Jack’s Arrival in Swingtown – The First Soft Swap With Swingers


First Soft Swap With SwingersI laid awake. Anne was beautiful and sleeping softly beside me. It was 5 a.m. and sleep had yet to find me. I was exhausted, but my mind was racing. Anne and I had just returned from our first lifestyle experience, a soft swap, less than two hours before.

Anne and I had been hanging out with two couples all evening. We had never met either of them in real life and only really talked with half of one couple prior to this meeting. We met them at one of their houses and they made dinner. Dinner was excellent, as was the wine. Anne and I had a wonderful evening talking and getting to know both couples. As it grew later, well past midnight, the Mrs. of the hosting couple was starting to fall asleep and opted to retire to the bedroom. The Mr. soon followed.

Left alone with the other couple, Anne and I went where the night had clearly been leading us. There in the living room Anne and I officially made it to Swingtown. Looking back, I realize that I was probably behaving awkwardly in the aftermath of it all, which given the circumstances probably isn’t unexpected. I wish I could say I was much more suave after the deeds were done. But sadly it wasn’t so; I was fairly awestruck from it all.

We left shortly thereafter. Anne and I hugged and kissed them goodbye and got into our car. I really don’t remember exactly what was said in the car on the way home. It pretty much boiled down it both of us agreeing that that was fun and weird.

Finally in bed, my mind was turning over the events of the evening. Over and over. Processing and analysing. My body desperately needed sleep, but my mind couldn’t slow down. So there I lay thinking.

This next part is hard. I am not sure I can fully pour my thoughts and feeling coherently onto the page, but I will try. So, bear with me, dear readers, as I overanalyze the crap out of this and myself.

First off, no matter how hard you try in your mind to prepare yourself for swinging, it will never be enough. I really wasn’t expecting to feel as weird as I do. I am not sure how I expected to feel afterwards. What I can say is that my feelings were similar to those I experienced after our almost-swinging with our vanilla friends. My feelings of general weirdness are not coming from the obvious places. Seeing Anne with someone else was totally fucking hot. No jealousy or anything of that nature. My feeling were solely based on the things that I had done.

Anne and I dated for at least six months before having intercourse (which is a long fucking time when you are 20 and 21). I had had sex before but she had not. However, most of the time waiting was because of me, not her. In the past, I had always linked sex and deep meaningful love. I was by no mean promiscuous in college or high school. I have since intellectually unconnected sex and deep love. However, I feel that at least partly some of my weirdness was coming from this. Now, I in no way feel guilty or bad about what I did. Though I suspect somewhere in the back of my mind at least part of me feels like I have betrayed Anne in some way, which really makes no sense. She was, after all, about 3 feet from me at the time and enjoying herself every bit as much as I was.

I am also fairly sure that part of my weird feelings came from having only really done anything sexually with two other women in my life. This single event upped the number of people to have touched my penis in a sexual way by 50%. Which inevitably lead to me questioning whether I had been good enough or not. I assume I was and have no reason to believe otherwise. However, it is very intimidating when you know your play partner is significantly more experienced.

Finally, some of the weirdness I felt was maybe not getting to know the couple as well as I would have liked before actual swinging began, but I have no idea if I would have even thought we ever knew them well enough. So I am grateful they took the lead. I certainly feel more confident about being able to take the lead in the future.

Despite this weirdness I felt, none of it was a bad feeling. I certainly do not feel guilty or ashamed or anything remotely bad. It really is just very surreal and took some time for me to process. In fact, I am still processing it all. My weird feelings are slowing turning to excitement for future swinging.

Our blog is called Road to Swingtown. We finally made it. Well, at least to the outskirts anyways. Even though we are here, in Swingtown, the name of the blog will stay the same. After all, there are many people and places along the road to see and do. I hope you enjoyed the beginning of our journey and continue to enjoy it with us. Maybe we can meet you on the road someday.


An average suburbanite barely into his 30s, Jack has recently begun a more exciting secret sexy life with his wife, Anne. These experiences have led him to preach the gospel of sex positivity and safer sex to anyone who will listen.


  1. It all seems a bit surreal, doesn't it?

    I can appreciate everything you wrote in this blog, and understand a lot of where you're coming from. (Well, as much as I can having never participated in a lifestyle encounter myself. I've appreciated the honesty in your story, as it helps me identify potential pitfalls and perils as well as analyze my own feelings. Yes, I have been known to overanalyze. Heh.)

    First, congratulations for reaching swingtown without it blowing up in your face! Not everyone is nearly as lucky as you've been. Careful planning works wonders, but indeed one can never be ready for the final jump. My personal belief is that whether one is merely dipping a toe or jumping right in, one must be fully committed to being a swinger.

    As you've already found, swingtown is not just a single destination, but a huge city with street after street of fun, excitement, and discovery. The road keeps going thataway, so in a way you'll always be on a journey there.

    Your weird feelings are very familiar to me. I, too, have had a limited number of sexual partners. I, too, feel the need to develop something beyond lust to enjoy a sexual encounter. I, too, analyze the hell out of everything. You'll probably be processing this for awhile. 🙂

    That you have emerged from this experience guilt-free and unashamed speaks volumes about your maturity as a sexual person, despite whatever you may think about your relative inexperience. That you can cleverly examine your own feelings and dissect them demonstrates that you are indeed the right kind of person for the lifestyle. Consider your hand shaken, sir.

  2. Well put and I couldnt agree more. As your journey continues, would love to see how your "weirdness" in your head evolves. Mine is still there. It changes. Sometimes I thrive off it and it helps me, pushing me deeper into Swingtown. Sometimes I question everything at the edge of Swingtown because of it and it really hinders the… biology… of the moment, making me question if I am even in the right town. Maybe my brain will eventually get used to it. Or maybe it will open new doors I dont even know are there yet as I learn more about myself.

    Thanks Jack for a great post.

    -G and S 😉

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