Page 9 of A Bossy Affair


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“I can and I am,” he said. “It’s my job. I look after you, like I promised your father and like I promised you when you came in. I will tell you the things you don’t want to hear. And while this has never been a problem before, I am just stating that it could be a problem now. I want to make sure you make your decision knowing that.”

“I think I can handle this,” I said. “I’m good.”

Shrugging, he stood.

“I would caution against any hint of impropriety. Even a whiff of it could be enough to make investors uneasy. They already reluctantly agree you are as successful as you are because of your talents and drive. Don’t give them another reason to doubt you.”

“Got it,” I said, effectively ending the conversation. Bobby knew when to stop.

He headed for the door, and as I watched him go, I wanted to be angry with him. How dare he question my ethics?

But he was right. I liked the girl. More than just as a potential employee. She turned me on. Not one woman had turned my head like she had in a long time. Usually, I just went to the club and let natural selection work itself out. Someone would eventually end up in my arms, I would spend the evening entertaining myself, and then I would leave her while she slept in the hotel room, making sure the bill was sent my way.

Yet Julia, she was something else. I was going to have to think about this one. I needed to source the opinion out to more people. Specifically, my best friends Leo and Sean.

I pulled out my phone and texted them in our group chat. Both guys were also successful entrepreneurs. Sean was the CEO of a major chain of hotels up and down the east coast, earning him the nickname Junior Hilton. Leo ran a multi-media conglomerate, one that was extremely influential in pop culture and news, meaning that he was one of the most important people on the planet, even if very few people knew it.

Me: Pepper House? Seven?

I got a response almost immediately from Sean.

Leo: Already here, bud.

Sean: On my way in about twenty.

I looked at the clock. It was just before four.

Me: You two are already done for the day?

Leo: Yes

Sean: Yup

They both replied, almost at the exact same time.

I had to laugh. As much as Sean especially was as driven as I was, he was also a bit keener to establish a cutoff time for work. While I would stay in the office all hours of the night, Sean believed heavily in getting eight hours of sleep, at the exact same time, every day. It probably had to do with being a hotel owner, and their whole MO being about sleep, but it was rigid for him. It meant that he clocked out at three sometimes and took his work to his indoor pool and called into video meetings in his swimming trunks.

Leo was… brasher. He had a crude sense of humor sometimes, something I chalked up to being around crew members all the time. As a young man, he had started out looking into being a television personality, but found his real talent was behind the scenes. It didn’t take him long before he was running his own media empire, mostly entertainment, but also some gossipy news stuff. Recently, he bought a group of syndicated channels, including their nightly news programs in local areas, and was dabbling in becoming a major mover and shaker in that field.

Both of them, like myself, were billionaires now. The Boston Billionaires or the Three Musketeers or whatever the local media liked to dub us, we were incredibly wealthy, successful, and loyal to each other.

Fuck it, I typed.I’ll be there in twenty too.

Packing up my stuff, my phone dinged a few times, but I ignored it until I was heading out to the parking deck. Most other folks had drivers, and I had a couple that would arrive anywhere I asked them to be at any time, but I preferred to drive when I could. Going to the Pepper House wasn’t much of a drive, just a few miles through the busy business district in north Boston, but I relished the chance to get behind the wheel.

When I pulled up, Sean’s and Leo’s limos were waiting in the parking lot. I could tell which one’s were which by the license plates, a vanity neither of them could escape. S3ANLMO and LEOLIMO. Creative guys those two.

Sean saw me across the room and held up his drink. The Pepper House was less like a bar and more like a giant study. Just a study with waitstaff, gourmet food, and fine whiskey. There were traditional tables for eating in various places, but for the most part it was filled with clusters of high-backed leather chairs and couches. It was a place where informal business deals could be made. It was also a place where men—as it was almost exclusively men—could come and drink alone or with colleagues and read in relative quiet. Off to the side and down some stairs was even a more traditional bar area with giant television screens to watch whatever sport was on. Often, Sean, Leo, and myself were the only ones down there.

“How are you, my friend?” Leo asked, slightly too loudly for the atmosphere, but completely expected volume-wise.

“I’m fine,” I said, taking a seat and accepting a drink from the waitress who knew me by sight. I always started with a Sam Adams, slowly moving to whiskey the longer I stayed. The glass was cold and reassuring in my hand. It represented a day done, though my thoughts were still racing. “I have some stuff to ask you guys.”

“What’s up?” Sean asked, tipping back his Bloody Mary. It was his traditional first drink, though he often moved over to whiskey as well.

“I’m looking for a new assistant,” I said. “I had someone come in, and, well, she’s perfect for the job.”

“Bully,” Leo said.

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