Raffle Girl
Copyright© 2025 by Lorn Skye
Chapter 15: Sailing
BDSM Sex Story: Chapter 15: Sailing - Dr. Sam White was not lucky. He had never won a single thing in his entire life. His colleagues at work had convinced him to attend a fundraiser for some cause that he knew nothing about. And suddenly, he won. The prize was not at all what he expected! Join Sam as he journeys from confirmed bachelor to the luckiest man in the world with a bevy of beauties surrounding him. ~43000 words
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Slavery MaleDom Anal Sex
The next couple of days were idyllic. We frolicked and played, the Bahama island way, sailing in a nudist wonderland.
Jokes and bad singing aside, we had a wonderful few days. We ate great food, swam in the beautiful clear water, saw some amazing wildlife, and drank beer and rum that seemed to flow endlessly. The only time we put on clothes was when we were near towns or the couple of times that other boats called on us to say hello.
Our days started in bed, with Eve and Olivia making sure that I was well-sated before I got out of bed. I would usually go for a quick swim and rinse off, and when I was done, Alex would usually have coffee ready for me, and we would sit in the cockpit and enjoy the quiet as we were usually the only two awake.
Alex and Angela had no problem with our nudity. In fact, they were usually just running around in bikini bottoms and a loose wrap to provide some sun protection. When we were underway and they were working, they might be in athletic wear to facilitate the work they were doing.
But they had no issue with our nudity, and so we wore no clothing.
The best part of that to me was getting to rub sunscreen all over Eve and Olivia, especially over their sensitive parts. While Olivia was of Italian heritage and tanned easily, Eve was a bit more sensitive to the sun with her pale skin, and I worked hard to make sure she didn’t get burned.
Besides, rubbing my hands all over her nubile body multiple times a day was a joy all in itself. And even though Olivia didn’t really need the protection, I just had to do the same to her when I applied sunscreen to Eve.
Of course, they had to return the favor.
Eve’s favorite way to ensure I was well protected was to squirt a large glob of sunscreen on her cleavage and then rub herself all over my body.
And somehow she always needed to make sure my cock was well coated. I suspect that she enjoyed the aftermath where I flipped her over and fucked her thoroughly.
After four full days of non-stop sun, swimming, sex, and sipping sun-downers, we needed a break.
Angela sailed us to Georgetown, and we all got dressed and headed into town. Eve and Olivia wore cute little sundresses with tiny thongs underneath them.
They enjoyed walking in front of me and flashing me by flipping up their dresses.
And of course, I made sure to grope them at every opportunity.
We all had fun shopping at the market. We bought some hats, a few mementos and knick-knacks. Then the girls found a swimsuit boutique, and we spent a couple of hours with the girls trying on swimsuits and modeling them for me.
We drew a small crowd, and the girls enjoyed the attention. Olivia, while initially a bit shy, quickly found she enjoyed the attention, and Eve’s enthusiasm and natural exhibitionism rubbed off on her.
I ended up spending a small fortune on clothing that likely wouldn’t get worn a lot, but I must say I enjoyed the show quite a bit.
As we were leaving, a very striking woman approached us. She was tall and lean, and Eve immediately recognized that she was wearing a very ornate collar that locked around her neck.
“Hello Sir. My Master would like to invite you and your companions to dine with him this evening.”
Her voice was captivating, a beautiful blend of Bahama and British English. She had a lovely lilt, and when she spoke there was a musical quality to her voice.
“Who is your Master?” I asked.
“He is Johann Orlov, Dr. White, and he would like to discuss a business proposition with you. When he heard you were in town, he sent me to find you.”
She paused and looked over at Eve and Olivia.
“My sisters will be well cared for and pampered while the two of you speak, and my Master has arranged a guard for Mistress Angela’s ship so they can also have a night off.”
Johann was a bit of a name in the venture capital world. He had a reputation for shrewd investments that made a lot of money. I had worked with him on a couple of deals, but where I mostly focused on the biotech space, Johann took on bigger bets in more diverse fields, from pure tech to energy, to banking and business mergers. A potential business deal could be very profitable, and shunning such rich and powerful people was never a good idea.
“Please inform Mr. Orlov that I am happy to accept his invitation. Can you please send us the details of the meeting?” I replied.
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