Dale's Women

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24-year-old Dale finds 50-year-old Gloria fascinating.
5.9k words
4.45
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Part 1 of the 17 part series

Updated 06/09/2023
Created 06/07/2019
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Dale's Women (Chapter 1)

Kathryn M. Burke

Dale Willis was an altruist.

At twenty-four, of independent means as a result of the early death of his parents, he was constitutionally disinclined to undergo the tedium of pursuing a career. He had had his share of dalliances with the debutantes in and around his hometown of Greenwich, Connecticut, but their frivolity and baby-doll prettiness had become unutterably wearying, and so he sought to expand his horizons with involvements with females of a very different sort.

In other words, he became interested in older women.

He was well aware that the women of his parents' generation, whether they were safely married, divorced, or widowed, were by and large unhappy with their lots. Those who worked found some diversion in their varied occupations; but the stay-at-home wives or widows seemed ineffably bored with ordering servants about or arranging one more garden party or bridge game. And it did not fail to come to Dale's notice that for many of them the single greatest factor in their dissatisfaction was a very obvious one.

They weren't getting good sex.

Their husbands, paunchy and balding, were hardly likely to be expert performers in the bedroom, assuming they could even take enough time away from their high-powered law firms or doctor's offices to do anything between the sheets. And many of the married couples had been together so long that any mystery or novelty in the sex act was a thing of distant memory. In Dale's opinion, the women had preserved themselves—both their bodies and their minds—far better than their spouses, and he found their ripe beauty, mingled with a certain world-weariness and even cynicism about life and their place in it, a powerful aphrodisiac.

In the two years since he had graduated from Cambridge College (a small liberal arts college in Ridgefield), he had been involved for a longer or shorter time with a number of older women. Their marital status didn't concern him: if they were married and took up with him, it was a clear sign that they were unhappily married, and he felt he was doing a kind of public (or, more properly, private) service in bringing a little cheer into their lives. He never used force; only persuasion and his mild-mannered good looks. Single, divorced, or widowed women were of course safer, but there was an adrenaline-pumping thrill to affairs with married women that was not to be denied.

Dale was rather short in stature—no taller than five foot six—and that gave him an unthreatening air that he found beneficial to his efforts. His soft brown hair and honest, regular features worked in tandem with a slim but muscular physique to lure women in their forties and fifties into his arms and into his—or their—beds with some regularity.

But let it not be thought that he was only after crude physical satisfaction. He knew that sex was better if you genuinely liked and admired your partner. He couldn't say that he had actually fallen in love with any of his inamoratae, but in a few instances he had come close. It was, indeed, they who had discarded him far more often than the other way around, and he was always on the lookout for a more permanent relationship—or series of relationships.

His methods differed depending on what kind of women he was at that moment seeking. The stay-at-home wives could be chatted up in grocery stores, drugstores, or coffee shops during the morning and afternoon—unless, of course, they were so wealthy and indolent that they had their maids do their shopping for them. Working women were most conveniently secured by way of the well-known New Haven Line commuter train that regularly left Grand Central Station in Manhattan for points east, making stops at all the major cities along coastal Connecticut up to New Haven.

That was where he found himself one fine spring day. It was late afternoon on a Friday, and everyone seemed relieved that the work week was over. Dale was too young to have had personal experience with the "bar car" that used to provide alcohol to the weary commuters at the end of the day—and he sensed that his luck would have been even better than it was if that car had still been in existence.

Right now he focused on a fine-looking woman—apparently in her early fifties, her blond hair appealingly pinned up in a bun but with random strands brushing her face, her figure trim and fit, and encased in a power suit that accentuated her gentle curves—who by some miracle had a vacant seat next to where she was sitting. Dale plopped himself down on the seat a little too hastily, slightly jarring the woman's elbow as she was reading a thick stack of papers.

"I'm very sorry," he said in his mild baritone voice. "I couldn't believe my luck in getting this seat."

She smiled at him out of one side of her mouth. "I was beginning to wonder if I was radioactive."

