The Rich Widow Next-door

by mattwatt

Copyright© 2018 by mattwatt

Romantic Sex Story: Newly minted Doctor, Jason Porter, meets his slightly older, widowed neighbor and the scene is set for a romance.

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

He walked out onto his balcony that day with a glass of iced tea. He he sipped the tea and made a contented noise. He was simply that pleased.

He gave himself a moment to think about it: newly minted doctor, and what a great sound it had: Dr Jason Porter. He knew that there was a possibility of a good position in a flourishing medical firm, probably allowing him to make more money than he had ever thought of even in his wildest daydreams.He’d already had an initial interview with them. It all caused him to smile.

Then he’d sought out and bought this lovely house on the hill. It was up near the top of the hill with a canyon of sorts that was back behind the house.

He didn’t mind at all the canyon. He wasn’t a fan of that much grass mowing in the first place. With the canyon there, that was not a problem. He did have a plunging side yard and lovely frontage for his house. But he was determined to find someone who he’d pay to do the front and side mowing.

He lived there on his hill top and being at the top of the hill, also there were other houses down the hill from his own.

Standing there on his balcony, he glanced down in the direction of the other houses then for a moment. His eye was caught by movement in a house down the hill from his.

He knew his neighbors already, having been introduced to them at a gathering that had occurred only the past week. They seemed like a very cordial group and he’d been welcomed to their neighborhood by one and all. It had pleased him.

It was just then, as he was standing and looking round idly, that a woman came out onto her deck, apparently to enjoy the sun.

Jason couldn’t tell, in just looking down at her deck from the vantage point of his, if she was wearing a bathing suit or simply her underwear.

He felt rooted to the spot.

He searched his mind, projecting it back to that evening gathering, when he was introduced and came up with the name May Weathers.

“Yes,” he said to himself, “May Weathers.”

He forced himself to turn from the sight and prepare to go in. He was feeling a bit guilty just then for spying on a neighbor lady.

Just then his phone rang. He’d carried it out to the deck with himself, always wondering if he might get a call where he would be needed at the hospital.

“Hello,” he said.

“Dr. Porter,” the soft voice said.

“Yes,” he said.

“This is May,” she said next.

“Um, May?” he said a bit confused.

It caused her to give off a tinkling laugh, little more than a giggle.

“Your down the hill neighbor,” she said then.

His head spun around and he saw her waving at him.

“May,” he fairly croaked.

“Yes,” she said, “I’m the older, rich widow lady just down the hill.”

“Ah,” he answered almost automatically, “The older, rich widow lady just down the hill.”

“Yes,” she said, giving off that endearing laugh again, “I’m also the one who is out her on her deck in her undies being gazed at by her handsome neighbor.”

“Yes,” he croaked, still staring, “Your undies.”

She laughed then outright.

“Have I rattled you, Dr Porter?” she asked in an almost coy voice.

“Yes,” he said before thinking at all. Then he recovered just a bit of his composure and started to apologize.

“Now, now,” she broke in, “None of that now.”

“Oh,” was his only reply.

“It’s just good that I wore my panties and bra out here to sun myself,” she said, giggling.

“Just good!” he said.

“I mean instead of being naked for my sun time,” she said then.

“Yes, instead of being naked,” he repeated, in a strained voice.

“Oh, you are so cute, when you’re rattled,” she went on.

His only reply, the only thing that came into his overworked mind was the phrase ‘yes, your panties and bra instead of being naked’; he caught himself, not in time, saying those words to her. It caused a new round of that tinkling laughter from her.

“Were you using your binoculars, Dr Porter?” she asked.

“Don’t have any,” he answered.

“Too bad, Dr Porter,” was her reply to that. “You should.”

“Yes,” he said automatically.

Then he looked on, as she set the phone down and actually waved at him. She grinned up at him and unhooked the back clasp on her bra and, setting the bra band wide, lay down on her pad for some sun.

He looked on for only a few more seconds, and berating himself for spying on her, though he wasn’t sure that he was actually intending to do that, went in.

He did notice that before he went in, she waved at him.

A GIFT: The next little episode in the drama that had begun that day with the ‘sun bathing incident’, as Jason kept thinking about it, occurred two days later.

He got home from his rounds at the hospital, thinking about what he might fix for his dinner, when he found a package inside his storm door.

“Hm,” he said to himself. “What’s this?”

He put his case down and went to the dining room table with the package. It had a note attached.

Opening the note he found it saying simply: “For Dr. Porter from his good friend.”

He was intrigued and opened the package. His hand went involuntarily to his mouth laughing, when he had opened the package and found a pair of good binoculars.

He went to his back windows and began to use them, looking out across the small canyon, to get used to how they were. They seemed to be really quite strong and gave him a great view into the canyon behind his house.

