An Evening Out Ch. 01

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Couple has an interesting encounter one night.
8.5k words
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Part 1 of the 2 part series

Updated 10/06/2022
Created 03/09/2004
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Everybody has sexual fantasies. Some people are fortunate enough to be able to fulfill some of them, others choose not to, and still others never take the risks necessary to experience them. Not all fantasies are meant to be played out; knowing which ones to risk trying can be difficult to discern.

My wife Sarah and I had for many years talked about sharing our sex lives with another person or couple. Sarah was very bisexual, and had been exclusively with women for many years before we met (I like to joke that I "saved" her from lesbianism, and she often referred to herself as a "wasbian"). We both enjoy reading erotica together, as well as the occasional porn video, and we both found ourselves turned on most by stories involving women together or a threesome among two women and one man.

These thoughts had remained as fantasies for many years, primarily because of the hurdles posed by children, jobs, family commitments, and the like. Even without those hurdles, I doubt we would have turned fantasy into action earlier in our relationship, because we were not emotionally secure enough to try it out earlier. But we finally reached the stage where the hurdles were low enough, and we were emotionally and sexually secure enough, that the fantasies began to evolve into discussion of possibilities.

The more we discussed the idea of sex with another person or persons, the more we both realized we wanted to give it a try. We weren't sure how to go about it, or exactly what to expect, so we went into it with an open mind. After surfing the web a bit, we discovered a few swingers websites, posted a profile on each, and began corresponding with some couples.

Besides being interested in sex with other people, there was another part of our sex life that we had been exploring. For about a year before deciding to embark on swinging, Sarah and I had been experimenting with dominance and submission, or D/s. I had known for a long time that I had a submissive side. I was always turned on by stories and videos that portrayed strong women who asserted their control over men (as well as other women). I had never shared this feeling with Sarah, though I suspect that she had begun to realize how I had felt based on my response to specific stories and videos.

It was not until about a year ago that Sarah began to playfully assert control over me while we were having sex. It started with her teasingly telling me what to do to please her, and as she quickly realized how turned on both I and she were by this play, it escalated to the point where she was into full femdom mode. She would tie me up and force me to service her sexually, with occasional "training" sessions where she would spank and verbally humiliate me into submission. Our D/s was not so much about punishment, however, as it was about her asserting control (and my giving it up) in order for me to please her sexually. It was a practice that we've seen referred to as "sensual dominance."

In many of our D/s sessions we would spend much of the evening with me paying attention to her body, which could include starting with my bathing her in our oversize bathtub, moving to giving her a nice warm oil massage, and then on to an intense session of bringing her to orgasm every way imaginable. If I did a good of pleasing her, she would reward me by allowing me to masturbate in front of her. And if I did an especially good job, I would be rewarded by being allowed to have sex with her. The D/s sessions were not an everyday thing with us, they were something we engaged in occasionally and were very special to us. Most nights (or days, as it were) involved more vanilla sex between the two of us. We were definitely not into 24/7 D/s, as were some people we had met online. Children, job responsibilities, and other things made it impossible for us to pursue it, and to be honest, neither of us was truly interested in a 24/7 relationship like that. But we certainly did enjoy it in the bedroom.

So as our discussions about swinging became more concrete, we obviously discussed just what role the D/s should play in it. We decide to be somewhat circumspect in our profiles on the swingers sites, because we didn't want to turn off any couples or women. You would be surprised how many profiles say that the person or couples are not into "BDSM," though it is not always clear what that means to people. Through conversations with people online, we determined that the majority of people respond to the BD – bondage and discipline – or SM – sadism and masochism – in the term BDSM. To Sarah and I, however, it was the DS that was at the center of our sexual role playing. We decided not to mention anything about D/s in our profile, and we would see how things progressed as we met people.

