Dale's Women Ch. 07

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Dale has a fling with a 60+ year old women--and likes it.
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Part 7 of the 17 part series

Updated 06/09/2023
Created 06/07/2019
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"So who was the oldest woman you ever had?" Gloria asked.

"Oh, there's no doubt about that: it was Laura."

"Who was Laura? How did you meet her? How old was she?"

"One question at a time! She was sixty-four—"

"Sixty-four! Omigod. How old were you at the time?"

"Twenty-three."

"Jesus Christ. What were you thinking? What was she thinking?"

"I have a feeling that's what she thought also. But let me tell you the story. I met her on the same train I met you—"

"Did you now?"

"Yes. The train was, surprisingly enough, not that crowded on that Friday afternoon, so I managed to sit down next to her. She was a fine-looking woman: gray hair impeccably arranged, rather short around her head; chiseled but delicate features with very few wrinkles, and brilliantly blue eyes that almost hypnotized you; somewhat thin lips, but very appealing when she smiled; quite slim physique, but under her power suit I could tell she had nice curves here and there."

"Do you think of all women as prey?" Gloria said acidly.

"Of course not!" Dale cried. "How can you think that of me? I just can't help appreciating female beauty, in whatever form it comes in. Women are the ornaments of our species, as I've suggested before. You'll note that in other species it's the male who's the more attractive, like peacocks and ducks. But for us it's women. Anyway, a man is allowed to look, isn't he?"

"You do a lot more than look, Dale."

"Yes—but only with their approval. I've never forced myself on anyone, and I never will."

"I'm sure that's true. Just go on."

"Well, it turns out she was the publicity director for a fairly major New York publisher. It took a while to get her talking, but I think the end of the work week loosened her tongue, as she was happy to put that all behind her and look forward to a weekend of doing nothing."

"But something else happened, I gather?"

"Yes, yes, but let me tell it. We actually got into a pretty intense conversation, and I told her a lot about myself and she told me at least something about herself. She was widowed—her husband had died several years ago, and now she lived alone in their house. She had one child, a son."

"I daresay he was older than you."

"Well, yes—he was about thirty-five, as I recall. Anyway, as we were gabbing, I saw that she was getting off in Greenwich, just as I was. How lucky! But I wasn't certain that we had established enough of a bond for me to—well, you know . . ."

"Proposition her?"

"If you want to put it that way. I really did want to get to know her better. So, as we were both making our way to the Park-and-Ride, I blurted out:

"'Let me take you to dinner.'

"She gave me this piercing look, as if she was staring right through me. I swear that she didn't respond for a full minute—which, in that context, seemed like an eternity. Then, when she finally spoke, all she said was: 'Why?'

"That question threw me somehow, and all I could think of saying is, 'We've had such a nice talk. I'd like to get to know you better.'

"Once again she looked at me with those blazing blue eyes. At last, with a kind of wry smile, she said, 'All right. Where would you like to go?"

"'Anywhere you like!' I cried out.

"Suddenly she was all business. Saying, 'Okay, follow me,' she got into her car. I almost ran to my car and started it up, not giving her a chance to change her mind.

"She took me to this nice place somewhere in the country—oddly enough, I didn't recall ever being there before. It was a super-elegant place, with brilliant white tablecloths and shining crystal goblets, all brightly lit with an elaborate chandelier. The maitre d' who seated us gave us a bland look and raised his eyebrow a fraction of an inch, but went ahead and seated us.

"Our conversation continued all through dinner. Of course, good wine and good food helped. I sensed that Laura was becoming more comfortable with me—at least as a dinner companion, if nothing else. She seemed flattered that I was taking a genuine interest in her—her life, her work, her attitudes. It was almost as if I were conducting an interview of her for a profile in New York magazine—but really much more intimate and engaging than that. I found her a fascinating person altogether."

"Why?" Gloria asked as bluntly as Laura had.

"Because," Dale replied at once, "she had lived a full and rich life—and wasn't in any way finished. She had been contemplating early retirement, but found the work she did too interesting—and she was good at it. Her company told her she needn't worry about stepping down anytime soon. She had had a long and on the whole satisfying and enriching marriage to her husband—a professor at NYU named Henry—and his sudden heart attack three years before had truly been a shock to her. But she was a trouper and carried on. She had plenty of friends, and her son was now happily married and living in the Chicago area.

