Wake Up Lisa Mitchell Ch. 26-27

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A different type of pleasure and a scary moment for Lisa.
13.2k words
4.75
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1

Part 18 of the 18 part series

Updated 08/27/2023
Created 09/11/2020
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JamesVI
JamesVI
66 Followers

CHAPTER 26

"Ladies and gentlemen, we have begun our descent. Please turn off all electronic devices and stow them until we have arrived at the gate. In preparation for landing, be certain your seat back is straight up and your seat belt is fastened," said the stewardess on the handheld PA.

Lisa put away her laptop and checked her seat belt. She rested her head back and closed her eyes. The businesswoman's first couple of months had started off slow at VBS. But now, the mature woman had figured out the formula in her approach as a Senior Account Executive.

Taking a deep breath, Lisa thought about the last few months. Not only had she turned forty-four, but her daughter had become a year older as well. Shelby celebrated her twenty-first birthday enjoying a glass of wine and dinner with her mother. Lisa smiled thinking about the maturity she had seen in her daughter lately. The day Ryan and Lisa shared with Shelby about the separation, the young Ms. Mitchell cried. She then followed this up with a barrage of questions, anger, and silence.

What it led to was the young woman shaping her own career decision. Her parents decided to sell their house and Shelby asked if she could be the agent. With a bachelor's degree and her real estate license, the young beauty felt good about her future.

Lisa smiled slightly at the thought of her daughter before thinking about Ryan. He had completed a transfer to Charles' region. She recalled how upset Ryan was when he found out Mark was given the promotion. Plus, he couldn't understand how Lisa was okay reporting to the scumbag. For the savvy woman, she framed the conversation in a way that supported her career aspirations.

About her old, well, new boss, she gently chuckled to herself on the plane. She appreciated his compliments and youthfulness. Not only that, but she found him extremely desirable in more ways than she would've imagined. Lisa pressed her thighs together, thinking through the night they both celebrated their career achievements.

Some slight turbulence broke up the busty woman's thoughts around her lover. Mr. Lipscomb had been integral in her onboarding process and ramp-up at VBS. His knowledge of their products and services was vast. Mark even invited her to some of his client meetings as he transitioned to the VP position he eyed. This helped Lisa network as well as develop her sales approach.

Her contractual partner was the last thought she had on this flight. Everything Charles had outlined for Lisa had taken place within the first few months of her arrival. What remained was the exit strategy Charles had in mind. Lisa wondered when he would execute his plan.

"Ladies and gentlemen, Sunwest Airlines welcomes you to Houston. The local time is 3PM. For your safety and the safety of those around you, please remain seated with your seat belt fastened and keep the aisle clear until we are parked at the gate. The Captain will then turn off the "Fasten Seat Belt" sign, indicating it is safe to stand. Please use caution when opening the overhead compartments and removing items, since articles may have shifted during flight," said the stewardess.

The unbuckling of seatbelts started prematurely as Lisa opened her eyes, patiently waiting to exit the airplane. Slowly the rows emptied and people filed out of the plane through the single aisle. Sitting near the middle of the plane, Lisa's turn eventually came.

She stood up and reached towards the overhead bin across from where she sat due to them becoming full quickly. Her calf muscles flexed in her high heels as she pulled her carry-on down. Some of the men in the aisles watched as the busty brunette's skirt cut just above the knee, and stretched across her ass as she did this. Lisa wore some pantyhose just in case she felt that a situation like this may arise.

After placing her carry-on down, she pulled up on the handle and walked down the aisle in her black stilettos. Her hips swayed with each step, like a model on a runway. Some of the same men peered between the seats to get a look at the sexy woman walking away.

Once she exited the terminal, the Senior Account Executive scheduled a ride-share. On the way to a hotel, she replied to some e-mails and text messages, especially the important ones from Mark and Charles in a group thread.

Mark: Sorry again team, good luck on this one.

Charles: All good, we should be fine. Lisa, I'll call you once I land so we can meet before dinner.

Lisa: Alright. I'm going to go ahead and get ready for the evening then so we don't lose time.

Charles: Good point, I'll do the same. Mark, can you be on standby?

Mark: Yes, for sure!

After arriving at her hotel, the mature beauty finished responding to some e-mails and then went to shower and get ready for dinner. They would be meeting a potential client tonight and were eager to win their business.

Charles called the sexy woman as she was getting ready.

