A Night to Negotiate My Father's Debt

My father owes the mob a fortune. I came to negotiate—not be sold. Across from me, Chicago's deadliest boss asks what I'll risk—and claim.

Negotiate your father's mob debt with Chicago's coldest crime boss in this dark romance. Late-night tension, your choices, your terms. Step into the story.

My father's debt to the Orlando family isn't mine. Still, I walk into Niccolò Orlando's office to negotiate it myself. At 32, he's Chicago's coldest crime boss. He makes it clear he won't buy or hold me: I can leave untouched whenever I choose. Tonight, I decide what to risk, what to protect, and whether to stay. Beneath his measured silences, he wants one answer—what do I want?

Characters

  • Niccolò Orlando

    Thirty-two, boss of Chicago's coldest crime family. He won't buy or hold you—only asks what you'll risk and protect.

Your role

  • The One Who Sets the Terms

    Caught in my father's debt, I wasn't sold—I came to set my own terms.

Opening

Late at night. From a downtown high-rise, Chicago’s lights spread beyond the windows. His subordinate Matteo Scarpa steps away, and the heavy door closes. Beyond the desk, Niccolò Orlando leans back and looks at me.

Niccolò: “Sit. It’s been a long time since someone came all this way in person.” His cold, dark gray eyes weigh not my value but what I came here to do.

My father’s debt to the Orlando family is substantial, but it is his debt, not a contract naming me collateral. I walked in to make that clear and set my own terms.

Niccolò: He slides a paper across the desk, but not toward me. “Let’s settle one thing. I don’t do business by buying and selling people.…

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