Bet On It: An Age Gap Billionaire Office Romance(5)

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Reed—one month later.





I really shouldn't complain. How many men in the world could make money hand over fist in business while spending the morning in their office drinking coffee and watching the hockey highlights from last night’s game?

I bet there were many who couldn’t, yet here I was, sitting at my desk while I watched the home team star player, Bo Tyler, score two goals on the big-screen TV in my office. I justified having the TV because as CEO of a billion-dollar daily fantasy sports site, I needed to know what was going on in sports. It was a fucking fantastic excuse to watch TV.

At the end of the game highlights, the commentators switched to showing Bo’s after-game antics in which he was caught celebrating his success by getting drunk and sneaking onto a golf course to play drunken golf with glow-in-the-dark golf balls.

I shook my head as I watched him get escorted off the course by the golf club’s security. I smiled wryly, wondering how my best friend, Pierce Jackson, coach of Bo’s hockey team, was faring this morning. He had to be happy about winning the game, but he wasn't going to be thrilled about Bo’s nocturnal golfing habit.

I clicked off the TV, tossing the remote on my desk. As I looked at all the paperwork scattered on it, I had to remind myself again how lucky I was. As the owner of the number-one daily fantasy sports company, I made more money than I could ever spend in my lifetime.

My kids—hell, my grandkids—probably wouldn’t be able to spend it all. Not that I had kids or grandkids because I didn’t and it was unlikely I ever would.

My dating life was shit.

I was a forty-five-year-old ex-hockey-star turned billionaire who couldn't find a woman who would stick. And it wasn’t from a lack of trying.

During my hockey days, I didn’t date. I hooked up. But once my business hit a million dollars in net worth not long after I started when I was forced to retire from hockey, I decided I’d find someone to share my newfound wealth. But every woman I dated dropped off the radar after a few dates. It was annoying, although today, I couldn’t remember much about any of them, except for one.

Analyn.

Ever since that night a month ago, she had become my fantasy sex sport, starring in my dreams and my daytime jerk-offs. I couldn't quite pinpoint what it was about her that stuck with me, compared to the other women I had dated.

Yes, she was beautiful and sexy, but so were the other women. There was something sweet and vivacious about Analyn. There was an authenticity about her that was refreshing. She said what she thought and didn't act with any guile or pretense.

When she'd first come to sit next to me at the bar, I wasn't sure what to think. To be honest, I wasn't in the mood to be picked up by a woman. I went to the bar to lament, as had become my habit, on how boring my life had become. I wasn’t sure I had ever gotten over the fact that my hockey career came to an end earlier than I would've liked due to an injury. Now I was a billionaire with the world at my feet, but I was alone and bored out of my gourd by life.

Sometimes, I thought I should have gone into coaching, like Pierce had. But at the time, I didn't think I could handle watching all the players on the ice and not be able to skate with them. Hockey had been my dream, and then my life, and then it had all come to an end.

Of course, I understood what a whiner complaining about my charmed life made me. When I quit playing hockey and started my business, my dissatisfaction only continued to grow. I thought maybe if I were to find a good woman and have a family, that would be the answer. As it turned out, finding a good woman wasn't so easy.

Now, over ten years since my forced retirement from hockey, I was still unmarried and childless. There must be something wrong with me that after a few dates, the women would disappear. It took Analyn one night. I woke up the day after having the most amazing sex I’d had in a long time, maybe ever, ready to fuck like rabbits again, only to find the bed empty. The disappointment was acute.

But it wasn't just that there wasn't going to be any more sex with her that bothered me. I really enjoyed her company. I would've liked to have seen her again. I was aware that she was from Chicago, but maybe I could have flown out to visit her or flown her here to visit me. On the one hand, it seemed like a lot of work to date a woman long-distance, but since she was the first woman in a long, long time to get me out of my funk, it would've been worth it. Imagine the phone sex!

But it wasn't to be. Not only had she left while I was sleeping, but there was no note. I wondered what happened when she woke up next to me. Had she regretted it? Had I done something to offend her? Maybe in the early morning light, without the haze of alcohol, she realized how much older I was than her. I had to be at least twenty years her senior, practically old enough to be her father. I shook my head free of that thought because it was disturbing.

The intercom on my desk buzzed, pulling me out from my ruminations. I poked the button. "Yes, Catherine?"

"I just want to remind you that you're interviewing for the new social media marketing manager today. The first candidate is in twenty minutes. Would you like me to bring in the file for the applicant now?”

I scraped my hand over my face. Sometimes, I really hated my job. "No. I'll look at it when it's time."

"Very well."

The line clicked off, and it occurred to me that Catherine often spoke to me in a tone that made me feel like she was disappointed in me. Considering I was a billionaire who spent his day whining, I couldn't blame her.