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.
“Sorry, but it has been a long time for me!”
He was pleased that things didn’t immediately shrink to normal size, and she was able to ride him for a few more minutes before he lifted her off. Another good reason to use the condom, he wasn’t overly sensitive after cumming to need to stop immediately. He sat up and by leaning forward was able to stand up with her still in his arms as he turned around and deposited her on the couch where he had been. “That was pretty amazing for me, but now, let’s take care of you! Let me grab a couple of towels.”
Popping into the bathroom around the corner, he snatched a couple of towels and ripped them out of the towel holder with enough force that it fell apart, the metal bar clanking loudly on the floor. He’d have to fix that later!
“You okay?”
“No problem, just in a bit of a hurry.”
He deposited the used condom in the sink and used one of the towels to give himself a quick wipe off before returning to her. He dropped to his knees between her legs and with little warning buried his face into her crotch, inhaling the sweet aroma as he did. It was only a matter of moments before his tongue was hard at work, tracing the outlines of her vaginal lips, slowly probing her sex. He licked the outer lips, teasing her a bit before moving into the inner area, running his tongue up and down the smooth, wet slit. A few flicks on her clit with his tongue and she was quickly transported to another level, her scream echoing off the walls. She pushed the back of his head into her crotch as she spasmed, covering his face with her liquid. After a few more licks and some rather dramatic aftershocks, he was finally able to come up for air and wiped his face on the towel. The couch was going to need some serious attention, but he wasn’t going to mind a bit.
He collapsed next to her on the couch, head still spinning. Madison’s breathing started to stabilize and she turned sideways, burying her face into his shoulder and holding him tight. She felt good in his arms. Matt grabbed the TV controller and flipped to Graham Norton, still not sure about what had just happened.
They watched the show in a bit of a daze and slowly gathered their wits about them. They got themselves dressed and finished watching the show together on the couch, a bit hesitant to touch. When it finished he walked her out to her car. It was cool, but fall hadn’t really taken hold yet.
“Thanks. I really needed that.”
“No, thank you! I’ve been having a bit of a dry spell myself!”
She giggled and gave him a hug. “I suspect we’ll do that again.”
“As I said, I’ll leave that entirely up to you, but I’ll be here ready and more than willing whenever you should need me.”
There was a marked change in their relationship at that point. Nothing that was obvious to most, but Madison took charge of his body in many aspects, and not just as a sex toy. Instead of meeting at the coffee shop as often as they had been, they would meet at the gym. She became his personal trainer, she’d put him on an aerobic machine for half an hour and then they would sit and talk for a bit, before hitting up some of the weight machines. They spent less time at his place, which was certainly a benefit for keeping suspicious thoughts out of the minds of others.
Madison took him shopping for some more current clothing, updating his wardrobe a bit. She didn’t mess with what he liked, just got rid of some of the older items that were starting to show wear and got him things that fit better, particularly as she got him to lose some weight. They also tended to eat together a bit more, as she made some changes to his diet.
Madison discovered that Matt was a pretty good cook when he wanted to be. If he felt like showing off he could go all out and present some very pretty plates, with a reasonable calorie level and a nice balance.
He actually did lose weight. There was a certain level of it which was due to the aerobic exercise their sexual activity provided, but most was due to a combination of training and a bit more conscious diet. She rewarded him when he hit the loss of 10 pounds. It hadn’t taken her long to realize what really turned him on, a nice ass was the first thing he noticed on most women.
“Is that your thing? You like women’s asses?”
“Pretty much every time I’ve been attracted to a woman it has been because of her ass. What tends to keep me around is the rest of the package, but the ass always seems to be what I remember.”
“For instance your wife?”
“Oh, yeah. Watching her walk down a hallway a few steps ahead of me. All I can say is that it was a good thing no one else noticed, or I could have been in big trouble.”
“So, you remember the first time you saw my ass?”
“Yes, actually my first memory of you is you bending over a table in one of the classrooms, working on a poster. You were wearing dark hosiery and a pleated skirt that mounded over your butt and split around your cheeks.”
“Okay, name some others.”
“Really? You want me to go there?”
She reached over and started to massage his cock through his pants.
“Alright. Your friend, Louise, wearing a pair of gray yoga pants. She’s got an athlete’s butt and I have admired it since that first day. Even went to her wedding and the wedding gown didn’t hide it’s charms. Then there is Chelsey, she was an ice skater and came in after practice one night to where I was doing some volunteer work to see her mother. I pretty much went crazy over the tight leggings and short skirt. That was another one of those that could have gotten me into a lot of trouble if someone had really noticed me looking.”
“So, always the ass?”
“Not always, mostly.”
“Legs?”
“Sometimes the legs, particularly if there are patterned stockings or tight leggings, your mother would be a good example.”
“Oh, you have a thing for my mother?”
“I wouldn’t call it a thing, she’s pretty good looking, after all, your beauty came from somewhere! And your smile is almost the same as hers.”
Madison had kept her fingers moving the entire time she was grilling him. The images in his mind as he brought these memories to the surface were pushing him toward orgasm and wondered if she was just going to finish him off with the hand. But she surprised him, “If you have admired my butt so long, maybe you should fuck my ass.”
He thought about how tight that would feel and before he knew it a full erection was standing between his legs. She went to the bathroom and returned a couple moments later with a pair of towels and a bottle of lube.
She proceeded to lube up his erection making it throb in anticipation, the pre-cum leaking out of the top. With his cock lubed up she smeared some more lube on her own ass and proceeded to climb on top of him. With a bit of careful placement she put her ass hole against the tip of his cock and slowly relaxed, letting her sphincter muscles slowly expand to allow his entry. Even getting the tip past the initial opening had him as hard as steel and he wanted to thrust up, impaling her on the shaft, but he held himself back, not wanting to hurt her. It took some will power, but he let her take control. He wiggled up further on the couch so she wasn’t at the edge, he didn’t want her to fall backwards and hit the floor.
