She had been flirting with me for five years. Though I was sorely tempted again and again, I had been trying to avoid an entanglement, while remaining friends and colleagues.
And now I found myself in the back of an UberBLACK car on the way to the airport with my right hand between her legs, my middle finger deep in her warm wet pussy, my thumb thrumming her clitoris, and my left hand fondling her generous D-cup breast through her silk shirt, while she moaned into my mouth.
"I need this so bad," she said.
The driver turned up the electronic dance music on the radio.
Andi lifted her hips against my hand in rhythm to the music and pulled my head back into a deep, tongue twisting kiss.
"How did I get here?"
The question floated through my head as I let myself drown in the moment.
"And what comes next?"
Truth be told, I had been fantasizing about this moment for five years, ever since Andi first recruited me to join her nonprofit board. She was smart, ambitious, persuasive, and attractive. She was about my age, and more intriguingly, for me, about my height. I'm 6'4" and I'd never been with a woman my height. My marriage was on the rocks. My wife had agreed to an amicable divorce, but we were taking our time, planning to finalize it when our youngest daughter finished high school.
Meanwhile, I had gotten a small place across town, and I was actively looking around.
And Andi looked good.
Plus, she was touchy, in a good, warm way, which added frisson to every encounter. We were sitting in an outdoor café outside my office when we first met and she pitched me on her board. She touched my forearm and elbow while talking me into the challenge of turning around an important cultural institution in the city, a diamond that had been through a long rough patch, a seriously undervalued asset.
I like turnarounds. I like the challenge. The conditions seemed right for a reasonable chance at success. And turnarounds are such a great story. My life was in turnaround, too. And I wanted to think I had a reasonable chance at scoring again.
I agreed to join her board. And when we parted, Andi gave me a hug. Was it just a friendly hug? Maybe. But it was borderline, I thought, as she walked away.
She definitely pressed her tits against me, and her body fit into mine in a way that startled me and gave me an instant woody. And then it was over. She smiled and said she'd see me at my first board meeting in a month.
As she sauntered away, I thought about her splendidly shaped pendulous, but firm breasts, bigger than my wife's or any woman I had been with, which had been on display in a sleek silk blouse, unbuttoned to reveal tempting smooth cleavage. I watched her long stride and couldn't help but imagine what it would feel like to run my hand up those long legs. And how would it feel to be fucking a woman who was built like me?
Now I had a real hard-on. And I had to sit for a while and read the newspaper until it went down and I could go back to my office.
Ever since, I had been pretty sure she wanted it. But I've always been unsure about reading women, and probably too cautious my whole life. Blame it on respect. Or maybe I'm just a pussy.
And she seemed to act the same way with a lot of men, which left me confused and hesitant. The close warm hugs. Her tits rubbing against my chest. Casually or meaningfully? The kisses uncomfortably close to the mouth.
I was sorely tempted a few times when we were alone in her office to push her back against her desk and take her right right there. Or in the parking lot on the way back from a fundraising meeting to reach across and fondle her ample tits. Or following her up the ladder to inspect the roof of the organization's historic headquarters downtown to reach up between those long legs. I was sure she was tempting me. Maybe, I thought. I was paralyzed.
"Down boy, this is a professional relationship," I reminded myself. I was, in a very real, fiduciary and legal sense, her boss, as a member of her board. We ran in the same professional circles. I was afraid of any whiff of impropriety, conflict of interest, let alone sexual harassment.
Plus, she was married. She rarely talked about her husband, though she talked about her sons all the time. I wondered what he was like. I was intrigued that his name was John, too. That irked me. Then I met him. He was instantly forgettable. I wondered how he landed her. And that irked me more.
But by then I was well into a good, steady relationship, too, with a great woman I could see spending the rest of my life with. I was in love with Catrina. And I didn't want to fuck that up. She was smart, fun, cool, we shared a lot of interests, and the sex was great, the best ever, in fact, over and over again. And, unbelievably, it kept getting better. She kept in shape. She had a great body. I loved everything about it. But she was shorter than me, as all of my girlfriends had been throughout my life.
And so I fantasized. There was no harm in that, I told myself. Especially when Andi casually rubbed her tits against my upper arms at a reception as she introduced me to city officials or donors, or against my chest when she kissed me goodbye on the cheek after a meeting, and the kiss slipped to the edge of our lips and then was gone.
I left the board after a three-year stint. We had turned the organization around and that was what had interested me. It was on a good, steady growth track. And Andi could take it from there. We still met from time-to-time when she was in town or I visited the city. We gossiped and I offered free advice, which may or may not have been worth any more than she paid for it. I always bought the drinks. She was still always touchy in the same friendly way. But tonight it had gone further.
We had toured a historic building her organization was thinking about buying. We talked about the structure of the building and the deal, and her strategy for expanding from the city into a new town. She seemed subdued, which was not a word anyone would usually ever associate with Andi.
"How are you doing otherwise?" I asked, as she sipped her red wine.
She looked at me with sad eyes. Her lips trembled. She dabbed at the corner of her eye.
"It's been a really rough few months," she said. "The boys are doing great." She perked up and seemed ready to launch into her usual, overly enthusiastic litany of their accomplishments in high school, good grades, success in sports. She stopped. "But John and I..."
