Finally, Our First Time!

My wife (Jill) and I (Jack) had been discussing the Lifestyle for several years. We narrowed down our opportunity to a trip to Sint Marteen. We stayed on the topless side of the beach. We discussed different methods to get our fantasy started. We even brought a top-up tent through customs in case there was an opportunity. While at the beach, I would often tell Jill to sit up with her tits sticking out when potential victims would stroll past us. We even visited the nude beach several times, but we found that most of the people we saw there were not people we would like to see without clothes. We visited several local hangouts in hopes that we would discover a potential victim for Jill. We did not have a rule book or a how-to book, thus leading to many unsuccessful attempts. Finally, after our fifth day on a seven-day vacation, I decided to turn up my boldness several notches. We visited the local beach bar close to our villa. FINALLY a possible victim.

The French Bartender

We found a single bartender who was French, about ten years younger than us, who was very attractive. We tried all of the usual forms of flirting without any success. Then I became a little desperate, thinking that our vacation would soon be over, and we had not had any Lifestyle experiences. I made my move around 10 pm. 

As I approached the bartender, I explained that I was a little nervous and unsure of what to say, and as I stumbled around in my conversation, I was able to finally look him in the eye and ask if he would be interested in playing with my wife as I pointed Jill out. The bartender seemed a little taken back, and he responded by saying he had never ventured into any playtime with a couple, and I explained that the contact would be between him and Jill, and I would be there to watch and make sure she was safe. I assured him that I was not a director, and I assumed that he and Jill would know where all the parts fit together. The bartender told me he wanted to think about the offer, and before I could return to our table, he came up and told me he was interested. YEA! We finally had something to fantasize about. 

Jill and I talked as the excitement level rose. After approximately 15 minutes, I went up to assist the bartender with completing his duties in closing the bar. The three of us then walked a short distance to our single unit, which had a private pool. After a few minutes of small talk, Jill excused herself and returned moments later, wrapped in a towel. As she neared the pool, she dropped the towel, and we saw that she was naked. Jill looked at our new friend and invited him to join her in the pool, and he hurriedly responded. 

They got into the pool, and I sat on the edge of the pool as nature took its course. After a short time, it was obvious that the bartender was displaying a hard-on. As they walked into our villa and approached the bed, I became concerned as to what my role was to be. Should I sit or stand? Get close or move away? Should I hold the drinks, or keep up with the towels? I was nervous beyond belief, and Jill was having a great time. They moved to oral sex with each other, and Jill looked at me and shrugged as if to say, “what do I do next?” I smiled and mouthed, “have fun.”

As the sex progressed, our friend put Jill in several different positions as he penetrated her. It was obvious from the sounds Jill was making that she had passed being nervous and was in heaven as the sex continued. After a long lovemaking session, our initial experience was coming to a close. After our friend left, we nearly killed each other. We had been married for ten years, and the sex that night was the best we had ever experienced together. 

That was our only experience of this vacation. But, during the past eleven years since that vacation, we have experienced many, many combinations of sexual experiences. First, with couples, but as we quickly learned, having four adults on the same page was rare. So, we continued our adventures with an extra male, which has always been our favorite setting. We have one night in Sint Marteen to thank for the next eleven years of the greatest sex we ever experienced, and we see no signs of the adventure becoming stale. We thank all of the people that have contributed to this experience and look forward to meeting additional people to add to the story.

This story was submitted to our SDC Erotic Writing Contest:
“Our First Swinging Experience” by one of our members.

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