A May-december Romance

by mattwatt

Copyright© 2014 by mattwatt

Romantic Sex Story: When his Momma died, Winston Knight left home and took to the road on a ramble to kind of discover life. What he hadn't planned was the lovely older lady in the shiny new red Cadillac, who offered him a ride and the love that grew between them.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   .

She breezed along and the one thing that she kept thinking, that kept rolling around in her mind was the new-car smell. She thought that it was wonderful. She breathed in deeply and just loved it all over again.

She gave a covert look around: dash board, seats and appointments! It was all grand.

After all, this had been one of her 'new' major decisions. The new car. She remembered the salesman and how accommodating he was. He seemed to know that he had a 'live one'.

She had made the decision and given in to this whim. So, it was a new Cadillac for her. It was a new red Cadillac with white leather interior for her. And it was grand.

She certainly thought so and breathed in the new car smell once more, loving it that much more.

"Good for you, Linda!" she said to herself. "Just good for you. It's about time."

Linda Ryder's life had been the business. She took it over from her Dad, before his relatively early heart related death. She grew with the business and eventually had her hands so completely on it that she knew it inside and out.

She had a head for it, devoting time and attention and watching it grow and prosper.

It had been her decision for a few decades to do that with her life. There was no time, really, for men, for suitors. She had a pile of good friends but had long ago given up on anyone coming for her in the form of a shining knight. She'd put off any number of efforts and offers from friends to 'fix her up'. She was stubborn that way and wouldn't allow it. She'd made that clear in what she thought was a forthright but kind way.

She wondered, at times, what she might have missed but the excitement of the business was always real for her.

With the death of her Dad and, eventually, her Mom, the family was gone, and she was the last one of them around.

It was with that in mind that she began, a few months ago, to back off and take her enjoyment. She'd put into place a really good management team for the business, and shared the profits liberally with them. They needed 'hands on' from her less and less these days. She knew that.

Then she kind of laid back.

The very first sign of this 'laying back' for Linda was the purchase of a new car, this lovely red Cadillac.

She thought of that and sniffed it all again.

Linda Ryder would be 58 at her next birthday, though celebrating those things was, for her, almost a thing of the past.

She had, over the years, given herself a few perks, especially with the business going 'great guns' and all. One such perk was the house. It was large and had beautiful land around it. She had a gardener who kept it in good shape. She lived there quietly but very contently.

She also had rescued two kittens and let them have the rule of the house. They were a gray and a tabby, named Miss Whimsey and Ned. They were her bed companions and doted on her, as she did on them.

This new car had been almost a surprise thought for her, and once it was established, she knew that it was exactly the right idea.

She'd even gone back to the town where she'd grown up to buy it. It was where she had always bought cars but up until now, it was always utilitarian vehicles. There had never been anything as lovely and flashy as this red Cadillac.

The thought, of course, made her breathe in deeply again and kind of let out a small giggle at what she'd done.

"But," she reasoned, "There was money and to spare. It would be going, once she was ready to join Momma and Poppa, to charities and so, why no enjoy it now? Why not indeed!" she said to herself.

Linda had, all her life, taken good care of herself. She was a workout fiend and took yoga classes and various other physical endeavors.

She was petite; maybe even small boned. She had small but what might be called, if you were looking —- and few had ever had the chance to do the looking —-'perky' breasts with large, dark, cap-like nipples.

Her small waist swept down to a lovely upside down heart shaped butt. Very nice indeed! And though her hair was now a shining white, she sported a 'vee' shaped nest of dark curly pubic hair, that made a lovely contrast with her white, white skin.

Over the years, her hair had turned gradually white. Actually, it turned long before she was half way into the late 30's. Now she wore it straight and it added a kind of distinguished look for her.

At her current 57, Linda Ryder was lovely! Simply lovely! She wasn't looking for a man! Not at all. She'd recently backed off from the constant push of the business. She liked that thought.

And she'd bought this red Cadillac! (And 'yes', the thought made her take in a deep breath again.)


