The Pilots - Cover

The Pilots

Copyright© 2025 by Wolf

Chapter 19: Positioning

Romantic Sex Story: Chapter 19: Positioning - 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  

I came back into the master bathroom. The scene before me belonged in a romantic but highly erotic pornographic video.

Trish lay naked and spreadeagled on her back in the middle of her king-size bed. She was panting, an activity that made her delicious breasts rise and descend in an inviting manner. The manicured tuft of pubic hair glistened with the wetness that the three of us had generated in that area since we started hours earlier.

Trish had a hickey on each breast – one from me and one from Doug. I don’t think there was a square inch on her body that I hadn’t kissed, licked, sucked, and made love to, and there certainly wasn’t an orifice that I hadn’t had my cock in for a goodly time prior to dumping my man juice inside her.

Doug lay on her other her side, also face up and panting from the highly energetic fuck the two of them had just completed with a matched set of orgasms marked his and hers. I felt sure that he’d also covered the acreage and orifices with the same love and enthusiasm that I had. Any modesty between Doug or me had quickly vanished in the interest of making Trish happy. Of course, at several points in time we were both doing Trish with a robust double penetration.

Trish for her part had been urging us on as she rippled from orgasm to orgasm. If I’d discounted her remark about being a ‘nympho slut’ earlier, she certainly earned the title with the two of us that night.

Doug said to no one in particular, “I’m done, empty, kaput, out of vital fluids and devoid of energy. Just tell them that I gave at the office.” He put at arm over his forehead and didn’t move.

Trish turned her head to me, cranked one eye open, and crooked a finger at me. I knew what she wanted. I had to chuckle. The woman really was insatiable just like Kim, my girlfriend. I thought that I might have one-more round of sex in me.

To get this one started right, and to milk a few more minutes of recovery time, I went down on her. I pulled her labia apart and started licking and sucking. Yes, it was gross. Further, the juices there weren’t all mine or even Trish’s. I’d learned years earlier with Mindy that it didn’t make any difference and it really wasn’t all that bad. Playing to my ego, I found that I could gross out other men and even an occasional woman, although many of the latter were already used to swallowing their blowjobs so it was no big deal to them.

I watched Doug’s eyes enlarge as he watched me and Trish started to moan. “Oh, God, you know just the right spots to light my skyrocket.” A few minutes later her whole body did a spasm thing as her orgasm gave her minutes of wild pleasure. I’d lost count, but I was sure that she’d had well over ten since we started. She was very gratifying to make love with that way.

I got a mouthful of the fluids from her pussy and brought them up to her. She grinned at me and then pulled me in for a French kiss. I gave her the fluids, obviously mixed with my own spit. As the kiss extended, I got them back. With more kiss, I reshared them with her. Eventually, we had to break the kiss and we both swallowed. She gave me a devilish grin.

I took my hardness, such as it was after two prior cums into her body, and slid into Trish’s interior by way of her well-lubricated vagina. I kissed her and she was passionate about kissing back and tasting all the residual flavors on my lips and face. Her velvet sheath helped me harden even further and I felt my libido go through the roof. Man this was hot.

Doug lay beside us watching our live porn show and idly toying with his flaccid cock. After a bit, he disappeared into the bathroom.

Trish and I lasted fifteen minutes before her sexiness, the scene, and some dirty words from her, set me off and I again came inside her. We’d ended in the woman-on-top position with some orgasms a few seconds apart. Trish just collapsed into my arms and there was no further movement. I was wiped out, too.

My next awareness came with morning light streaming in Trish’s bedroom windows. Trish was face down in a pillow beside me. Doug was sleeping on the other side of her on his side facing the wall. The area around us smelled like the inside of a French bordello, not that I was expert on that subject.

I slipped out of bed. It was six-thirty and despite going to bed on the late side I was juiced up for the day. I got my dopp kit and went into the bathroom and tried to quietly spiff-up and shower. I put on my business suit, and then checked on my bed mates. They were still asleep.

In anticipation of the flight to Camp Forge, I did some preliminary flight planning and even filed my flight plan. Later, I’d check the weather, but the other parts of the flight were already laid out.

About that time, I heard some groans from the other room. I thought that Doug and Trish might be having sex, but she came out into the living room deliciously naked. I got a hug and kiss. “Thank you for last night. You and Doug were spectacular and really satisfied every itch. Of course, by tonight I’ll be horny again, but then I’ll be back home.”

“Can I do breakfast for you and Doug?”

When Trish shook her head her breasts shimmied in the nicest of ways. “No. Breakfast places on the way to work for all of us. I’ll need about thirty minutes. Doug went off to shower and shave. You were up early.”

Thirty minutes later, looking very upscale and professional, the three of us walked out of Trish’s Boston condo into a beautiful sunny morning. Any visage of the storm the day before was gone except for a few puddles. We took time for a cup of coffee and, in my case, a doughnut for breakfast.

After seeing Trish to the building her marketing and ad agency was in, Doug and I walked another fifteen minutes to his office at Fidelity Investments. He set me up in a conference room, and then went to check his emails and gather the others on his staff that he wanted to hear my pitch.

The day, including a catered lunch, went well from my point of view. I got to give a detailed overview of TNA or TransEnergy NA. Doug also brought in a couple of his staff and then a few more for my half-hour version of an intro to TNA. He seemed impressed and so did his staff. They would be primed to jump in as the IPO came to market.

Having Fidelity, one of the largest investment institutions in the world buy up some of our initial shares would be like having the pope bless your new child. It was someone major giving their blessing to the offering and in no small measure. What was a small investment from them would be like a mammoth investment for TNA. Others would soon pile on based on that news, and hopefully drive the price up a little.

Off the record, Doug also made a suggestion that we come on the market at $40 per share. He had more depth of research behind him for that recommendation than I did looking across the entire sector, but that was the number that I’d been thinking about. It also reflected the approximate value of the outstanding pre-IPO shares, but some of that was ‘funny-money’ estimating TNA’s goodwill and brand development.

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