The Pilots
Copyright© 2025 by Wolf
Chapter 18: Advances
Romantic Sex Story: Chapter 18: Advances - 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
Kim was mostly in her North Carolina office over the next three weeks. On the other hand, I was in Houston, Little Rock, Denver, New York, and D.C., using commercial flights for the longer hops.
One thing I was doing that Kim urged me to pursue was establishing the baseline for her initial public offering (IPO) sometime late in the year. Apparently, the various market gurus believed that November was the perfect time to launch a new company into the public arena.
Over dinner on our second night back in Camp Forge with the Circle, Bob asked me what my travels were about. Since it wasn’t any secret, I told him about scouting for ‘small’ energy companies that TNA might acquire and the upcoming IPO.
“What are you using for cash?” he asked.
I shrugged, “We’re almost out of it. Our next round of acquisitions will have to wait until after the IPO, assuming that a few people buy the stock.”
Bob frowned, “Two things will probably happen, right? The price for your targets will go up. The due diligence process will become more complex. Further, if you have those acquisitions under the roof before the IPO then TNA looks much more attractive, you can command a higher strike price, or you can go in low and let the market drive up the price.”
I had to agree with all of his points.
Bob said, “So, a private angel investor would do well to invest in TNA before the IPO, right?”
I nodded, “Sure, but we’re not all that attractive now. Kim has already taken on some debt, but that’s been at a reasonable level. She has been using her own resources the past three months to get things to happen. I’m heavily invested, too, and so are a couple of her other execs. If we extend any further, my friend at Goldman Sachs tells me we start to become less attractive financially.”
Bob said, “Could you use ten million?”
I about choked and said something dumb. “Dollars?” I was gawking at him.
“Duh,” he laughed. “Yes. The Circle would like to invest. What would you do next?”
“Complete the purchase of a small tidal power generation company trying to get started up in Canada near the Bay of Fundy, and the purchase of a geothermal outfit outside of Denver.”
Bob asked, “And those would look really good on the books for the IPO?”
Kim and I both nodded. She said, “It’d be like adding gold ingots to the foundation of the company. We would look like what we’re trying to become – a full-tilt alternative energy company.”
By now, I realized that Jim and Trish had also been tuned into our discussion, and that other conversations on the patio had ceased.
Bob said, “Then by unanimous vote of the Circle, we hereby pledge ten-million dollars to TNA in exchange for pre-IPO stock of equivalent value in the current company.”
Kim got tears in her eyes. She blubbered out, “Thank you. I’ll do everything in my power to make sure you get it all back with a lot of interest and capital gains. I need you to know that Goldman Sachs thinks we’re a bit of risk at our current level. One guy did say that if we had those additions that everything would change.”
“And this will help establish more of that stability?” Bob asked.
Kim and I both nodded.
“Good. That’s what I thought.”
I was numb and Kim was nearly comatose as she just about got down on her knees and worshipped Bob. He explained that he was the head of the Circle’s informal investment committee.
He said, “After hearing more about TNA on your last visit, we did some research on our own and decided to shift some of our portfolio over to a riskier endeavor, like your company. I assume you have some lawyers available that can make up the right papers to facilitate the transfer? Both of us need to have it all legaled up, especially for the IPO.”
Kim stuttered, “I’m going to call my lawyer tomorrow and have that ready first thing on Monday morning. Is that okay?”
Bob and the others grinned, “That’ll work. We’ve already taken the steps to have the money liquid and ready to wire into your account. We just the banking details to make it happen – on Monday.”
Kim popped up from the picnic bench and went around the table to where Bob sat. She turned him for access, plopped down in his lap, put one of his hands under her top and onto her breast, and then launched into a series of very passionate kisses. She said, “You say the sexiest things.”
About ten minutes later after a hot make-out session, the two of them got up from the table and went inside Jan’s house. That was also where Bob and Trish ‘lived’. I got aroused knowing that my girlfriend would try to have Bob fuck her stuffing out in thanks for what he’d just done for her.
I had to ‘suffer’ the evening with June. Jim welcomed the attentions of Jan and Trish. I really liked this Circle thing. The five of us stayed in the back yard and made love. There was some trading around until Jim and I had each had our cocks in the women that were with us. I found the night highly arousing to be able to see the others making love and eating or sucking on the right places in one another.
I slept with June in my arms and we also made love in the middle of the night. It’s what exceptionally horny people do.
Sunday, we lolled around the house and patio. It was a warm, sunny day in the area. Jim goaded us all into getting into athletic gear and taking a jog through the local trails and parks. The activity did get the blood pumping and the exercise was an hour well spent.