That was a good sign: she didn't glower at him for jostling her, and even made a little witticism. She had a somewhat low voice for a woman—something he didn't care much for, but he figured he could live with it in light of the woman's other virtues. He noticed no ring on her finger, but didn't know what to make of that. It could mean anything or nothing.

"You're certainly not that," Dale said gallantly, but she paid little attention to the weak compliment.

After a pause he went on. "You shouldn't be working—it's a Friday, and time to relax."

He didn't think there was a double entendre in that, and in fact he didn't intend it. He found workaholic women even more troubling than workaholic men, and wished people would come to their senses and chill out once in a while.

Without looking at him, the woman said: "I may have to be working all weekend. This job doesn't give me much time off."

"And what job is that?"

For a few moments the woman debated whether she even wanted to have this conversation. At last she said somewhat warily, "I'm a literary agent."

Dale's eyes widened as he looked at the big pile on her lap. "And that's some great American novel by some unknown genius?"

That made her smile again. "Hardly—it's a purportedly rousing blood-and-thunder spy novel by someone you might actually have heard of."

"Is it good?"

"No, but it'll sell."

Dale frowned. "Shouldn't you be in the business of promoting good work rather than stuff merely meant to tickle the rabble?"

He worried that he'd gone a little too far: perhaps the woman would think he was insulting her, or at least insulting her profession. But she merely glanced at him with a cynical little smile and said, "If I did that exclusively, I wouldn't be eating very much. 'Stuff' like this"—she tapped the thick manuscript—"is what pays the bills so I can focus on that great American novel by some unknown genius."

"Good point," Dale admitted. "But are you going to be tied up with that all weekend?"

She sighed heavily. "I probably should finish it by Monday, but I suppose the world won't come to an end if I don't."

Dale thought she was close to putting the manuscript aside and devoting her entire attention to him. He realized the next few moments were critical.

"I'm surprised you're not reading that on a tablet, or even on your Smartphone," he said.

She now looked at him right in the face. "If you were your age, maybe I would; but I'm of a generation that still remembers what print is like, and I feel it's only fair to an author—even a hack like this one—to read him the old-fashioned way."

Dale wasn't entirely sure he liked the sound of that: it made him think she was overly concerned about their difference in age. But perhaps that very point could be used to his benefit.

But he didn't want to harp on that issue—yet. Instead, he boldly extended his hand and said: "I'm Dale Willis. I live in Greenwich."

She seemed taken aback by his words and his gesture. No doubt she had lived in the New York metropolitan area long enough to be suspicious of strangers who sought to cultivate one's acquaintance: almost always it would be for something nefarious. But he counted on his open countenance and neat, well-dressed appearance to put her at least somewhat at her ease.

But it took her several seconds to take his hand and say quietly, "Gloria Washburn. I'm getting off at Stamford."

How cagey! She didn't say she lived in Stamford—maybe she left her car at the Stamford Park-and-Ride and drove many miles inland to a house in some remote enclave.

As Dale continued to gaze at her, he found Gloria more and more appealing. Her soft, gentle features, accentuated by just the right amount of makeup, were ones that he could never tire of looking at for weeks, months, maybe years. She was obviously supremely intelligent, and her profession no doubt instilled in her a skillful use of language. He couldn't believe she was unattached: such a woman would have made a tempting prize for some fat-cat banker or stockbroker.

The Greenwich station was several stops before Stamford, so Dale had to work fast if he hoped for any success in this venture.

"You must really like your work, if you're going to waste this lovely weekend with your nose buried in that book."

Gloria smiled wryly. "Well, now that you mention it, it doesn't sound like the most interesting way to pass the time."

"I'll second that motion!" Dale said enthusiastically.

Gloria gave him the courtesy of shoving the hefty manuscript aside and devoting more or less her full attention to Dale. He could tell she was still wary—she had probably endured many pestiferous males trying to pick her up, regardless of her age or marital status—but she seemed just a tad friendlier than before.

"So what do you do for a living?" she said, glancing briefly at the worn leather satchel that Dale had placed at his feet.

This was going to be a bit awkward, on several levels.

"You might say my occupation is observing people," he said flippantly. "It keeps me pretty busy."

