The Pilots - Cover

The Pilots

Copyright© 2025 by Wolf

Chapter 38: Progress

Romantic Sex Story: Chapter 38: Progress - 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 first night that Patti Arlington was with us was four weeks before the wedding weekend. She stayed overnight with us, and was a full and eager participant in everything that went on after dinner. She couldn’t have enough sex to satisfy her hypersexual urges. Like everyone, she was a genuine nymphomaniac. On the other hand, all the men liked the perky little wedding planned and made it a point to spend time with her, usually in a popular sexual position working on mutual orgasms.

Dinner, as usual, had been a special treat that Vanessa had created. Kim knew of the affinity that Van had for me, and she encouraged it. “Make that woman happy. Help her heal. I think your love can do that for her.”

Darren, our newest male member and Ally’s husband, Scott, and I helped Vanessa with the dinner clean-up process in the kitchen. There were a lot of people for dinner, and she was learning to cook for a large number of people. That gave me an idea that I’d run by Kim on Sunday morning.

The wooing and loving had started by the time Darren, Scott, and I returned to the large living room. I found I was starting the evening by making love with June. She had some sexy make-up around her eyes that enhanced her sex appeal. She was also draped in a gossamer shawl that gave an extra aura of attraction to her nude and luscious body.

June and I started some serious making out. I told her that I expected special privileges when she was my sister-in-law. She laughed, “I can’t think of anything special that you haven’t already tapped into.” She was right. From the time Kim first had us mate, June and I had done everything sexual you could think of that didn’t break the barrier into BDSM. Near as I could tell, no one in the Circle was motivated to cross that boundary.

I saw Vanessa peek around the door jamb at the large rooms entrance. She’d gone off and changed into a very short robe that was open and pulled back off her shoulders, revealing her front. I could see her body and breasts. She was already stroking herself and looking at us.

I asked June, “Can I ask Van to join us. I don’t know what that means – maybe not sex with her, but she likes to watch and get turned on. We have to play it by ear and not force anything on her. There’s some bad history there.”

“Oh, yes. See if she’ll come and let us love her. I’ll be careful. I know she’s brittle.”

I stood, my naked body rising from my embraces with June. I strode over to the doorway and to Vanessa. She looked surprised to see me approaching her. I gently pulled her to my naked body making sure I could see her eyes. I didn’t want her to panic.

“Vanessa, June and I want you to join us. You don’t need to do anything or have anything done to you. We just want you with us, while we make love. We want you to feel that love and feel included more than standing here as a horny spectator.”

Van shuddered, “You don’t mind me being ... right there ... as you fuck?”

I gently led her into the room; the flaps of her robe giving those that noticed a first glimpse of the sexy body beneath. I made to help her off with the robe, and she looked at me for a few seconds and then turned so I could remove it. She was beautifully naked. Pert breasts. A perfectly shaped ass. Beautiful legs, that like the rest of her screamed I’m beautiful.

I kissed her and then June stood and asked, “May I also kiss you?”

Van nodded. June leaned to the woman and carefully gave her a long sensuous kiss that sent a message of love and caring, and of passion and desire. Van stood, almost like a statue as the kiss evolved, she moaned in obvious appreciation, and then she raised one hand to June’s breasts, carefully fondling and stroking the fleshy mound.

I said to June, “I invited Van to be here with us as we made love. I hope she can feel what we feel for each other and also how we love and care for her.” As I spoke, I moved in and caressed June. We sat on the sofa, and I gestured for Van to sit nearby.

I moved in front of June, and I started to finger her pussy slit and use my tongue on the sensitive parts. She had well-defined inner and outer lips. I loved to suck the inner labia into my mouth and almost gnaw on them. June was especially turned on, in part, by having an observer only three feet away.

Van let a hand drop to her own bit of pubic hair, and she started to lightly stroke the sex area as she watched us. I put my all into bringing pleasure to June, and soon I elicited her first orgasm. I sat back and pinched her labia between two fingers at a rapid rate, making sure to show the excited and swollen labia to Van. My rubbing of June intensified her pleasure and I got a moan. One signal that I’d hit the right spots was that her nipples had turned white hot as they became erect.

June said, “Vanessa you don’t have to touch us, but anytime that you want to do that is fine with either of us.”

Van smiled slightly and nodded in understanding.

June pulled me around so that she could perform fellatio on me. She was good, and also one of the Circle women that could deep throat me when I was at full staff. Van watched but there was little reaction. I wondered whether she was comparing what we were doing to the things her ex-husband had forced on her with strangers. I hoped not.

I nudged June, and she lay back and spread her legs. I came over her with the stiffness in my hand. I moved the head around the wet slit, and then slid inside. We joined together and also kissed tenderly and then with increasing passion. Both of us got vocal and told the other of our love, lust, caring, desire, and more.

We changed position so that June was on top. I could fondle her breasts and we could also kiss more easily. We let our tongues dance in the air between our mouths. We moved to the spoon position. I was behind her and holding her body to mine, as my cock sought out her vagina for more loving. I could kiss and fondle my love, and did.

Vanessa slid off the sofa onto the thick carpeting. She got right next to us, where she could watch my cock moving back and forth into June’s body only inches away. We were still talking to each – loving phrases and dirty phrases; words pledging lifelong devotion and words about cum, fucking, lust, and more.

To my surprise, and no doubt to June’s, Van reached out and touched where my cock was slowly sawing into June. She followed my shaft from my balls along my length dripping with June’s lubricating juices, and then to June’s gaping slit and over her clitoris. I had stopped moving when I saw her approach, and as Van’s fingers crossed over the right area, June not only jerked in response, she also had an orgasm – eyes closed, body shuddered, moaning her pleasure. As part of June’s orgasm, her vaginal muscles went wild, spasming around my hardness.

 
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