Her e-mail address was listed on the bottom of the card with the binoculars. He went to his computer and sent her a thank you note.

He got a return to his thanks that said: “For your peeping activities.”

He laughed, realizing how much of a challenge this woman was, this ‘rich older woman’, as she styled herself, and sent her a return: “Didn’t know that’s what I was doing.”

He got an immediate: “Of course you were; I was wearing only my panties and bra and you were leering.”

His return was: “Don’t think I was leering at all.”

Then came the next note: “Yes you were; I could hear you!!”

He was laughing again and sent back simply an admission: “I give!”

“About time,” came her response with a smiley face.

He spent some time that evening trying to bring back up to his mind all that he could remember about that meeting with the residents, at which he certainly met May Weathers.

His impression was of a fairly petite, but also fairly big breasted woman, whose age he really wasn’t very much sure about.

That wasn’t really too strange for Jason, since he wasn’t all that great about assigning ages to people with whom he was not closely acquainted.

It did, however, leave him grinning and ruminating about the whole incident.

He got a note that evening: “Hope you’re over your leering.” It wasn’t signed but it didn’t need to be.

“Wasn’t leering; I don’t think,” he wrote back. “At least that’s my story.”

The next note was: “Likely story!” And then:

“Good night, Dr Porter!” appended to the note.

“Oh,” he sent back to her, “I am probably so out of my league here!”

“Dr Porter,” she said, her final note of the evening, “I will take such good care of you!” The signature on the note went: “Sent from a now naked May Weathers.”

Appended to that note was one final short note: “Play with yourself now please.” It was signed ‘May’.

He hardly needed to be encouraged to do that. He was really tempted to go out into the darkness of the evening and jerk off right there out on his deck. He thought about it only for one more minute and out he went.

The darkness surrounded him and he looked down seeing only barely a light on at May’s.

“Probably a night light,” he thought.

His cock was standing out at attention and he began to play with himself, looking down at her house, her deck.

He came all over the ivy vine that covered the side of the railing on his deck. He thought about May all the while he was jerking off, imagining her out on her deck to sun herself, wearing, he guessed, only her underwear.

Before he went to bed, he sent May a note telling her what he’d done. It made him chuckle.

Her response in the morning was to the effect that now she was pouting, since she didn’t watch him do that. He chuckled over that too.

That day was a Sunday, an off day for him. He had his breakfast, and took coffee out onto the deck. He was wearing running shorts and his underwear but no shirt.

He noticed May sitting out on her deck with coffee also. She saw him and waved. He waved back, and saw her pick up her phone. It made him grin.

When his phone rang he answered by saying:”How’s the angel this morning?”

“Well, aren’t you sweet as well as sexy!” she answered.

“Thank you, beautiful,” he continued. which got a giggle in response from her.

“Here’s what I want this morning,” she said.

“Yes,” he responded, “I was waiting.” He chuckled.

“Well, listen and do as you’re told,” she went on.

“Yes, ma’am,” he said.

“Ah beautiful to look at and polite is the doctor!” she said.

“Yep!” was his answer, and he heard her kind of giggle then.

“Now, you were saying,” he said into the phone.

“Yes, I want you to take off those running shorts, and you’d better not have ‘tightie whities’ or ‘boxers’ on; I do not allow those.”

“Oops!” he said.

“Aha,” came her voice, “Confess.”

“Boxers!” he said.

“Won’t do, not sexy at all; I refuse to let you wear them. Got anything sexy?”

“Not sure I do,” was his answer.

“Okay, I’ll take care of that,” she said, with finality in her voice.

“Yes, ma’am,” was his response. “So, off with it all?”

“Yes, now,” she said, raising a pair of field glasses and holding them up for him to see.

With a grin on his face, he did what she was demanding. He slipped the running shorts down and off, and then the plaid boxers, which he held up and then deposited in the waist receptacle that he had on the deck.

The whole incident, and her actions from the beginning had him, by now, riled up; when he got his boxers off, his erection stood up against his stomach.

“Good!” she said. “Now look at who’s beautiful! Beautiful and yummy looking.”

“Thank you!” he said to her, into the phone.

“And now,” she said, and hesitated;

“And now,” he put in.

“I want the beautiful doctor, the lovely naked doctor, the doctor who doesn’t wear boxers or tightie whities any more, the stiff cocked doctor to jerk off!” she said.

“Jerk off?” he repeated, almost overcome by his lust.

“Does the doctor know how?” she asked, giggling into the phone.

“I guess!” he said, and noticed that she was intently watching him with her field glasses.

He had a stool and got it. It raised him up enough so that she could see him from the knees up. His erection stood out into the night.

