Prologue: I don’t know about you, but sometimes the more erotica I read, the more everything sounds the same. You know, like the coveted cocks are always 10 or 12 inches (always an even number, though) and “as big around as a wrist.” There is always precum dripping. And the Sex proceeds in more or less predictable ways (maybe that’s because the variations are relatively finite with three orifices in women and two in men. And finally, there is rarely any suspense or tension created, rarely any character development. I know a lot of readers want the turn-on experience, “so cut to the chase.” To me, though, it’s the frisson or friction between characters that creates the sexual interest, and it’s how that develops and manifests leading to character change that makes the piece believably interesting and unique. There are Literotica writers here that do all that very well, and for me are really fun to read.

Just to let the reader know, this story has no cock size mentioned, no precum, and the Sex may, in some reviewers’ opinions, be relatively tame, but as it really happened that way, it should be totally believable. It tells an origin story and only begins to introduce the characters. But Chapter 2 is in rough draft form and Chapter 3 is steeping as i’m sleeping. Thanks for reading this intro, and a bigger thanks for reading the entire piece. And, by the way, it is gratifying to have you leave a number rating, even if you don’t have time to write a comment.

Lisa sat cross-legged with her back to me in her sexy silky underthings: deep plum bikini panties, fashioned with one side solid and the other, lacy. On top she wore a matching bra. Considering her age, and despite a little extra skin folding over the waistline, she still had that iconic hour-glass form from behind.

I was likewise naked except for the red silk thong she had requested I change into, and although I was relatively thin and tall, age had given me a little extra padding as well. She had smiled, as I re-entered the room in my silks, so I took that as affirmation that at least she was not turned off.

We sat on a twin-bed-size slab of memory foam covered with a flannel sheet in front of a roaring woodstove fire, which made the room invitingly comfortable. A Loreena McKennitt playlist was filling our space with music from a cylindrical speaker on the coffee table. The only light came from lancinating yellow-orange flames through the stove’s glass front, providing a warm glow to our skin and a glistening fluorescence to her red hair. Rounding out the sensations were a hint of rosemary fragrance from her shampoo mingling with trace scents from the split birch, oak, and maple logs stacked nearby.

Lisa reached over to the coffee table, retrieved and handed me her hairbrush. I began dragging it through her thick, flaming hair. It had been earlier washed, toweled off, then air-dried, she had explained, apologizing for the tangles at the ends. That compelled me to linger with each stroke, not pulling the brush through too quickly. When I reached the snarls, where resistance was met, I gingerly extracted the strands so that there would be no uncomfortable jerk.

Sometimes I pulled her hair from her left scalp over to the right, covered her ear, and then combed it out from the middle of her forehead down her back. To continue some semblance of symmetry though, I repeated the mirror-image action.

Stroke after stroke after stroke, I repeated the motion and soon the tangles vanished. Combined with the music’s swaying effect, her rocking motion, gently left and right, or back and forth with my brushing direction, signaled that my patience with her hair care was having a seductive and hypnotizing effect.

I don’t know if it’s a sense of power it gives me to pleasure a woman and to bring her slowly through arousal to Orgasm, but I wanted that experience. Maybe it was to be regarded as a good lover. Perhaps I was on a quest for the quintessentially perfect erotic experience with both of us climaxing at the same time. Or maybe it was something else. I didn’t really know. But right now half of what Sex and Love-making was to me was missing with my Wife.

I’m a man, a bisexual man, or maybe a pansexual man. I’ve heard men explain the terms differently. My therapist called me undifferentiated. So I’m that: open to all genders. I am 69 years old, and I really enjoy Sex. I guess I Love Sex with someone I know and trust and with whom I can have an emotional and intellectual connection, because Sex is transformed into making Love when that happens. Or at least that’s how woman-Sex has been for me.

I still get erections, but they’re not exactly with the spear-chucker’s rigidity that they used to be. I’ve taken Viagra just to see what it was like and that does give me an 18-year-old’s boner. I’ve kept some on hand as a treat for the rare occasion when my Wife wanted a “big fuck” as she called it. The operative word was “when,” because for the last several years she’s really felt no desire at all to have Sex or to make Love.

