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.
"I've been snipped, so there are doubly no issues from that perspective. I'm open for the opportunity, I mean, what male could possibly resist? But we should probably set some guidelines to avoid problems in the future."
"Okay, what did you have in mind?"
"No leaving either of us hanging! Finish off what was started. No hickeys or bite marks or anything that would indicate something more was going on between us."
"A big agree on that, I never know when I might get a photo shoot, and don't want to worry about having to cover up some marks."
"No overnights. Anything said during our romp is not to be taken seriously. And even though we are going to be intimate, no invading each other's personal space in public. If we show a lack of respect for the space, people are going to figure things are more intimate pretty quickly."
"Seems reasonable. Might I suggest the use of a condom at all times?"
"Really? Even though we are doubly protected?"
"Yes, for several good reasons. It is easier to clean up things afterwards. Less chance of the smell being obvious to others. And you will last longer, meaning less chance of me being left hanging. And if one of us should happen to have something the other doesn't, it doesn't get spread."
He certainly wasn't going to make an issue out of it! If she wanted him to wear a condom, it would be a small price to pay in exchange for getting with her. And he knew that her points were valid, he often used a rubber when masturbating for the same reasons, it prolonged his pleasure and it sure beat having to wash the sheets every time, making it a whole lot easier to clean up. Matt never got the mucho gotta go bareback train of thought. The longer the better as far as he was concerned.
"Okay, and I will add this, partially for my own sanity. I will not initiate anything. I'm sure you will know when I'm interested, but will pretty much abide by your desires and needs." It sort of felt like he was putting her in charge, but any opportunity would be better than no opportunity and he figured letting her pick would make her more comfortable with coming to him for some relief.
Not hearing any further objections, Madison quickly flipped off her t-shirt, lifting it over her head revealing a taut belly and just a hint of the ab muscles. The light green bra was fairly utilitarian, but that didn't stop his erection from throbbing a bit more at the sight of it. She tossed the shirt onto the couch and walked over to him and began unbuttoning his shirt. He figured if she was going to back out of this, his shirt coming off would be the time. He wasn't a body builder by any means, but he was at least toned and not overly flabby. His waist was definitely bigger than it should be, but part of it was due to the scar. It ran from his sternum down to his waist line, cut with a surgeon's scalpel. It had been an exploratory cut to find out what was causing the pain and fever after the appendix operation came up empty, no organ in sight.
She tossed his shirt on top of her own, and ran her finger tips over the scar. Even after all this time it was still somewhat red and stretched, a smooth keloid that was about half an inch across. "Knife fight?"
"No fight to it, the knife was in the hands of a surgeon."
"You'll have to tell me all about it, but later."
"I shall regale you with tales of the attempt to sacrifice me to the Whirly Bird of the Eastern Med." She giggled and proceeded to unfasten his belt, she struggled with the unfamiliar buckle, but it only took her a moment to figure it out. His pants slid to the floor as she gave the tented briefs a pat before dropping her own blue jeans. She dipped her hand into her pocket as they fell to the ground, a slight gleam revealed that she had come fully prepared. There was no doubt he was getting a bit light headed, a combination of sexual desire and the situation, but he picked her up, she was a feather in his arms, and moved to the couch. Fortunately the curtains on the picture window were already closed.
Matt slid down on the couch with her still in her arms. Madison popped up and slid off her panties, a light green that matched the bra. He wondered if she always wore matching underwear or if she had been planning this. And realized, while it didn't really matter, both were probably true statements.
Her skin was nicely tanned with a variety of lighter tan lines around her hips and breasts, pulling his attention into those areas, not that it was needed. She was clean shaven, not surprising considering the modeling she did. He flipped his hips up in the air as she reached for his briefs and slid them down. She didn't waste a moment of time, ripping open the condom and after a quick glance to orient it, she rolled it over his penis. The unfamiliar hand coupled with the aroma of her arousal and his lack of a sexual partner for over a year made it difficult for him to control his passion. It was everything he could do to not cum right then and there.
Madison slid her knee onto the couch beside him and pretty much impaling herself with his rigid tool. He winced a bit as things weren't as well lubricated as he would like. But he wasn't about to slow her down. She quickly removed her bra, the front fastening providing a fast release. The nipples were a light coral color, not the darker red that he usually encountered. Her breasts were right in front of his face, so he did the natural thing and kissed them, giving them each a flick of his tongue. She moaned as she settled into place, slowly sinking the last inch or so of his eight inch erection into her hot tunnel. He filled her nicely and she was definitely pleased by that. He began thinking about some deadlines he had coming up for various art commissions as she began slowly moving up and down with her thighs. The sensation was fabulous and it was only a matter of a few moments before he lost all control. With a yelp and a thrust he ejaculated, spewing his cum into the condom with enough force that she felt the warmth spreading inside her.
