A Kind of Loss:
In a move that at first appeared to be a disaster, Tim Murphy discovered that his neighbor, Agnes Winfield, was moving. She had a new job to go to that was out of state and was just going. The final meeting between the two of them proved to be an emotional one for Agnes. She said to him 'how close' they'd been.
(In reality, they had not only been close, she'd been, Agnes, the next door neighbor, who was indeed his Mom's age, had been his lover, his project, his passion, his challenge and his toy for over a year and a half. It had been a fortuitous ass slapping that had set them out on the road.
Slapping his Mom on the butt had become a kind of form of horse play between Tim and Judy Murphy. It had occurred almost by accident and was taken in fairly good humor by both of them. Judy was often apt to complain about how big her butt was. Tim argued, at the same time, that it wasn't indeed too large. One day that kind of discussion was going on and Judy happened to bend over at the wrong time. Tim, in a playful mood, simply swatted her behind. She jumped and kind of squealed, and he stood there and grinned at her, with her returning the grin.
"Enough of that big ass talk!" he said.
"Yes, sir!" was her sassy answer and they'd left it there.
He had some work to do at Agnes Winfield's shortly after that, and the same kind of situation presented itself. Agnes was wearing a skirt that day. They were working in the basement, and she bent over to get something out of a tight spot. She made a quip, just then, about her butt being too big to fit into such a little spot and Tim swatted her on the ass, hard.
Agnes was silent for a long minute; she straightened up and Tim was sure that he was in trouble. Agnes Winfield looked at him and said softly: "You slapped me on the butt!"
"Yes, uh..." was as far as he made it.
He was almost rendered stupid by what she did next: She resumed her bent over attitude and hiked her skirt up to her waist. Tim was now presented with Anges' magnificently shaped ass encased only in a pair of panties!
"Do it again, please!" she said softly.
Tim obliged and their relationship was launched.
In the process he learned a good bit about women. He learned that by using the spanking, which Agnes dearly loved, he could leverage her into doing whatever he wanted. In successive bouts of spanking, using various instruments for the spanking, Tim began to get blow jobs from Agnes, and then it was screwing and finally, the cap on his successful 'Agnes Campaign', he began to butt screw her.
He learned how to use her compliance to get her to do what he wanted. It also served to produce, develop in Tim a kind of sense that allowed him to be able to discover when a woman was the kind of submissive that Agnes had been. That was the coolest result of his dalliance with Agnes Winfield, and he would be, he knew, sorry to see her go.
He staged one last event with pretty and complaint Agnes. He'd told his Mom that he was going out, while she watched her tv shows and slipped off to Agnes'. She let him in the back door and he didn't waste much time. He had her on her knees and sucking him off, as soon as he was in the door. As a kind of lark, he hauled the submissive woman out of her house and took her to the bushes outside of the room where his Mom was watching tv to finish the blow job. Agnes was resistant, but then she was often resistant to his wilder ideas, but she complied and, with Tim gazing in on his Mom, who, he noticed, idly stroked the crotch of her running pants now and again, much to his delight, Agnes blew him.
He took her then back home and, without the normal beating this time, stripped her and began to screw. He tied her hands together and draped her over the bed, with her hands tied to the head board. Then he greased himself and was fucking Agnes, this one last time, in the ass right away, with her protesting and yelling into a pillow but never insisting that Tim stop what he was doing.
It was a very successful night but then Agnes was gone. Her moving happened the next day!)
(Tim Murphy had begun his dalliance with the mature neighbor, when he was all of 15 years of age. He was athletic and slim with big and very expressive blue eyes. He was pretty much a beautiful boy and would certainly be a beautiful man. That alone, his looks, got him constant attention from women, women of all ages.)
At this point in his life, Tim was in need of a new kind of focus; it had been Agnes Winfield for so long. His one immediate answer was to focus somewhat on his Mom.
The picture of his Mom, when she thought that she wasn't being observed, idly playing with herself, was an image that stuck in Tim's mind. Their relationship continued to be casual and very affectionate but Tim now was being much more observant.
