The Prince of Chicago

Chapter 11

Isabelle

After being led back to my room, and locked in of course, I had about an hour to kill before the 6pm dinner Rose mentioned earlier. Man, one of those books from downstairs would’ve been handy right about now. Or a TV. Or something! I also hadn’t had my phone since I arrived, for obvious reasons. I’m sure Angelo had it stashed somewhere. It’d been over three days with no contact to the outside world. Then, I realized something: Marie.

I rarely went more than a day or two without talking to Marie. Plus, when I had left the club Saturday night, she told me to text her when I was back home, which I never got the chance to do. Surely, after over three days of silence from me, she’d be sounding the alarm bells. Hell, she was probably tearing up the city by now looking for me.

For the first time since I had gotten here, I breathed something close to relief. Someone was out there, worried, looking for me. And that someone just happened to be one of the most headstrong people I had ever met. I was sure that if I couldn’t get out of this myself, Marie could get to me. She had to.

But then again, who’s to say I couldn’t get out of this myself? After today, I felt like I had a window inside Angelo, one that I hadn’t had before, and one that was of the utmost value. He seemed to be warming up to me a bit, or at least attempting to, and he responded positively to many of my jokes and banter. Could that be the key?

While I had considered making a run for it while downstairs, I was glad I hadn’t after more thought on the matter. Yeah, I’d been left alone in the office, but even if no one was outside the door, or even in the penthouse, I was sure there were men close by. Angelo wouldn’t be stupid enough to leave himself unprotected, let alone a witness who could end everything for him. I would never have gotten far enough to actually escape, and my life was still on the line. If I proved to be too much of a problem I’m sure they’d have no issue in silencing me permanently. No, running in the traditional sense wouldn’t be a good option.

I shuddered at the direction my thoughts had taken me, then flopped myself down onto the bed and stared at the ceiling, sorting through the day in my head. The one thing I knew for certain was that Angelo would never let me go if he didn’t trust me to be out on my own without bringing him or the Outfit down. Trust was the leverage I needed to gain my freedom. And while I wasn’t sure how exactly I could most quickly earn that trust, I did know that having him warm up to me was the best start I could get.

And that moment in the doorway of the filing room today - I swore I could’ve seen lust painted in his eyes. I’d pegged Angelo as a playboy for sure, but I’d never considered how this trait could positively impact me. If I could get him to want me enough, then I could leverage that to gain what I wanted: my freedom.

A plan slowly emerged then. I’d befriend Angelo, to build a rapport with him, maybe even go beyond friends if I had to – and that would be the ticket to getting out of here. It wasn’t going to be easy, but I was pretty sure I knew his weakness now, and that was all that I needed. I’d need to play the playboy.