Disclaimer: This work of non-fiction is for entertainment purposes only. You must be 18 or older to read this story. It contains acts of betrayal and stupidity, jealousy, and graphic descriptions of heterosexual cisgender sex including virgin anal sex and bare skin-to-skin contact. If any of these topics disturb you, please read no further. Neither the author nor this website condone any of this. Remember, virtual is tantamount to virtue.
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Chapter One: So Lucky I Was Unlucky
I laughed when I first thought of writing this, because I realized that I was uniquely blessed/cursed to tell my dating story with utter thoroughness. While y’all I’m sure have all kinds of amazing early dating stories from high school to share, you can’t nya nya, because all non-fiction must be 18+ here, and three cheers for that! But it puts me in an enviable position in only this one respect.
I went on my first date at the age of 48.
How did this happen, you ask? How is it that an incredibly articulate, incredibly attractive, incredibly financially well-off man (granted, I’m being humble here) manages to avoid his first date until the age of 48?
Although I had virtually no appreciation or understanding of it at the time, I had been so lucky I was unlucky. My first wife and I divorced when I was 26. We had been high school sweethearts and divorced after three years of marriage, ending a tumultuous eleven year relationship. My first wife and I had both been virgins. The only other woman I’d ever slept with I’d met in my college Chemistry class while wife one and I were on the outs one time. It lasted two weeks; she smoked way too much grass.
My first wife was a genius and became an opera singer, but my second wife, Lisa (not her real name), was much smarter and craftier. Lisa was originally married to my best friend Dan (not his real name), but he always adamantly never wanted to have kids, and Lisa desperately wanted lots of kids. At the age of 26, I had practically no social skills, being that I’m high functioning Asperger’s to begin with (though it wasn’t a thing back then) and deep childhood trauma to boot. How difficult do you think it was for a brilliant, socially adept, sexually experienced woman of 24 to corner me in a hot tub? Of course, I thought it was all my idea. That said, I want to make it clear I was not some kind of victim in this relationship. There were many other factors, as there always are, not the least of them that Lisa and I both had good paying jobs while our spouses decidedly didn't.
Here’s the story of the beginning of my relationship with Lisa, written near the end of that relationship in 2008, at a time when Lisa was still my everything:
From the moment I first saw her back in the summer of 1981, I knew life had to be so good with Lisa. She was a calm kind of girl who took young men's souls with a sidelong glance and a wicked half smile. Back then she was a dangerously curvy eighteen years old, bursting with vivid and saucy tales of her months long walkabout in Canada as we moved her boxes out of the farmhouse she had been living in. "Are your eyes two different colors??" I asked incredulously as I leaned in, and sure enough, one was a brilliant green, the other blue, flecked with radial golden streaks. She said nothing at all, and I held my breath.
Alas for me, the renowned, mature, and resoundingly girlfriended-up University man of our gang at age 20, she was The Fruit That Shall Not Be Plucked. No, she was all for my very good friend Dan. I had been sent, an honor guard of sorts, to escort her to her new place by his side. And so off limits. And not only that, they were so obviously in the passionate first bloom of love. They were transfixed and orbiting in each other's webs of adoration. At one point Dan stepped aside with me and asked me in an excited whisper, "So what do you think?"
And the envy was probably palpable in my voice as I raised it to make sure she could overhear. "You sir," I said, swallowing hard, "are a Very Lucky Man."
Forward to a fresh October night in 1987 at Dan's parents' house in Santa Cruz. Lisa and I found ourselves alone together facing each other across the backyard hot tub, she perched in her gloriously rounded nakedness out of the water on one end, the steam rising between us into the cool air like a promise. We had been talking all night. My high school sweetheart and wife of three years, along with Dan, were asleep in the house somewhere, or as we might have been imagining, locked in some similar struggle with themselves and each other. Her eyes had been inviting me to get on with it for some time now and I was done with thinking that I must be misreading her intention. What harm would it do to get cozy?
Falling silent, I advanced slowly so as not to startle her. As I approached, she slid back into the tub. I descended to sit next to her. Again I looked at her. Those eyes she had been making were still there, shining in green and gold splendor. The adrenaline fluttered in my chest as I was drawn inexorably into a kiss, and then a hot kiss, and then my arms rebelled and encircled her, swept her up, and pressed her fully against me into a Desperately Hot Kiss. This Was Not Right. My arms and heart grew weak with the thought and she floated back down onto the bench, looking up at me silently, expectantly. There Was No Going Back. More relaxed now. Slowly kissing. Feeling her breast, firm and floating in the water. Rubbing the nipple hard. She reached down and cupped my package, and I grew hard and desperate almost instantly. Could she be ready? I reached down and found her to be slick and trembling with readiness, even though the tub should have cooked her dry long ago. Must preserve the fluids! Standing, I plucked her out of the tub and set her gently on the ledge, asking in a whisper "where can we go?" Silently, she rose and gently took my hand to lead me into the house.
It was dark and quiet inside, with the shadows rolling along her steaming body as she led me with purpose to the location. It was a futon couch of some sort, in Dan's old bedroom, where with all the guys Dan and I had wiled away our infinite hours of youth in role-playing splendor. The couch was long and narrow, far too narrow for me, with a tall gently sloping back. She, hopping onto the couch and pacing it, me peering at it though the darkness, grasping mentally for the way to Get This Thing Done. I pressed her back against the gentle slope of the futon and checked her vitals with my trembling hands. Still willing. Still wanting. Moist. Tasty. She reached out and touched me up. Rousing, I press her legs apart and upwards and enter her easily in a single motion.
