Grand Prize Winner Fantasy

This is a fun fantasy scenario for almost any type of bondage, experimentation or prisoner fun that can go in a wide variety of directions.

I never win anything so I was very surprised to get a call that I had actually won something. Not just anything but the grand prize in one of those big giveaways for one of those dating sites you see on TV. I had just broken up and wanted to get back into the dating scene, but hadn’t had much success with it yet. They said I had won a free trip to a beautiful exotic island resort in the Pacific. Usually these type of things allow you to bring someone I thought but this one specifically said it was just for one person and wasn’t transferable. It did seem a little odd that it was just for one person, but it was from a dating site so I figured it did make some sense. I didn’t really have anyone to bring though so I didn’t care and they made it sound really beautiful.

It wasn’t until I got there that things started to get a little strange. It was a private island and I had to take a boat to get there. That is okay but I expected a larger boat. This looked like a little more than an outboard motor fishing boat. There several boxes of supplies on most of the seats and only one empty directly in front of the operator. The driver smiled a lot but seemed more than a little creepy and I had the feeling he was watching me the whole time.

We bounced along the waves for at least two hours and finally pulled up to a small empty dock. He pointed to the buildings up beyond the beach and as he helped me with my bags I looked around wondering why there weren’t any other guests on the beach. He told me to relax in a large sitting room that was open to the beach and that the owner would come to greet me in a little while. He offered me a drink which I gladly accepted. It had been a long trip and I sank down into a large lounge chair and must have fallen asleep. When I woke up…