Raffle Girl
Copyright© 2025 by Lorn Skye
Chapter 1: I Won?
BDSM Sex Story: Chapter 1: I Won? - 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
I’m not sure how I ended up in this affair. A friend of a friend invited me and explained how they were raising money for some cause that he thought was worthy. Even after he had just invited me, I couldn’t have told you what cause we were supporting.
I’d come, because I didn’t have anything better to do this evening, and I was trying to be more social, after, essentially, being a hermit during the pandemic. I’d gotten rather used to spending time at home alone. Sure, I was on video-conferences all day, so I talked to a lot of people, just not face to face.
I enjoyed being able to go for a run after work, eat some dinner, and read, or watch a movie, before heading to bed. It was comfortable and familiar, but it was a little lonely.
And so it was, that I found myself at a luxurious estate on the north side of the city with a view out over the lake. I’d taken a car service and the driver promised to be in the area for the next several hours. I think he had a ‘friend’ that he was going to visit.
After arriving and getting a drink from the bar, I found myself chatting with a couple of people who I had overheard talking about baseball. Since I was a huge Blue Jays fan, I had joined in, as we discussed the latest trade that had been announced that morning.
When the young woman came around selling raffle tickets for a hundred dollars each, I had bought a hundred tickets. I had the money, and I had come to help raise money for whatever fund it was that this party was intended to support.
Of course, this prompted the others in the group to also buy a few more tickets than they had probably planned, so I felt like my donation was already multiplying! The girl selling the tickets was blown away by my purchase, and I wondered for a moment if I had overdone it.
“You must really want to win her!” the girl said as she sauntered away.
I really should have paid more attention to the rules and the causes that were being supported!
The rest of the evening went as these things typically go. There was a lot of drinking and schmoozing going on. Dinner was served, and it was rubber chicken, or stinky fish, as usual. Word got out that I was an investment manager for a large venture fund, as it usually does, and the number of people who wanted to chat with me, and gave me their card, went up dramatically. It seems like I never get to just be social at these things!
Finally, the host took the stage to thank everyone and announce how much they had raised. I was relieved the evening was coming to an end and I was ready to head home.
The host announced a few minor prizes, there was a spa day that someone had won, and there were VIP tickets to some club I had never heard of before, and finally, a shopping spree at some boutique that I was sure was quite expensive, based on the amount of money that was announced as part of the price.
And then it was time for the grand prize winner to be announced. But before they could announce the winner, they had to thank everyone who was part of the organizing committee, and the caterers, and Tom, Dick, and Harry too.
I was getting impatient and was just about to call for my driver when the announcer said, “And now for the Grand Prize Winner!” And then he said my name! “Your winner tonight is, Dr. Sam White! Come on up here Dr. White!”
I had already been primed to stand and leave, and so I just naturally stood, even as the other people around the table started congratulating me. But then they were also saying weird things like, ‘She sure is beautiful,’ and, ‘Better take your Viagra,’ and even, ‘Hope you survive the night!’
I never win anything, I mean never. I’ve never won a single thing in my life. Sure, a game of skill, like bridge, I might win, but my luck is so bad that people refuse to go to Vegas with me, for fear that my bad luck might rub off on them somehow.
I once bet on a football game and the team I bet on got the flu the night before, so they were starting players who hadn’t played in years. That is what my luck was like.