MILF in Office Trouble Pt. 08

She checked herself in the mirror to make sure her lipstick looked good after having a dick in her mouth for twenty minutes. To her surprise, it was mostly ok. She touched up her lipstick, got out of her car, and walked into the office building. Her short skirt, red lace thigh-highs, long red fingernails, highlighted hair, and long eyelashes made her look far sexier than she would have liked for this meeting, but she had no choice at this point.

Mary knocked on Kelly's office door and entered. She almost dropped her purse and laptop bag when she saw who was sitting in the chair in front of Kelly's desk.

"Mary...what are you doing here?" Mike answered, getting up and looking surprised and very annoyed.

Mary broke out in a cold sweat and her pussy clenched in panic.

Her ex-fiancée Mike Hubbert was standing there looking at her with hatred in his eyes. Mary could not blame him. It had been fifteen years since they parted ways in the aftermath of Mary's betrayal.

Mike was married until Mary came along. Bored with her job and life, Mary played the home wrecker, seducing Mike away from his wife Helen and their three kids. Mike proposed to Mary soon after, then Mary cheated on him with Helen's sister's husband. Mike was devastated and eventually got his ex-wife to forgive him, but Mary was on their shit list for good. Mike, Mike's Wife, Helen, and Helen's sister Becky and Becky's husband Ronald, all loathed Mary. Mary could not blame any of them for hating her, and her actions remain a very sore point in her past. She swore to never let the slut in her control her life in that way again.

"Mike! I had no idea the bid proposal was from a company you worked for. I thought you owned your own IT service company." Mary said, not knowing what to do.

Kelly sat back and observed the carnage. She could tell by Mike's body language and expression that Mike was very disturbed by Mary's presence.

"Will she be the project manager for this bid?" Mike said, turning toward Kelly.

"Why yes! She is the team lead for the project and will be working quite closely with you to make sure the project stays on target. Her Team leads the technical implementation end of the contract." Kelly said enthusiastically, knowing something was close to blowing up between them.

"That's all I needed to hear," Mike said and stormed out of the office past Mary.

"What the hell was that!" Kelly said, looking upset, but internally she was thrilled.

"He was my fiancée. It's a long sad story, but I really fucked up, and he hates me for what I did to him and his family." Mary said, knowing it was a mistake to divulge any of this to Kelly.

"Well, it's none of my business, I guess, but earlier, Markus (the CEO), Mike, and I had a great meeting and worked out the financial part. I was just going over the contract, and it was looking great until you walked through the door." Kelly said, loving the look on Mary's face.

Mary was shell shocked and cursed the gods or whoever for this horrible luck. Who would have thought that Mike would show up out of the blue after so long? Mary did not know what to say. She was still quite shaken.

"You already talked with the CEO about Mike's bid? Wow...I don't know what to do. I am so sorry, Kelly, but I don't think I can fix this." Mary said, almost in tears.

"I suggest that you do your damnedest to try and work it out, Mary. Markus was thrilled that Mike's company would do it for the price offered. No other company came close to HotWire's bid. I don't think it would go over well for Markus to find out that the deal fell through because of a personal conflict between you and Mike."

"Can't we get another person at Hotwire to work with me?" Mary said.

"I suggest you find out, Mary! Here is Hotwire and Mike's contact information. Get back to me by tomorrow." Kelly said, handing Mary a slip of paper.

"Ok, I will contact them and see," Mary said as she turned and walked out of Kelly's office.

"Not so fast, Mary. I need the video of your drive into work, and don't forget, you are almost late for your morning meetings with your Team." Kelly said with a smile.

Kelly knew that sucking cock would be extra hard considering her stress over the situation with Mike, but it made it all the sweeter for Kelly.

"You mean, making me suck cock is more important than this!" Mary said, exasperated.

Mary's pussy lit up with voltage as Kelly pushed the button on her chastity ap.

"Yeow! Ok..ok... I'll do it...please stop!" Mary said as she fell to her knees from the pain in her poor pussy and clit.

"That's better slut! You won't admit it, but you love to suck cock. I am doing you a favor, and besides, you'll feel better with a stomach full cum. Now get out of here before I zap you again!" Kelly said with an evil smile.

Mary could not deny that she was dripping wet, but her ego and arrogance refused to recognize the connection.