We had a number of responses to our profiles, and messaged some people – both couples and single women – on our own. We were primarily interested in finding bisexual women, as sexual contact between the women was going to be an important part of the relationship for us. Our experience on these sites, I suspect, was similar to that of many others. Ninety percent of the contacts that we made led to nothing; either we realized that we weren't compatible, or more commonly, the other couple really weren't interested in swinging but were on the site for the titillation factor or to collect nude pictures of other people.

Some of the connections we made did turn into actual meetings with people, and some of those meetings turned into "dates." We had some good experiences, where Sarah and I really connected with the couple on both an emotional as well as a sexual level. And we had some not-so-good experiences, but the one thing we always tried to do was learn from the experience.

One thing we had not had any success in finding was a single woman with whom to play. Many couples on these sites refer to single bisexual women as "unicorns," because they are as rare as the mythical animal. But like other couples, we kept searching and messaging women in the hopes of finding one to bring into our bed.

After about a year on the sites, we saw a newly listed profile for a woman who called herself "FunnGrrll." She didn't live too far from us, and was about the right age (we tended to stick with people around our own frightfully-close-to-middle-age range). There was not much information in her profile regarding her likes or dislikes, and just one picture that didn't show very much of her, but we figured "what the hell, we've got nothing to lose," so we went ahead and composed one of our witty little messages and fired it off. Based on our previous experiences (can you say "struck out" in 47 different languages?) we did not have very high expectations.

Like many others we messaged, we didn't hear back from her so we removed her from our "friends" list and went on with our lives. Then about two weeks later, we had a message in our inbox on the site. When I looked at it I saw it was from FunnGrrll. I quickly opened the message, expecting to find the familiar "Thanks, but not interested" message that we considered to be one step above those people who never replied at all.

But much to our surprise, I found a short note thanking us for our message, explaining that she had been out of town on vacation, and that she would be interested in finding out more about us. She shared her Yahoo ID and invited us to look for her online for a chat. I had Sarah come over and read the message over my shoulder. She was surprised also, but not particularly optimistic given our lack of success in this department. But she said, "Well, go ahead and look for her online and see what she sounds like." I tended to instant message more than Sarah, who had little patience for it, so I was the one that usually made the first contact with couples we met on the swingers' sites. I replied to FunnGrrll, giving her our Yahoo IDs and first names, and telling her I would look for her online.

I sent a request to add her to my friends list, and Sarah did the same. I didn't hear back from her in a few days, so wrote her off and figured we'd never hear from her. And then about five days later when I logged on to Yahoo I received a message that FG (as Sarah and I now referred to her) had accepted me and added me to her friends list, as she had Sarah. I checked to see if she was online, but she wasn't. I messaged her anyway, in case she was signed on in invisible mode, but didn't get a response.

A couple of days after that, after we had put the kids to bed, Sarah was on the computer checking her e-mail. Her computer beeped and she saw the flashing icon that indicated somebody was messaging her. She clicked on the icon, and up popped a window titled "FunnGrrll." The window said, "Hi Sarah, Jill here." Sarah called me over to the computer to read over her shoulder as she began to chat with her. They chatted for awhile, engaging in the getting-to-know-you kind of banter that we had gotten very familiar with over the last year. Most of these initial contacts led to nowhere, but we had learned that it was a requisite step in finding another couple or person online.

As Sarah and Jill chatted, aided by my occasional question I suggested to Sarah, they got to know each other a bit more. Nothing too deep at the outset, but they exchanged enough information to determine that there may be a possibility of a connection among the three of us. After awhile they signed off, Sarah shrugged and said, "Well, we'll see," and we went back to our activities.

The next day I looked to see if Jill was online, but couldn't find her. I checked the next few days (as a college professor, I tended to spend long periods of time in front of my computer), but never saw her online. I concluded that she was one of those people who either was never online or always signed on in invisible mode. After a few more days of this, I checked in with Sarah to see if she had heard back from Jill at all. She said that in fact she had, and that she and Jill had chatted for a short while every day so far. I was surprised, but not stunned, and decided she was just somebody who liked to chat with women. We had been very upfront from the beginning that we were only interested in her as a couple, and that Sarah did not play alone, so I wasn't too worried about this.

