Getting Back in the Dating Pool - Sex Stories

Getting Back in the Dating Pool

Matt couldn’t believe it. Here he was sitting on his couch with a gorgeous woman half his age bouncing up and down on his cock. He certainly wasn’t going to complain about the situation, but it sure messed with his sense of reality. Maybe he was dreaming, but if he was, he didn’t want to wake up for a while!

The two were a very unlikely pair. But the friendship had built up over the last six weeks. Matt had literally known Madison all her life, being friends with her parents when she was born. Various events over the years had maintained some semblance of contact, and she was comfortable enough with him to give him a big hug whenever she saw him.

And Madison had grown into a real beauty, of the model quality beauty. Which meant for him that she was too skinny for his preferences, he liked a more solid build. But that certainly didn’t prevent him from admiring her modeling photos when her parents shared them online. She had paid for college with her fees and graduated with a job in marketing. And a steady boyfriend that proposed after a couple years. For whatever reason it was called off after another year. He didn’t hear the reasons behind the cancelled engagement, but it was a generation away from his normal circle of friends and interests and just didn’t think it was any of his business to ask her parents about it.

But there they were, Matt and Madison chatting away together. They had both suffered a pretty devastating loss, Madison’s broken engagement and ...

... Matt’s wife had recently passed away from cancer. It was a mutual support friendship more than anything. There was no real sexual tension between them, their age difference was enough that neither one of them looked at the other as a possible sexual partner. Well, at least neither of them would admit it to the other, or to anyone else. It would just make him seem too creepy. There was no need to create any sort of facade, they were two individuals that needed some company, someone to do things with while they processed their losses.

Madison found him fascinating in many ways. He had experienced so many things in his life that there was little he couldn’t talk about, or show an interest in. His career had started in the military out of college, a combat tour, getting out of the service and going to work as an engineer, making good money managing projects all over the country, and once in a while in other countries.

As Matt contemplated what he wanted to do next, he took some art classes at a number of the local venues for such things, and found himself enthralled by the works of a Danish artist. This artist gave classes online and Matt took every one that was offered, learning to turn his thoughts into quirky drawings that stretched the boundaries of reality but still allowing his viewers to identify with the characters and situations. At one point a friend had written a children’s book and asked if he would illustrate it. He had put together a couple dozen spreads for the ...