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Edit: Found it through inquiries at a romance novel forum; it was "The Bartered Bride", by Mary Jo Putney.
Hey, I just wasted a couple hours searching for this book to no avail after it suddenly popped back into my head; I believe I came across a review or plot synopsis online about 5 to 10 years ago and it stuck in my mind, but I don't remember the title or the context in which I found it. I do remember quite a few details about the plot, though, although I haven't had much luck using any of this as search terms.
I think this was a romance novel, although it might've been more in the adventure genre. The protagonist is an English (or possibly American) businessman of some kind (I think), who travels to another country (I think some kind of carribian island) on business. The local boss he's talking to (I think some kind of Sheik or Emir, or maybe just a rich businessman) is showing him around, and when they're passing through the slave market, a woman catches his eye because she's English/American too. That night, he finds that the boss has left the woman in his hotel room in her threadbare garments as an intended bribe through sexual service, having noticed that she'd caught his attention, but the protagonist has no interest in taking advantage of her. I believe here the woman tells him the story of how she was forced into slavery in a foreign land and begs him to help her escape.
The protagonist goes to the boss and tries to buy the woman's freedom, but the boss, taking advantage of his concern for her, won't simply sell her, and makes the man agree to a bet. The protagonist must attempt to pass a series of challenges, each randomly selected by dice; if he succeeds, he will win the woman's freedom, but if he fails, he must offer him favorable business concessions. The protagonist accepts, and goes through a series of challenges, including I believe fighting a tiger and drinking the boss under the table. Eventually, the final (or perhaps penultimate) challenge ends up being to bed the woman in public, and although the protagonist wants to forfeit to spare the woman from further disgrace, she's been through so much already that she wants him to go through with it. That's where my memory of the plot synopsis cuts off.
I can remember these details so clearly, but just not enough unique details or exact wording to find the book through searching. If anyone can help me at all, I'll be grateful!
Edited by SSDG