He took time, while his Mom was away, to look into her underwear drawer, and see what kind of panties that she had. He was pleased to discover that the drawer was full of frilly and sexy kinds of panties.
It made him wonder. He knew enough about his Mom to know that there were no men, casual or otherwise, in her life but she seemed, as he was observing her now, to be pretty steamy. It also made him smile.
Judy Murphy was casual around the house and that gave Tim, now that he was 'on the hunt', opportunities to come across her in stages of undress.
Tim worked, hard, to keep those kinds of thoughts at bay; he just wasn't sure that he was ready to take on his Mom as his next 'Agnes' project, although he was also was sure that he wanted and was seeking out another 'Agnes' figure for himself.
He was both confident and had experience with this kind of 'hunting', since his times with Agnes but his next 'Agnes' came to him as a kind of surprise, even so.
Margaret Karney And Her Underwear:
Margaret Karney, Peggy to her friends, was a history teacher. She also, deny it as she would often enough, had a thing for Tim Murphy. She was simply stirred by his beauty, and frequently enough devised secret and sly ways to let him know that she was interested. In fact, Margaret Karney was interested enough to not really be willing to put any kinds of 'boundaries' on what she might do with this lovely boy/man, should he return her obvious, to her, interest.
For a brief time, all that Tim was aware of was that Ms Karney, whom he had for U.S. History, was very kind to him. He had her for his last period class and one day had some questions about homework assignments. It was spring turning hot already that day.
After he'd asked his questions, Ms Karney posed a question to him:
"Tim, um, would you be able to help me move some things around in the storage closet? They are a bit on the heavy side."
"Sure, Ms Karney," he said and followed her into the closet.
She pointed to the things that she might want to have moved and Tim had a sudden and almost blinding revelation. The thought struck him, plainly and with force, that Ms Karney, his history teacher, was acting in exactly the same manner that Agnes had acted. It made him wonder, as he watched her and she stooped down to look at the things that were on the floor and she might want to have moved.
(At this point in her life, Margaret Karney was 38 years old. She was fairly thin but not either in the breasts or in the butt. She had long auburn hair but wasn't one of the 'faculty foxes', as the guys had named a few. She was, however, at that precise time, radiating a kind of aura to Tim that he was strongly familiar with and that reminded him of Agnes, his lost and gone Agnes.)
Then it happened. In that closet, she made a move and Tim made his counter move and he was, once again, in the driver's seat with an older woman.
Ms Karney, as she was stooping down, turned her knees toward Tim, who was watching her like a hawk, and she spread her knees, in a kind of accidental fashion, and there Tim could see, between her spread knees, the front of, crotch and belly, her yellow panties.
He was immediately in the 'zone' with Margaret. He lifted his foot and, without hesitation, pushed his foot into her crotch.
"Ohhhhh," she said, letting out a harsh breath.
Tim simply grinned down at his teacher. Then he took his shoe off, while she watched, and his sock, and now he was able to let his toes play, wiggling and poking, in her panty covered pussy.
Margaret Karney simply sighed and sat on the floor, spreading her knees out to the side, to give this lovely boy/man better access to her pussy.
"Yes, yes, Tim, do that please! I beg you do that!"
He grinned and wiggled his toes into her slit for about five minutes, and she began to shake and writhe on the floor. She was cumming, and in giving her that orgasm, Tim had a new Agnes Winfield on his lucky hands.
She stood then and clutched him to herself.
"We can't do more here!" she said urgently. "I'm sorry but we can't. But soon, I promise."
"Then give me something to seal your promise," he demanded.
"Yes," she said immediately, "What?"
"I want your underwear!" he said.
She giggled. "My underwear? Here in school?"
"Do it, Ms Karney!" he said.
"Peggy," she whispered.
"Do it Peggy!" he said.
She did. With him watching and smiling his 'I've got you' smile. Peggy Karney took off her blouse and camisole and gave him her bra. Then it was her skirt and half-slip and she gave him her panties.
He took them, grinning, and began to walk away.
"You wait five minutes now," he said, "And then dress."
"Yes, Tim," she said breathlessly, "Five minutes."
He wrote down on a slip of paper his cell phone number.
.... There is more of this story ...