Every time Anthony would make his rounds I made sure to be obvious that I was checking him out. I complimented him on the fit of his pants and how strong he was when he brought out another case of beer for me. I didn’t even try to be subtle. He was a man after all, and I had a suspicion he was a top from the way I caught him checking out my ass when he got a chance. I started having fantasies of what it would be like to have such a muscular, hairy Greek man lying on top of me, pressing his weight down onto my body, and eventually working his cock into my hole.
When the night finally started to wind down close to 2AM, Anthony walked behind the bar and half-whispered into my ear, “Why don’t you settle the register and bring everything back to me in the office?”
“Sure thing, boss,” I said, grinning and letting my gaze settle onto his hairy chest for good measure.
I gathered the cash from the register after the bar closed and walked back to Anthony’s office. I knocked on the door, and when I heard, “Come in,” I entered.
Anthony was sitting behind his desk with a big smile on his face.
“Just set the cash here on the desk,” he said.
I did as requested. If I could get him to trust me, I could find out if all of this cash gets reported.
“Thanks again for letting me join your team. I had a great night. The tips were amazing!” I said, dropping more compliment bombs.
“Why don’t you shut the door for a minute?” Anthony said. “Let’s talk about how things went tonight.”
“Sure,” I said, knowing that talking probably was the last thing on his mind.
I shut the door and stuck my hands in my pockets. Even though I was getting close to my mid-twenties, I knew I could still look like a teenage boy and how that hardened the dicks of a lot of total top guys.
“Did you have everything you needed tonight?” he said. His eyes examined me from head to toe.
“I did,” I answered. “Everyone was very helpful. All the guys who work here are so hot, but…”
“But what?” he asked while stroking the stubble on his chin.
“I’m a little embarrassed to say it,” I said. I tried to give my best innocent, boyish look.
“You can feel free to say whatever you want, Oliver.”
“Well…I think you’re definitely the most handsome man here,” I said, letting my eyes drift down to his crotch.
“Oh, really?” Anthony said, cocking an eyebrow.
“Yes,” I replied. “I hope it’s okay that I said that.”
“Of course it is.”
“You’re just so my type,” I said. And it was the truth. If I hadn’t been there to investigate him, I would have been wondering if he was single.
“You’re cute. You sure I’m not too old for you. I am getting close to forty,” he said with a sly smile.
“I think you’re perfect,” I said, and I meant it at least when it came to physical attraction. “This whole night I’ve been thinking about…”
I paused for dramatic effect.
“About what?”
“What you taste like?” I answered, and then looked away as if I had suddenly gotten shy.
“You want to taste me?” he asked, spreading his legs while seated in his chair.
And I did. Even though I was undercover, that part wasn’t a lie.
“I do. Badly.”
“Why don’t you lock the door for a moment?” he suggested.