I ended up taking a shower with Trish. We didn’t stop until we were both squeaky clean, although there were a few moments during the long shower when she had an injection of my semen into her body as I held her against the wall and pounded into her as she urged me on.
Trish whispered that she loved me and wanted me around her whenever I could. I mentioned my plans to be in Boston in a week and she made me promise to stay with her and to come prepared for some serious loving.
That afternoon, Kim and I flew back to North Carolina, this time in her Mooney. We compared notes about our encounters with the Circle, and that made us both hornier than we’d been the night before.
After landing, we rushed home, made love, and then went out for a late dinner. Once home, we made love again and then happily went to sleep together. I was the luckiest guy in the world.
Tuesday night, I flew on the red eye to London on Kim’s behalf to talk to another company doing tidal power generation in the Thames estuary. Yes, they were interested in being acquired by a U.S. company and the group of engineers that had started the company were glad to kick around the idea of being a subsidiary with ties to at least one other similar company in the U.S. I left them on Thursday morning to consider a proposal and also the conjure up their asking price and other terms.
What with connections out of New York, I didn’t get to Kim’s home until nearly midnight. I crept into her bed and after a kiss, went to sleep with part of her on my chest after a short lovemaking session.
Friday, I worked on some my own client projects from Kim’s dining room table. Kim and I worked over the weekend on TNA’s strategic plan and on some of the paperwork for the IPO. We got a run in each day and made love frequently, but were pretty dedicated business people otherwise. Overall, it was a working weekend.
Monday, we spent with Ken Wheatley, TNA’s CFO, and Brian Daley, the company’s lawyer, and two other outside attorneys on the IPO ‘package’. There were many phone calls, including with the NASDAQ where we hoped to be listed before the end of the year. Ken and his crew, including some outsider consultants, had been working on all the required financial statements.
The lawyers had reviewed the financial stuff, but were more focused on the registration statement that had to be filed and approved by the Securities and Exchange Commission.
Everyone on our task force was also glad to see the Circle’s investment in the company. Each of the five in Camp Forge became an ‘official’ shareholder to help build up some of the numbers for the SEC filing that wanted a minimum number of existing shareholders.
The meetings and work to complete the filing went on the rest of the week. I left Kim to worry some details and flew up to Boston to have some investment talks with Fidelity and the analysts in their Energy Sector.
Wednesday night I called Trish in Boston to ask whether her invitation was still open for a Thursday afternoon arrival and late Friday departure, even offering to fly her down to Camp Forge so I could connect with the Circle for the weekend as Kim flew up from her home. I told Kim about my meetings at Fidelity and went into a little detail about the filing and also what I hoped to set up at the big investment house. She probed and I had the feeling she was really into my visit, including success at Fidelity.
Trish had a combination door lock on her condominium, and gave me the code to get into the building and into her unit. I told her that I was buying dinner, and that ended the call.
The flight up from North Carolina to the Bedford, Massachusetts, airport took about four hours. I had favorable winds, but from Hartford north the area was pretty solid IFR – instrument flight rules. There was a light rain falling, and it really pelted onto the windshield at 140-knots. The plane did get a ‘free’ wash.
I got vectors and various altitude assignments from Boston Center and then Approach Control vectored me to the LOBBY waypoint, the Initial Approach Fix, for the ILS 11 approach. I picked up the glide slope there, adjusted the power slightly and added, flaps. I was handed off to the tower then. I reported into the tower and was cleared for the ILS 11 approach and landing. They also had a reported ceiling by another aircraft that came in ahead of me. I had information Oscar with all the winds and visibilities, so was in good shape.
I broke out of the scud at 600-feet, well above the landing minimums, called the field in sight, and was acknowledged. Tower had me stay on their frequency after landing, even as I taxied to the FBO parking area. I was waved into a parking spot by a lineman that came out in the rain to direct me. He helped me by tying down my right wing as I got the left one. One advantage of a high-wing plane is that you can get out of the plane in the rain and not immediately get wet. I got my gear together, my raincoat on, and then hustled inside to check-in and leave my contact information. I also got an Uber to take me downtown.
Trish had called her Boston apartment a pied-a-tier. I had a vision of a tiny studio where the bed doubled as the couch, and so on. Such was not the case.
Trish’s apartment was a two-bedroom, two-bath, piece of luxury living overlooking Louisburg Square on Beacon Hill. The condo was meticulously decorated, neat as a pin, and looked like it had just been photographed for a special edition of Better Homes & Gardens. I was very impressed. I took a selfie and texted it to Trish so she could see that I’d arrived.
She replied, ’Home soon. Bringing my local BF. I’m so glad you’re here. Love. T.’ I wondered whether BF meant best friend or boyfriend. I vaguely recalled her mentioning that she had ‘a piece on side’ up in Boston.
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