My co-worker, Sally, and I had just finished running a training workshop in Miami for 75 nonprofit managers. We were working on pure adrenaline after four 18-hour days in a row, but happy as hell because it had gone so well. Our flight home wasn't until the next day, so we went back to our hotel rooms and changed clothes for a night out to celebrate.
As we were waiting for the valet to bring the rental car back around, Sally said, "Jill, don't turn around right now, but the guys at the bell stand are checking us out. I guess we don't look too raggedy after all!" We were headed to a little jazz club down the street that had been the favorite hang-out for some of our workshop's participants.
I casually glanced over my shoulder and caught one of the bell hops leering at my legs; I was wearing a short white linen skirt and sleeveless blouse. As flattered as I was, it reminded me that it had been a long time since I'd been unattached and away from home.
My boyfriend and I had broken up a few months before. After three years, we both knew we would never make it in the long-run. I had done my grieving and then lived a nun's life spending all my time at the office to prepare the workshop. Sally and I had worked together for five years, climbing the corporate ladder and ending up managing our division. We had been teaching eight workshops a year together, always on the road, and Sally was the only one who ever got to indulge herself when we traveled.
She was a party girl, and good-looking. Her mother was Italian, and Sally had long black hair, a curvy figure, and olive skin. I had been living vicariously through her for years. She loved to kiss-and-tell, right down to the last spine-tingling detail, and I loved to listen. She was a little wilder than I had ever been, but I was ready to let loose that night.
"Sally, you know you look good in that little bitty dress, and that's why you put it on. You look like you've got some serious plans for the night," I said.
I couldn't help but laugh as Sally shot me a mischievous look while we got into the car. "Yeah, I've got some serious plans," she said. "I am seriously going to make sure that you're the one with the story to tell tomorrow." She started laughing like she knew something I didn't, and I wondered for a second what I was getting into.
We headed down the street to the club. When we walked in, the band was playing classic jazz, but the percussionists were giving it a funky Latin treatment. Sally and I were looking around for a table when someone - a tall someone - stepped up behind me and slipped an arm around my waist, pulling me close into him. I stiffened and almost stepped away, but I recognized John's voice when he leaned his head down and quietly said, "I've been wondering for years when I might get to spend an evening out with you. Is this my lucky night, Jill?"
John and I had known each other since I'd been at the company. He was a consultant we brought in to teach part of our workshops. We lived near each other, but we had only seen each other at planning meetings or conferences. He was a genuinely nice, handsome guy - he had a rugged look that I really grooved on - and I'd had a crush on him since I'd known him. I'd felt school-girl bashful about it, and had only flirted with him a little. I never had a clue that he might be serious about it.
Sally had told me that he and his wife had "an open relationship," and that she knew his wife and knew that it wasn't some kind of Lothario BS he used to get into other women's beds. He'd never done any prowling at our workshops, but we'd heard stories now and then that had piqued our curiosity. John was more of a fun little fantasy than anything else; my ex-boyfriend and I had been monogamous, so I'd never pursued anything with him.
It took me about two seconds to decide. I leaned back into him and turned my face up to his, put on my best sly come-hither look, and said, "Actually, I think tonight is my lucky night. Good thing for you that I know how to share." I figured it was now or never, so I got bold - bold for me, anyway. I stood up on my tiptoes and tongued the underside of his jawline where it met his neck, and I felt his cock instantly harden against my back. "Mmmm. What a nice surprise!" he whispered. "This oughtta be even more fun than I imagined!"
He took my hand and guided me over to his table against the wall, and he ordered a couple of double rum punches while I scanned the crowd for Sally. She gave me a big thumbs-up, and I could tell by the look on her face she and John had talked about this. No wonder she told me to change out of the blue jeans. The drinks arrived, and after a few more rounds and an hour of good music, feeling the heat coming off his body, him stroking my thigh ever so lightly under the table, I was so aroused that I could barely think.
"Is it OK if we head out of here?" I asked him. "I can't take any more of this."
"Whatever you want," he said. "But we have to get Sally first; I promised her we wouldn't leave without her."
The short ride to our hotel seemed to take forever. Sally was sitting up front, and her victim of the evening, Adam, was driving. I had slid as close as possible to John in the back seat, and he had one arm over my shoulders, caressing the top of my chest, while his other hand rested in my lap. The entire trip back, he rubbed one finger from the top to the inside of my thigh along the hemline of my skirt. Every now and then he'd sweep it beneath my skirt and skim my panties. I was barely able to breath by the time he worked his other hand into my curly blond hair, slipped his finger under the edge of my panties, pulled my ear to his mouth and said, "Oh, this is going to be so good."
With that, Sally turned around and smiled - not at me, but at John - and asked, "So, are you up to this? Jill's been out of the saddle for a while."
