The Pilots - Cover

The Pilots

Copyright© 2025 by Wolf

Chapter 25: The IPO

Romantic Sex Story: Chapter 25: The IPO - A chance meeting between an older gentleman pilot and an accomplished younger woman pilot triggers a relationship that starts rough builds into long-term partners. They build a remarkable business and launch it into the public domain. Their loving connections with a larger group flavors their lives through romance, polyamory, sex, family and lesbian sex, and creative lovemaking.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Lesbian   Heterosexual   Fiction   Workplace   Sharing   Incest   Group Sex   Polygamy/Polyamory   Anal Sex   Exhibitionism   Masturbation   Oral Sex   Voyeurism  

My children lived in a Chicago suburb – two daughters born to Mindy and me, two years apart. They were twenty-nine and twenty-seven. Marcy, the older one, taught social studies in junior high school and loved her job. Karolann, the younger, had a job as a physical therapist for a small company specializing in supporting the nearby orthopedics doctors’ patients in healing.

Both daughters were married. Marcy’s husband was Todd. He was a burgeoning photographer in their small town, and had managed to capture the contract with the local school system to do the various individual and class photographs that went in the school yearbooks. He also covered the local school sports teams.

Karolann’s husband, Scott, was an electrician. He was eight years older than my daughter, and established in the town where they lived, so had more than enough business to keep himself and ten other electricians and ‘apprentices’ busy. Kar also helped with Scott’s back-office stuff such as the weekly payroll, calendars, scheduling, and other admin stuff he didn’t like to do.

After Mindy had died, so had part of my relationship with my daughters. Mindy was the one of us that was intimately involved in their lives from the time they were born until she passed when they were just finishing college. She did get to attend Marcy’s wedding, but barely.

I routinely emailed the two of them and we had a common ‘Hume News’ text group where we could post various milestones or events, often humorous, in our lives. In person conversations had become rare

Thus, I shuddered with some intrepidation when I read a long text from the two of them: ’Dad, the four of us are coming to stay with you in North Carolina for the Thanksgiving Holiday. If you can’t house us, can you arrange something nearby? We love you and don’t get to spend enough time with you, so prepare for the four of us to arrive on Tuesday afternoon and depart Sunday morning. Details to follow. Love, Marcy and Kar, Todd and Scott.’

I showed the text to Kim. She gave me a great smile, “Oh, good. I’ve wanted to meet your kids. I think we can be great buds. Heck, we’re all about the same age.”

That evening, I explained to Kim that I hadn’t been exactly forthcoming with my girls about our relationship. I explained that since Kim was more or less their age, I thought they might not approve.

Kim asked, “What have you told them?”

I sighed, “I’ve never mentioned your age, and if anything might have used a word or two in my communications that suggested you were more my age.”

“More,” Kim gestured.

“I said that I’d ‘gotten a room’ in a house because I was doing so much work for your company. I later said that I’d developed a ‘nice friendship’ with someone and that we ‘shared some interests’, including flying, and ‘liked to spend time together’.”

Kim laughed. “They are going to hoist you on your own petard, my dear, as Hamlet said. I think I may end up being on their side of things. You should have told them more as we went along – not the juicy stuff, but that you and I are serious.”

I did an eye roll at my own situation. Kim was right, but it was too late to fix it until they arrived. I did send a reply text that I hope suggested something slightly more significant than what I’d previous led them to think. ’Re: Your Visit. Wonderful. Kim and I look forward to your visit. Lots of room in the house for all of you. Come and stay – we have multiple guest rooms. Love, Dad.’ I hoped they’d key off the word ‘We’ and not be as shocked by what was going on.

I had two weeks to worry about what else I might say and how to defend myself for my lack of specificity and detail about my relationship with Kim. Hopefully, my daughters would immediately overlook the deficiencies.

While that was going on in our social life, our business life was going much better. We finished up the submission to NASDAQ in mid-October. I flew up to New York and hand delivered the entire data package in person, hoping to make a good impression about our eagerness to be listed as a publicly-traded company.

Since the submission, we’d had a few questions that we clarified within a day, but there was still no indication of acceptance or rejection. Mostly, in terms of the submission, we sat around with our fingers crossed. We got a friendly email that indicated that a decision was likely before the end of the year. I was let down since that meant we might have to wait six or seven weeks.

Kim tasked me with being sure the two guest rooms were in proper shape for my daughters and spouses that we wanted to impress. I didn’t think about impressing them, but Kim did. She wanted to be on their good side ‘for the rest of time’, she said.

I worried not only the bedrooms, linens, pillows, dressers, luggage racks, and so on, but also the hall bath that they would share. I bought new towel ensembles so that each person would have a color-coded set to use. I got some girly shampoo and conditioner, some manly soaps to go with the girly soap bars, and cleaned the place until it sparkled.

On Tuesday before Thanksgiving, I drove Kim’s SUV to Raleigh-Durham airport to pick up our four visitors. The flight was on time, but the airport was mobbed. Finally, with everyone in the car, we headed towards Chapel Hill.

Of course, the first question that I got after we got off the airport property was, “Dad, tell us about the woman you like?”

You would think that with all the time before they got there that I would have rehearsed some of the questions I’d have to field. I was in denial or numb or something.

“Errr, her name is Kim Winslow. She’s also a commercial-instrument pilot. We actually met over a year ago in Orlando when we’d both flown in for an energy conference. She was one of the keynote speakers, and she did a great job at it. She’s a good communicator.

“She has a business that I’ve been helping her with. I guess I should mention that I’ve actually gone to work for the company as their EVP. We’ve made a submission to be listed as a public company on the NASDAQ Exchange. It’s a big deal and we should hear any day.”

Todd asked, “Do you own pre-IPO stock?” The man knew his stuff.

I was grateful for the redirection of the conversation to business rather than relationship questions. “Yes. I’ve been taking stock in lieu of my consulting fees initially. Now, I’m a one-dollar-a-month employee, with the rest in stock. I think that’ll change as soon as we go public, so I look like a more normal executive on the books. Also, in case you didn’t know it, I’ve gifted you each an early Christmas present of a thousand shares each. That sounds like a lot, but pre-IPO that’s not worth much.”

“Do you know the offering price?” Scott asked.

“I think it’s a wise investment, but we’ll know soon enough. We’re seeking a $40 per share initial price. Obviously we’re then hoping that the stock rises in price. We think it’ll be a hot commodity. The company needs money for some of its strategic plans.”

The discussion about stock, valuation of the company, and such continued for a while, until my other daughter asked, “What’s Kim like?”

I chuckled at that point, “You’ll find out soon enough. We’re almost at the house. She’s lovely, kind, sweet, professional, competent, and ... well, as you’ll soon see.”

Hot damn. I’d made it from the airport home without becoming nailed to the dashboard by my daughters.

At the house, I helped with a few of the luggage items. It was a nice sunny day and warm in our part of the world, so we were all in shirt sleeves by then.

Kim came out of the house in shorts and a colorful top. She looked crisp, and her smile was welcoming.

I knew I was in trouble when both my daughters started to bounce the looks between the two of us. Kim looked young, and I was obviously old enough to be their dad and then some.

 
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