I asked Sarah what they had been chatting about, and she replied, "Not much, the usual chitchat, getting-to-know you kind of stuff. But I think she would be interested in meeting us, and she definitely seems to have some interests in common with us." I was a bit surprised to hear this, simply because I had assumed we would never find a single woman interested in us, and had little hope that Jill would be our unicorn. So I said to Sarah, "Great, I'm all for it. Is she willing to share some pictures?" Sarah said that Jill was supposed to send some in the next day or so, and when she did, Sarah had promised to share some of ours (we had only body shots in our profile; we were careful not to share pictures with our faces until we got to know somebody a bit).

The next day, I was in my office working on grading papers, when I received an e-mail message from Sarah. There was no text in the message, just a subject line that said, "Take a look." After making sure my office door was closed (didn't want any pesky students coming into my office and looking over my shoulder) I opened it up and found three attachments. Clicking on the first, I opened a jpeg file that contained a picture of a blonde woman who appeared to be in her late 30s or early 40s. She was not what many people would describe as pretty, but she had the kind of look that both Sarah and I liked – short hair, with a look that some people would describe as "dykey," and she definitely would fall onto the "cute" page in my book. It was, in fact, a look that Sarah carried off quite nicely. She always joked that she could still walk into a lesbian bar today, after almost fifteen years of being a "wasbian," and do very well for herself. And I would never dispute her on that.

In the photo, Jill was dressed in a very pretty, somewhat formal black dress with spaghetti straps that clung to her and showed off her body quite nicely. Again, I would suspect that most people would look at her body and not find her very attractive or sexy, but she had a look that I knew Sarah liked as much as I did – not really fat, but very well rounded with great curves in all the right places, a figure not unlike Sarah's. Needless to say, I was quite intrigued about the possibility of getting together with this woman. I was trying not to get too excited, however, because there had been plenty of other people with whom we had traded pictures, and the contacts had amounted to nothing.

I clicked on the next attachment, and up popped a photograph that clearly was taken on a nude beach. This one showed just the top half of her body, which was naked, with a big smile on her face and sunglasses covering her eyes. She had a beautiful set of breasts – quite large, yet not overly so, with very prominent nipples. In fact, her breasts were very well proportioned to the rest of her upper body. Once again I was struck by the fact that most people would look at the picture and think of her as overweight, but I found her incredibly sexy and arousing. She clearly was a woman who was quite comfortable with her body, enough so to be lying there on a nude beach with a figure that was far from model-perfect.

With anticipation I clicked on the third attachment. I could see that this photo was from the same nude beach, but this one was taken from a few steps back, so that you could see Jill's entire body. She was lying on her side, and the shot was taken from behind with her looking back over her shoulder. She had the same wide smile on her face, and the perspective provided a wonderful view of her ass – like the rest of her, nicely rounded, not too large, but definitely one I would like to get my hands and lips on. I looked back at the previous photo, and again at this one, and was struck by how nicely proportioned she was. Everything from her smile down to her muscular legs seemed to fit nicely together, even though I knew that many would look at her and scoff that she was too overweight.

I replied to Sarah's message, saying "Great – when do we meet?" Much to my surprise, just a couple of minutes later, I got a reply from her saying, "This Saturday night." I was shocked, and immediately picked up the phone and called Sarah. Before she said, "Hello," I asked, "For real?"

Sarah replied, "Yup. The kids are going to Rob and Marcia's for a sleepover and we're meeting her for dinner in Maywood." Maywood was a town about 15 minutes from us, about halfway between where we lived and she lived. Rob and Marcia were our best friends; they had two kids the same ages as ours, and Rob was a fellow professor at the university. We often shared childcare duties in arrangements like this, though the two of them had no idea what Sarah and I were doing when we left our kids with them.