"She was smart, capable, quick-witted, and vibrant. And she was lovely. The more she talked, the more beautiful she looked—her eyes twinkling, her lips forming words in such a seductive way that I just wanted to bend forward and plant a kiss on them, her hands delicately but precisely cutting up the food that she daintily placed in her mouth. Everything about her was appealing.

"And so, when the dinner ended, I picked up the tab (she acknowledged it with a gracious nod of the head, but said nothing), and we walked out to the parking lot. Our cars were parked fairly close together, and we stood at the driver's side door of her car facing each other.

"'Well, Dale,' she said, 'I've had a wonderful time.' But her tone of voice clearly implied: It's been nice, but I don't imagine I'll ever see you again.

"I said with great enthusiasm, 'So have I!'

"I know that sounded a little childish, and she gave me a kind of condescending glance. But she seemed pleased. There was this pensive half-smile on her face—so luscious that I took her by the shoulders and gave her a quick kiss.

"For some reason that seemed to take her aback, and she pulled away from me abruptly. But I held on to her. I could see her blushing in the dim light of the parking lot. Her mouth opened as she seemed about to say something—but I didn't give her the chance. I wrapped my arms around her and kissed her again, this time keeping my lips firmly glued to hers.

"She wriggled for a while, then stopped. I couldn't help thinking of how long it had been since she'd been kissed like that—or kissed at all. At least three years, I figured. I guess she must have liked it, for eventually she put her arms around my waist and kissed back.

"Then I put a hand on her bottom."

"You didn't!" Gloria said.

"I did. I may not have mentioned that it was a pretty cool fall evening, and she was wearing a fairly thick wool skirt. But I could still feel the wonderful curve of that bottom. That's all I did: I put my hand there; I didn't stroke it, I didn't try to go under her skirt—"

"Glad to hear it! You were in a public space!"

"Yes, well, nobody seemed to be paying us any attention. But she made no move of any kind: she didn't push my hand away, she didn't slap my face, nothing. She just let me kiss her and hold her bottom in my hand.

"Finally we broke the kiss, but I kept my hand in place. She gave me a long, ambiguous look and finally said, 'You've got to be kidding me.'

"I knew what she meant. I'm forty-one years older than you—you can't possibly be interested in bedding down with me. But I made it clear how wrong she was in the simplest way I knew how: I rubbed my erection into her belly."

"Good Lord!"

"Well, she'd made me hard! I couldn't help it. That long, lingering kiss—and the heady smell of her perfume, not to mention the exquisite feel of her bottom—had had the predictable effect. I felt huge, and I wanted to let her know it was all her doing.

"I knew she could feel it, because she then said, 'You're serious about this?'

"I just nodded.

"She pondered that for some moments. Remember that all this time my hand was still on her bottom—just placed there, not doing anything. After a long while she said almost the same thing she said before: 'All right, follow me in your car.'

"Thankfully she didn't live too far away, and within minutes we had pulled up to a nice big house with a large yard, with a garage that could accommodate at least three cars. I pulled up right behind her in the driveway, and we both got out of her vehicles. We slowly made our way to the front door. There, she gave me a strange look over her shoulder—I imagine she was thinking, I can't believe I'm really doing this—before she stuck the key into the lock and opened the door.

"When she turned the lights on, I found myself in a very large living/dining room that extended practically the whole length of the house. It was a fine old colonial-style home with leaded glass windows and elegant molding on the ceiling and wainscoting on the walls. She clearly took pride in keeping that house looking clean and spruce. She gestured to the couch, indicating that I should sit down, and said, 'Would you like anything to drink?'

"I didn't want to get too soused—I'd already had plenty of wine—as it hinders my, um, performance. But I did say, 'I'd love some sweet liqueur.'

"She smiled that condescending smile again. Bending down in front of a cabinet, she opened it, fished for something way in the back, and came out with a bottle of chocolate mint liqueur. She held it up to my gaze, and I nodded enthusiastically. She poured some out for me, giving herself a little shot of brandy.

"We drank our beverages quickly. Afterwards, with only a moment's hesitation, she took my hand and said, 'Let's go upstairs.'