Not that she’s against my having sexual fulfillment when we’re together. As a matter of fact, for her, the pleasure has recently come in bringing me to the proverbial edge a number of times, watching me hover there on the precipice, arms metaphorically flailing to keep my balance, then sending me hurtling over into an Orgasm chasm. That has been fun for her, and for me as well, but as she didn’t enjoy being pleasured in return, that part of my sexual play was therefore lacking.

But from what I am coming to understand, she is not the only one—the only woman over 60—who feels that way about Sex. I shouldn’t be surprised that a woman who is 68 would not have the libido that a woman in her 30s, 40s, or 50s does. After all they’ve gone through menopause, and not only are their estrogen and progesterone diminished or gone, but so is their testosterone, which is the source of the Sex drive, from what I understand. But somehow, Lisa was different, which both mystified and excited me.

Lisa had asked me to brush her hair because it had always been arousing to her in the past. But that had been almost a decade ago. It seemed obvious to me that her responsiveness hadn’t changed. Brushing her hair was so entrancing in fact, that she did not need to speak and let me know by voice the pleasures she was succumbing to. Her beguiling movement told me all. And as I was repeatedly drawing the brush down and through her hair, I became aware of what was drawing up and against the red silk of my thong.

How I got into this position was both direct and circuitous; intentional and serendipitous. I had reasoned that although post-menopausal women may lack testosterone, older men still have plenty of it, and therefore a potent Sex drive. So being bisexual, it only made sense for me to search for other like-minded married men, whose wives were not interested in having Sex, but who were, like me, interested in a physical connection with another married man. I also felt it would be easier to justify having sexual intimacy outside the marriage if it were with another man, reducing the risk of my Wife feeling inadequate as a woman and as my life-partner. That was a reasonable assumption and it had potential, as long as I could find a man whom I liked and therefore with whom I could feel vulnerable and thereby develop an emotional connection.

But it wasn’t as easy as I had hoped. The first man that I really felt close to, and got to know really well, found me “not his type” after we made Love one night. Eventhough he told me that he had never had a man who really took his time with him, and knew how to handle a penis like I did that night, that relationship didn’t go anywhere sexually afterwards, except that we stayed close friends.

I met another man who I initially liked, but who talked so incessantly about himself that I never felt important to him. He was the first one to have taken my Anal cherry, so to speak, and although it was pleasurable, I didn’t feel like it was out of Love, more out of compliance with my request to be fucked.

My third married man I liked, too, but it didn’t seem like we were going to get anywhere because, feeling fearful of discovery, he wouldn’t allow me to even know his name, just his initials. Moreover, he didn’t want to be seen in public with me, even though I countered that we would just be appearing as two men who were friends. His resistance, therefore, made it hard to get together spontaneously and to share experiences, and therefore, prevented our becoming Intimate. So I emailed him that we should break it off.

So, my three failures to find a married man made me even more pessimistic about giving it a fourth go.

Maybe it was that, or perhaps something about myself that I hadn’t figured out. For some reason, I began craving a relationship with a libidinous woman again. That changing polarity—finding myself fantasizing about men one day, but then about women the next—bothered me. Why couldn’t I make up my mind, settle on one gender, and be satisfied with that. But I couldn’t.

What that ambivalence did, however, was lead me to the internet in another direction: to look for couples, married or attached and either bisexual, bi-curious, or at least open to the possibility. That way I could get both gender-needs fulfilled simultaneously.

I initially looked on one site and narrowed the search to within 75 miles of my locality. My first observation in looking at couples was that most often the man was in his 50s, or 60s, or even 70s, and the woman in her 50s, 40s, or 30s. The second observation was that there was only a smattering of concern regarding Covid. Also, no one seemed to prioritize safe Sex, although the claim was occasionally made of a couple being drug and disease Free. My question was how did they maintain that disease-Free state when they seemed to list so many partner-couples, and how did they obtain proof from others that they were also disease-Free. Was it just the honor system, or did they have to show a battery of negative test results from Planned Parenthood? No one specified.