Winston trudged along the side of the road. There were few people out today, and, though he was headed south and was making progress with it, to get out of the northern climes for winter, it was still a little cool.

But he was, as usual, thoughtful about it. He smiled. He liked the freedom.

Once his sainted Momma had finally died of the ravages of the cancer, he felt free enough to break out and go his way.

He had his education. It had taken him a good 6 years to get that, since he had decided that he'd pay for it himself.

His Mom had tried for years to reconcile Winston and his step Dad but it never worked. The man was simply jealous of any and all attention that Marge had ever directed toward Winston.

Early on, while Winston was growing, that meant constant back hands from him but those days were over. Once Momma was gone, Winston was gone the next day.

The house was jointly owned by his Momma and step Dad and he wanted no part of it. The place had simply too many bad memories for Winston.

He thought of the oft repeated phrase that his step Dad had used with him over the years: "It's my way or the highway."

It made Winston chuckle that he'd left and had actually decided on 'the highway'.

In his mind he wished the old man well but suspected that his stubborn, bull headedness would earn him a very lonely end of life experience. He knew that he didn't wish that on his step Dad but he expected it to be true nonetheless.

(In this respect, Winston was accurate in his thinking!)

He was far enough south now that the weather was getting fine. The rain of a few days ago had stopped and he was dry and in good fettle. He swung along the highway and now and then put out a thumb to try to attract passing motorists. It didn't seem to be working for him that day.

Winston Knight was coming up to a 25th birthday. It made him smile to think about it.

"Will have to get a cupcake or something for that!" he mused.

He was very careful about his money but had learned early on to find odd jobs that were always around and replenish his stash of cash. His needs were slight.

He was whistling to himself as he walked along. He carried his knapsack easily. He kept the 'stuff' that he toted to a minimum and it made it easier.

Then he heard a car. There hadn't been one along this road for a good long while.

As the car approached, a red Cadillac, he saw a white haired woman driving.

This time, instead of putting out his thumb, he simply waved. He also grinned at the driver. She gave him the same kind of warm smile back and waved to him. She went on.

Almost as soon as she'd passed the young man on the road, Linda was getting, giving herself, notes about the fact that she should have offered a ride.

"Are you crazy?" came a small voice from within.

But it was a voice that, over the years, Linda had gotten used to suppressing and casting off its oft repeated messages of gloom and doom.

The voice, these days, even made her angry.

That was part of the reason why, at the next cross road, she did, in fact, turn around and headed back the other way.

As she passed the young man, he noticed her and waved again. She smiled at him and waved back.

"Twice in one day," he said to himself, "Maybe it's a sign of luck!"

(He had a thing about considering red cars to be a sign of luck.)

But Winston was flabbergasted, when, hearing a car approaching, he looked back and saw the red Caddie coming his way again. What's more, he was even more flabbergasted, when the caddie pulled into the side of the road ahead of him.

He walked slowly in the direction of the parked car, with a huge smile on his face.

One thing was certainly true of Winston Knight; it was his always sunny personality. He always supposed that behind this mind set was a lifetime of messages from his sainted Momma about how special he was.

She had certainly been aware of her husband's attitude toward Winston and seriously strove to not let it get Winston down. In that, the wonderful woman had also been pretty much successful.

Winston's smile grew broader, as he watched the woman get out of the car. She was petite and white haired. She was also smiling.

He gave her a huge grin and Linda Ryder found out immediately what Winston was basically like.

"Hey, sunshine!" he said brightly. It made her grin widen.

"Hi!" she returned his greeting. "How's the walking?"

"You know, not bad today," he said, leaning on a long stick that he had. It helped him to keep a kind of rhythm to his walking and served as protection against stray dogs that might not be friendly. Though Winston also found that he got along well with dogs. "Rain is gone and it's cool but not too much and I'm headed south where it won't be so much of a problem."

Then Winston's eyes swept over the car.

"Lovely red Caddie!" he said, the smile never fading.