Distracted and pissed, she left Kelly's office after showing the video of her blowing the cop. Kelly loved that part where Mary's tits were being abused. Kelly downloaded the video and let her leave.

"Well, hello! Just in time. Sandeep is on his way at this very minute!" Shelby said, not knowing anything about Mike or how fucked Mary was considering the situation."Well, yes, I am late, but I need to get this over with to deal with a fire concerning the project. Can you make sure that they come right in after I finish each one?" Mary said as she took her seat at her desk.

"I'm sorry to hear that. Kelly must know as she wants you completely naked today to encourage the Team to cum quickly. I now see the reason why." Shelby said, curious to know what's going on but happy to have Mary's humiliation heightened by being forced to be naked.

"Shit, really! Ok, give me a second." Mary said with a red face as she removed her clothes except for her red high heels, thigh-high stocking, shelf bra, and garter belt.

Shelby's pussy moistened at the super sexy site of Mary's outfit, or what was left of it.

Mary sat down on her desk chair and looked up at Shelby, waiting for her to let Sandeep into her office.

"Aren't you forgetting something....your little helper... Kelly insists on it every time." Shelby said, but in fact, Kelly had said no such thing.

The humiliation surged through her as she opened her legs, spread her pussy lips, and sighed as she pushed the button on her desk. The thick dildo moved up between her legs and slipped quickly past her pierced pussy lips and into her hole. Mary wiggled her hips as the dildo buried itself deeper until she was fully impaled.

"It felt good being stuffed with cock even if it was plastic." Mary thought as Sandeep came in, walked around to the back of her desk, and into the slot that led back to Mary. She swiveled her chair to face Sandeep and leaned forward to hide the fact that she was sitting on a dildo.

Mary was blushing bright red as she looked up at Sandeep. For as many times as she sucked off her Team, she never quite got used to the idea, especially now, naked, with a pussy filled with a long thick dildo.

Sandeep looked down at Mary and took in the sight with relish. Mary's perfect breasts, hanging down right below him, with a gold chain connecting her huge puffy pink nipples, her long red fingernails combined with the eyelash extensions, put the icing on an already perfect cake.

"Love the look, Mrs. Davies! You should dress this way all the time!" Sandeep said, and he whipped out his nice size cock, which was almost fully erect, and pointed it at Mary's bright red lips.

Mary sighed and went to work. After over 200 team blow jobs, she got to be a master cocksucker, and knew the best technique to use on each of them. She was also in a hurry today and wasted no time. She deep throated his cock and let him play roughly with her tits and face fuck her. Sandeep was bucking his hips and blowing his load down her throat in only eight minutes.

"Holy shit, that was awesome!" Sandeep said as he pulled on her chain one last time, lifting her tits up.

"Ouch! Careful with my tits!" Mary wined.

Sandeep let go of her chain as Mary cleaned his cock and put it back in his pants.

Sandeep cupped her breasts one last time and left satisfied.

Mary blew the rest of the Team in under forty-five minutes. They each seem to have had an enormous load of cum to deposit down Mary's throat. She was full and felt the cum swimming around in her stomach as she got up off the dildo to get dressed.

She was also highly horny after sucking so much cock, but she had to act fast to save the contract. Kelly will not let her cum anyway, so she put it out of her mind as she wiped the pussy juice from her legs.

Mary called Hotwire and found out that Mike was the CEO, and he specialized in this type of server installation. They said that if the bid was accepted, Mike would have to supervise the install; there was no one else.

Just as Mary got off the phone with Hotwire, she got a call from Markus.

"Mary, I need to see you right away! I have some great news!" Markus said excitedly.

With nerves building up to a breaking point, she walked into Markus's office on the top floor of the office building.

She walked into his office and sat down at his desk. He greeted her warmly, which was out of character considering their past. Once the small talk about the project was over, he told her about a new client that was on track to be the first to use the latest software from Mary's project.

"We just found out that an overseas client is willing to install and use your new software. They plan to invest heavily if the beta program is successful and the icing on the cake; they are willing to cover all the costs and give us a guaranteed 50 million dollar contract! But they are only interested if the increased speed is achieved with our server center. What do you think about that!" Markus said with a huge smile.