"Hey Lisa, did I call at a bad time? If so we can talk later," he asked politely

"Well, if you don't mind, I'm just finishing getting ready," she shared with him, just as polite as he asked.

"Yup, sounds good, see you downstairs at five-thirty. Dinner reservations have been made for seven," he added before hanging up

The mature beauty finished blow-drying her hair before applying her makeup and pulling on her dress for the evening. Lisa looked at herself in the mirror before leaving the room.

She wore a black Susana Monaco mock neck, sheer mini dress. The pull-on styling and mesh fabric at the neckline gave it elegance. The length of the dress which came down about mid-index finger didn't leave much of her long legs to be concealed. On her feet were some black Michael Costello, x Revolve Sonia Sandals. The four-inch heels with wraparound ankle straps and buckle enclosure finished up the look.

After sitting down on a couch in the lobby, Lisa texted Charles that she was there. Then she replied to some messages from her lover and ex/new boss.

Moments later Charles joined her and they embraced professionally before he sat down. The two of them started to discuss strategy.

"Did you get the proposal finished?" Charles asked

"Yes, Mark and I looked over it last night and we have mostly everything covered," Lisa replied

"Great! If we can close this then I can put in my notice next month. Oh, and in terms of our deal, if VBS lands this, I'd like to see how Eric and I can get the add-on or supplemental work. Think about that," Mr. Grant added

Lisa listened attentively and hung up on what he just shared. Eric had just left last month. To her, it sounded as if she would have to help in more ways than she thought. Plus, Lisa thought he may want to see how honest and in what way she would direct business their way.

"Sounds good Charles. I'll work that angle in," she said

He let her know they had their ride-share and they went to the car, heading towards the restaurant. Once they arrived, the VBS team stepped out of the car and Charles called the client.

"Hey Kimberly, we are here.... Okay great... We'll wait for you," Mr. Grant said

Lisa and Charles chatted as they waited for a few minutes.

"Charles?" A woman's voice asked

Mr. Grant turned around and greeted her.

"Hey! Kimberly, thank you for joining us, this is Lisa," he said while shaking Kimberly's hand and introducing her to the Senior Account Executive.

"Hi there! Pleased to meet you," Lisa greeted Kimberly with a warm smile, holding her hand out.

Kimberly shook the beautiful brunette's hand, "Pleased to meet you Lisa, I love your dress!"

The two women analyzed each other. Kimberly was near eye level with the busty brunette. She stood at five feet, seven inches, and wore three-inch heels. She had on a dark woman's business suit which contrasted against her copper blonde hair. Kimberly was intent on ensuring people knew she was a professional. If one had to compare her appearance, it would be similar to actress Laura Linney.

Meanwhile, Kimberly eyed the outfit and the bust of the brunette in front of her. She admired her build and was intrigued to learn more about the busty beauty.

After a little more small talk, the trio made it to the front desk and were led to their table. It was a half-round booth. Lisa scooted in first with Charles sitting on one end and Kimberly on the other. This left the busty brunette at the head of the table.

Once they settled on a bottle of wine, the introductions went on some more.

"So... Mrs. Lisa... Tell me about you," Kimberly started

"Yes, of course. Lisa Bailey. Ms. Lisa Bailey. I've been with VBS for a few months and before that was in the financial industry. Charles asked me to join for a few reasons so I'm very glad to be a part of this meeting tonight." Lisa said

"Oh, how nice, Ms. Bailey, I'm really glad Charles had you join," Kimberly added, directly looking into the busty brunette's blue eyes.

Charles Grant caught Lisa's last name and still found it strange but knew why she wasn't Mitchell anymore.

"Thank you so much! May I ask for the same?" Ms. Bailey asked

"Kimberly Wolf. I've been the COO at ByteSize for two years, before that, I was at DreamPath and then Heritage Holdings. A variety of sectors but really enjoying tech." she shared. Her tone was confident and friendly

The waiter arrived with the bottle of wine and he poured them a glass each while the conversation continued.

"Thank you so much, Kimberly and Lisa. Now for why we are here..." Charles started before Kimberly jumped in.

"Of course! Sorry Charles, I wanted to share with you what I know," she was direct now

"I spoke with the rest of our C-Suite and this is going to be difficult. We have other services needed that VBS does not offer, yet the competition does," Kimberly shared, waiting for a response

"Oh, I get it. What if we can be competitive with two partners versus using just one? Sure, you lose continuity of resources but I guarantee you that the VBS partner knows their business inside out," Mr. Grant said

The dance of negotiation had begun and Lisa Bailey watched with much interest.

