At a certain portion of my life, I was in an unhappy marriage, but basically was 'staying for the kids'. There were a half dozen lady friends, who had been friends for 5-10 years, where there was always some attraction, but as they were married and I was married, nothing had happened. Eventually circumstances caught up with us, and we had a physical relationship.
The most striking was a clerical assistant that I had for 5 years. We clearly liked each other, and both had said, out loud, "if I wasn't married.......'. But nothing happened. It came time for her to move to a better job, so on the last day of work, she came to my office to say good bye. A hug and a kiss on the cheek, turned into a real hug and a real kiss on the mouth, with tongues involved. As it was the end of the day, the office was empty, the kiss continued, and hands started to roam. Being a 'good boy'(e.g. idiot), I pushed back and said that we shouldn't do this. But, she said, 'I'm not going to let you use that boner on her (e.g. my wife at home)'. She, quickly unbuckled my pants, pushed them down, and began to suck my very hard cock.
After a few minutes, I stood her up, looked her in the eye, and told her that I had wanted to fuck her for a long time, and wasn't going to waste the moment on just a blow job. That elicited a very big smile on her part. In only a few minutes, our clothes were on the floor of the office, and my fingers were in her very, very wet pussy. Quickly, we wound up on the floor, with her sitting down on my cock.
It was a very good fit. She was 40, and had had one kid, but was an amateur ballet dancer, so she was trim and tight, but very wet and not so tight that she was hard to enter. Over the next 30 minutes we fucked in several positions, and I got a taste of her pussy. From her reactions, she also came several times, at least she would tense up, breathe very hard, then relax with a nice smile on her face.
When it came time for me to cum, I stood her up, bent her over my desk, and entered her from behind. Damn, ballet dancers have pretty and tight bottoms. When I came, I pulled out and came all over her lower back.
Over the next couple of years, we would get together for lunch, just to catch up with each other, about every 3 months or so. We always wound up having a good fuck. Given that she had started by blowing me, I found that she liked to give oral, and liked to swollow. After I knew she was on adequate birth control, I found that the best for her was for me to cum in her pussy, and then eat her clean.......it turned her into a bucking broncho as she came. I tried to get into her ass, but she objected every time I even put my thumb back there, so I guessed that wasn't her thing.
Eventually, I moved to another city, so our get togethers became limited to when I traveled on business back to her city. The last time I saw her, we were traveling on business to the same city, so we had the opportunity to share a hotel room, and have two nights together. The first day, within 5 minutes of her arriving at the hotel, we were having a nice fuck, doggy style, and she let me put my thumb in her ass, then came very hard. Encouraged, after she had recovered, she didn't object when I put the head of my cock against her asshole and entered her. She quite liked it, and did her bucking broncho thing as I fucked her ass long and slow. It turned out that her hubby had quite a large cock, didn't have much finesse about anal sex, and sort of insisted on fucking her butt regularly, so it always hurt her. Over the next two days, I taught her to really like anal.
Unfortunately, for me, she eventually got tired of her hubby, and quickly connected with another guy, and remarried. I saw her again, and made it clear that I still wanted her, but she said she wanted to be faithful to this guy......as he reminded her of me.
So, she's the best example of half a dozen ladies, most of whom I worked with who, just at a certain moment of their lives needed what I had to give, for a little while. I think the slowest was over 12 years from when we first started flirting until we did the deed. Remarkably, I wound up doing anal with 5 of the 6, which is a much higher percentage than I have with my other lovers, including 2 wives who never wanted anal, I don't know if it was their age, their trust in me, or their willingness to do something a little more outrageous in a different situation. Interestingly, all are still friends, even though I don't see them often, but I'm not fucking any of them at the moment.
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