My Threesome with Nancy

Nancy and I had an affair which lasted from 1987 through 1990, although we continued having sex whenever we happened to see each other for another ten years. She finally found the man she planned to spend the rest of her life with and she announced that for once in her life she would give monogamy a try.

When I first met Nancy, we were both commuting from homes in Philadelphia to jobs in New York City. I spotted her one morning on the Metroliner, noted her dancer’s legs, stylish outfit and stunning face and unleashed one of my best lines as we stood in line to disembark: “Do you have the time?”

Nancy knew what I was up to and treated me kindly. We walked out of Penn Station chatting and by the time we reached Seventh Avenue, I had her card and a dinner date. We had a wonderful dinner at Palio, went dancing at a club in the 30’s and spent the evening fucking at her hotel.

She was perfect for me. At this point I was 39, married, the father of three. She was 37, married, childless and unhappy in her marriage. Shortly after we took up with each other, she got a sublet in Manhattan and I was able to give mine up and stay with her the nights I stayed in New York, which became many. We both worked late and would agree on a restaurant where we’d meet for dinner. After dinner, we might go elsewhere for more drinks, but generally were anxious to retire to her place for sex. We usually got no farther than just inside the door before we were in each other’s arms. After kissing passionately for some time she often dropped to her knees, unzipped me and started sucking on my already erect penis. In short order, we’d each get naked and feverishly start fucking.

We always had sex twice in the evening. When morning came, Nancy liked to wake me by burrowing under the covers and taking my cock in her mouth. What was most thrilling about this was the way she just held it in her mouth at first, letting it start stiffening in the moist warmth of her mouth. Our morning sex was passionate, but brief. Wonderfully, Nancy seemed to reach orgasm very quickly in the morning. After we had both uttered our last moan, we became all business, preparing to face the day. Nancy would shower quickly, and then turn the bathroom over to me. While I showered, she placed her daily call to Doug, her husband.

This satisfying routine went on with minor variation for months. One of the charming things about Nancy was that in the midst of our passion, she would invariably murmur, “Tell me what you want me to do.” At first I dismissed this as a simple habit whenever she had a dick in her pussy. Finally, though, I decided I needed to make a demand. As we rocked in missionary position, I told her I wanted her finger in my ass. Now she had done this on her own a few times, but I decided I wanted her to establish it as a regular part of our sex. She knew enough to put her hand between us and get her finger wet from her juices, and then she inserted her middle finger deep into my rectum. She was immediately rewarded as I began thrusting harder, faster and deeper. As hard as I thrust forward into her vagina, I pushed back into her finger. After a time, she began inserting her index finger alongside the first. I started making animal noises as the pressure in my rectum and against my prostate began an ejaculation like no other I had experienced. My ecstasy triggered hers and we shared explosive orgasms.

That night launched adventures in anal sexuality that I dream about. After we recovered from our first orgasm, Nancy moved down my body, kissing and licking. But my penis, which I was sure was her objective, received only a quick suck. She was focused instead on my anus. She hooked my legs on her shoulders, widened my crack with her hands and inserted her tongue into my asshole. My reaction was immediate and wildly enthusiastic: “Yes, yes, yes! Deeper!!! Yes!!!” My depleted penis stood up in no time. When Nancy felt she me sufficiently aroused, she straddled me and inserted my penis in her own fully lubricated ass.

From then on, I guess I ejaculated in Nancy’s bowels about as often as in her vagina. For her part, she showed up at dinner one night with a present for both of us – a strap on cock. She could tell from my immediate and intense responsiveness to her anal ministrations that I was a man who would enjoy being fucked in the ass. Indeed, if I never had sex any other way but on my back, my legs hooked around her as she fucked me with her eight inch black cock, I would be quite content. As it was, she could clearly understand how much I enjoyed this aspect of our sexuality. She seemed to enjoy it too, since the pressure of the base of the penis on her clitoris produced regular and multiple orgasms for her. Her cock was perpetually hard, and I never asked her to stop. She would ultimately collapse on me, exhausted from the exertion of thrusting and enervated by her multiple orgasms.

