The Pilots - Cover

The Pilots

Copyright© 2025 by Wolf

Chapter 42: New Boundaries

Romantic Sex Story: Chapter 42: New Boundaries - 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  

The twin-engine set down on the runway as though I was landing a feather; I greased it. I smoothly brought the throttles back, and adjusted the props one more time. We slowed over about one-thousand feet as I gently braked, and then I took a taxiway, and headed back to the parking area by the FBO.

Next to me in the plane, riding in the co-pilot’s seat, had been Warren Dittmeyer, the FAA Examiner for my multi-engine rating. We’d been flying for one-hour from takeoff to landing. I’d been under the hood on instruments, done several engine-out recoveries, answered about one question a minute, and also done stall recoveries in the plane with engines on, off, and on single-engine. This was all stuff that I’d practiced. When I got my commercial rating, I had an instructor that demanded precision. I thought that I’d delivered precision.

We parked, and I set about tying down the plane while Warren walked to the office. He had been able to maintain the most inscrutable face of any person I’d ever seen for the entire flight. When I nailed a maneuver, I looked to him expecting a nod or frown, but ... nothing; only a suggestion about the next maneuver and a question.

After tie down, I collected my flight gear, locked up the plane, and went inside. Warren sat in one of the ratty looking chairs that surrounded a table littered with flight magazines going back decades. He gestured for me to take a seat.

Warren said in an even tone, “Congratulations. You’re now a multi-engine-rated pilot. You did well, and you know your stuff. What are you going to do next?

“Learn to fly that.” I pointed out the window where the Challenger 350 sat waiting for the next day’s flight up to Camp Forge. If I remember correctly, the prior weekend Bill had taken it over to a service center at PHL to replace the two main landing gear tires. I still lusted over getting into the pilot seat on that craft. I added, “I’ll probably go up to a training center for a couple of weeks or more.”

Warren looked over his reading glasses at me. “I wish I was able to give the check ride in that, but that’s way above my pay grade. Good luck and enjoy. You should get your CFI, too – become a certified flight instructor. How do you happen to have that plane?”

“It’s the one and only business aircraft where I work. My boss will be taking her multi-engine check ride with you in a few weeks. Kim Winslow. I hope she does as well.” I presented him with the requisite check, we signed some papers, and I’d get a new FAA pilots license in the mail in a few weeks with new rating listed among the growing list of qualifications. In the meanwhile, should anybody ask, I had a copy of the paperwork that Warren would send in.

Warren left and I went back to work at TNA. Kim did give me a kiss and her congratulations. She had a lesson in the same plane I flew in the next morning.

Thursday, riding in the jet from North Carolina to Camp Forge, I quizzed Kim with as many questions as I could remember from what Warren Dittmeyer had asked me during my check ride. Kim was doing pretty well answering them, but she did have to think about a few before responding. She was taking notes about her weak areas to study over the weekend.

We were greeted by a security man in our car, as we’d arranged. This man was new – Stu Meyers. He rattled off his qualifications that sounded close to some of the others. He had taught Krav Maga, and in response to a question from me, he said he’d be glad to teach me the craft. I suggested Saturday morning after our run. Usually, we had a security guy tagging along on our group runs, often lagging slightly behind.

I got greeted by Vanessa like a long-lost relative, and to my surprise she even kissed me quite passionately in front of some of the other members of the Circle. I saw a couple of surprised looks, but wisely nobody said anything. I still didn’t know how recovered that Van was, so wanted to play it safe.

Vanessa had prepared swordfish steaks for us as the entrée – and we gave her a five-star rating and a round of applause. Several suggested that she be sure that dish, the sauces, and the accompaniments were on her menu at Vanessa’s when it opened.

Todd gave me a report about the restaurant. He and Heather had negotiated the price of the property they’d chosen down to $1.6 million. They’d also lined up a contractor that knew the building codes for restaurants, and had rebuild several within the past six years. Further, the fire marshal knew him and approved.

Todd also had a growing number of spreadsheets estimating the cost per meal based on what Van was itemizing for him for some of her popular choices by the Circle. He’d made guesses about the number of patrons, and could show the profit or loss per meal, even based on seat occupancy in the restaurant. I congratulated him for thinking in the right way about the business.

Bob turned out to be an oenophile – a connoisseur of wines. He was helping out Van and Todd by preparing a Wine List for the restaurant to use. He’d been talking to some wholesale vendors in the area about supplying the restaurant, and the availability of the selections that made his list. I congratulated him; I barely knew the difference between reds and whites.

After dinner, our group migrated to the ‘loving room’, as usual. It seemed that some of us were unusually horny that evening, and they were quickly naked and united in a making love kind of way. Jan and Jake were one couple just about putting on a fucking show for the rest of us.

Tori had captured Sawyer and they went off to a different area of the room, where they too quickly started without much foreplay.

June came to me and we took our time getting started, making out, playing orally with each other for quite a bit, and then making love in a range of fun positions for each of us.

June said, “You’ve done wonders with Vanessa. She’s actually circulating among us during the day, asking for input about meals and being chatty. She was so shy before; the contrast is startling. I know that you spent all of last Saturday afternoon with her. I think you’ve done good, grasshopper.”

“Thanks. I’d still tread lightly with her. I’m trying to take baby steps, but she did surprise me last Saturday.”

As June and I made love, Vanessa appeared at the living room door. I expected her after our intimate time together. She was naked and immediately focused in on June and me, and started to massage her lady bits in a masturbatory manner.

I whispered to June what I saw over her shoulder. She said, “Ask her to join us again. I’ll behave with her, but I did like her touches.”

I commented, “Kim did give her passionate kiss last week. Yor might ask whether she’d like another – that is, if I can get her over here.”

I extracted from June and walked over the Van, whose eyes got big and worried as I approached. She stood still, however, and didn’t flee. When I got to her, I leaned in and kissed her very tenderly. She accepted that and kissed back. We didn’t use our hands, yet were both completely naked.

“Vanessa, June and I would like you to join us ... if you feel up to it. I especially would like that, but no pressure. We love you.”

I could see a burst of anxiety fill her and her brow wrinkled, but then she seemed to take control of herself. The whole time she looked at me. I leaned in and kissed her again. I said, “You don’t have to. I’ll love you either way. Perhaps we can do something later or tomorrow. I think your decision might depend on how much you want to stretch yourself – to stretch your thinking. Just remember, this in no way is what Michael had you doing. That was just criminal.”

Vanessa was completely naked and barefoot. She held out her hand in a gesture for me to lead her. I led her to where June waited for my return. When we got there, I introduced them as though they’d never met. “Vanessa, this is the lovely and very horny June. She loves you unconditionally. June, this is the beautiful, somewhat shy, but equally horny Vanessa. She is relearning how to love and our love for her will help her grow and evolve.” Van smiled at my statement.

June said, “May I kiss you?”

 
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