Mary never saw him more animated or excited about anything in recent memory.

"That's great Markus! The project is almost ready for the beta phase. We just need the server farm install. I am running into issues with the current bid company. Can we hold off until I find another?" Mary said, trying to hide her emotions. She was beyond excited but knew this could turn on her if she did not get the extra time to find another supplier for the server farm.

"What issues? I spoke to the CEO of Hotwire only this morning?" Markus said, looking very disappointed.

"Well, it seems like they had some issues about timing when I spoke to Mike, the CEO." Mary lied, trying to think of a way out of this horrible situation.

"Well, Mary, please let me know asap. Suppose this install is successful, and we get the contract. In that case, I will shorten the time frame of your promotion to full partner immediately. Think of it, Mary!" Markus said, wondering what the issue with Hotwire might be.

Mary was stunned. She started to sweat, thinking about her options. She could not say no to Markus now or let him down. Her promotion to partner depended on it. An idea came into her head as she looked at Markus.

"No worries, boss! I will get Hotwire to do the work!" Mary said with false confidence.

There was no other answer to give Markus at this point. It was live or die with Hotwire. Get Mike to build the server room or fail and fall back into the clutches of Kelly.

"That's my girl! I knew I could count on you and do not worry about Kelly. She is out of the equation. The decision stands with me about your promotion, now that we have a potential 50-million-dollar contact!" Markus said.

Mary was surprised at Markus's admission that Kelly had that much influence on him.

"Much appreciated, Markus. I will let you know about Hotwire's schedule for installation by the end of this week. I still need to meet with Mike to settle the details." Mary said.

"Do what you have to! You have my 100% approval to move this forward. Come to me if anything gets in your way!" Markus said as he got up to shake her hand.

"Thanks, Markus. I won't let you down!" May said.

"I know a future Partner of the company can be depended on!" Markus said, hinting strongly at the reward if she succeeded.

Mary left his office already thinking about the next steps. She had a plan but needed to consult her lawyer friend to check on the reality of her idea.

She got back to her office and immediately called her longtime friend Kevin, who she dated back in the day. He was the best lawyer she knew, and she would need a great one to pull this off.

"Hey, Kevin! Long time to talk to, how have you been?" Mary chirped.

"Well, if it isn't Mary Davis. I'm good! Last time we spoke, things were not going so well for you." Kevin replied, wondering what Mary could be calling about.

"I need to talk to you about a certain type of contract, but I need to speak with you in person. Can you and I meet you at your office later today?" Mary asked.

"Sure, stop on by!" Kevin said, fondly remembering the sight of the best set of tits he had ever laid hands on.

"Ok, see ya soon!" Mary said and picked up her things and left the office without a word to anyone.

She also disconnected her chastity cage app so Kelly could not bug her while she worked out the plan's details. She left the cage attached to her pussy because she liked the feeling of her pussy lips being locked uptight.

"Markus must have already talked to Kelly as she had not tried to contact me since my meeting with him." Mary thought as she walked out to her car.

She drove to Kevin's office, took the elevator up to the top floor, and walked into his office area. Kevin saw her right away, much to Mary's surprise.

"What can I do for you, Mary?" Kevin said, staring her up and down but always coming back to her huge rack so blatantly exposed.

They had a sorted history but never really dated officially. They were primarily old drinking friends and fuck buddies; at least that is what Mary thought about their past. They parted ways when Mary changed her life and entered the corporate world.

"Well, the last time I knew, you specialized in personal contracts, specifically in NDA (non-disclosure-agreements) contracts. I was wondering if you could make one for me for a very unusual purpose?" Mary said, hoping Kevin would understand the extreme nature of this NDA.

"Well, that is still my specialty. What would this contact contain and for whom?" Kevin said.

Mary explained in vague terms. She wanted something that would prevent the parties, locked in by the NDA, from divulging anything that happened between her and the NDA signees during a specified time. She gave a few examples of the behaviors covered and what would be happening. The distribution of any audio or visual media would also be a violation of the NDA. She wanted intimidating verbiage throughout to discourage abuse of the contract.

