The Pilots - Cover

The Pilots

Copyright© 2025 by Wolf

Chapter 34: Girls’ Night Out

Romantic Sex Story: Chapter 34: Girls’ Night Out - 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 Circle was in full swing when we arrived on Thursday evening. Vanessa had produced a magnificent dinner again. Further, we learned that she was doing portion control on an individual basis. Thus, although I could have eaten the table, I got a modest portion of the entrée, and no dessert. I guess she’d heard me worrying about my weight. I asked for seconds, but got nicely told, “No.”

My daughters and their husbands had finished their move into Acre Woods that week, so the meal was also a bit of a celebration of that event as well as Debbie’s soloing in the Cessna. The condo they had in Chicago still had furniture staged in it, so it would hopefully sell soon. Most of their important possessions had arrived by truck on Tuesday. I did note a few boxes still around.

Doug had also flown down from Boston with Trish, bringing his wife Karyn. Thus, there were sixteen at the long table for dinner. I was pleased to discover that Bob had insisted that Vanessa have a seat at the Circle dinner table. She wasn’t participating in other activities, but she had obviously become a beloved member of the overall family.

I gave Vanessa a warm and loving hug when I caught up with her in the kitchen. She cuddled into me and asked for me to hug her tighter. Then, something magical happened. We kissed. It was very tender and lasted perhaps thirty seconds. We didn’t want to part, but we did.

I smiled at her as we pulled apart and got a shy smile from her, too. I could see that just maybe she was coming out the shell I had felt she was in when we’d first met. I arranged for Vanessa to sit next to me. In a brief aside, she said, “Everybody here can call me Van. I don’t mind, and I kind of like it as a nickname.”

People helped carry dishes to and from the table so that Van didn’t have to serve the large group of us by herself. I put myself on the clean-up team, and we made short work of putting dishes in the two dishwashers and saving leftovers in the giant refrigerator. The house also had a walk-in freezer built into the garage building.

Vanessa disappeared after the kitchen was neat and ready to serve breakfast. The rest of us settled in a dimly lit living room that soon became the loving room. My pleasure that evening included Karolann, Karyn, and Trish. I cuddled Kim and Debbie in our bed overnight.

Again during our lovemaking part of the evening, I saw Van peeking at the larger group of us from the foyer doorway. She was wearing a long dark t-shirt, but had it hiked up so that she could finger herself and rub her clitoris. She was very attractive and even sexy dressed that way. I was pretty sure that I saw her have an orgasm before she disappeared.

Friday, Kim, Debbie, and I did remote work for TNA after a morning run with some of the others in the house. I noted that Doug was also doing some remote work for Fidelity. He and I also had a good discussion about the energy sector of the economy over lunch.

Friday’s dinner was a cookout – the first of the season. Van rushed around putting side dishes out and making sure the volunteer grill chefs knew what to do, how long to cook the steak medallions, and so on. When it came time to serve, she also played the nutritionist again and divvied up portions for weight control by each of us.

The evening got chilly as the sun set, so the group migrated back to the ‘loving room’. Except for engaging with different partners, we duplicated the evening before. The six men were outnumbered by the nine women. Van had disappeared again, but only temporarily. When sexual liaisons were seriously underway, she reappeared at the place where she could peek at much of the room and the open and loving sexual liaisons that were taking place.

I was with June and Jan when I spotted Van. I made a gesture for her to join us. She smiled and waved a finger back-and-forth at me. I wasn’t sure what the gesture meant, but she didn’t come into the room. That night I had Kim and June in my bed. They were still cranked up, and proved to me that they were more than capable of another half-dozen orgasms each. I was the happy voyeur, but allowed them their sapphic time together.

Saturday, we did another run in the morning. Penny paced me on the run and we kind of talked as we ran, which was hard to do at our pace. She’d engaged a lawyer in Denver to handle the divorce. Bart had been served, complained bitterly that he didn’t want a divorce, yet wanted to negotiate the settlement. Her lawyer told her that he used outrageous language regarding her and the situation she’d left him in. They did not have a prenup and Colorado was a community property state, so the deal was fifty-fifty unless there were some extenuating circumstances.

