Last summer, the company I work for hosted a conference in New York City. I'm based in their west coast office, and though I think I live in the greatest city in the world, I was excited to spend a few days in New York. I looked forward to taking advantage of some cultural experiences not readily available in San Francisco. Broadway shows, the best jazz clubs in the universe, and oh yeah...Yankee Stadium.
The conference itself was predictably boring. Sales and marketing strategy meetings, corporate pep talks, etc. On the next to last day, I attended a marketing break out meeting with about 20 other reps from offices across the country. In an effort to stay awake that afternoon, I found myself fantasizing about a woman from the Boston office who was seated across the large table from me.
Her name was Shay. She was thirty-something, stunning, and very tastefully dressed. While I sat and listened to a marketing VP drone on about whatever he was droning on about, I thought about Shay's fingers wrapped around her pen, and what they would feel like wrapped around my cock.
I am as subtle and discreet as the next guy, so of course Shay busted me at least twice while I was checking her out. She gave no reaction whatsoever. I assumed that she was fairly used to guys checking her out. Anyway, no harm, no foul.
When the meeting ended for the day I remained in my seat momentarily, as the Shay-induced boner in my pants prevented me from jumping straight up. She collected her things and gave me a quick glance before she turned and walked from the room. I watched her ass all the way out the door, which only made my boner situation worse. I pretended to look over my notes until I could stand up without drawing attention to myself.
Much later, I returned to our very nice Times Square hotel from my solo evening out. I took the elevator to the 21st floor where the hotel bar was located. One nightcap to top things off, I thought. As I walked through the bar, I saw Shay and two other women whom I recognized from the conference seated at a table. I waved, and was somewhat surprised when they waved back. They looked happy and a little buzzed.
I went to the bar and ordered a wee dram of single malt, and told the barman that I'd like to buy a round for Shay and her friends. He told me that he'd bring the drinks over.
"Hi, you guys." I said as I approached their table. "Mind if I join you?"
"Please do." answered one of Shay's companions, an older woman whom I recognized as being from the Boston office as well.
"My name is Ben and I'm from San Francisco." I said as I sat down.
"We know!" blurted Shay's companions in unison, breaking into laughter. Yep, they were buzzed.
We covered the rest of the introductions. For her part, Shay was a bit more reserved. The drinks arrived and the women told me about the Broadway play they had seen that evening. Shay added her comments in a quiet manner. I had to lean forward to hear her.
"And you? What have you been up to tonight?" asked Tina, the older woman who had taken on the role of conversation ringleader.
"I took the train down to the Village. Saw Tom Harrell at the Vanguard." Blank stares from Shay's friends.
Shay looked right at me and said, "He's one of my favorite trumpet players. I didn't know that he was in town. I'm sorry I missed him. "
"He's playing there for the next three nights." I said.
"I'm flying home tomorrow." answered Shay.
We continued the fairly pleasant banter until the other two women finished their drinks and got ready to leave.
"We're heading up. Are you coming, Shay?"
"Not yet. Just going to finish my drink. I'll see you in the morning."
"Okiedokie." said Tina the Ringleader. She gave me a quick but very obvious raised eyebrow, as if to say, "Lucky boy."
Shay and I talked about music for a bit, and then I asked her what she thought of that afternoon's meeting.
"I found it every bit as boring as you did."
I looked at her and asked, "You caught me checking you out, didn't you?"
"Yeah, you and about seven of the other guys. At least you weren't making googoo eyes at me like Chad, that annoying fuck from Chicago."
"Mr. Smooth."
Shay chuckled, "Whatever. None of you guys were exactly discreet about it. I noticed that you didn't leave with everyone else. Feeling a little stiff were you?" Shay laughed again.
She lifted her glass to her lips and continued, "Actually, I was checking you out too." She took a sip and paused for a moment. I let her go on.
"I was thinking that I wanted to stand up and walk around to where you were sitting. I wanted you to take my clothes off and fuck me right there on the conference table. In front of everybody."
