The Pilots - Cover

The Pilots

Copyright© 2025 by Wolf

Chapter 20: That Kind of Man

Romantic Sex Story: Chapter 20: That Kind of Man - 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 eight of had pizzas and salads for dinner. We ate outside at the picnic tables and the conversation was lively, especially the others catching up on what Doug had been up to in Boston.

Doug reported on the affair his wife Karyn was having with Dr. Carl Rappaport, a noted Harvard professor in psychology that often appeared on television for various reasons, and was also quoted when an authority on some aspect of motivational behavior was needed.

Doug chuckled, “Dr. Carl is staying in Cambridge this weekend for some special events at Harvard. Karyn will be on his arm tomorrow night at some lavish reception at the college.”

June asked, “Do they care about his or her behavior?”

Doug shook his head. “I think most of the staff know what’s going on. We don’t hide it, and we don’t flaunt it either, although going to this event might be a little over the top. There were other ramifications. Karyn told me once that he’d told her that half the faculty was fucking the other half anyway.

“Carl’s weekend away, mostly shacked up with Karyn, means that his wife Joan can consequently have Ben in her bed all weekend. I’m told that Ben thinks that Joan is just a randy married woman with unique sexual needs that require her to have outside help for satisfaction. That’s kind of true, but he will get the full scope of what’s going on this weekend – meaning, she’ll tell him about the chain of events – the dominoes, all the way to the Circle here.”

Kim asked, “Has Carl or Joan ever some here to visit?”

Heads shook. Bob responded and turned to Doug, “No, but perhaps you could extend an invitation to that whole daisy chain of people to come visit for some sex-filled weekend. I think they’re all horny enough.”

Doug laughed, “That’ll blow some minds along the chain. Trish and I have had Carl join us, but I’ll definitely extend the invitation. Maybe I’ll text Karyn later so they have the weekend to conjure up all the possibilities a visit here engenders. I’ve shared just about everything I know about you all. She’s expressed interest.”

“What’s she do for work?”

“Karyn is a clinical psychologist and also teaches at Harvard. That’s where she met Carl, although she isn’t on the tenure track by her own choice. I guess you could say that she splits her time between those two activities.”

After dinner there was a rush to put away the leftovers and clean up the tables. The night was warm so people wanted to be outside on the patio and the various chaises and sunning mats the Circle had.

June sidled up to me, with a long, sexy kiss. I felt her erect nipples on my bicep, and discovered that she had shed her crop top. She’d pushed down her shorts far enough to reveal the top edge of her tuft of pubic hair. She said, “I’m a needy girl, and I just know that you know how to cure that situation.”

I kissed back and quickly got rid of my t-shirt so we could rub our bare skin together. Our shorts were quick to disappear, too.

Only a few feet away, I watched Doug putting the make on Kim. One of his hands was under her thin little crop top, pawing at her breasts. He raised up the fabric and latched onto her left breast with his mouth. I knew enough about Kim to know that attention to her lovely breasts like that guaranteed access to all of her other charms without any restrictions.

As June and I lay down on one of the wide chaises, I kept watching Kim. She pushed down Doug’s athletic shorts and grabbed his cock with both hands, doing some quick fondling as she led him to her mouth. I noted the broad smile she gave just before ingesting his shaft to start one of her erotic blowjobs.

June was fondling my equipment and then duplicated what Kim was doing to Doug. Between what June was doing to me, and watching my great love interest, I became harder than diamond. June had me fuck her mouth as I watched Kim’s talent oral play.

Doug stopped Kim from totally bringing him off. Even in the dim light I could see not only that he was erect, he was also on the edge if the purple color of his cockhead was any indication. He leaned over and picked up Kim, planting an immensely passionate kiss that she responded to in kind.

Doug danced around the patio with her in his arms and ended quickly by carefully seating her onto an outdoor sofa. He sat on the ground in front of her, put her legs over his shoulders, and started to eat her pussy like the world depended on it. I thought he was trying to drive his tongue as deep as he could into her pussy. The light glinted off the wetness Kim was making. She was turned on.

June whispered in my ear, “Just think, in only a few minutes that purple headed cock will be sliding into Kim and driving right up near her cervix. The two of them are going to fuck each other blind, with Kim squirting her juices all over him, and Doug leaving a major load of sperm right up at her more inner doorstep. They look like good fuck mates.”

As June talked and teased me, I could feel myself getting harder and longer and more intent on leaving my load of sperm deep inside her. The sister relationship with Kim wasn’t lost on me either. My friends used to tease me in similar ways when I would watch Mindy fucking some other man. It was arousing then and still was.

I got that worried feeling about losing Kim in some way to Doug, but then he had a wife and a complexity of relationships that he was managing. I hoped this wasn’t doing damage to our interactions and the love we felt for each other.

I stoked deep into June with my cock, even imagining that I was plowing new territory inside her body. She was such a looker. Her breasts were swaying in time to my strokes as I bore down on her in the missionary position. I leaned in and sucked on each nipple and areola area until I brought the nips to a rigid state. I lowered my chest to hers, so we could scrape those hard teats across my chest.

Nearby, Kim was just mounting Doug as he lay back on the patio sofa. His rod was pointing at the stars, and seemed to have the potency of a ballistic missile ready to fire.

Kim toyed with the cock, running her hands up and down his shaft a few times, and then she used the bulging end of his shaft to wipe back and forth through her sodden sex. I could see her juices appear on his cockhead. She made sure he touched her clitoris over and over.

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