A couple of years ago I decided I really needed a holiday in Jamaica. Having been there a few times before I knew I wanted to be in the Ocho Rios area and started searching online. One place really caught my eye... Couples - Tower Isle. Now being a single older man I just needed to find a partner to make the "Couples" part work.

An attractive close friend who is about half my age was my first choice. I called her up and she didn't hesitate to say yes. While we are very close and familiar this was something new for us. This was going to be interesting.

The time came for us to head south and things were fantastic. The resort was excellent and our little excursions off the resort were fun too. Saint Ann's Parish Market was fantastic and the Green Grotto Caves were amazing. We had a lot of fun turning heads everywhere we went and we had a blast. Tripping around with locals opened my eyes to a side of Jamaica I had not experienced.

One afternoon we took a catamaran cruise and swim that was sponsored by the resort. It was on that boat that we sat next to another couple who said they were from the Toronto area. After a bit and some friendly conversation where it was assumed that my friend and I were a regular couple, I told them we had an "unconventional relationship". That opened up a whole new discussion about their previous trips to Hedonism in Negril and such. The outing ended and we returned to the resort.

One of the interesting features of Couples - Tower Isle is their island that is restricted to 'nude only' sunbathing. We had visited the island a few times and on our last day at the resort we thought we would head over there for some last minute sun. To my pleasant surprise the couple from the catamaran was there, sunning by the pool. I can't recall anything about the gentleman but I can tell you the woman was stunning. I would guess she was in her late forties give or take a few years. We chatted for a bit and then my friend and I retired to the lounges for a bit more sun before catching our shuttle to the airport. The woman then came over and chatted with us there.

Looking back, I think all the indications were there. I wish so badly I had asked for contact information for when we returned home. In the worst case scenario I would have been told no and we were leaving. My companion wouldn't have cared a bit. I think about this encounter often and wish I had taken the chance.