"Wow, this would take a Trump-level type NDA, like the kind used to silence Stormy Daniels. It's not cheap, but ya, I could make one. You would have to have him sign in the presence of a notary to make it valid. I never knew you were into this type of thing Mary, it's none of my business, but are you sure you do this for what looks like 2-3 weeks?" Kevin said, starting to sweat from the hot blonde talking about the details of the NDA.

"I know it seems crazy, but there is a huge payoff for me that makes this all worth it. You don't really need to know all the gory details. Still, yes, I know what I am doing, and attorney-client privilege covers our interaction, so I am not worried about you, Kevin. I know I can trust you." Mary said, feeling more confident about the process.

"I can have it ready by the end of the week if you are willing to pay the expedited fees for registration and application," Kevin said.

He could easily have it ready sooner, but the way Mary looked with her prodigious chest, flowing blonde hair, short skirt with thigh-highs, and red fuck-me pumps, he could not help himself.

"That is way too long, Kevin! I need it by tomorrow afternoon at the latest!" Mary said, looking distressed.

"Sorry, Mary, there is no way I can get it ready that fast," Kevin said sternly. He was going to hold out for a flirtatious date or something close, but his mouth dropped open as he witnessed Mark leaning forward, exposing her massive cleavage.

"I can make it worth your while Kevin. I really need this tomorrow!" Mary said as she used her arms to squeeze her tits together, pushing them up and out, so her nipples started to show.

"What's one more blow job at this point after filling my stomach with six loads of cum not two hours ago?" Mary thought as she looked Kevin in the eyes and slowly opened her blouse and cupped her breasts while teasing her barbell pierced nipples. She still felt ashamed of her breasts labeled with "I LOVE TO SUCK COCK!" so she cupped them to hide both tattoos.

"Holy shit...I almost forgot.... what perfect tit's you have! Maybe... we can work something out!" Kevin stammered. His cock started to engorge as Mary removed her blouse and bra. Her barbell pierced nipples connected with a gold chain stood out front and center. Kevin drooled at the sight, gaping at her, entranced by the perfect set of tits, as she walked around his desk, swiveled his chair to face her, then kneeled on the carpet, looking up at him with her hands rubbing up his thighs. Her tit's swung back and forth as she rubbed closer to his cock, straining in his pants.

"I think we can definitely work something out, Kevin. Oh my, you are hard as a rock!" Mary said as she unzipped his pants and released his stiff prick.

Mary slowly licked around the sensitive head while she spoke.

"I remember this cock...umm", Mary said as she licked up his shaft, "...so...do you think you can make this happen by tomorrow?" Mary continued as she slowly sucked his cock down her throat until her nose was buried in his pubic hair.

"Oh god...I forgot...what an amazing...cocksucker you are! Yes...I...think...I can!" Kevin said, stuttering as Mary sucked the life out of his shaft.

"That is good to hear!" Mary said and continued to blow him for another few minutes until Kevin's balls retracted high up in his sack. Mary felt that she knew the end was near.

She popped his cock out of her mouth, enclosed her large, soft breasts around his stiff shaft and pumped her tit's up and down while looking up at him.

"That great news Kevin!" Mary said cheerfully as she covered the tip of his shaft with her lips to receive the hot jets of cum spurting from his rock-hard cock.

Kevin exploded with an intense orgasm that made his balls ache as cum filled Mary's cocksucking mouth.

Mary put the icing on the cake by showing Kevin a mouth full of cum before she swallowed it down in one gulp to join the six other loads of cum from her Team, swimming around in her stomach.

"Oh my god, that was fantastic. I can't remember the last time I came that hard. You really like being a slut!" Kevin said with a smile.

"A slut with a mission Kevin...a slut with a mission!" Mary said as she reached out and grabbed Kevin's hands and placed one on each breast.

Kevin sat memorized as he fondled the most perfect set of tit's he had ever seen. They were large, perfectly shaped with a gold chain connecting her large barbell pierced nipples. He had never seen, let alone felt such a perfect set of tit's displayed in this way.

Mary took full advantage of his fascination with her chest by finalizing the deal. At the same time, Kevin cradled her globes and played with her stiff, puffy nipples.

"So we have an understanding Kevin? You are going to make me an unbreakable, "Trump-style" NDA by tomorrow afternoon, correct?" Mary said, trying to get his attention.

Kevin was leaning close to her nipples. He was very distracted, but Mary knew what he wanted.