Since we had not only an adulterous relationship, but one that was unusually intensely sexual, we had no inhibition about discussing our sexual history and experiences. When the subject of group sex and swinging came up I admitted to her that beyond discussing swapping wives with a good friend of mine, the closest I had come to group sex was having sex with my girlfriend in a room with another couple. They were screwing as well and we watched each other fuck.

Not surprising to me were Nancy’s many experiences, with much older men when she was in her teens, with much younger men currently, and with women of all ages. It seems that her only group sex took place with two male colleagues with whom she was taking a business trip some years ago. She had already slept with each of them, so to avoid the awkwardness of making a choice that evening, she invited them both to her room. She recounted with great pleasure how much she got off on kneeling before them, taking one, then the other, and finally both penises in her mouth at the same time.

I asked if her partners seemed uncomfortable having their erect cocks in contact with each other. She assured me that they seemed to enjoy it so much that she would make a point of rubbing them together. The highlight of that night was her first double penetration. Nancy looked at me meaningfully and told me she wanted to experience that with me.

Well, as a man who never turned down a sexual encounter of any type, I was ready to oblige. I admitted to her that my idea of a threesome was two women and I, to which she responded that she would enjoy that experience, but that she called her fantasy first. I conceded the point, and we began discussing practicalities. Nancy was a very effective person and I had no doubt that she would have a plan and execute it with energy. What surprised me was that she already had our third in mind. I imagined that we’d go bar hopping and troll for a likely looking guy in a suit, the right age, the right look and make his night by telling him that he had a sure thing in front of him, just so long as he didn’t mind another guy fucking her at the same time. I thought I’d be gracious and give him the choice of vagina or anus. Instead, Nancy strongly recommended we go with a known commodity, known to her that is. Thus I was introduced to James Carey the very next night at the Zig Zag Bar, down the street from Nancy’s apartment.

Nancy and I were coy about whether we were currently sleeping with other lovers. I had several women between New York and Philadelphia and I was certain that she was getting other action as well. As soon as I met James and saw them relate, I was certain he was more than “an old flame”. He was about my height and build, grayer and possibly a few years older that I, good looking and personable. He was a commercial banker and carried himself like a man who knows how to do relationship business.

“Hi Joe”, he greeted me; “Nancy’s told me a lot about you.” I replied that I was at a disadvantage, and he proceeded to give me a brief life story, telling me of his wife, kids and dalliance with Nancy. As he told it, his wife uncovered evidence of his affair, which he denied. He thought it best not to push his luck, so that currently he and Nancy were simply “close friends”. Of course, I didn’t believe this for a minute, nor did I much care; I liked the look of the guy and, to my surprise was increasingly anxious to see the three of us naked together.

He had been thoroughly briefed on the plan for the evening and our conversation at the bar, lubricated by several rounds of martinis, “to overcome inhibitions” as Nancy so neatly put it, became ever more sexual. Each of us in turn recounted an outrageous tale of sexual conquest or kinkiness. I know that I was getting aroused and judging by the flush on Nancy’s cheeks, she was as well. Significantly, when it was James’ turn, he talked about being picked up hitch-hiking by a gay photographer and his seduction. It turns out that somewhere in the world of porn are a number of photographs of a younger James sucking on the cock of his patron.

That anecdote seemed to signal that the time was right to head down 23rd Street to Nancy’s. We walked past the bored doorman who undoubtedly knew more of Nancy’s secrets than I. We were oddly silent on the elevator, each of us probably wondering exactly how this encounter would play out. Nancy, true to form, opened the door, stepped in, turned on the light and dramatically leaned against the entry wall, inviting us to begin making love to her. This is just as she did it with the two of us. What would happen now?