Starting gently, measuring the size of her, legs up, arms grasping, body pinned by my weight to the back of the couch. I pressed into her hard and felt her gasp, tremble, clip in her first coming. She Likes It Hard. I grind into her, and then begin to slam into her, and her face squeezes into a rictus of ecstasy, her teeth, incisors sharp, baring. Her breath hissing out raggedly between her clenched teeth as she cums again, barely containing the animal scream written on her face. That's It For Me. My semen arrows hard into her as my body arches every muscle and dissolves into hers.
Coming to our senses, we look around for something to catch the juices already getting everywhere. The house rouses and there are people staggering around in the hallway. We separate and Lisa grabs something to cover herself and contain the flow. I wipe myself off somewhere and venture into the hall. It's my wife, staggering around in the living room, cranky, sleepy, dressed. Regarding me with hurt. I turn away and retrieve my clothes and sling them on. Dan stirs in the background, puttering around the hot tub. As I turn towards her again, she glares at me and says "You'd better say good bye to your friend." She cannot utter the name. Back to the room, a brief hand clasp to Lisa, a whispered endearment, and then it's back out to the living room to be led out to the sparkling night in shame, a whipped puppy who has Done A Bad Thing.
At least, that’s how I remembered it back in 2008, more accurately than I would now.
Wife one and Dan were both very understanding, and let us have our cute little fling. We flung very hard on camping trips where we dragged them sullenly along with us. We flung extremely hard in my condo in Larkspur while wife one was away, earning a note from the downstairs neighbor informing us that we had permanently emotionally scarred her daughter. We flung at the place she shared with Dan. We flung at the beach and in cars. We flung everywhere two lovers who don't have a socially acceptable place could meet. I remember one time when the four of us and a pile of our other friends were all there in Larkspur for some event. Lisa and I were throbbing and wetting ourselves for each other, so we snuck out over the sleeping bodies of all our friends out to my carport storage shed and had unrestrained sex there for hours until dawn. My friends had all seen us leave, of course.
Our spouses were both outrageously in love with us, but Lisa knew that all she had to do was wait for wife one to do something extremely stupid, being that wife one was already extremely unstable, and that would be that. And sure enough, it wasn’t long before wife one decided that it would be a good idea to start an in-call massage business in our bedroom. I found strange men in there multiple times with her. It annoyed me, and I thought it was unsafe.
Then she brought a teenage homeless waif girl she’d found on the street home to live with us. She mentioned to me that the teenage waif girl thought I was cute and would be happy to accommodate me. I kicked everybody out and divorced her instead. After she signed the divorce papers, wife one voluntarily checked herself into a mental hospital. I’m not proud of that, but I was 26. As soon as wife one destabilized, Lisa kicked her husband out the door as well, and that was that.
There's no convenient place in this narrative to mention The One Who Came Between. She was a very memorable one night stand. She approached me at our workplace and started chatting with me. I had my own private room at the office because I had a lot of moderately noisy electronic equipment to wrestle with. It didn't take long for her to get asked over one evening when I was technically single and Lisa was not around.
I thought that we could talk and get to know each other. On this visit, and maybe when she visited next, we could maybe kiss, I imagined. She had different plans. She set down her wine glass, climbed her tiny Asian self into my enormous lap, and hauled up her shirt to show me the most perfect pair of tits I'd ever seen in my life (though to be honest, I hadn't seen many by then).
I took her to the bedroom, not MY bedroom, which was for Lisa, but the other one. She threw off her clothes rapidly, and when I saw her perfect naked body, I said, and I'm not kidding for a moment, "I surrender." And I had. She could have my car, my bank account, my condo, my life, whatever she wanted of me. She wanted my dick. She wanted it in her ass. Remember, she was only the fourth woman I'd ever made love to. I'd never done that, and thought it to be violent and hurtful to women. So it took me a minute. Then I did it. It was wet as a pussy, and in retrospect, she must have prepared it. It was heavenly. I was so freaked out, I lasted a long time. She came many times.
Then we showered, with me talking about all kinds of things. Then she started to get dressed, and I thought, great, we can finish our wine, get to know each other. I went into my bedroom to get some fresh clothes. By the time I was dressed, she was out the door. I ran after her. She was leaving in her car. She kissed me, complained about my wine breath, and drove off. After that, she avoided me at work.
What Lisa and I started with a bang, she ended with a whimper. In October, 2008, after 22 years, 18 of them married, Lisa told me she was bored, and that was that. I spent a year trying to convince her, if only for the sake of the kids, the youngest of whom was 8, but she was adamant.
Really, the breakup was as uninteresting and devoid of passion as that, as it probably was with her first husband, come to think of it, whom I still know, and who, without ever saying anything because he’s a dear sweet man, told me with his eyes, “I told you so.” Or, maybe I’m still not over it. Maybe I’ll never be over it. She kept telling me to broaden my horizons, and I tried, for her sake.
That’s when I started trying to date women.
(To be continued)