Her [male best friend/coworker/boss] has been interested in her for awhile, but she's always resisted crossing that line. But when several things go wrong in a row, she's in need of a good amount of money that she doesn't have. She knows he'll lend it to her, but there's gonna be a cost. He'll give her the money, but she's his for the weekend, with very few limits. When she agrees, he surprised her by giving her the best sex of her life.
Looking for someone to play the male in this line. Would especially love the version with her boss, possibly played by Jeffrey Dean Morgan (but I'm open to others), with a bonus where it can/does develop into a sugar daddy type situation. I'd also be open for the male best friend version becoming a relationship after.