Then she surprised him again. This time with a small vibrator that she slid into her pussy and turned on. His cock was immediately excited by the sensation of the vibrations through the thin walls separating the vibrator from his temporary anal home. She was just as excited, the stimulation sending her quickly over the top and shuddering with orgasm after orgasm. He finally couldn’t take any more and rolled over on top of her, pulling her legs up to her chest and the peaks of her skinny ass grinding deep into his crotch. He pounded for almost five minutes before his balls crinkled up and shot another load into her, coating her tunnel. Truly exhausted, they lay motionless for several minutes before she made him move off of her.
That became his incentive for hitting various milestones of weight loss and fitness levels, a good session of anal when he reached them. It proved to be a good motivator as his waist thinned down and his upper body strength improved. Not only was his body getting healthier, he was learning to prolong his love making. Part of it was to make sure that Madison was satisfied, but also to prolong his own pleasure. He never knew when she might decide that she no longer needed a friend with benefits.
Madison’s parents were a bit concerned with the amount of time she was spending with him, but she explained it as that he was her latest project. She was trying to get him ready to go out into the social world with the idea of finding a girlfriend and stop being a recluse. And when she was working on him, she wasn’t thinking about her own situation, it was helping to buffer her pain and helping her adjust to her own need to go out and find someone. Her parents would have been more concerned if the two had been closer in age, but given their age difference was over 25 years, they really didn’t think anything long term could come out of it.
A couple of times a week, she would follow him back to the house after the workout, or show up at his door after work and push him back into the house. Most of the time she would start by laying him out on the floor and riding his face, letting him lick her to ecstasy over and over. During their time together she never went for oral sex on him, something he wasn’t too upset about, after all, he was getting laid on a regular basis. His tool was a bit on the large side, it would certainly have caused her some trouble. That wasn’t to say she wouldn’t give it a lick or two as she teased him to full size. But Madison much preferred having him plugged into her vagina, stretching it as she rode him to an orgasm or two. And true to their agreement, she always made sure he had an orgasm before they finished up for the session.
And there was certainly an increase in interest in him from other women. Before when he attended church, Madison and her parents were the main interface, along with a couple of other widowers and a few couples that had been good friends. No one pushed him to change, but Madison made it happen. There were a few women that had divorced that would give him a smile that at first was a bit uncomfortable, but his younger sidekick could read the signs and worked to encourage him to respond and would surreptitiously excuse herself so that they could chat alone.
Then Matt got a great opportunity to head to a major theme park and teach a couple of one week art classes, followed by a week on a cruise ship doing the same thing. It was a great deal, he was paid a nice sum and the company setting it up provided full room and board for the entire three weeks, along with full access to the park and all the other cruise amenities. He thought about asking Madison to go with him, it would have been amazing to have her join him for some uninhibited coupling away from people they knew. But reality butted in and he realized it would be very difficult to explain both of them being gone at the same time and lots of questions would be asked. It was much easier for him to say yes given that Madison could look after Krazy Kat. He could never remember the name that the cat had been officially given when she had appeared in their home, but Krazy Kat fit her to a T.
When he returned, well tanned and without having gained more than a pound or two, Madison met him at the airport. They chatted about what occurred over the last three weeks as she sped up the highway to his house. They barely got into the door before she was all over him, stripping off his clothes in the mud room, which was probably going to have happened anyway, as the laundry room was right there. She dragged him down the hallway to the bathroom and started up the shower, stripping herself as the water warmed up. There was no doubt she wanted him and wanted him immediately as they climbed in under the warm shower. He was glad to clean off the travel dirt, but was even happier to run his hands over her body.
He snuggled in against her back and wrapped his arms around her, his right hand sliding over her left breast and massaging it firmly, with the occasional tweak of the nipple. She leaned back into him as she felt his erection prodding into her lower back. His left hand slid over her belly and worked its way carefully into the folds and began rubbing her clit. Her first wave of orgasm was over with quickly, the fastest he had ever gotten her to climax. It was obvious that she had needed the release. He soaped her up and enjoyed the feeling of her body sliding against his. The soap foam slid down her body and dripped off her breasts. She did the same to him, the lather lubricating their skin and making for a very erotic situation, but also threatened to send them flying on the slick tub. By the time she got both hands to his cock, he was immediately sending an eruption of cum across the tub, splattering on the wall and sliding down to the drain.
They rinsed off and dried each other, before moving to the bedroom. The bed was one of the few places in the house they seldom used for their sexual release, but this was unusual. He’d had a number of women approach him during the cruise, but they were either underage girls or grandmothers with more than a few extra pounds on them. So he had essentially been without any relief other than his hands for almost a month.
She was in full control as she pushed him back on the bed, not even allowing him to get his feet off the floor before she came at him. For the first time, she attacked his cock with her tongue, slathering over the eight inches of flesh as it throbbed in her hand. She slid it between her lips and rolled her neck, her tongue continuing to dance around the bottom of his tool as the top of her mouth stimulated the head. Sliding her head up and down, a few gags caused all kinds of strange sensations on his bare dick. More and more of his penis slid down her throat until it was firmly swallowed, her nose tickling his pubic hair. It was only a few moments after getting there that she started humming, at first he thought she was choking, but her eyes let him know she was alright. And that was enough to push him over the edge, spewing cum down her throat as he yelled in pure bliss.
She sucked him slowly as she removed his tool from her mouth, no saliva or cum left as the suction cleaned him off. Madison wiped her face off and climbed up on the bed beside him.
“We need to talk.”