"How can you guarantee a partner like that? What are you hiding?" Kimberly playfully asked. Serious but still light in the delivery of the question.

"Well, first tell me this, how far are we off on the initial estimate?" Charles asked,

Kimberly Wolf looked at the sexy brunette before looking back at the man she was conversing directly with, "It's a big difference. About fifteen percent."

Adjusting his neck slightly, Charles continued to discuss terms and what they could do at VBS. He was able to provide discounts and such where Lisa would've leaned on him anyway.

"I can get us closer, trust me there." Mr. Grant said

Lisa used this as a cue for the other services Kimberly had mentioned. "And to those other services, I believe VBS has a wonderful partner in this space. If you may, give me a few days and I'll get you more information. What I can say is that they know VBS inside out."

The mature client looked at the VBS employees before looking to leverage the situation. Just as she was about to speak, the waiter interrupted for dinner orders.

"Steak, medium rare please," Kimberly requested

"Sea bass," Charles added

"Caesar with the salmon please," Lisa said

The trio resettled before continuing.

"Charles, you've got a tough sell on this. We both know in this space, even a company that has initial and post-project support can be dysfunctional. With these other services, honestly, we can't fuck around." Kimberly was a little more stern and direct now

Right before he was going to speak, Lisa interjected, "Mrs. or Ms. Wolf, let me get you the details on that alignment. What we have at VBS is continuity for sure with initial and post-project support. It's the same consultants working the project through. No other partner does this. With the other services, I know you will be happy with who I bring to you."

Kimberly eyed the busty brunette as if sizing her up. Charles Grant meanwhile was interested to see how Lisa would navigate the conversation. But he also didn't want her to be set up for failure as it impacted his business.

"Lisa, tell me if I'm wrong, but you were going to tell Kimberly about AppTech," Mr. Grant added. He was helping her with his plugin during this conversation.

The COO let Lisa know her thoughts nicely but sternly before shifting to Charles, "Mrs. Wolf, Lisa. And Charles, who is AppTech?"

Ms. Bailey was going to jump in but paused long enough for Charles to answer.

"AppTech is new to the scene. They are a partner to VBS and have SaaS solutions for the VBS product offerings. Remember Eric? He's there now," Mr. Grant shared

Kimberly eased up some, she'd met Eric when she started out in tech and had seen his growth from afar. "When did Eric go there?"

"It's been recently," Charles said.

Their food came out at that moment and while they ate, the trio discussed the connection between AppTech and VBS.

Once dinner was over, Charles and Lisa had positioned VBS for another estimate, one from VBS and another from AppTech.

"Lisa, care to join me for a nightcap? I always appreciate speaking to another woman in a male-dominated industry," Kimberly said with Charles still at the table.

Mr. Grant took her comment as well as anyone could, showing no emotion but listening to hear Lisa's answer.

"I, uh, thank you, and sure," Ms. Bailey said

"Great, is that okay Charles? I can drive her back to the hotel. We can just reconvene at the bar back there," Mrs. Wolf said.

Lisa replied calmly but still enthusiastically, "That's great! I'd like to learn from you too if you don't mind Kimberly."

The copper-blonde executive was impressed. Once Charles paid, they exchanged goodbyes before Lisa and Kimberly walked together to the bar.

"How can I help you tonight?" asked the bartender

Kimberly looked at Lisa, "Same as me?"

Ms. Bailey nodded in agreement

"Dewar's, straight, double," Kimberly told the bartender.

From the order, Lisa Bailey put together that this may be stronger than what she would prefer. Once the drinks arrived, her concerns were validated.

"To powerful women!" Kimberly raised her glass eye level for them to celebrate.

Lisa clinked her glass with the COO and they both took a sip. Ms. Bailey could feel the burn go down her throat from the brown liquor as it settled in her stomach.

"Where are you from Lisa? I know you told me somewhat about your career, but what about you? Kids? Etc." Kimberly asked. She didn't dance around many questions.

Ms. Bailey answered the questions as they were asked, finishing up with, "And...recently separated."

Mrs. Wolf raised her eyebrows, "Oh god, fuck him. Sorry... What did he do?"

Lisa took a deep breath, "He cheated on me with a stripper."