I tended to like the couples that professed they were new to the lifestyle, or that they were newly trying something like this to spice up their happy marriage. That latter rationale made me wonder because in my marriage, happiness would not be spiced up by another man or couple joining us to have Sex.

I got excited on my first foray: a woman writing for the couple wanting a man who was really bi—not just into Sex with her, but also willing to pleasure her husband. I wrote back believing I had hit the jackpot on my first messaging. She replied with a question, which I answered, but then I never heard back. Maybe I lived too far away, but I never knew. I tried others on the same site and got no replies. Not even an acknowledgment with a polite, “No thanks.” Nor a “Not interested.” Where was the etiquette, I asked myself. Or was this the culture of this site: silence if you’re not interested?

So I tried a different pond to cast into: a promising site called Fantasy Friend Finder, boasting a much bigger pool, where people want to live out a fantasy they’ve only been having in their imagination.. With more people, though, the asks got more nuanced. Specificity broadened out. Couples wanted “men, women, couples.” One couple wanted to host a gang bang. Another couple wanted a man to take the cougar Wife while the husband watched, sometimes stipulating that the man have a cock bigger than 8 inches, preferably thick, and/or it had to be black. None of that appealed to me, nor did I qualify in the size or color categories.

I had “advertised” myself as a bi-man looking for a couple for a three way, but hoping for more of an ongoing relationship, not just a one-night hookup. No one responded to my offering, and no one, whom I messaged, even replied to me—even though they explicitly promised to!

So I pivoted. I had a radical thought. My erstwhile lover-man, who had only given me his initials and who was reluctant to be out in public with me, was married. He had children. So he had had Sex with women and might still be having Sex with his Wife, I understood, had she not abandoned ship. So would he team up with me if I found a woman who wanted to have a three-way with two men?

I didn’t know. I just knew his interest in me hadn’t flagged, because several months after I had broken off our relationship, he had gotten back in touch with me again, telling me his name for starters—let’s call him “Al”— hoping that we could get something restarted. I wasn’t sure, but while I politely kept up a conversation, I didn’t include anything about this trio idea to him; I just quietly worked alone on my own fantasy.

I reset my filters on “She for Them.” I searched for a woman in her fifties or sixties, as Al and I were in that age range, and I liked middle-aged women. I liked their wrinkles, their slightly sagging breasts, their battle to maintain their appearance in the face of aging, sun damage, arthritis, and weight gain post child-bearing. I was exhibiting similar age-related failings, and so too, was Al. In other words, I wanted to make Love with a mere mortal, not with, say, a goddess half my age. It would be like having Sex with my daughters-in-law, for goodness sake!!

As before, the search was proving to be fruitless. My ideal woman was scarce. I figured it would be. But then it happened. A new woman named Lisa had joined FFF. She was 66, twice divorced, living alone and uninterested in another LTR. But….., she was looking to have a long-time fantasy fulfilled: to have a threeway with two men. Not much to go on, except her two photographs. She obviously colored her hair—it was a flaming red—and she wore makeup, something that really turned me on. She appeared buxom, happy, and attractive. So, I went into action.

I had to act fast. Meaning, I had to woo her to my cause with honesty and sincerity, before scores of cunning man-wolves got to her first. I had read tantalizing posts from single women looking for unspecified Sex with men, who unabashedly posted days later that they had had so many responses that they couldn’t guarantee “getting back to you for a long time.” That might happen here. I didn’t bother conferring with Al. I just figured he would be in—he could have me as part of a trio, after all.

I stretched the truth a bit, but it was essentially honest. I wrote to Lisa that I was a 69 year old man, friends with another man of 64, both of us married, so she wouldn’t be worried we might want a LTR. I related that our wives were not interested in having Sex any more, and being very sexual beings, we were exploring our same-Sex attractions. However, we both loved women and were missing the kind of Love that only a woman can provide. So would she be interested in our helping to fulfill her fantasy as a threesome, as it would certainly provide a rewarding experience for all three of us.

