The Pilots
Copyright© 2025 by Wolf
Chapter 31: Another Surprise
Romantic Sex Story: Chapter 31: Another Surprise - 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 took Penny’s arm and gently led over beside Kim and Bob, who were dancing and kissing. I gestured to Kim, “9-1-1, Foyer. Right now!” That was our code for we need to talk immediately. Penny was still in my arms and had started laughing.
Kim looked somewhat puzzled but started to follow us. Bob went to the two women that were dancing together.
Kim, Penny, and I went to the large welcome foyer. I sputtered, “Your mom has us figured out, completely it appears, and...”
Penny interrupted, “And, I want to be part of it all – tonight – the sex. I even want your fiancé as my first partner, with your permission, of course. I need some serious and sexual loving. God, I’ve gone without for so long. I hope I haven’t forgotten what to do.”
The silence was ear-shattering. Kim silently sized up her mother and then said, “Wait a minute.” She went back to the living room and reappeared less than a minute later with June in tow. The two daughters faced off with their mother.
Kim stated to her sister, “Mom wants in on the sex – the group lovemaking. She apparently wants to be a full member of the Circle, although we need to talk about that.” Penny kept nodding in agreement. “Lastly, she wants to be with Ron to start with.”
There was more silence as the two daughters looked to see whether their mother was yanking their chain. She wasn’t. Penny nodded that what had been said was exactly what she wanted. She did maintain her smile. I was glad the daughters were both present.
I suggested, “Penny, tell them why you want this.”
Penny nodded and began. “I have been in a loveless marriage for almost twenty years. Bart turned out to be a huge disappointment on all counts, except he was providing me food, shelter, clothing, and a few other nice things I couldn’t have had otherwise. I suppose you could say that I prostituted myself to keep that lifestyle. Just to be blunt, he was and is a terrible lover. Early on, I was in survival mode and too proud to say anything to anybody else, and then I couldn’t see a way out. I didn’t want to call on you because of ... pride, the burden I’d be, and my inability to return your kindness.
“A week ago, on their overnight visit, Kim promised me an out from the ogre if I needed it. I knew she could help me financially because I have figured out that she is beyond rich. I took that as a sincere sign that I really had a way out although I’m not happy about taking the charity. Bart was so rude to the two of you. I popped or whatever you say. I just knew that I couldn’t last any longer. Lord knows, I’ve tried. I wanted a good marriage with a loving husband, but with THAT MAN, I just couldn’t do it. I don’t think anybody could. My mind is made up; I’ll file for divorce. I want him out of my life.
“Those were the huge reasons for pushing me out of the marriage and into something else. But then there was something else pulling me towards all of you. The ‘something else’ I pieced together from bits and snippets of what the two of you told me about your lives over the last few years and months, how you talk about your husband and fiancé, and the Circle. What you cut yourself off from saying – uncompleted sentences and such when you’d catch yourselves.
“You were never explicit about the sex, but you may as well as written it across the sky. I know what the two of you are like, especially when you were younger. You think I didn’t know about what you were doing growing up and in college. Guess what? I did. Also, just to set the record straight and so you don’t feel alone, you were just like me. You both were wild about sex and variety; well, me, too. Sometime soon, I’ll tell you about what your two fathers were like when we were together. The short-hand version is that we were wild, highly sexed, and had a lot of variety in our sex lives. Their deaths made me have to give all that up.” I’m so sorry I took a third marriage and made you Bart’s step-children.
“You’ve basically told me that you share yourselves with the other men, and also that they’re wonderful lovers, partners, and the best of friends. I want that. I need that. The only friends I had in Denver were the few wives of Bart’s associates. He had to approve them and then manage any interaction that I had with them. I stopped trying after a while and focused on being in shape, my dental work, and such.
“I want to be loved – and made love to. I want to give my love to others. I want to be wanton, and have wild and crazy sex when the mood strikes. I believe that’s what your Circle environment is like. Please let me participate. I won’t be a problem, I promise. I will make you proud of me.” She bit her lip, almost on the verge of tears. I heard her sharp intake of breath.
Silence again prevailed. Kim looked at me and since Penny was looking at June, I winked and smirked. June saw the interaction.
June finally shrugged to indicate she didn’t care what the decision was, and said, “Come on, back to the living room. I am so horny I might spontaneously combust and I need to get laid about ten times before I sleep.” She turned and walked away.
Kim nodded at Penny and said, “So be it.” She turned and winked at me. She made a gesture that Penny couldn’t see with one hand making a fist, and then plunging the forefinger of her other hand into the hole the fist made a few times – fucking. She mouthed to me, “Do her!” and then pointed back at her mother. She then walked back towards the living room leaving Penny and me.
I guess that I had clear directions from my fiancée to fuck her mother. I knew she’d want me to pour on the love and do a good job of it, too. I had that thought that if I did, I would have nailed all three women in that family. I heard Kim tell the others in the living room that if it was alright with them, Penny would be participating. I heard a few positive replies and missed a few others.
Penny said to me as we stood there, “Are we okay? Have I screwed the pooch, or whatever it is people say about messing up?” She tried to laugh, but she was tense.
I just took her hand and led her back to where we had been dancing. The difference this time, was that Jan and Trish were both nearly naked and totally loving the pawing and sucking they were getting from Bob and Jim. Debbie was removing her clothes to join them. Doug had intercepted Kim, and the two of them were in an epic kiss that didn’t seem to end.
I leaned in and kissed Penny – definitely not a future ‘son-in-law to future mother-in-law’ kiss, especially after our tongues got seriously involved. Penny also started to grind her lower body against mine, and I returned the favor, only with a growing bulge that was hard to miss.
Penny whispered, “This evening now has signs of turning out to be the best night in my life.” The next kiss her arms wrapped around me like she was desperate to hang on. I liked her grinding and returned the favor by reaching down and holding her ass cheeks. I didn’t feel any seams under her short dress.
I suddenly had a realization. “Penny! Are you commando?”
She grinned in a lecherous way. “Yes. I don’t want anything to stand in the way of you slipping into me with what I feel growing in your pants.” I was sure she blushed making that admission. We were in the shadows of the room so it was hard to tell.
A dozen feet away, Doug had just stripped away the last of Kim’s clothing. She was undoing the last of his clothing as fast as she could. Penny said in a demure tone, “I know the big picture that I pieced together, but not the nuances about what to do when. I’m sure you’ve all got some implicit behaviors to start the sex, do it, and then end, that you might not even know about. Help me navigate them. It seems as though you should take my clothes off at this point ... and I guess I should remove yours.” She gestured to the other couples near us in the large living room. Some were naked, and everyone else was headed in that direction.
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