"I'm sure it does," she said. "But it doesn't sound very remunerative."

Okay, let me just take the plunge and say it. "Well, my parents left me with a fair amount of funds to sustain me if I'm frugal and prudent."

She frowned, not quite knowing what to make of that. "What exactly are you saying?"

The words came out of Dale's mouth in a rush. "They died in a car accident five years ago." He turned away from her and looked to the floor.

The fact of the matter was that he hated to elicit anyone's sympathy on the matter. He didn't want to secure a woman's interest or affection out of pity—the very idea disgusted him. But at some point, he realized that the truth would have to come out.

Gloria seemed to turn pale, as the blood drained out of her face. She too looked away and said, "I'm so sorry." She tentatively extended a hand and put it over his own.

"Oh," Dale said lightly, "it's all right. I have some aunts and uncles who've taken me under their wing. They've been a good family to me. Anyway, I like living alone—it suits me."

"You live alone?"

"Yes—in my family home in Greenwich."

"I live alone too."

"No, you don't," Dale said at once.

Gloria was confused. "What do you mean? I'm telling you I live alone."

"No woman as beautiful and intelligent and capable as yourself could possibly live alone. It—it isn't right!" he concluded with a flourish.

She smiled cynically at him. "How galant of you, but I've heard that line before."

"I mean it," Dale said earnestly. "Here's my take on things. Men are, in their heart of hearts, fundamentally uncivilized. They don't really belong in polite society. That's why it doesn't bother a lot of men to be alone. I mean, you hear about 'mountain men' and such—you never hear of 'mountain women,' do you? That's because it's women who tame us, who bring us to heel, who civilize us. That's why it's—it's an obscenity for a woman to be alone. It's not natural to her whole state of being."

Gloria was clearly nonplussed at this extravagant venture into pseudo-sociology. She was looking at Dale with increasing wonder and skepticism as he spoke; but she couldn't doubt that, however much might have been trying to seduce her, on some level he truly believed what he was saying.

With a kind of awe in her voice she said, "You're a very strange young man." Dale wished she hadn't added that word "young," but let it pass. Gloria went on:

"Well, if it makes you any happier, I haven't always been alone. I'm divorced."

"I'm sorry to hear that," he said formulaically. Then, realizing his words might be misconstrued, he went on hastily: "I mean, I'm sorry you're divorced. How did that happen?"

Gloria hesitated only a second before speaking. "It's an old story. Harvey went through a midlife crisis and came to believe he couldn't live without his twenty-five-year-old secretary at his side—and in his bed. He ran off with her. Six months later he discovered she didn't have a brain in her pretty little head. He discarded her and begged to return to me, but I told him where to get off."

"How incredibly stupid of him!" Dale said with unexpected venom.

Gloria shrugged nonchalantly. "Yes, well, there it is. It happens more often than you might imagine. But I'm well rid of him."

"When did this happen?"

"He left me a little over three years ago."

"And you've not, um, found someone else in all that time?"

"I've not exactly been in a rush to take another man under my wing. And, no matter what you think of women in general, I really do like being alone."

Dale sensed that the time for a definite move was right. His next words came out in a rush. "Let me take you to dinner somewhere. Maybe somewhere in Stamford? You can pick the place—I don't know the town very well. Anyplace you choose would be fine. I really would like to talk with you some more."

It was several seconds before Gloria replied. When she did, she said, "Well, we can't dine in Greenwich—you just missed the stop."

Dale glanced casually out the window. The train was just pulling out of the Greenwich station.

"Oh, I don't mind. I can always catch another train going back the other way."

Both of them knew that the matter wasn't settled. Gloria hadn't definitely rejected his dinner offer—in fact, she had implicitly endorsed it. She well knew that the time would soon come when she would have to decide what to do with this persistent but curiously appealing young man at her side. She also knew that his ultimate aim was to get into her pants; and whatever she thought of the mental state of such a young man pursuing an older woman, she couldn't help being flattered by the thought.

Looking at him straight in the face and heaving a sigh, Gloria said, "I have a better idea. I'm pretty tired and don't want to go out anywhere. I was looking forward to a quiet evening at home. Why don't I give you a nice home-cooked meal?"