"She led me to what I assumed was the master bedroom. There was a huge king-size bed there, and the first thing I thought was: Omigod! This poor, lovely woman now has to sleep in this magnificent bed all alone!

"I said to her, 'May I undress you?'

"She smiled at that but said, 'That's okay. I'll do it.'

"So she turned her back to me and began undressing. I did the same. As usual, it took me a lot less time to strip than it took her. Very much the way you did, Gloria, on our first time, she carefully placed her clothes on an easy chair in a far corner of the room. I took it all in: suit jacket, blouse, skirt, and then—after a fraction of a second's hesitation—bra, stockings, and panties. As she revealed herself, my impression of her overall beauty was confirmed: she was gorgeous. From the back, I could see gently sloping shoulders, a firm, straight back, slim but muscular thighs, rounded calves, small feet—and, of course, a curvy bottom to die for.

"Then she turned around. She now had a sort of worried or apprehensive look on her face, as if she thought that I would be disappointed by what I was seeing. I can't imagine why should would have thought that, for her delicate face, moderately sized but perfectly shaped breasts, flat stomach, and thick bush around her delta would have stimulated a man of any age.

"And she could see what she had done to me, for her eyes widened as she saw the size of my erection.

"'Oh, my goodness,' she said, swallowing hard.

"I didn't think she was the kind of woman who would fall to her knees and service me, and she wasn't. She almost pushed me down to the bed—it was very high off the ground—and had me lie flat on my stomach. Bending over my groin, she placed about half of my cock into her mouth and worked it with her mouth and tongue. She did a good job of it, too, and I felt even bigger than before.

"But I wanted to give her some pleasure before taking my own. So I flipped her over onto her back, kissed those luscious firm breasts with their hard nipples, then worked my way down her body to her sex, where I parted her labia and began licking and sucking with gusto. She was already quite wet, and at the first contact of my lips there she let out a gasp that made me think I was on the right track. I kissed and sucked and licked her sex for ten or fifteen minutes, while cupping her bottom with my two hands. She had put both of her hands on my head, making sure my mouth was firmly lodged on her nether lips, and sometimes even pulling my hair in her passion.

"Then she let out a kind of choked scream. As I looked up at her, I saw her eyes, which had been closed tightly shut, pop wide open as if in surprise. I continued working her sex more gently, wanting to prolong her climax as much as possible. It did in fact go on for minutes, until finally she pushed my head away—she just couldn't take any more stimulation.

"She went limp like a deflated balloon, her eyes looking dazed and confused. I slid up her body, looked down at her, and said, 'Was that nice?'

"She chortled and said, 'Of course it was, you silly boy.'

"I wished she hadn't said that, but I didn't really mind. As soon as she had settled down a bit, I inserted myself into her. I did it gradually, for I knew that she hadn't experienced something like this for years and was probably a bit out of practice. She moaned when I first entered her, and again her eyes widened as I went in inch by inch. When I was in her all the way, I pasted my lips to hers as she wrapped her legs around my own.

"I pumped her strongly as I kissed her mouth, her cheeks, her neck, even her eyes. I nuzzled her ear lobes and placed my warm tongue in her ear, making her squeal. I squeezed her breasts, bending down to roll her nipples around in my mouth. In minutes I exploded, and she clutched me spasmodically as I emptied my essence into her.

"I rolled off of her, exhausted. I saw her body drenched and glistening with sweat. We were both breathing hard, but she managed to say, 'That was incredible. You were incredible.'

"'So were you,' I said.

"But I wasn't finished yet. After we cuddled a bit, I whispered into her ear, 'May I go into your bottom?'

"She seemed to freeze in my arms. She looked me straight in the face and said, 'I don't want to tell you how long it's been since I've done that.'

"'But you have done it,' I said.

"'Yes, I have,' she said, almost as if she were embarrassed to admit it.

"I hope," Gloria put in, "you didn't say it was like riding a bicycle!"

"No, I didn't. Laura gave me a long look, as if deciding exactly what to do or say. At last she said, 'All right.'

"'Really?' I said. I was convinced she was going to say no. But maybe she was thinking: I've gone this far with this lad—I might as well go the distance.