Apparently on Friday, the women had decided that they wanted a different kind of evening, so they’d planned something different for everyone. They wanted a girls’ night out, but with the safety net of having the men nearby in case they got in ‘trouble’ – whatever that might look like. After describing a few scenarios, the males decided to join them, but not be with them. The evening became a night off for Van, and, no surprise, she opted not to go with the group. She wasn’t ready to be that social yet.

I think deep down I knew we were in trouble when the women appeared ready for their evening. Every woman looked eager to party and have a good time, with a strong hint of sexual readiness. Their cocktail dresses barely covered their pussies they were so short. Most also were highly suggested that a wardrobe malfunction was about to occur in the breast area. Cleavages were deep, and in several cases the navel was winking at anyone interested. They were all wearing CFMs – come-fuck-me shoes. Kim’s were her black stilettos that turned me on so much.

After some teasing, we gentlemen learned that most of the beauties were commando. All they had on was the dress and the shoes. Oh, yeah, there was a lot of ‘come hither’ make-up to make each of them even more alluring. If they were planning on chumming the clubs of Philadelphia for unwitting males, they were dressed for it.

The limo we engaged filled with people and there was a lot of pussy and breast flashing that I certainly appreciated. We drove into the ‘hot’ district of Philadelphia. The first stop was for dinner at Barclay Prime, a nice upscale restaurant. We had to break-up into smaller groups, so, in the spirit of the night, the six men sat together at one table, and the nine women divided themselves into two adjacent tables. I arranged with the maître d’ before the meal got started to put the entire throng’s drinks and meals on my card. Other than that, the males tried to pretend we’d never seen them before.

Dinner was a long and pleasurable affair, and the guys certainly bonded more than ever. Our observation of the women was that they were a little loud, laughed too hard, and were having a good time. There was a lot of shifting around at their tables, too. We did get some pussy flashed at us from some of the girls that were best positioned to do that to us.

When we were through we reconnected with the limousine, but didn’t go too far, to a club on a secondary street called Duke’s. I think I could hear the music at the club about a block away. Several of us rolled our eyes at where we’d be. Fortunately, that was some special event, and the volume did drop, but not by much.

Bob, Jim, Doug, Todd, Scott, and I went in as a group, paying our covers. There were still some tables available, so we pushed a couple of small ones together for starters. Our cute waitress had even less clothing on than the Circle women. She had a G-string on, and a halter top with her nipples punching through the thin material. She also wore CFM shoes. We ordered a round of drinks and I also kidded around and flirted with the young waitress.

The women came in behind us. The unescorted ladies got in free – no cover charge. They managed to command a corner of the club with a semi-circular sofa and several tables. I could see Debbie in there organizing everybody and pulling chairs around. I found it interesting that they got a male waiter. He was muscular, wearing tight dark shorts that clearly showed his ‘package’, plus white cuffs and collar, no shirt, manly chest, and looked like pure hunk. I think he’d modeled himself after one of the Chippendales.

The other men in the club sure paid attention to the nine stone cold foxes that had arrived. I could see the drooling over all that unescorted pussy starting to begin. I speculated they thought the girls might be a bachelorette party. There had been a few other women in the club, but our nine really tilted the scales and if I say so myself, they were sexier and hotter until you got to the waitresses. It took about ten minutes for everyone to get served. That round let to a second, and by then each of the women were being asked to dance and whether a guy could buy them a drink. I didn’t think that I heard a slow song since I walked in the door.

Our waitress was also handling another large crowd of guys more or less in the other corner of the large room from the women. I guessed that there were about a dozen men. She told us it was a bachelor party for Jake, a guy wearing a Philly’s baseball hat with a couple of cheap plastic necklaces around his neck to indicate his ‘important’ status that night. His buddies were obviously trying to get him shitfaced, and it looked like he was resisting. I noted at one point that he kept picking up and supposedly glugging from one of the empties on the table. Smart man. Good ploy.

Many of the guys had started to ask the women to dance. I texted Kim: ’Bachelor party guys mostly – the groom is Jake. How’re you holding up?’

She replied, ’Moderating my intake of alcohol. How bad can I be? I like some of the men that I’ve danced with.’

My reply was, ’I promise I’ll still love you in the morning. Use condoms – all of you.’

 
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