"Yes," she said, "Still has the new car smell!"

"Cool!" he replied.

"Want to try it out?" she inquired.

"You know," he answered, "I love the walking, especially on a grand day like today is but a ride in a new red Caddie would just about make my day! Not something that I'd dare refuse." He said that with a huge grin for her, which was matched by her own grin.

"Then let's do it!" she said.

He held up a hand then and said: "And I want you to know that I'm not a rapist, or a murderer or a sinister character. Just a guy that's following the road."

"Good to know!" she said, giggling at the way he'd presented himself. "Then step into my new red Caddie!"

He did that.

They put his pack and stick and stuff in the back seat of the car and he climbed into the front.

He sniffed. "My, my but you're right. Total new car smell!"

"Yes," she said, grinning at him. "Picked it up today, and I love it. Was even hoping to get someone to go for a ride with me so that I could display my pride and show it off."

"Well," he said, "Here I am!"

"Where to?" she asked. "Oh, I'm Linda Ryder."

She stuck out a hand as he said: "Winston Knight."

"Hey, Winston Knight!" she said. "So, where to?"

"Well," he answered, "I'm just kind of following the road these days, walking away from cold and winter."

"Sounds kind of exciting," she said, "As long as you can keep the bad guys away."

"Well, I've been okay at doing that," he said. "Have said 'no' to any number of offers of the wrong sort so far."

"I can imagine," she said, and smiled at him. What flitted through her mind just then, in the wake of talking about such 'wrong sort' of offers was how lovely this young man was. She even surprised herself by actually saying that to him.

He grinned. "What my sainted Momma always told me."

"She's?" Linda asked.

"Gone!" he said wistfully, "And then so was I!"

"Look," she went on, "I'm going back home from picking up the car. I still do some shopping back in Waynesville, where I was raised. Had a friend that sold cars and went to him for this purchase. So, if you want, you can ride with me for a while. I'm going to Adair, and that's gonna be another hour or so."

"Sounds perfectly fine to me," Winston answered. "I'll just sit back and rest my legs and let you and the new red Caddie take care of me for a bit."

"We can certainly do that!" she said, still smiling.

They rode on companionably for just a bit, exchanging information about each other. It was just basic stuff. But they both noticed a comfort level that was quickly established with their exchanges.

"So," Linda said at last, "Following the road, a story there?"

"Yes," he said, and, feeling a great deal of confidence in her, launched into the whole issue of his growing, how wonderful his Momma was, how nasty his step-father was and his decision, after college, to get away and be his own person for a time period.

"Both sad and exciting," she ventured.

"Yes," he agreed.

"She must have been a wonderful woman!' was Linda's next comment.

He looked at her and said seriously: "She was! She always caused the light to shine for me! It's what I miss the most these days, though the walking and journeying itself are a true treat."

"Hard to lose someone like that!" Linda said and he nodded.

Then she spoke, talking about her life and the start she'd had from her Dad and how she'd devoted so much of her life to the business.

"How is it?" he asked.

"Fabulous!" she said. "Got it to the point where I could hire managers and just kick back. It was a kind of a birthday decision for me."

"Great!" he said. "Birthday, when?"

"Next Saturday," she said with a smile.

"Wow!" he ventured.

"What?" she wanted to know.

"Mine too!" he said, "Next Saturday, all of 25! And I won't ask you how old you'll be! My Momma taught me manners!"

"Not ashamed at all," she said, "I'll be 58 on Saturday. This car is my 'happy birthday' gift to myself."

"A grand one!" he said.


"And you," she asked then. "Birthday gift for yourself? New red Caddie?" she was giggling at the end of the phrase.

"Guess not," he said, "But I'm determined to root out a cupcake somewhere and treat myself."

"There's a grand bakery in Adair," she said. "I'll show you where."

"Finances?" she asked, holding up a defensive hand then and adding: "Tell me to mind my own business; I won't seriously mind at all."