He took hold of it, closed his eyes and jerked off, only this time it wasn’t into the night; this time it was aimed at her, at the lovely, rich, widow, as she described herself, of, as far as he was concerned, uncertain age.

He came powerfully and it left her clapping.

He picked up the phone again and she said to him: “You are so yummy, Doctor Porter. Yummy.”

“Thank you, sexy lady, Sexy May,” he answered.

“Is that who I am,” she asked in a soft voice.

“Oh, yes,” he said. “Sexy May.”

It was a few days later, very late in the evening. He had to work late at the hospital and came home determined to have a drink to settle himself down before bed. It was a fairly balmy, warm night.

He left the car in the driveway and went up the front stairs. That’s when he saw her.

It was May and she was on his porch lounge chair, kind of curled up and was sound asleep. She was wearing a robe, which, right then, hid not very much. It had ridden up and was showing him her shapely butt and pretty bluish panties.

He chuckled to himself and, reaching down, simply picked her up from the lounge chair, with his arm behind her neck and the other under he knees.

She fluttered her eyes open.

“Oh,” she said in a very sleepy voice. “It’s the doctor.”

“Yes,” he said. “Let’s get you inside.”

“Oh, yes,” she sighed, her eyes fluttering closed again. “Inside.”

He was carrying her across his living room. He noticed that she was smiling up at him, as he carried her.

“Hi, doctor!” she said softly.

“Hi, beautiful May,” was his answer.

He hadn’t had a chance to notice previously but now realized that she was probably about his age, of 27. (She was actually 32 at the time.) He thought her lovely, in her sleepy innocent looking state. It pleased him very much.

“Where taking me?” she asked.

“Putting you to bed,” he said.

“Ohhh,” she sighed. “To bed in the doctor’s house.”

“Yes,” he affirmed.

He got her settled into the bed, where she lay, smiling at him with the covers pulled up to her chin. The grin never left her face, as he took his clothes off, hanging his trousers up in the closet and putting first his shirt and then his tee shirt into the laundry hamper.

He stood there smiling at her, while wearing his thigh length off blue Calvins.

She put her hand to her mouth and giggled at the sight of him.

With her watching and making noises, he took the Calvins off, putting them too into the hamper.

She reached out a hand to him: “Please, please,” she said, with a beseeching tone, “Let me kiss him once.”

He smile and walked to the bed, where she took his semi erect penis in her hand and placed a loud kiss directly on the head, causing it to stir.

She lay back then, grinning up at him, as he went into the shower.

“Nice ass on the doctor!” she said. He grinned back at her.

She drifted off then, hugely content. He came to bed in a few minutes and snuggled up against her, simply getting a huge sigh from her.

“Pretty May,” he crooned into her ear, “Lovely May, Pretty May!”

It got him another sigh.

That night he discovered himself in the midsts of a lovely, wild erotic dream. He was simply being ‘done’. She was there, that May, that Pretty May, and, in his dream, she was riding him as a stallion rides a mare in season. It was erotic, it was graphic, it was sensual, it was wild.

His eyes snapped open. In that nano second he went from sleeping to wide awake. There, directly in front of his eyes were her nipples!

She grinned down at him.

“Hi, doctor with the fabulous ass!” she said.

“It’s Pretty May,” he said.

“Yes,” she said, shifting around, and, in the movement, causing him to groan. “Pretty May what fucks the doctor!”

She moved again and he groaned louder than before.

“Open your mouth, doctor with the beautiful ass,” she said softly.

He did.

She stuffed a nipple into his open mouth and he began to suck on the offered nipple, now getting loud groans and even more movement from her.

“Fucking me, fucking Pretty May very nicely now,” she crooned, as he continued to work on her nipple, letting his hands snake around behind her to take possession of her ass cheeks.

It simply made her wild! Their sounds, not to be confused with any kind of conversation, in the next ten or so minutes were almost primordial. It left them sweating, breath heaving and simply holding onto one another.

He stroked her hair and said, repeatedly, “Pretty May, Pretty May, my Pretty May.”

She opened bleary eyes the next morning and his smiling face was the first thing that she saw.

“Doctor, doctor,” she sighed ini a voice hardly awakened.

He moved and she felt his morning erection rubbing against her thigh. It made her giggle.

“Yes?” he asked.

“Doctor with the fabulous ass, would you May a favor?” she asked softly.

“No,” he said, shocking her, “But I’d do anything at all for Pretty May.”

It made her giggle.

“From the bureau fetch my lipstick please,” she said, smiling at him.

“Ohhh, lookie, lookie!” she crooned, when he’d gotten out of bed. “Look at the ass on the doctor.”

He brought her the lipstick, which she amply applied right away and then she grabbed him by the hips, turning him and began to plant lipstick kisses on his ass cheeks.

It fairly made him howl with laughter.

