she tried to hide her body.

"Absolutely amazing! Lower your arms, we want the full view." Dave said.

Mary lowered her arms and felt strangely good after the compliment from Dave.

Mary began to realize the power shift now that both of them were transfixed by her naked chest on display.

"Like what you see, boys! I hope so...if this is what it takes to get the work done, then here they are in all their glory!" Mary said as she lifted each breast up, squeezed them, and then let them fall back in place.

Dave and Mike were taken aback by her attitude and more than a little intimidated.

She was shocked that she did this, but found it exciting at the same time.

"These two could almost be my sons, and they love my body," She thought.

She also felt cheapened, but she couldn't deny her feelings and rush of adrenaline.

"I should take this opportunity to get work done right now!" She thought.

She moved closer to her side of the desk until her thighs touched, then she bent over and placed her hands on the far side of the desk facing the guys. Her breasts were now hanging down right in front of them, two feet away, at eye level.

Mike stared directly at the pair of gorgeous tits hanging right in front of his face. They were perfect globes with nipples set high up. He wanted to touch them so bad that he raised his hand to do so.

"Not so fast stud. Here is the deal." She said as she wiggled her tits back and forth. "Get me the estimate report, by lunch tomorrow, fully vetted with accurate estimates. As a reward, you get your hands around these." She drew her head back and pushed out her tits, so they were almost touching Mike. Then she pulled back quickly.

Mike and Dave just stared forward dumbly for a while, then finally, Dave looked up from her tits and said, "You got a deal, Mary, I can't wait!"

"Shows over, boys, now get me that report and get back to work!" She said as she retrieved her clothes and started to get dressed.

"You got it, Mary. That was wonderful. Thank you, and yes, I have a good feeling that more work will get done!" Mike said as they both got up and left the office.

Mary sat back in her office chair after she finished dressing. Then she got up and locked the door. She did not want anyone coming in.

"What the fuck have I got myself into," she thought as she sat back down in her chair and spread her legs as far as the skirt would allow. She slid her hand under her skirt and into her panties, then slid her fingers past her blonde pubic mound and in between the tender folds of her moist pussy. She was obviously very turned on by the whole situation. She unconsciously started to circle her massive clit with one hand while the other reached into her bra and pulled on her erect nipples.

She pictured herself in front of Mike and Dave with her breasts being manhandled by them as she pulled and pinched her nipples.

"Oh God, what am I doing!" she thought as she continued to work her clit and nipples until she raised her hips up off the chair and began to cum. It surprised her how quickly she came with just her fingers. Usually, it took a vibrator and a dildo, working her pussy for five to ten minutes to make her cum that hard.

She had never thought of playing with herself at work, and now she was masturbating to the thought of them touching her.

"What the fuck!" She thought, arguing with herself as she was trying desperately to deny the feelings she was having.

She pulled herself back together and tried to get some work done, but she just couldn't help thinking about the new "deal" with her team.

She went home after all the other employees had left. She did not want to face Dave or Mike on the way out.

She arrived the next day at work dressed in the same way. Her generous bosom was on display along with her legs in a short skirt. She added high heels to magnify her long shapely legs. Also, the heels had the effect of pushing her ass out and chest forward as she walked.

She was very nervous as she came into the main cube area where the programmers sat in their cubes. All of them stared at her as she walked by, impressed with their boss's new look. She smiled at them, which was quite a change. She passed Mike and Dave on her way to her office.

"Well, boys, how is the report coming along,'' she said as she stood before them, her blouse showing major cleavage.

"We will have the report done today, Ms. Davies, you can count on it," Dave said right away as he stared directly at the DD's on display. He could make out her stiff nipples pressing on the inside of her lace bra. It made his cock engorge.

"Good news! I have been asking for this report for 2 weeks. I am glad you found the motivation to finish it," she said, winking at them, then turning on her heels, she swung her ass around as she walked away.

"Wow! I really think she is going to go through with it," Dave said.

"I sure hope so, we have to make sure we remain in charge, though. Mary needs to pay for everything we have done for her on this project!" Mike said.

It was almost the end of the day when she heard a knock on her office door.

"Come in," Mary said.

Dave and Mike came in and sat down in front of her desk and handed her the report.

"It's all there, all the estimates for the major milestones, but these estimates assume our special understanding," Mike said.

"We have only agreed on one part of it, for now, until I see this list you talked about. If the report is complete, then I will honor my part," Mary said, in a very business-like voice.

They both sat there for 30 minutes as she read the report. She wanted the report to be unfinished in some way, so she did not have to fulfill her part of the bargain. The other part was filled with nervous excitement as she remembered her self-pleasure at her desk the day before. The report was not only complete, but they had also estimated the full project and, in much more detail, then was asked for.

Mike sat there, staring at her breasts that he hoped he would soon see and feel! He had the report, that she so desperately needed, mostly done for a while, but held out on giving it to her knowing the delay would upset her. She indeed was a stuck up bitch and treated them all like shit. Typically projects just got delayed because of her attitude. There was nothing any of them could do about it, and it really did not matter that much. The CEO, Mr. Davies, spoke to Mike weeks ago about the desperate situation Mary was in, telling him that Mary was in a bind. The CEO wanted Mike to delay the project so he could have a reason to fire her, but now Mike had different ideas. Mike could still screw her over and make the CEO happy, but not until he got what he desired, her fabulous body, of course. He also wanted to humiliate her as payback.

"Man, these little shits had this report or most of it, done already. They were holding out on me! Well, at least I have it now and know how to get more out of them. I just hope the price is not too high!" she thought as she stopped reading and looked up at them.

Even though she was excited and now that the time had come, she was very apprehensive. If she went through with this, it would be so humiliating as well as crossing a line with them.

"Letting these little shits get off by letting them touch my breasts! Fuck what have I done!" she thought.

"Is everything in the report as promised? If so, a deal is a deal, Mary," Mike said with a sly grin on his face.

"Yes, Mike, it looks complete to me. I will honor our agreement. Before I do, is there any other way I can compensate you for the delivery of a report that you owed me anyway?" She said, feeling more and more powerless.

"Sorry, Mary, you have very little leverage, except your body at this point. It's perfect!" Mike said as he turned toward Dave, smiling.

Mary felt like punching him in the mouth. She was at a crossroads. Mary hesitated and thought briefly about giving them the finger and telling them to fuck off, but the thought passed. She was heading down an unknown path now, which she hoped would lead to a better place in the end.

"Fuck it! They are just breasts," she justified to herself, as she stood up from her chair, moved to the other side of the desk, and leaned back on the desk in front of them.

She started to unbutton her blouse slowly, exposing more and more of her ample breasts, sitting snugly in her white lace bra. Tears began streaming down her face, smudging her mascara. Then she pulled her blouse out from her skirt, fully opened it, then took it all the way off and set it on the desk behind her. She turned back around, facing Mike and Dave. Her nipples were fully erect, betraying the excitement she felt, as waves of humiliation washed over her, looking down at her tormentors.