"No, it's okay," he said. "I find odd jobs around wherever I go and keep myself in needed cash. Can certainly afford my birthday treat!"

His eyes lit up then as he said: "And speaking of birthday treats!"

He leaned over the seat and was rooting around in his pack. When he sat back down, he'd come up with a small, dark recorder, a soprano.

She gave him a look of joy, as he began to play 'happy birthday'. Then she sang along with him, using the words 'happy birthday to us'. They were laughing at the end of the song.

"That was lovely!' she said. "You play so well."

"Momma taught me!" he said.

"Yes," she said, "Your lovely Momma."

Their conversation was both easy and relaxing. It was a treat, especially for Linda to have found a ride companion as easy to get along with as Winston. She told him that. He smiled.

He asked then about her business.

"Be very careful!" she said at first. "I'll not only talk your ears off about the business but will likely bore you to tears."

It made him laugh and he said: "I doubt that. I'm a really good listener."

She went into it then: the business, how it had been, when she took over, at a young age, from her Dad. How she'd learned the business from the ground up and then began to inject her own ideas into it.

He was fascinated.

(It was one of the strong points of Winston's personality. He had a genuine interest in people, in what they were doing and how they were getting along. He showed that constantly.)

He had questions for her about the business and how it was these days.

She was both surprised and pleased that the questions were so 'right on' and answered. A discussion ensued.

Linda didn't really know, when it was that she'd made the decision. Maybe it had come gradually right along but she got to a point where she knew exactly what she was going to do.

There was a brief silence, after their discussion about the business.

"See," she said, "I told you!"

He held up a hand and said: "No, really! I think it's fascinating."

"You're so nice!" she said.

He turned to her and said: "And truthful!"

"Yes," she said next, "I can sense that."

"Well, Mr Truthful!" she went on.

"It's Winston actually!" he said and they both laughed.

"Yes, Mr Winston Truthful," she ventured again. "I have a suggestion."

"Yes?" he said, "I'm all ears!"

"Oh," she said, giggling before she even got the sentence out. "That sounds so painful!"

He gave her a wry smile and said: "Okay! Proud of ourselves are we?"

"Indubitably!" she replied.

"Your suggestion?" he prompted.

"Why not interrupt your odyssey and come to me for a little bit? We can celebrate our birthdays together, and I promise you a first class cup cake. Might even bake it myself!"

His grin was world winning. "What a nice, nice suggestion. Are you sure?"

"Yes, positive!" she said.

"I don't want you worrying about taking in a stranger!" he said earnestly.

"Stranger? Heck!" she snorted, "We share a birthday, and besides I'll have you vetted by Ned and Mrs Whimsey."

"And who, may I ask, are Ned and Mrs Whimsey?"

"My attack cats!" she said proudly, "A gray and a tabby."

"Sound lovely," he said. "Never had pets, growing up," he ventured. "Step Dad didn't like them. Promised to kill anything that I brought around!"

"Beast of a man!" she said.

"I'm afraid so!" was his answer.

And then he told her of his suspicion about what kind of old age the step dad was going to have.

"You're probably right about that," she said.

Then she said to him: "But here we are in Adair."

"Great!" was his reply.

"There's the bakery!" she said, pointing it out, as they drove down main street.

"Yes, but you promised to make a cup cake yourself!"

"So I did!" she said, "And I too am truthful!"

"I never doubted it!" was his reply.

Then they were pulling into the drive way.

"This is gorgeous!" he said, "The home of Ned and Mrs Whimsey?"

"The very same!" she said.

She drove around the back and stopped in front of the garage. It was a three car garage, which came with the house, but she used only the one stall.

"See," he said, "Room for growth!"

She grinned at him then.

From somewhere then the little voice came and accused her of a kind of selfish behavior, what with the new car and the big house and all.

"You must think I'm terrible," she said, waving her hand, "I mean with all of this, and you out on the road and all."

He smiled at her and put a hand on her arm. "First of all," he began, "I'm out on the road by choice and most of it is grand. Secondly, you work hard and get to enjoy what your hard work has earned for you. That's what I think."

