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 story, and to his surprise, a publisher picked it up and printed it. And a few months later he was awoken in the early morning by a call from the American Library Association telling him that he had won the Caldecott Medal for his illustrations.

She supposed he wasn’t bad looking. His hair was salt and pepper, and the salt was taking over. His beard was neatly trimmed and off his neck and cheeks, covering his chin. A bit of a dad bod, but seemed to be in pretty good shape. He stood almost six feet, which meant she was looking him in the eyes when she was in her heels or cushioned joggers.

His clothes were a bit dated in one respect, but he tended to wear loose polo shirts and had a penchant for Hawaiian shirts, even in the cold northern winters. Shoes were typically something that slid on rather than tied, unless he was in a full suit and then he always looked sharp. His hair was short and usually a bit of a mess when he wasn’t in a social situation. It took several minutes with some gel to tame it and he couldn’t be bothered most days.

The two of them would spend several hours just sitting in a coffee shop sharing stories, talking about their dreams, their heartache and their experiences. He enjoyed her company, she was smart and intelligent and was able to provide cogent arguments when they disagreed on something, or were just trying to solidify their position on a topic. She had a dry sense of humor, with a touch of wit that caught him off guard. It wasn’t typical of her age group to approach things the way she did, but that was probably one of the reasons he liked her.

It was many weeks after they started actually doing some things together. Mostly coffee several times a week. He’d take her with him for an exhibit opening or if he had tickets to a show. His schedule was pretty flexible, few deadlines to meet, so when she could slip away from her job he could join her for a quick lunch and chat.

So six weeks after their first discussion, she had come over to his place after they had been to a movie and they were standing in the living room. He was about to suggest putting on the Graham Norton show, but she was looking at him with a thoughtful look on her face. They had been in enough in-depth conversations that he knew the look and knew that she was pondering something pretty deeply.

“Look, I’ve been considering something for a while. I’m a human being and I have needs. I have no desire to get involved in a romantic relationship right now. I know I’m not ready for that, it would be a rebound if nothing else. But, frankly, I’m horny as hell. I propose a friends-with-benefits situation. We both know it isn’t going to be a long term thing. I’m on the pill, so that isn’t an issue. How do you feel about that?”

“I’m speechless!” Matt paused before continuing, so many things running through his head. “I’m more than twice your age!”

“Guess I hadn’t thought about the actual numbers, I’d have put you at about the same age as my parents.”

“I’ve got at least ten years on your folks!”

“Really? You certainly don’t look it. And it isn’t like you would be robbing the cradle, geez, I’m closer to 30 than 20!. You’re in pretty good shape. Unless you have performance issues?” She glanced down and grinned, the obvious bulge in his pants told her that she had him. “And that does not appear to be the case!”

There was no question the idea appealed to him on a physical level, her quick glance had shown that his body was responding very positively to the idea. She was, after all, a beautiful woman. Madison’s hair went a bit below her shoulders, a golden brown with some highlights. Green eyes in a gorgeous face. Even being on the skinny side didn’t detract from her beauty, nice firm breasts well suited to her size, enhanced by the rather tight t-shirt, he wasn’t sure how much they were assisted by the bra that she was obviously wearing. The nice curve of her waist accentuated a pretty nice butt, even as small as it was. And despite his firm belief that he didn’t stand a chance with her, she had been the focus of more than one fantasy in the shower.