Here is my story of a delightful affair I had with a married woman some 8-9 years ago. It lasted a little over year. She would always bring sushi and a small bottle of red wine we’d share after lovemaking, and after a few sessions she asked me to take her anally as well. And of course I did.
This began like most of my other affairs, with her responding to an ad I had placed on craigslist, looking for an ongoing sensual friendship with a married woman. My ad was very similar to the one that had attracted Katie, and the one that drew in Louisa whom I had to cut loose after she proved to be crazy (details in my earlier posts). In fact, this woman — let us call her ‘Helen’ — saw the same ad Lousia had answered, and finally screwed up the courage to respond, but not till right after I had pulled it down. So we just missed each other at first. This unfortunate turn cost our affair a number of months.
Helen had been married to her current husband for over three decades, about as long as I had been married to my wife. They had one child, a daughter, who suffered chronic pain owing to a medical condition she could never quite shake. This led Helen to leave her job years ago– she’d been some kind of corporate somebody — and dedicate herself to raising the daughter. The husband was some kind of computer whizz, so they had plenty of money, with a nice home in the hills and a lakeside house as well. Though the husband is a bit younger than she is, he had developed ED and he could not take meds for it. Instead of exploring other avenues of sexual pleasure, which Helen pleaded with him to do, he became surly and withdrawn. Some men think it’s all about the penis and nothing else! Poor souls; if only they knew. So Helen began to feel restless, all the more so since her daughter seemed to be mostly healthy and ready to spring into her own adulthood. Helen had had some rich sexual experiences between her two marriages (she broke with her first husband in her 20s), and she had cruised the porn sites so she knew what she was missing.
Helen is one of the most practical women I have ever known, and very careful. Helen feared her husband, very adept at monitoring electronic signals that entered and left their premises, might discover what she was up to so was constantly on guard. For a time she even created a new yahoo account and only emailed me from a computer in a public library. I never learned her cell phone number and she never asked for mine. We communicated exclusively via secret email.
I had placed my ad in the Men Seeking Women section, and it made clear that I was married and looking for a married woman not wanting to leave her husband. There was a time when ads like that in this category would get flagged off right away since they weren’t asking for marriage or normal dating, but I guess the community had become more tolerant of philanderers like me. My ad checked off all Helen’s boxes: educated, traveled, attached and planning to stay so, patient, a good listener, and sensual. She told me more than once that everything I had written about myself turned out to be true! That still feels good.
She was a bit older than me but very fit and attractive, a regular visitor to the gym. She had brownish-blonde hair almost touching her shoulders that was always exquisitely coiffed, with a beautiful smile and the cutest of dimples. Her body craved touch, long slow light caresses across her sides and stomach and thighs and shoulders and back and legs and yes, there too. We always eased into our lovemaking, and cuddled at the end.
We first met in a hip cafe on the north side of town to look each other over a bit and then we went walking along a nearby greenbelt. When I felt the moment was right, I reached out and kissed her, gently but hungrily, and she responded in kind. She was nervous about doing that in public but we were far away from her part of town. She always insisted that we meet well away from areas she shopped dined and lived in.
We agreed to get together in a Motel 6 a few days later. This might sound strange for a woman like her, but I assured her this particular one was safe enough for an afternoon tryst, and it was and probably still would be if not for the pandemic. I always smile when I drive past it. This is how careful she was: she would not drive to the motel but insisted we meet in the parking lot of a large shopping center across the interstate from it, and then she’d ride over to it with me. I had already checked into the room. We did it like this five or six times before she finally felt safe enough to park at the motel herself. After a time we moved our clandestine get-togethers to more upscale places, and she would cover half the cost. And she would bring wine and sushi!
We soon learned / shared our ‘real’ identities and spoke of anything and everything. Sometimes we’d meet in cafes and flirt and talk, sharing little kisses in her vehicle before rejoining our ordinary lives. She liked telling me how she felt during our most recent sexual escapades, and whisper her desires to me via email, always with delicate words, never vulgar.
Sex with Helen was magnificent. She was oh so hungry, in no hurry and her skin was like silk. Her stomach was firm and her breasts were soft, and she liked her nipples to be caressed and licked just so, just so. She had a neatly trimmed patch of hair above her sex, and a piercing just below her navel. She loved it when I’d get on top of her face to face, grab her hands and pull them above her head, and grind away. She loved feeling my weight on her pearl. That’s what she called her clitoris: my pearl. And she loved how I licked that pearl, slowly, gently, kissing the fleshy folds as I pulled them aside to reveal … her pearl. Of course sometimes I took her from behind and she liked that too, and once I pulled her to the edge of the bed and massaged her pearl as I stood and pushed myself in and out, in and out. Oh! she exclaimed, this is one of my fantasies! This was not the last time we did this.
Helen always came for me like a good girl, and I always came for her, inside her, sometimes also in her mouth. She liked that and she liked how I tasted. She was the first woman who licked and kissed her juices of my beard after I had eaten her. And she had anal longings, and after a few wonderful encounters, we gave that a try.
This is how that went down: we’d make love, this way and that, and she’d cum and I’d cum. We’d then take a break, and when my manhood was ready to soar once again — by this time I was taking Levitra as had prescribed by my MD, to the maximum dosage allowed — we’d spoon. Then she’d guide the head of my hardening penis into her rear opening, and I’d push it in not too deep, just the head and maybe a little more. I’d rock gently back and forth, and she’d finger her pearl until she came. It never took long. I never came this way though wish I had; I was usually spent by the time we reached this point, though still able to stand tall. But she always came, and told me it felt not better, just … different. I would have been willing to plunge deeper or take her anally from different positions and angles, but this is all she craved and this is what I gave her. It was all so very delightful.
My affair with Helen was about as perfect as an affair affair can get. I regret none of it. Intimacy is for me the intersection of friendship and the erotic, and this is what we had. We enjoyed each other immensely and gave ourselves delightful encounters to look forward to again. But we were measured. We found balance.
Of course it had to end and it did, after some 15 months. This came about gradually, as Helen’s daughter’s health deteriorated again and she had to focus on that. And my own mother was fading, and passed away suddenly after a surgery. I had to focus on that. We’d still meet occasionally for coffee — we were comforts to each other — and emailed each other, first daily then every few days then less often.
Then one day my email bounced back. Her address never worked again. I can only speculate what happened. Perhaps her husband called her out on those electronic signals. Perhaps her practical side counseled her to move on. Or perhaps she found another lover. I’d like to think that she did. She deserves joy, and I would not be at all jealous. And yes, I would meet her in a cafe to talk over old times and new, and yes, I would meet her in a hotel anytime, to share sushi, wine and more, today, tomorrow, and next week. Yes, I would.
Source: reddit.com/r/gonewildstories/comments/imiyfy/i_m_share_sushi_anal_pleasures_and_more_with_milf