"Oh yeah, then fuck him!" Kimberly replied

They continued the small talk further. The tall blonde was impressed by the sexy brunette. She also found her very attractive. As they chatted and the liquor started to creep in, Kimberly brushed and touched Lisa's shoulder, hand, and hip in an unassuming and non-sexual way.

About an hour and a half later, Mrs. Wolf paid the tab and they walked to her car. So far they had just talked generally and non-business.

"So Lisa, do you think that Charles can bring the cost down and do you believe in AppTech?" Kimberly asked

Looking in the mature woman's direction, Lisa replied, "I do. Charles and Eric have both been exact and true throughout my time with them."

After some more mixed conversation, Kimberly parked in a visitor space at the hotel.

"Well, we are here," she told Lisa.

Ms. Bailey smiled at Mrs. Wolf and their eyes made contact for a second longer than Lisa may have noticed. Kimberly took a quick gaze at the busty brunette's lips before leaning in to kiss her.

Both women closed their eyes as their soft lips touched. Lisa felt a jolt of lightning strike through her body as Kimberly pressed gently before moving away.

Lisa was shocked and in awe, unsure of what to do. Her face was flushed and her chest and neck were visibly red.

"Oh god, I'm so sorry, you just, you are breathtaking Lisa," the COO apologized along with the compliment

"It's, yeah, it's, it's okay, no problem. Um, have, have a good night," the sexy brunette replied, fumbling with the handle and lock before swinging the car door open and exiting.

Kimberly Wolf felt the touch of desire between her legs as she watched Lisa Bailey walk away.

After reaching her hotel room, Lisa changed and thought about the evening. She felt in control and confident with how she approached the COO. What threw her off was the kiss at the end. The last time she remembered an incident like this was during a college party. It was a dare between her and her friends while out on a girl's night.

The sexy brunette closed her eyes and went into a deep slumber. In the morning after connecting with Charles on some details, Lisa checked out of the hotel and made it back home in the late afternoon. She was glad that the week was over. After texting Mark and Shelby separately, Lisa went out for a run before coming home and taking a bath.

That evening, she received a text from Charles that Kimberly wanted Lisa to come out again next week to share the estimate with her. The mature brunette agreed but was a little nervous after the kiss. Ms. Bailey spent her weekend with her lover one night and tended to some of her own tasks the other. During the middle of the week, she flew back out to meet Kimberly Wolf.

Kimberly texted the busty brunette an hour before Lisa's departure: Here is the address. I have some other friends coming in. Cocktail is the attire. Be there by six thirty

Charles Grant had confirmed with Lisa it was okay to share Lisa's cell phone number with the COO.

Ms. Bailey grabbed a dress quickly with heels and packed it in her carry-on. Once she arrived, Lisa unpacked her belongings and noticed that she had brought a dress that may have been a little contemporary.

Sighing, Lisa picked up her attire for the evening and laid it out on the couch in her room. After showering, she wrapped her hair in a towel and applied some light makeup.

Next, she moisturized her arms and legs before slipping on the mid-thigh dress. The black B Darlin product had double spaghetti straps and was lined and fitted through the chest, waist, and hips. It had ruching all over and most importantly a little keyhole cutout at the chest. The material was polyester and spandex. After clipping on her earrings and clasping her necklace, Lisa Bailey slid up a black thong.

To be somewhat tasteful, the mature beauty didn't want underwear lines to indent her dress. On her feet, she wore the Stuart Weitzman Gemcut 85 Sandal. It had hand-applied teardrop-shaped Swarovski crystals. The modern square-toe sandal had nearly a three-and-a-half-inch stiletto heel. To finish off the sandal was an adjustable ankle strap with a crystal-embellished buckle.

Lisa felt guilty wearing such expensive shoes with a dress like this but didn't concern herself too much with the contrast in price. Checking herself in the mirror one more time, the mature beauty adjusted the spaghetti straps of her dress to conceal as much of her big boobs as possible.

Once she was ready, Ms. Bailey scheduled a ride-share and made her way to the address provided by Mrs. Wolf. On her way, Lisa texted Mark and Charles separately about different topics. Mark was more interested in her outfit and Charles more about the potential deal.

When she arrived, the sexy brunette noticed that it was to a residence. Thanking her driver, Lisa walked up to the door and rang the doorbell. About ten seconds later, Kimberly opened the door and greeted the busty brunette.

"Wow! Thank you for coming tonight and for looking so stunning Lisa," Kimberly said. She was seemingly happier than during their meeting the prior week.

JamesVI
JamesVI
66 Followers