The Pilots
Copyright© 2025 by Wolf
Chapter 6: Trouble in Paradise
Romantic Sex Story: Chapter 6: Trouble in Paradise - 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
We walked the beach some more each of us deep in thought. Kim finally said in a downbeat way, “You’re seriously worried about our age difference, aren’t you?”
“Yes, but it’s more than just my age,” I admitted. “I’m twenty-years older; I know I shouldn’t worry about it but I do, even if fifty-two is the new forty-two? Somehow I think I won’t live up to your hopes and expectations for a partner and that I’ll lose you because I’m too ancient. You’re young and athletic; as I get older I’ll be even less resilient that I am today, especially in the sex department – ‘use it or lose it’ notwithstanding. Hell, I’ll die years before you even start to get old. That’s been my biggest worry since last Wednesday. I’m scared, too, and I don’t know what to do about any of this except brood over it all, which I’ve been doing whenever we’re not together. You caught me out just now.”
Kim stopped and hugged me. She looked deep into my eyes, “Nothing I can say or do will make you feel adequate except to say ‘Thank you’ for what you’ve given me these few days and in particular the last two hours.”
She paused and hugged me again; “I should share my big worries with you. You’ve arrived; you are where I want to get to in my life, in my career. I mean you have this wonderful house on the beach, a place in Maine you mentioned, and the condo right in downtown DC – and next to Lincoln Center, wow! I’m blown away and I’m even intimidated by it all. I’m thinking how I can ever achieve such greatness in my life, have the toys I want, and make the kind of contributions to society and business that you’ve made?”
She glanced at me then went on, “More importantly, you have such wisdom and have done such deep thinking about life and relationships and family and all. It scares me to think about it. You’ve got answers to questions I didn’t even know existed! Moreover, I know that we’ve only scratched the surface of that whole topic. I feel like a little kid looking up at a super-hero. I’m not worthy to even be in the same room with you. I’m not near your equal; I’m so far behind that I’ll never catch up.”
I offered with a forced chuckled, “Well, that’s what twenty-five years of bumping into the right obstacles will get you, as well as the balls to charge $ $1,000 to $2,000 per hour as your billing rate. You end up with possessions, and while they’re nice, they’re not a light in my life like you are for me. I don’t see you as a kid and it’s not a race. Take your time; enjoy the journey. He who dies with the most toys, does not win. I can see by the look on your face that there’s not too much I could say to you to make you feel adequate right now is there?”
Kim shook her head “No.” We just smiled weakly at each other. I was suddenly at a loss for words. I was wrapped in my own insecurities. She was wrapped up in hers. I mean here was the this most beautiful young woman, and I had fallen for her head over heels. Yet, even as we stood in the sand I could feel her slipping away from me. I wanted her, yet the gods were against our union. Our grip on each other was failing.
I said, “Can we learn to live with our inadequacies? Can we create a lasting relationship here – the two of us?” I looked at Kim and she had tears rolling down her cheeks. She clutched at me and just whispered, “Oh, Ron; Oh, Ron.” I was starting to choke up, too. In that brief instant we each knew we’d lost the other.
We walked back to the house in silence still with our arms around each other. Neither of us felt worthy of the other. The sun was gone from the sky leaving only a rosy hue as the evening twilight fled. The eastern sky above my home was almost dark when we reached the house.
We cleaned up, dressed up, and I drove us down to the Amelia Island Resort for drinks and dinner. Our dinner conversation was ‘neutral’ and often touched on the expansion of her business. We strolled around the resort after dinner talking about nothing in particular and everything in general. We stayed away from the sensitive subjects we’d found in each other’s lives including our ages and our relationship. I remained at a loss for words. I know we both had a million things to tell each other but nothing came out. I couldn’t think what to say to hold us together. I was glad it was dark; the people we passed on our stroll couldn’t see the tears in my eyes – and probably Kim’s.