I read over my response a couple more times, making sure the grammar and spelling were correct. A sloppy first appeal might actually be ignored by someone who wanted men who took their time, both in bed and with getting their messaging correct.

I tried not to keep checking the app. I figured some people put out a batch of appeals and listened for the returning pings, like baiting several hooks, and waited for the bobbers to dip below the surface signaling a nibble or bite. But I resisted spending my day like Pavlov’s conditioned dog. How quickly she replied—if she even did—might indicate the intensity of her interest, but, also, too many other things, like that she was a working woman with a day gig, or worse, that she had found a man-pair more appealing to pursue.

I sent my message in the morning. My picture was of me taken from below as I was standing on the top of a step ladder. Even less for her to respond to, although my face was clearly visible, and even more so was my crotch in blue jeans! But it was something she could pair with my prose. I checked in the mid afternoon. Nothing. I began feeling discouraged.

But then the following morning, I got a reply: she liked my proposition and wanted to chat a bit more before committing fully to anything. Over the next several hours spanning into days, we chatted a lot. In the end, she wanted to meet me alone first, and get to know me more intimately-she used that word-before going all in on a threeway.

So here we were, beginning an intimacy. Aside from the e-exchanges we had had, Lisa was completely new to me. And with a physical intimacy, how she responded would be something like how a pair of new Tango dancers would dance to a Tango tanda. In that situation, partners are granted three songs to dance to. The first song is exploratory to find out the communication between lead and follow. The second song allows those patterns to be explored further, maybe with some additional ones added, and the third song is to go all out with what each partner has learned about the other’s lead-and-follow, and letting the music guide them.

I had found out her response to the hairbrush and decided to add something new. I started moving my freehand behind the hair brush following it to the hairs’ ends, but then I veered off, letting my Free hand wander down her back across the seam of the panties and then up to her abdomen and over the warm belly fat that had folded gently over in the front. As I made circles with my Free palm, I let my hand adventure across the lower line of her bra, nudging from below her pendulous breasts, and then back around up to her left shoulder. I then waited for another stroke of the brush to follow down her long red hair, and I wandered in a somewhat different direction.

As she kept swaying, and didn’t make any effort to turn away from nor push away my hand, I interpreted that to mean I could continue—or maybe even go farther. With my right hand continuing to brush her hair in long sweeps, my left hand was Free to also explore along the tops of her thighs down into the inner thighs up to her covered groin then initially teasing her by avoiding the groin entirely, going along the elastic of her panties both in the front and then in the back.

I was giving her all the time she needed to relax into me. Her sexual experiences with men had been a decade ago, she was straight, and although I was a man, I was a relative stranger, so I wanted to affirm in my actions that I was open to whatever she wanted and at whatever pace. I wanted her to gain trust that I was not going to take advantage of her.

I had begun cross-legged, too, but decided to unfold my legs and curve them around her from behind. Now my gradually stiffening cock pulling up into the silk fabric of the pouch rested against the small of her back as my thighs encircled her buttocks and her outer thighs.

Her responsiveness augmented mine. She moved from her initial position, with outstretched arms and palms in between her crossed legs, to placing each hand on my shins. That was followed by her moving her back tighter against me as she slid her hands up to my knees, then onto my thighs. She retreated from me when she slid them back down the shins to my ankles, but soon returned, continuing this play in a repetitive motion. The see-sawing was alternately compressing and releasing my swollen, cocooned cock. I kept brushing her hair, and the new sensations from our contact points, further invited me into taking more risks.

I reached up to trace my hand along the line of her bra strap, across the back, and then around and over each breast in its covering of silk. She uttered that pleased sound of “Oh,” and surprised me by reaching back, undoing the double clasp and shaking the bra off from, first her shoulders, then her breasts. It was like permission given to repeat the action without the encumbrances of straps and cups.