A Cougar by Any Other Name

Before we had a name for it, Donna was a cougar. Though I didn't know it at the time, I was far from the first younger man to whom she'd taken a shine. I could never understand quite why we clicked, but we did nonetheless, and she was the engine driving the works. We met at church, of all places, where she was not shy in sharing her interest in me. She made direct eye contact and flirted with me after worship was over, while all who had participated in worship were chatting with each other during social hour.

One older church member in his seventies, a total introvert, noticed that the appeal and bond was so strong that we'd even exchanged a kiss on our way out the back door. He was good not to point it out and acted as if he hadn't noticed. Had it been someone else, we might well have been gossip fodder. The church was theologically liberal. No one was going to imply that we were going to hell, but tongues often waggle when parishioners start up relationships, romantic, sexual, or somewhere in between. The age difference was the most notable contrast.

I was in my mid-twenties then and she was pushing fifty, though she looked slightly younger. She dressed like she was my age, in t-shirt and jeans, plus black Chuck Taylors. It amazes me how that style of footwear has transcended generations, including baby boomers, a particular group of men and women who still refuse to age. I had a pair or two of Chucks myself earlier in life, but they always hurt my feet terribly. No padding. Only some rubber and canvass. Not much else.

She suggested we meet for coffee at a local shop on Wednesday evening. I eagerly agreed. Though she'd come directly from work, she was wearing an absurdly short skirt with white sheer pantyhose, giving me an obscene amount of view up her crotch. I could clearly view the V-shape of her vagina when she sat across from me. I wasn't sure at first whether this was purely accidental or deliberate, but her continually flirtatious behavior let me know that it was not. Things were going very well for me and I could see myself getting laid very shortly.

We made a second date for the following Saturday, over at her tiny little house. She was a secretary for the state, a career employee who had never been promoted, even once, which was why her residence was old and cramped. Our stated intention was to watch a movie together, which we did, but anyone with half a brain knows where two people viewing a film together in an intimate setting inevitably heads following its conclusion.

At the time, I'd started baking homemade bread. I could never get much consistency. One loaf would turn out perfect and another would be a total dud. But I made sure that what I brought over to her house was of the highest possible quality. It made the desired effect. She was impressed, more impressed with me than she'd been earlier in the week.

"I'm going to end up fucking you," she said, ecstatically. And as she quickly unrobed, I could see the tale tail evidence of her age. Her pussy hair was patchy and sparse in places, even a little scraggly. In a younger year, it might have formed a solid bush. Her small tits slightly sagged but were not unappealing. She was still an attractive woman and very slender for her age. There was no telling what her original hair color had been. It was now blonde, but she was the first older woman I had ever slept with, and I was intrigued and aroused by the prospect.

"You can fuck me no problem. I had my tubes tied years ago."

I usually start out with oral first. I try to be an unselfish lover, and I love to perform it. Nothing gets me off faster than making a woman orgasm with my tongue and lips. And nothing gets them wetter and more lubricated for the fucking to follow. I dipped my tongue between her legs and began aggressively licking her. Some of my lovers have preferred it faster or slower, harder or gentler, but most have thoroughly enjoyed it.

"Damn, boy," she said, a smile plastered upon her face.

I sat stationary and motionless on a chair in her tiny kitchen while she rode my hard cock cowgirl. We kissed with great force as I penetrated her. As I thrust into her, I took her breasts in my hands and squeezed gently. We kept at it for several minutes, when I began to feel the force involved beginning to make a detrimental impact, soon to very negatively influence both of us.

"We're going to break this thing if we keep it up," I noted.

"Good point," she agreed.

In saying this, we retired for the satin sheets of her bed and made love with great passion for the next two hours. She knew every trick in the book, which was quite surprising, because I pride myself on creativity in the bedroom. I had an older girlfriend once, a few years later, who was obsessed with the television show Sex and the City, whereupon an entire episode is devoted to all the reasons why younger men seek older women. The quick capsule summary review? Smart pussy.

And we had many subsequent sessions of highly pleasurable sex, homemade bread or not. If only that had been enough. My issue was not the intimacy, but the frequent late night, frantic phone calls and the sometimes-crippling insecurity that was on constant display. I could sometimes calm her nerves sufficiently, but their frequency began to slowly wear me out. I did six months with her until I could take it no longer and then moved on. But I always thought of her fondly.

How did we end up, in the final analysis? More as lovers than as partners, I'm afraid. It was disappointing. I wanted us to last a long time, but I very quickly learned that she had significant issues with clinical depression, which from time to time rendered her unable to do much of anything but lie in bed and cry. I'd tried my best to be compassionate but discovered myself needing to distance myself from her, pushing away periodically. I knew this would never work for long. One day, I told her about a woman I'd nearly married a couple of years before, and from that time forward she justified my resistance to her needs by believing I was still in love with the other woman.

As it turns out, that wasn't the case at all. I'd long since gotten over my first real love. Donna was the problem. I just didn't have the heart to tell her that she was too emotionally unstable for us to be a successful pairing. We lost touch for years, but one day she arrived at church, an emotional wreck, sobbing throughout the whole of the service. But she perked up when she saw me. Apparently, she still held a torch for me and may still, for all I know. Shortly before COVID, she appeared again, sought me out deliberately, and insisted we take a picture together.

She was sixty now but had kept to her old ways and most of her looks. I was now forty. Her new boyfriend was forty-four, according to her, but, as I soon realized, he was phenomenally jealous. In my trying times, she'd send me sympathetic Facebook posts or a text message expressing concern, and I was thankful for those gestures. The boyfriend, however, was absurdly possessive. Calling merely to chat, I discovered that he had recorded her voicemail message for her, and after I left a message merely to say hello, she disappeared into the ether once again.

I still think of her. I've had several partners like her who were cursed by the scourge of chronic illness. For a time, I thought through my love for them that I could cure them, or at least ease their pain. And I did some of that, but not nearly enough. One came down with cancer and wasted away to nothingness. A second was always in and out of hospitals. I can relate to a Fiona Apple song lyric that concludes her first album, Tidal. "And all I want is to save you, honey/or the strength to walk away."

She was skilled enough in bed that I periodically dream about bedding her and wake up with an erection. If only sex was enough to make up for a multitude of other serious issues. I sometimes pleasure myself thinking about the first time I saw her naked and the thrill it gave me. Other times I jerk myself off remembering the good days. There's no harm in that, is there? Those memories are as much mine as they are hers.