“Lipstick kisses for the lovely ass,” she crooned, kissing his ass cheeks again and applying more lipstick.

“Now turn, doctor, doctor,” she said and he did.

Now it was his morning erection that was getting the attention, getting the lipstick treatment, ending with his upstanding member covered with her lipstick kiss marks.

MAY’S TURN: It was a few days later. It had been a long, long and, at times, hard day for Jason. It seemed that Dr Porter simply ran and ran. That kind of day.

He wandered home and was ready to just pack it in. When he got to the door of his house, he noticed a note attached to the door: “Come to my house, please” it said and was signed ‘May’.

His innate tiredness almost prompted him to ignore it but he did turn and go to her door. He knocked and the door was opened right away.

She was wearing a short and lovely pink nylon robe.

“Oh, Doctor Porter!” she said with obvious relish.

“May,” he said, “I’m so tired.”

But that’s as far as he got.

“I know, I know,” she said. “And I’m all ready for you. You just come with me.”

As she said this, with him just looking on, she took his trench coat and hung it up and then took his sport coat, hanging it up also.

By then he was simply smiling, and actually interested in seeing what she was going to do.

“Come, come,” she said, taking him by the arm and walking him into the bedroom. “Tub is all ready for a tired doctor.”

“Yes, tired doctor!” he said, going along with her.

Once she got him into the bedroom, she sat him on the bed and then took his shoes and socks off.

He was simply grinning at her like a fool, or so he thought.

“Not going to be very much good,” he said.

“No, I’ll do everything,” she said, now unbuttoning his shirt.

Then his shirt was off and on a pile, followed by his tee shirt, then she was working at the belt on his pants. The belt was opened and then his zipper and she had his pants folded up and on the chair with his sport coat.

It left him wearing only a pair of thigh length shorts. They were light blue in color.

“Light blue!” she said with relish. “My own blue boy!” Then with a grin, she took off his blue shorts.

She took him by the arm then and led him into the bathroom, where she had a very deep tub. It was already with hot, scented water.

“In you go,” she said to him, helping him into the hot water.

He sighed and settled into the tub, and she began to wash him.

“Ohhhhh,” he groaned as she proceeded with his armpits, and chest, tweaking his nipples and giggling, as she did.

She used a cloth to wash his face and neck, and then, with him now standing, she washed, first, his back, giving herself a chance to bounce his ass cheeks as she washed, with more giggles. She paused then, grinning to herself, and lightly, very lightly bit each of his ass cheeks, prompting him to jump a bit and make a noise.

She giggled.

Then it was his front, after carefully washing between his ass cheeks, taking extra care to wash his balls and penis, actually cooing to them and talking to them, as she did.

“You guys are so pretty!” she said directly to his penis and balls, “But don’t tell him that I called you ‘pretty’; you don’t say that to a man.”

It made him grin.

Then she was done with the bath. She helped him out of the tub and, using a huge towel, dried him off, again subtly playing with his ass, cock and balls in the process.

She took him into the bedroom then and sat him on the edge of the bed, while she pulled the sheets and blankets down to accommodate him. She snuggled him into the warm bed. She had an electric mattress pad, which she’d used to heat the bed in advance.

“In you go, doctor,” she said, once the bed was ready for him, and she proceeded to get him up and into the bed.

“Yes, in I go,” he said. Then, looking at her, he asked: “What you gonna do?”

She grinned at him and giggled again. “Well,” she began;

“I think that I’m going to play but you just rest here,” was her answer.

“Yes, rest,” he said, lying down on the warm bed.

She sat in a side chair and watched him. He was asleep in no time.

It was only later that he woke, noting that it was totally dark. But the sensations that had brought him up swimming through the dark water of sleep and tiredness was the feel of her nakedness, pressed against him.

At the moment, she was facing him, as he rested on his back. The scratch of her pubic curls could be felt against his thigh, and the pressure of her right breast, with a poking nipple, was against his arm.

“Oh, dear!” he said softly.

“Hi, doctor!” she said into the side of his face.

“Hi, May, beautiful May, naked May, exotic May, sexy May, wonderful May!” he crooned to her.

“Oh,” she sighed, “You talk to me so nicely, doctor, doctor!”

“It’s the way that you treat me,” he said to her.

“Yes,” was her response, “How I treat you.”

“Doctor,” she said next, softly into his ear.

“Yes, May,” he responded.

“Do you know who I am?” she whispered.

“Yes,” he said, wondering, “You’re May, next door neighbor, who’s taking such good care of me.”

“Yes,” she said, “But I’m also May your rich next door neighbor; but no, that’s not the truth.”

“No?” he asked, his head up on his elbow as he looked down on her, lying next to him, with the covers down and her breasts showing.

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