The Pilots
Copyright© 2025 by Wolf
Chapter 36: Vanessa
Romantic Sex Story: Chapter 36: Vanessa - 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
Debbie spent Friday in a plane with her instructor. He didn’t want to turn her loose for her solo cross-country required flight until he’d taken on one. He had her chart a round-robin course of more than 150 miles when all the legs were added together. He also wanted her to have to deal with the Philadelphia Terminal Control Area, so one leg of the flight went from Camp Forge to Trenton, New Jersey, and the second leg to Atlantic City.
During the flight, he had her fly with the hood on, the kind used for instrument flight instruction, and then he’d let her take it off and then show him exactly where they were on the sectional map of the area. No fair using the GPS or other navaid. She had to do it by looking out the window and comparing what she saw to what the sectional map showed. Big difference, but she figured it out pretty quickly each time.
Her instructor also ran the drill with her: ‘What would you do if you got so lost that you couldn’t figure out where you were?” Debbie instantly parroted back: Stay calm, and Aviate, Navigate, and Communicate. Right start. She went on from there.
Debbie knew this because I’d run through this drill with her during my help with her ground school. There were a range of things, such as picking up obvious landmarks – rivers, mountains, radio towers, and such; various ways to ask air traffic control for assistance, even using the 121.5 MHz emergency frequency if you were in real trouble. Real trouble included encroaching weather, getting low on fuel, or starting to panic, to name a few.
As part of Debbie’s flight reward, TNA bought her a hand-held radio that covered all the ATC frequencies and that could pick up bearings from the nationwide VOR navigation aids. The other present was a tablet GPS or Global Positioning System receiver, complete with a good-size map display that could show position either on a Sectional or on an instrument or IFR chart. She was religious about keeping both of them charged up and in her flight kit where she could reach them.
Saturday, she did maneuvers and received instructions for what she’d do the following weekend, weather permitting – her solo cross-country flight. He gave her three airports that she should plan into her solo round-robin flight: Harrisburg, Penn Valley, and Wilkes Barre. She was to take photos, if not on the approach then on the ground to prove that she’d been there.
The week passed quickly. We were back and forth to Chapel Hill in the jet from Camp Forge. From what I could tell, Debbie knew every inch of her upcoming trip. She also kept studying the weather. I couldn’t tell whether she way praying for good weather to get the trip over with, or praying for bad weather so she wouldn’t have to make the trip. In any case, a nice bulging high drifted over the country from the west and created a CAVU weekend for her – calm air visibility unlimited.
Friday morning, Kim and I were up as usual and saw Debbie off to the airport for her trip alone. We were having coffee on the patio when we saw her plane lift off the Camp Forge runway and fly over the property. We had our own portable air band radio, and could hear her calls on the Unicom frequency as she departed Camp Forge, and then opened her flight plan with Philadelphia Departure. After that all was quiet.
She left me a copy of her Flight Plan. Her stop in Harrisburg would only be to turn around and takeoff again, after her full stop landing. I knew she’d also be taking a picture or two of the airport or runways. After that she had a nice leg to Penn Valley, where she’d repeat what she did in Harrisburg. Her stop in Wilkes Barre would be longer because she planned to refuel the plane at the FBO there. She then had the longest leg of her flight heading southeast back to Camp Forge. The total trip length, according to Debbie was 188 miles.
I was working outside on my laptop about noon when my hand-held radio came alive and I heard Debbie call her arrival to the Camp Forge traffic pattern on the Unicom frequency. She’d taken a little longer than she planned, and I figured that was time when she refueled.
She appeared at Acre Woods about one p.m. She had to park the plane and check-in with her instructor. There was probably a significant time to enter everything in her logbook, too. She was religious about that and carefully counted every minute of her flight time that she could. This trip was probably worth over two hours to her totals.
Debbie was about as high as her plane had been when she showed up at the house. She yelled, “I did it!” and we appropriately feted her deed. All that nervous energy that she’d had for a couple of weeks draining away. I took her on a long run, and then made love to her.
Other things at Acre Woods estate motored along as the place achieved some stability with all of us living there. Weekdays were quiet with most of the residents away at their jobs. Any group sex that took place had limited participants, rather than everyone in the house. Saturday and Sunday were filled with both individual errands and tasks, and community events, such as dinner out, a trip to a fair, or, for Debbie, her flight lessons or practice.
The evenings we were there, were events where we all gathered to be with the people we loved. Our group sex events constantly attracted one voyeur – Vanessa. She was ‘damaged goods’ and brittle, so except for her duties as our chef, we left her to her own devices. Bob might have known more, but he respected her privacy and no one pushed him.
I seemed to have a unique opening with her. She liked having me wrap her up and give her a loving hug and kiss. I didn’t make any move to do more with her. I figured when and if she was ready, she’d send up a signal.
The signal came after lunch about three weeks after Debbie’s solo cross-country flight. Van came to me while I was reading on the patio. I didn’t hear her approach until she was right next to me. I turned and smiled at her, as I always tried to do. She said, “Will you come with me. I need a special kind of hug.”
I followed her through the house to the wing over the garage, going up the stairs behind her. I’d only been to this part of the house once when we were about to buy the place. The security team also used the bedrooms up there.
Vanessa’s room was neat as a pin. She turned and said, “I want you to hold me on the bed, and I want us to be nude. I’m not ready for anything further.” I understood. She looked to be sure that arrangement would work for me.
She carefully stripped her clothes away, almost mechanically. I also got naked, using a chair for my clothes. When we were finished, I got on the bed and following her lead, lay down and she lay down next to me. I spooned in behind her, wrapping her in my arms. I kissed her gently and she kissed back and then we just were. I got hard being with the pretty young woman, but over time, with no further action, I deflated with my cock nestled in the crease of her shapely butt.
We stayed like that for a while, and I did gently smooth her body without becoming too sexual. Van said, “I need to tell you my story. No one else really knows. Bob knows some of my story, but not that much. I want you to know all of it. You are my best friend.”
I told her, “There’s no rush. Take your time. If you feel you need professional help, just know that we will pay for it without question or need to know anything further.”
She shook her head. “I need to tell you – just you.” A minute went by and she started, “You know my life fell apart about a year ago. I was married to Michael and I loved him. I would do anything he said so that I could bask in that love. I think we drifted into a relationship where he was my dominant person, and I was his submissive. We never used those terms, but that’s what seemed to happen in hindsight. I was independent, but if he told me he wanted me to do something, I did it without question.
“Michael is a hunky man – very attractive to women. Some girl at his work turned him on, and I think they got together. He asked me one day to be in a threesome with the two of them. At the time, I thought it was the first time they were together, but as I think about it, they were too comfortable about fucking that day. We did all kinds of sexual things together, and he especially liked watching me interact with Sharon.