The Pilots
Copyright© 2025 by Wolf
Chapter 14: Life in the Circle
Romantic Sex Story: Chapter 14: Life in the Circle - 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
Jim, Trish, Jan and I ascended to the large bedroom. Once in the room, Trish melted into my arms in a loving embrace and we spent a long time just kissing and exploring with our tongues and enjoying the feeling of our naked bodies pressing and rubbing together. The feeling of yet another new naked woman against my body shot my arousal into space it was so high. She quite intentionally trapped my cock between us when we’d rub together.
She had been through the foreplay stage with Jim, and even gone a full round. However, I repeated the sexual foreplay with her using my own techniques. I ran my tongue around the outside of her mouth, along her neck, ears and eyes. I gave her butterfly kisses with my eyelashes and we French kissed for a bit.
Slowly, I descended to Trish’s generous breasts. I again tongued all but the areolas for a moment or two before I gently worked my way in from the outside into the center of each mound where her nipples were. I sucked and then pulled on the nipples. I rubbed lightly on the small Montgomery bumps that graced her areolas before turning the job over to my tongue. Trish was alternately purring and moaning. We were both breathing heavy.
I glanced next to me on the bed. Jim was repeating my actions on Jan. Jan was lying back with her eyes closed savoring the erotic sensations he was giving to her. I finally lowered my head to Trish’s damp pussy. Again, I started with my fingers and tongue far away from the target zone and worked my way towards her sex a short distance at a time. Trish seemed more anxious that we couple than I was.
Finally, I sought out her clit that turned out to be rather stimulated and large from her session with Jim. I then thrust my tongue into her slit and savored the mix of juices I found within. I heard Trish moan loudly. Jan also moaned as Jim duplicated the move on her.
I used two fingers to search for Trish’s G-spot and found what I thought was a likely candidate area inside her beautiful and slick vaginal walls. She twitched and writhed signaling to me that I was close enough. I massaged the area frequently as I worked over the outside area with fingers and tongue.
Trish and Jan clutched each other’s hands as they lay next to each other. Jim and I were kneeling in front of these two beautiful women. They both climaxed together. Both women arched their backs and moaned as the light orgasms Jim and I’d delivered to them took effect.
I moved up over Trish after she’d come down a little from her high and gently penetrated her, only a little at a time as Jan had done with me about an hour earlier. Trish loved every mini-thrust that I delivered as I sunk deeper and deeper into her body. She held her legs back affording me optimal availability to penetrate her however I saw fit.
When I was fully into Trish I stopped and just made love to her breasts for a few minutes. Every now and then I would pull out and thrust back in, just enough to remind my cock that we were busy and not to deflate. I repeated the process on Trish’s neck, whispering words of endearment and love to her. I repeated the process on her face.
Trish was vocal back to me, first with loving phrases and pledges, and then she shifted to some dirty talk about how my cock and her cunt were destined to keep fucking in a long-term relationship as we keep pumping love into each other.
Then, while remaining connected, I showed Trish how to repeat the process on me. She did my face, neck, ears, and eyes, taking her time to really make love to me one little area at a time. We often made a little thrust in and out of each other. Trish made love to my breasts that can be extremely sensitive; she had just the right touch to extract maximum enjoyment from me.
We repeated the process in different positions and talked more to each other. We talked to Jim and Jan, telling them of our love and affection for them. They spoke to us.
Jan told us how Jim had taken her virginity several years before. Trish told us about how she’d had a lover several years ago and how they had enjoyed each other; she described one particular tryst that happened over a lunch hour with her friend.
We were silent and meditative, first as individuals then as couples, and finally as a group. We kept a slow, methodical thrusting in and out of each other, staying just below the line of too much pleasure where we’d lose it. We adjusted positions several times: on our sides, Trish’s legs over my shoulders, our legs intertwined, and so on.
After a while, I asked Trish how she wanted to finish. She looked surprised and checked the clock. An hour had passed since we started.
She said, “I want to be over you with you firing your lovely cannon up into me.” Trish moved and straddled me. I told her I loved her again and we increased our pace.
Beside us Jim and Jan duplicated our moves and position, and our speed. Jan arrived first. She gave a little scream and announced her climax with mewling and some very heavy panting as the burst of pleasure washed over her. Jim immediately followed. The two of them writhed in the gratification of finally achieving something they’d been working on for a long time. I think it was the orgasm of all orgasms for them. They clutched and whispered words of love to each other.