She hugged him then and said: "You're so nice!"

He smiled at her and kissed her cheek.

She noticed; she noticed right away. Even the cheek kiss gave her a tingle. She mentally put a quick clamp on that kind of thinking immediately. She just wouldn't have it, wouldn't at all! That was her resolve. She just filed the 'tingle' feeling and the resulting dialogue with herself back into the back part of her mind.

"Well," she said, brightly then, "Let's go and I'll introduce you to the demons and then we'll do the cook's tour."

"I won't have Ned and Mrs Whimsey defamed!" he said with mock severity, "I just won't have it."

Her response was a kind of tinkling laugh. The laugh made him grin at her. He was surprised, and had been constantly at how much he felt at home with her. He even said that to her and she agreed.

"It's very nice!" she said. "And here we are!"

They went from the garage, via a passage, to the back door of the house. As soon as they entered the house, they heard the two cats making their way toward the door.

He was being sniffed by the cats immediately.

"Mrs Whimsey, Ned, this is Winston, Winston Knight! He's going to stay with us for a few days," she said broadly.

Winston was now being rubbed, first by Ned and then by Mrs Whimsey. They alternated, with one working on him, while the other worked on her. Doing their rubbing and purring.

He had put his pack down and was paying some attention to the two cats, as they came to him for the proper amount of adulation.

He looked around then, as she led him farther into the house.

"This is plain lovely!" he said.

She smiled at him and thanked him.

"It's been one of my main sources of pleasure!" she admitted.

"That and the red Caddie!" he said, grinning.

"Yes," she said, shaking her head in response, "This and the red Caddie!"

"Good for you!" he said.

"Tour?" she asked.

"Love one!" he answered and they set out.

The hose had a bit of a divided plan. It had the master suite upstairs on one side, covering the entire side of the house upstair. There was a lovely kitchen off to the right and a dining room adjacent to it. A bit to the left was a sunken living room and off to the left of that, a kind of tv and family room.

On the other side of the house was the guest wing. The guest rooms, two of them, were upstairs. They shared a bathroom. On the lower floor, on that side of the house, was a powder room and the laundry room.

There was a finished basement with a few rooms, not all of which were used. Down there was a workout room, where Linda had her workout machines and practiced her yoga.

As they made their way through the house, with him appreciating all of it, and saying so, they were accompanied by Mrs Whimsey and Ned.

"This is so grand!" he said to her.

"Thank you," she answered, "We have grown into it. It feels so comfortable now."

She hesitated a few seconds and went on: "But what do you need now? I'm going to show you to your room and let you get settled."

They went to the guest wing side of the house and she showed him into the main guest suite.

"Lovely!" he said.

"And now?" she asked.

"Mind if I shower?" he asked.

"Fine!" she said.

"What a grand idea that is! On the road, it's cleaning as best you can, and when you get an opportunity kind of thing."

"I can certainly understand that," she said to him. "So, I'll leave you to it."

Then she showed him the bathroom and where the towels were. He thanked her.

Before she left, she said: "I'm going to be starting dinner. It might take a little bit of time. I'll likely be in the kitchen. You can find me there."

"Bet I can!" he said to her.

She was about to leave, when she turned to him and grabbed him into a hug.

"Welcome!" she said.

As they were hugging, he said a soft: "Thank you for inviting me to your, Mrs Whimsey's and Ned's home."

"It's our pleasure!" she said, and turned to go, her mind, however, reeling from the memory of that hug.

She gave herself renewed 'watch it, girl' message, that were accompanied by a line of thought that told her that she was old enough to be his Mom and almost his grandma.

"Yes, I know," she said almost snappishly to herself.

She went to the kitchen then, with a nagging sense in her mind that not far away he might be naked. The thought came unbidden and undefended against.

She was giggling before she knew it and again clamped down on that kind of thinking.

She took the time to change her clothes from her good slacks and blouse to a droopy tee shirt and a pair of tight, black capris and sandals.