"I leaped up from the bed. Saying over my shoulder, 'We need some lube,' I rushed to the bathroom. She actually didn't have any cold cream, but moisturizer would do the trick. I came back, applied the stuff in the proper place, had her lie flat on her stomach, and gently went into her.

"I knew I had to be careful, for I really didn't want to hurt her. Still, it was clear that, at least at the start, she was in a bit of pain. I hate to say it, but even the frown that covered her face when I first entered her was seductive—but I restrained myself and proceeded very slowly. A little later she let out a cry of obvious pain, and I said: 'Should I stop?'

"'No,' she said. 'Let me just see if I can get used to it.'

"I simply kept still as she became accustomed to the unfamiliar sensation. After a little nod from her, I went in a little farther, and then started the pumping action. I was trying to get her to relax, but she was clutching the bedsheets with both hands in a kind of desperation. I kneaded her bottom, and eventually she got the message and tried to go limp. It took me several minutes to finish, and after I'd filled her with my seed she at once said between gritted teeth, 'Please come out now.'

"I pulled out, quickly went to the bathroom to wash up, then returned and held her in my arms. She looked as if she'd been through the ringer, but she did give me a broken smile that made me think she hadn't totally regretted the experience. After we'd rested a bit, I did her in a more orthodox fashion, making sure I rung her bell as well as my own.

"By this time, Laura was pretty drained, and lay on her back as if she never wanted to get up. It was pretty obvious she hadn't expended this kind of energy for a long time, and I also suspect it had been years, perhaps decades, since any man had expressed such a devotion to her physical charms. I'm sure she was flattered, but she was also exhausted.

"I looked over to her and said, 'Is it okay if I spend the night?'

"She gazed at me in that penetrating way she had: she was taking deep thought as to what her answer should be. I got a little unnerved by her silence and went on to say:

"'You really don't want me to go home at this time of night, do you?'

"At that, she broke into a pensive smile and said, 'No. You can stay.'

"I bent over, kissed her, rolled over, and fell asleep.

"I woke up refreshed, with the sun shining through the windows and birds chirping in the trees. When I looked over to Laura, I saw that she was wide awake: she was staring not at me but at the ceiling, once again lost in thought. What was she thinking? Well, I got through the night without this guy plunging a knife in my back . . . How could I have let this stripling abuse every part of my body the way he did? . . . What would my son say if he ever found out?

"But when she saw that I was awake, she gave me a gentle smile and said, 'How about some breakfast?'

"'That would be great!' I enthused.

"Sharing breakfast with someone you've just slept with is an incredibly intimate experience, and she knew it as well as I did. She was partial to pancakes-and-sausages, and I helped cook the latter while she expertly prepared the former. We said very little during the meal, but I could tell that she was thinking all the time about what had just happened and what would happen in the future. I wished she would just yield to the moment, but that wasn't the kind of woman she was.

"When we finished, I quickly showered and got ready to leave. I could sense that she didn't wish to prolong our acquaintance just yet, and I didn't want to press my luck. She lounged around in a robe over her nightgown while I dressed. As I made my way to the door, I took her in my arms and just held her. The contours of her body through the thin fabric of her robe were keenly evident to me, and I felt an erection coming on almost at once. She felt it too, and broke gently out of my embrace.

"'May I see you again?' I said.

"She again gave me a piercing look and carefully weighed her words.

"'Please?' I said.

"She sighed heavily and said, 'All right.' There was no doubt what she was thinking: This is all against my better judgment . . .

"'When?' I said, with some urgency.

"'I don't know,' she said wearily.

"'How about Monday?'

"'Okay,' she said. I think she was now just trying to get rid of me.

"'Great!' I said. 'I'll come here around dinnertime and we can go out somewhere.'

"'I'll cook something for you,' she countered.

"'You don't have to do that.'

"'It's fine. I'd prefer it.'

"'Well, that's very nice of you,' I said, not wishing to get into an argument that would led to her banishing me forever.

"So that's how it went. We generally met twice a week, Mondays and Fridays, and I think I had some role in getting her to appreciate how splendid her body was. And not just her body: everything about her was splendid, and there's not a man in creation who would have thought otherwise. She was obviously not used to a man of my, um, stamina, and it took her a while to learn to keep up with me. She'd probably not had multiple orgasms since she was in her twenties.

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