While excited at this news, I was trying not to set myself up. We'd had too many of these meetings where the people we met turned out not to be anything like the couple we had been messaging with, or worse yet, they looked nothing like the pictures they had sent us. But nevertheless, I said to Sarah, "Okay, we'll see. I hope she doesn't turn out to be psycho," with thoughts of Glenn Close and Fatal Attraction swimming through my mind.

The rest of the week dragged on as I looked forward to Saturday night. Sarah and I talked quite a bit about what it might be like. We had certainly had experiences as swingers, but all had been with other couples, and this would be the first time we even got to meet a single woman. While some people had a rule that they wouldn't play on the first date, we didn't stick to that, and had met some couples that we had sex with the first time we met them. We didn't know how things would play out with Jill, but figured we would just play it by ear and hope for the best.

Finally, Saturday night arrived, we dropped the kids at our friends' house, and we headed out for Maywood. As we were pulling out of the driveway, Sarah said, "Oh, by the way, did I tell you that Jill is into D/s?"

I shot her a quick glance, trying to keep my eyes on the road and not kill us on the way to our first meeting with a unicorn. "Ah, no, you neglected to mention that. How did you find that out?"

Sarah replied, "Well, you know, when we were chatting about what we liked, I asked if she was into anything kinky. And she said that she liked to be dominated on occasion."

I said, "Really?", just a little bit astounded that my dear wife had neglected to mention this little fact. "Anything else about her you'd like to share with me?" I asked.

"No," she chuckled, "nothing else really important, I just thought you would be interested to know that about her."

I certainly was interested in that little tidbit of information. For the year that we had been swinging, Sarah and I had yet to find another couple who was interested in D/s. We had discussions with some about the topic, but never found anybody who was really into it like we were. One couple said they'd give it a try, but before we had the chance to try anything, they backed out. We had great sex with some of these couples, but still kept thinking that it might be fun to play around with D/s with another couple. So when Sarah let it drop that Jill was into it, I was quickly interested and excited at the same time.

"Did you tell her the nature of our relationship, that you're dom and I'm sub?" I asked.

"Of course," she replied, "Don't you think she would have asked?"

As I thought about this for a split second, I realized it was a pretty stupid question on my part. Anybody who is into D/s and talks about it with others very quickly inquires as to whether somebody is a top, a bottom, or a switch.

Anticipating my next question, Sarah said, "She said she'd be interested in trying it out with us. And I told her we certainly would be, too."

While Sarah and I had talked about the possibility of playing with D/s with another couple or person, we had never really gotten far enough along in these discussions to talk about the specific possibilities of how this might work. So I was not quite sure I was ready to jump right into this with Jill, but Sarah clearly was interested in giving it a try and, speaking for the two of us, told Jill this.

If we did engage in D/s with Jill, I knew what my role was going to be – that of the submissive. It was unclear to me where Jill would be in all this, for Sarah had said that Jill liked being dominated on occasion. But did this mean Jill was a switch? Or just that when she did fool around with D/s, she preferred to be the bottom?

Next thing I knew, we were at the restaurant. Sarah and I had been here before, in fact, had met other potential swing partners here. It was a relatively quiet place with widely-spaced tables that was conducive to intimate banter. We walked in, did a quick scan of the room, and spotted Jill sitting facing us in a booth near the back of the room. We nodded to the hostess, gestured toward that table, and started walking in that direction, Sarah first, then me.

As we approached the booth, Jill spotted us, flashed us a big smile (the same one I had seen in the photographs from the nude beach), and stood up. She gave first Sarah, then me, a quick hug and peck on the cheek while she said, "Hello, so great to meet you finally." She scooted back into the booth, and I waited for Sarah to get into the other side and slide over. Much to my surprise, Sarah slid in next to Jill, and pointed to the other side, saying, "Bob, why don't you sit over there." I was frozen for a second, but quickly recovered, saying, "Sure," and slid into the booth facing the two women. I wasn't quite sure what Sarah was up to, but figured I'd just go along for the ride.