We made love again back at the house but it didn’t reach the intensity or touch us on as many levels as it had earlier. We cuddled and slept pressed against each other throughout the night. I took comfort in it and I think Kim did, too. We were both hoping that some overnight miracle would solve the impasse we’d reached. In the end, it was wistful thinking on both our parts. Nothing had changed by morning.
When I woke up, I knew Kim was leaving; she wasn’t going to stay the full weekend. She packed and I drove her to the airport and helped put her luggage in her plane. We kissed goodbye. I told her I loved her and then she was gone into the sky on her way back to North Carolina. I stood and watched her plane takeoff and bank to the north and then climb until she was out of sight. I sighed and drove back to my empty and lonely home. I cried a lot that day and the next ... and the next. I grieved my loss of the most fabulous person I’d met since Mindy.
I convinced myself that I was right about the age thing. Twenty-two years was too great a gap. I was ready to wind down my career and she was just starting hers. She was a go-getter, I’d already gotten. She wouldn’t have wanted me making suggestions to her throughout her life; I had all this ‘wisdom’ I’d called it. What good was it? God, I was such an ass thinking that we could develop something.
Further, I figured I’d grossed her out by telling her about the foursome and ménage-a-trois that figured so prominently in my life when I was just a little older than she was. What was I thinking to share that highly unconventional situation with someone I’d just met? To her I am just a dirty old man with a sordid past and kinky sex habits.
And then I beat myself up over my wealth. I had to admit to myself that I was trying to snow her with the Porsche and houses and all. I overdid it. I scared her. She’d even used those words; “It was scary,” she’d said.
And then there was my own insecurity. Women don’t like insecure men; I shouldn’t have shown weakness. I should have been the rock for her and her insecurities. But I am the way I am, and she should have loved me just that way. Love is forgiving, especially unselfish and unconditional love. Or is it? Was my basic philosophy of life and love all wrong? Was my philosophy and vision for relationships just totally warped so much that it could never work in a lasting way?
I moped around through the start of the following week. I finally flew up to Washington and lived out of my Watergate condo. My clients were tolerant of my heads down attitude that week. I told them I had a lot to do to keep adding value to their projects and this was just one of those weeks when I was in “production mode.” The problem was I kept moping around the week after that and the week after that and so on. I think I hid it well though.
I tried to call Kim a couple of times but either I hung up before the call was completed or her secretary told me she was busy and couldn’t take a social call. I didn’t leave a message. Perhaps she’d told her assistant not to take calls from me. I finally stopped. I wasn’t exactly sure what I would have said. My bad crying jags went on for several months and then I decided I had to do something to turn myself around. I steeled myself to life without Kim.
Washington has more single women than men, and over two-thirds of the population is single. Doris Miller, an acquaintance in her mid-forties, was surprised when I called in early February and invited her to dinner and an evening performance by the Paul Taylor Dance Company at the Kennedy Center. I’d been away from Kim for four months by then, and decided I just had to get out and do something to help me move on.
We had a lovely dinner nearby the Center, and then strolled over for the performance. About all I could think about was Kim. Calling Debbie had been a huge mistake. I couldn’t even envision taking her to bed, which was quite a change from how my horny brain should have been working. I even reminisced about Mindy, but didn’t say anything out loud. I was Mr. Suave and Cool, and I struggled to be a good date.
After the performance, we took an Uber to the Marriot for some late drinks in the bar, and then then I escorted Doris back to her nearby apartment. I was sure that she wanted me to come in. Instead, we shared a polite kiss at her door, and I left and went home. Damn! I cried again over losing Kim. I wanted her, but without all the complications and insecurities we both seemed to invoke.
I thought about Kim for hours every day in spite of my resolutions to the contrary. How could that beautiful young woman have touched me so deeply, so fast? Would I ever get over her? I knew I eventually would, it would just take a lot more time than I was allowing myself. My heart ached and grieved.
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