But what did that mean for Cal and me? I quickly found myself playing a big round of what if.
What if we tried dating? I owned my own plane. We could visit each other whenever we wanted. Hell, he was between jobs. Maybe he could find something in Chicago. Maybe I could put him in touch with the Northwestern Sailing Center.
I pictured him bundled up in cold weather gear October through May when the sailing center was closed to actual sailing. It wasn’t ideal, but then again, how long was the sailing season in Hobie?
What if we didn’t date, but we simply met back up here a few times a year for fun in the sun and sheets?
I could do that. In fact, that would be perfect for me. The rest of the year I could focus on work and then maybe once a quarter take a break and enjoy Cal’s company on the ship. Surely, that would be enough sex and fun to tide me over until the next visit.
But what if he started dating someone else?
Okay, the what if game was going in an unpleasant direction, but I’d humor myself. If he started dating someone, he wouldn’t want to meet an old man for sex anymore. That would be disappointing. So much so, my stomach hurt even thinking of it.
But no. That would be good, actually. I wanted him to find someone. He deserved it.
I pictured him with a man closer to his own age. What if the guy didn’t like sailing? Or what if he didn’t support Cal’s love of it? What if he tried convincing Cal to get an office job in the city?
You mean like the one you have in Chicago?
I sighed. He wouldn’t be happy in a place like Chicago. I couldn’t even picture him in my penthouse apartment with its windows covered in sun-blocking film and the climate controlled precisely by a home-management system.
What if I changed? What if I was the one to move for him?
I let out a soft laugh. Me, Jonathan Worthington, billionaire venture capitalist and son of the country’s largest agribusiness conglomerates, chucking it all to move to Podunk, Texas—or god forbid a boat in the islands somewhere—to follow a twenty-three year-old-camp counselor.
Now who was being ridiculous?
I packed all of the thoughts away in a little box labeled Don’t Be An Idiot and turned my focus to the funding deal I’d just green-lighted. My assistant had already reached out to the attorneys to start drawing up some contract language, but I needed to be the one to start drawing up a potential path to IPO to present at next week’s meeting.
As I thought through our goals for the deal, I played with Cal’s hair, lightly scratching his scalp and pulling my fingers through his spiky locks as they dried. Eventually, he woke up enough to make appreciative noises.
“We should probably get up,” I suggested. “Julo was already setting out appetizers when I came down here.”
“Mm, I’m hungry, but I don’t want to move. You feel too good.”
I leaned down and pressed a kiss to his head. “Thank you for teaching Lucas today. Maybe if he falls in love with it, I can trade this ship in for something with sails.”
“I don’t want you to get rid of this one though,” he murmured. “I like it. Besides, it’s where we first met.” He opened his eyes and batted his eyelashes with a teasing look.
“Ah,” I said, trying to ignore the unsteady feeling in my gut, “I see. Maybe we should dip the ship in copper and display it on my grandma’s dresser like the pair of weird baby shoes she always kept there.”
“Yeah, what’s with that? My grandfather has those, and it’s creepy.”
I lifted his chin up and kissed him on the mouth, wanting to get a taste of him again before spending the next few hours around everyone else. Within seconds of fusing our mouths together, Cal crawled on top of me and began gently thrusting his hard cock into my side. I reached down to stroke it. We could fit in a quick frot before getting dressed, and it would go a long way toward calming down my wayward thoughts.
Just as I was turning to reach for the lube to help smooth the way, Cal’s phone rang.
“Ignore it,” he said, taking over the search for the lube in the drawer. I squeezed his ass as he fumbled for the bottle. After he pumped some into my hand, I reached down and gripped both of us together, slicking our shafts and lining us up better. Cal began sucking on my neck and chest which made me ten times harder.
“That’s it,” I said, unsure of whether I was talking to him or myself.
His phone rang again.
“No,” he said. “Keep going. Close. Feels so good.”