Leigh Whistler, 51, Long-Time Math Teacher

So said the headline of her obituary. She died after a long illness. I knew a little bit about that.

At my age, you start to get nostalgic for past loves. In that vein, this is a tribute to one that remains very special in my memory. While the story has a sad ending, it’s all about friendship and intense sexuality.

Six or so years ago, I met Leigh, a polyamorous teacher in her mid-forties, via an online dating site. She was looking for generous gentlemen companions – not something you would expect from a woman her age. But there was something about her profile that intrigued me. I sent her a message and a key to my pictures and got access to the following picture in return.

We got to know each other via exchanges of emails over the following couple of weeks. She was recently divorced from a guy who wasn’t doing his part to take care of their two teenage kids. So she was supporting herself and two teenagers on her salary as a high school math teacher – and it was a struggle. Leigh was highly intelligent – she had been a mathematics major in college who had later decided that teaching was her vocation – and also highly personable. Aside from her intelligence, what impressed me about her was her sweetness. In spite of her bad experience with her husband, she obviously loved and appreciated men. Her divorce had given her the opportunity to explore her polyamorous nature – and she had both enjoyed and profited from her experiences. She had established satisfying, ongoing relationships with five men who were successful, attractive and generous. I was to be her sixth.

Here is a description of her other men friends that she included in an email message after we had established our own relationship:

“I do think about the men in my life often ... There are five, in addition to you, that I will continue to see. There is my doctor, who was my ‘first,’ I suppose you could say, in this different type of lifestyle. We’ve been seeing each other for well over two years. Then there is Dallas, whom I see when he comes here on business. It was much more convenient when his New Jersey office was located in Cherry Hill, but more recently he has been working out of New Brunswick. So it’s a bit farther for me to see him now when he is in town. Then there are the single friends. My young Jack is about 8-9 years younger. We have a basically carnal relationship, yet he is still very sweet and caring. He’s extremely intelligent and fun to talk to, but we are definitely in different stages of life. There’s Phil, who is the sweetest, kindest man on the planet. I have to be careful with him because he often crosses the line into wanting much more than I have to offer. And then there’s my other Jack in Florida who is also one of my oldest and dearest friends. I’ve known him since middle school. He lived around the corner from me and was my prom date. There was never anything romantic or sexual until a couple of summers ago when I flew down to visit him in Jacksonville after I separated from my ex. I rarely see him, but we speak, at least, when we can. There have been a few other men in my life that I have liked, but none that I have been intimate with recently.”

Leigh and I met about three weeks after we began getting to know each other via exchanges of emails. The photo of her above doesn’t begin to do justice to her body, which was truly extraordinary. Her breasts were large – DD – and quite firm for a 40-something-year-old woman who had breast-fed two children. Her face was also very pretty and looked much younger than her years. She had long, brown hair and lovely, soft brown eyes that were filled with affection and warmth.

I don’t have any other pictures of Leigh. But I want to think of her as a younger woman anyway, when she was unmarried, childless, and living a life that was joyful and fulfilling. So with the help of AI software I’ve developed images of what I imagine she looked like in those years when, she said, she was a bit curvier. Let’s start with this one, which looks very much like a younger version of the woman I met on our first date, though her skirt wasn’t quite that short.

When I opened my hotel room door to meet her for the first time, I was surprised to see how pretty she was, as I hadn’t seen any pictures of her face. The second thing that surprised me was how intense our first kiss was. She melted into my arms as soon as the hotel room door was closed as if we had been intimate for years. After we had spent a few minutes kissing each other passionately and lightly caressing each other, I sat her down on the couch and pulled off her panties.

I knelt between her legs and began kissing the insides of her thighs without quite touching her pussy and clit. When she started moving her body toward my kisses, I finally pushed the tip of my tongue into the lower part of her pussy, which was soaking wet with her natural fluids, then followed the inner lips of her pussy upward to begin tonguing her clit. Encouraged and rewarded by Leigh’s gasps of pleasure, I pushed my tongue more firmly against the delicate spot, finding a rhythm that led to louder gasps and slight spasmodic movements of her hips and legs. After only a few minutes, her body stiffened and her gasps turned into rhythmic moans. I continued to thrust my tongue against her clit, gradually reducing the pace and pressure as her moans diminished, not stopping until they had faded out entirely.

I slid two fingers into her pussy and began rubbing her g spot, then resumed pressing my tongue against her clit, and occasionally sucking her clit between my lips. She moaned loudly, “Oh Bob, that feels so amazing! I’m about to cum again!” And soon she was there, writhing, gasping, moaning as she was overwhelmed by her body’s response to the stimuli of my fingers and tongue. Her orgasm went on for what seemed like minutes before it began to diminish, when I also began to ease off the pressure on both of her pleasure spots.

When her orgasm had finally dwindled off entirely, and there were no more aftershocks, she gently clasped the sides of my face and pulled me upright to give me a deep, passionate kiss. “Oh, that was so lovely, Bob. Now let me do the same for you and see if I can do you as well as you did me.”

“That’s a lovely compliment, Leigh.” I smiled at her, “but I hope we won’t really be looking at this as a competition!”

She turned her back to me and quickly pulled her dress over her head and tossed it on the couch, revealing her beautiful ass.