Trish and I watched and then picked up our pace again. She looked at me and started to talk dirty, “I want you to fuck my brains out. I want to be the slut, the whore, you always wished you could find and here I am now with your cock fucking my cunt. I’ll suck your cock, swallow your cum, fuck your friends, and let you fuck me in public. I’m your dream girl. I’ll do anything you want, anywhere, anytime, anyway. Just fuck me, fuck me, fuck meeeeeee!”
We both came. I splashed a load of cum on the walls of Trish’s cunt. She squeezed around my cock with her convulsions. Trish’s breasts swept across my chest as she leaned to kiss me, her nipples erect and stimulating mine as her breasts swayed. The waves of pleasure washed over us and over us and over us. We clutched to each other.
“Wow!” Trish said finally from her collapsed position atop my chest. “Big Wow!”
“I have the same feeling my darling Trish,” I said. “I love you.”
I peeked and Jan and Jim were watching us from their still coupled position right next to us. I was amazed that I had shut them out of my experience so completely I couldn’t have testified if they were in the room or not I was so focused on Trish and where the two of us were going.
“You guys are amazing,” Jan said.
Jim said, “Thanks for the refresher course. I’d forgotten some of the things we did, and I never lasted this long before. This was a spiritual experience.”
“I’ll tell you more about it tomorrow,” I said. “It actually is a mind-body-spirit experience. There are some things that will help you extend and also make the experience more pleasurable for you both.” I turned and kissed Trish.
“Can we sleep four to bed?” I asked.
“Tonight, we can,” Trish smiled. We all snuggled into together, I turned out the light and we went to sleep but not before lots of words of endearment were shared amongst us. My thought immediately shifted entirely over to Kim. I prayed that she was happy and that we were still the couple that had arrived her
Kim kissed me good morning and I opened my eyes to see my beautiful friend and lover smiling at me. Sunlight was streaming in two of the bedroom windows. The other three people in bed with me were sleeping very soundly. She motioned for me to go with her. I got up carefully so as not to awaken the others, and tiptoed out of the room as I admired Kim’s naked butt. I was thinking how I remained horny all the time at my age and even after fucking half the night away.
In the hallway, Kim turned and pressed her naked body against mine. We kissed and looked into each other’s eyes. “Do you still love me?” she asked, smiling.
“Oh, yes indeed I do and with all my heart,” I said as I hugged her tight. “I’m glad you came and got me. I wanted to see you when we first got up and be sure you were okay and still in love with me! How are you feeling about last night?”
“Slightly sore,” she snickered and rubbed her pussy fuzz, “but not enough to slow me down today. I had fun and I feel so embraced by everyone in the Circle. I never imagined the warmth, the companionship, and the sense of family that I feel here. I can understand why June became such a ready convert years ago when they created this five-person ménage.”
I teased and said, “I think we made it seven people last night.”
Kim had started rubbing her pelvic area against my pelvic area, only I had something sticking out of it that was getting harder and harder every second. She also was occasionally rubbing her erect nipples across my chest as we stood and talked. Someone else was horny, too.
“Come with me,” and I pulled Kim downstairs and into the living room where Jim and Trish had been going at it the night before.
Kim and I picked up where they’d left off on the sofa when they joined Jan and me only a few hours earlier. I sat back on the couch extending my legs outward and Kim came over and straddled me. She was still damp and sticky from the lovemaking she’d done the night before and it didn’t bother me one bit. Rather, I was turned on by it.
I knew that about half of heterosexual men in partner relationships wanted to see their loved one having sex with somebody else. This was even better because of the loving atmosphere that the men and women of the Circle propagated and rained on us.
Our foreplay consisted of the time we’d spent talking and rubbing against each other in the hall and the seconds it took for Kim to position herself over me. She held my stiff dick at the entry to her moist cave and lowered herself all the way down until I was buried deep within her. We kept looking in each other’s eyes; I was caressing her breasts; we kissed frequently. I told Kim how much I loved her and was so glad she felt good about our experiences since we’d arrived. Then we fucked, thrust, drove and pistoned into each other with renewed passion. I tried to be gentle, mindful of her aches resulting from her activities the night before, but Kim inflamed our union in her own way.