Dale was dumbfounded. He wasn't expecting this at all.

"Um," he stammered, "that's really kind of you, but it's way above and beyond the call of duty. I couldn't ask you to do that for me."

"Hey, don't expect haute cuisine. I was just planning to make pasta and a salad. Maybe there's some Italian sausage that can be added to the mix. Anyway, it's a lot easier to cook for two than for one."

"Maybe so, but—"

"It's what I'm offering," she said flatly. "I'm really not up for a night on the town."

"Even a quiet restaurant?"

"Even that." She peered at him closely. "You don't look like an axe murderer. You aren't, are you?"

"I don't even own an axe and wouldn't know where to get one," he said honestly.

"All right," she said. "Then it's settled."

Dale was, oddly enough, tongue-tied for the rest of the short trip to Stamford. He simply couldn't think of anything to say, even the most inane small talk. He wondered whether Gloria had turned the tables on him: was she now trying to seduce him?

But he didn't think so. And he also didn't think seduction—in the conventional sense of the term—was even involved. He realized that, even from their brief acquaintance, he genuinely liked her—and he hoped she liked him.

At Stamford they filed out with a mass of other white-collar wage slaves who were eager to put the dust and grime and craziness of New York behind them. Like overactive lemmings, many of them headed to the Park-and-Ride and bundled themselves into their vehicles, heading for parts unknown.

Gloria led him through a labyrinth of automobiles to her own car—a reasonably new and shiny red Mazda 3 hatchback. A sensible and not super-expensive car, but far more than a machine to get you from one place to the other. She pushed a button on her remote to unlock the doors, and Dale bundled himself into the passenger seat.

As he had expected, Gloria headed toward a state road that would take them quite a ways northeast of Stamford, into a suburban or even rural enclave. She may have been a high-powered literary agent, but he sensed that she didn't care for city living. If she had, she could no doubt have afforded a place right in Manhattan, or perhaps Queens.

Dale didn't follow the twists and turns of the route, but in due course of time she pulled into the driveway of a large house set quite a ways back from the county road they had been on. It was by no means a mansion, but it was an imposing edifice nonetheless.

"You live here all alone?" Dale said incredulously.

"I got it in the settlement," Gloria said dully. "Anyway, Harvey had flown the coop—there was no way he was going to pull this house from under my feet. He thought he wanted to live in Florida, the poor sod."

Dale didn't want to pursue this particular subject, as it was clearly still a sensitive issue with her. But he couldn't help asking: "Where is Harvey now?"

"I'm not quite sure, but I think he came back to the metro area somewhere."

"What is he? I mean, what does he do for a living?"

"Stockbroker," she said shortly, sounding as if she wanted to put an end to this phase of the conversation.

Dale was happy to oblige—and, even though he was aware that Gloria and her husband had occupied this house for years, perhaps decades, and that therefore it might have both good and bad associations for her, he was effusive in praising the general layout of the exterior, with expansive gardens and an old-fashioned white picket fence around the entire property.

When they stepped inside, Dale found more to please him. The house was impeccably furnished with tasteful but not outrageously expensive pieces—some antiques, some modern. It clearly showed a woman's touch, but there was also a certain austere elegance that might have stemmed from Gloria's husband. The place was not overdecorated, and each room seemed larger than it was because the furniture had been arranged sparingly but sensitively.

"Fix yourself a drink," Gloria said, gesturing to a sideboard that contained an array of bottles of various sorts. "I'm going to change. This suit feels like a straitjacket."

As Dale drifted over to the sideboard and made a Scotch over ice for himself, he wondered what outfit Gloria would change into. Surely she's not going to come down in a nightgown or something like that?

It was not to be. She tripped downstairs in a surprisingly short time, wearing a comfortable print dress that seemed to Dale a little thin for the time of year, but which emphasized her curves—above the waist and below—in a pleasing but not lascivious manner. It was clearly a dress she felt at home in.

For his part, Dale took off his suit jacket and draped it over an easy chair. Otherwise, he preserved his false appearance as a dynamic young businessman.

12