Then she went to the kitchen to begin the dinner preparations.

She had some chicken and a good masala sauce and decided on that combination. She also had some spinach in the 'fridge' and also decided to put the spinach into the combination. She began to simmer the chicken in coconut oil, giving a good smell and taste to the whole combination.

After a bit, he found her in the kitchen.

"Look at you," she said, "All clean!"

"Yes, a wonderful feeling," he replied. "Thank you. Something smells good."

She explained to him what she was making and offered him a drink.

"I'm having a glass of white wine. I'm afraid that I'd make a terrible wine snob. I like white from a box.

He grinned at her.

"Beer?" he asked.

"Yes," she said and fetched him a beer and a glass.

He sat then to watch the progress of the dinner, and they talked during the preparation.

"After dinner," she said, at one point, "I'm going to do some laundry. I can throw your stuff in with it, if you want."

"Why, thank you!" he said. "That would be great."

"How good is my fortune in running into someone as wonderful as you!" he said, and she grinned at him.

They ate companionably and then cooperated in the clean up.

"Don't know how tired you might be," she said. "Maybe a little tv?"

"That would be great," he said, "It's a kind of domestic scene that I have hardly had a chance at."

"I'm sure that Mrs Whimsey and Ned will be pleased to join us," she explained. (Which turned out to be the truth, for the two cats did join them, and Mrs Whimsey, early on that evening, established herself on his lap and went to sleep there.)

After a bit of tv, he apologized and said that he really was tired.

"Being on the road is a tiring past time," he said.

"I'm sure it must be," she agreed. "Well, I'll be in my library for a bit," she indicated the room that was next to the family room.

"I'll say 'goodnight' then," he said.

"Yes," she said, "Good night."

She went to him then and they hugged. In the process, he kissed her on the head.

"Thank you for the ride in your new red Caddie," he said softly. "Thank you for being so nice to talk to, and than you for taking me in!"

She looked up at him, just barely suppressing the desire to kiss him and said a 'you're welcome'.

"There are extra blankets," she told him, "In the closet in that room. You'll see them."

"Time in the morning?" he asked.

"I'm up at about 7 AM," she said, "But you take your time."

"Never got the habit of sleeping late, while I'm on the road," he explained.

"Fine," she concluded, "See you in the morning!"

"Good night, Linda the angel!" he said and she grinned at him, as he left the room.

She did sit in the library and went through the house finances a bit. She tried to keep a good, tight grip on her thoughts and feelings.

There were questions that were assailing her: "What did he wear to bed? Did he wear anything to bed? —-that question caused her to giggle into her hand. (The truth was that he didn't wear anything to bed.)

She worked at putting those kinds of thoughts out of her mind, but now and then erupted in a giggle due to the same thoughts crossing her mind again.

She did put some laundry in, and noticed that some of his clothes were fairly ragged around the edge. it put a plan in her mind.

She allowed herself only a pair of thin panties for bed that night and had Mrs Whimsey and Ned with her, as usual.

(During the night they did go off exploring, and she discovered the next day that they spent part of the night with him also.)

She was up early in the morning and, after combing her hair, put on a long robe and went to the kitchen. She hadn't been there very long, putting the coffee on and getting out breakfast supplies, when he entered.

"Hey!" he said.

She turned and gave him a broad grin and a 'good morning'!

She went to him then and collected a hug from him, before continuing the breakfast chores. He sat and watched her, talking about how peaceful his night had been, how the cats did indeed spend some time with him and, again, thanking her for the opportunity for him to have such a peaceful night.

"One gets used to night noises, when you're out and walking," he said.

"Yes," she agreed, "And I guess this was a 'heed no nightly noises' kind of experience."

"Exactly," she said.

"Plans for today?" she asked.

"Well, if you don't mind," he answered, "I just intend to hang out kind of."

"Sounds like a plan," she said. "Oh, and there's something that I want to ask you."

"Yes?" he replied.

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