When Barry Met Sally

As in the case of the last sex play session, the subject didn't come up again for a number of weeks. Sally came home one Friday afternoon and said that she wanted to go to a hotel out on Long Island. The lounge in the hotel played host to a pretty active swingers club, she'd found out from online chat rooms and the hotel itself rented rooms by the hour for those who cared to make use of them.

"You don't have to come with me of course," Sally said, "but I'm going either way. Single women are always welcome I'm told."

Giving in to what seemed to be the inevitable, Barry said he would go. It took a while to make the fifty-mile trip out to the hotel, but when they got there they found that the information Sally had gathered wasn't wrong. There had to be at least forty couples of all ages in the bar.

They hadn't even had time to order drinks when one man his age came up to Barry with his wife in tow and tried to strike up a conversation. Sally abruptly cut them off and said she was sorry but they weren't what they were looking for.

It would've been much more accurate if she said that they weren't what she was looking for. On the ride out there, she had made it very clear to Barry that if anyone approached him, he should refer them to her. She was the one who would decide if anything was going to happen, and with who.

Content to just hang back with the drink he had finally gotten and let Sally do her thing, Barry was surprised to see her pass on several rather good looking couples who had expressed an interest. As was the case with the Warrens, Sally had told him that she was looking for something new and different. He was on his second drink when Sally reappeared at his side with a couple in tow. Taking a look at them, Barry had to say they certainly were indeed different.

The man, who Sally introduced as Clayton Hiller looked like he juggled cars for a living rather than repaired them as he said. A hair under six feet, he had a shaved head topping a body even more muscled than Larry Warren's had been. It was the kind of body that you got from hours a day in a gym or a lifetime of heavy physical work.

Bridgett Hiller, was almost a total opposite. A half foot shorter than her husband, she had to outweigh Barry by a hundred pounds at least. What the attraction was between the two of them he couldn't imagine.

Still he had promised Sally he would go along with tonight's venture so he just told himself he'd make the best of it. After all, he'd never been with a woman as large as Bridgett, so if nothing else it would be a new experience.

An experience he found little to say about on the equally long ride back home later that night. Once more, Barry would've had to be deaf not to know that Sally had her usual great time. He, on the other hand, had the most disappointing sexual encounter of his life.

Worse than even the night he'd lost his cherry to Connie Mason during senior year of high school. He'd been so excited about winding up in bed with her, even though all of his friends had told him that Connie was a sure thing if there ever was one, that he'd climaxed less than fifteen seconds after getting inside of her.

In Connie's case, he had at least come out of it having lost his virginity, however brief the experience had been. In this instance, he didn't even have that to fall back on.

No sooner had he been left alone with Bridgett, she slipped out of her clothes and laid out on the bed. This time, Sally had graciously offered him and Bridgett the use of the sole bedroom, leaving the couch for her and Clayton. Barry had climbed on top of the larger woman and without any effort or help on her part, slid his manhood inside of her.

Her expression barely changed as he pumped in and out of her. In fact, she just laid there and didn't even move or utter a word. It was so depressing that after a few minutes, Barry did the unthinkable and actually faked an orgasm just to be done with it.

Once he rolled off of her, she disappeared into the bathroom and didn't emerge until her husband called out to her that it was time to leave. Just before she walked out the bedroom door, she turned to Barry and said her first words to him.

"I fuck you good, yes?"

Unable to even say that he thought that was good, Barry simply nodded his head yes. An action that brought a smile to the woman before she turned and left.

It was also on that ride home that Sally had said that she thought she would place an ad on some of the bulletin boards she had heard about in the chat rooms. Totally unhappy at the evening, the words didn't even register with Barry as he kept his eyes on the long road back to Manhattan.

-=-=-=-

Back in the here and now, Barry again looked at the letter and photographs. His first reaction still held true, these people were old enough to be their parents. Only a few minutes before, Sally had joked about fucking Mrs. Merriman. With these two, they were more than half way there.

"Is this is the only reply you got?" he asked, buying himself a little more time before he had to give a serious answer.

"No," Sally replied. "Actually I got over a dozen but this was the one I found the most interesting."

Interesting wasn't the word that first came to mind when Barry looked at the images of the man and women in his hand. From the letter, he learned that the man's name was Dave Carter and he was a fifty-five year old retired Police Officer. Six foot two with a muscular build, he had a closely cropped white hair and an equally trimmed beard and mustache. For an old guy, Barry had to say he was in pretty good shape.

The woman with him, the letter said, was Beatrice Carter, who was three years younger and with equally white hair cut just above her shoulders. Her body was what one would expect from a woman her age, with time and gravity having taken their toll on her five foot four form.

Looking deep into her face, Barry guessed that she might have been quite attractive when she was younger. Not to say she wasn't still pretty. Beatrice just wasn't what he pictured as a woman he wanted to go to bed with. And the encounter with Bridgett Hiller had soured him on just fucking someone for the experience.

"I don't know," he finally said, surprising Sally with his show of reluctance.

"Oh come on," Sally said, putting on her sexiest pout, "haven't you ever been curious about what it would be like being with someone really older?"

"Actually, no, I haven't," Barry said as he put the pictures down.

Her pout turned into a scowl in response to her lover's disinterest. Especially after she had just rocked his world. Usually, that was when he was the most compliant.

"And before you fall back on that old you'll go alone bit," he went on, "I'll tell you right now that if that's what you want, then go right ahead."

If Sally were to take a step back and look at the situation, she might consider the idea that she was pushing a little too hard. That it might be wiser, in the long run, to back off and let this particular one of her adventures pass. Unfortunately, all that occurred to her was that she didn't like to lose and she pushed ahead on a different track.

"I would," she said, responding to his suggestion in what she considered a conciliatory tone, "but they were quite clear that they were only interested in swapping as a couple. They aren't interested in a three-way with a woman."

"Then I guess you're out of luck this time," Barry said, not feeling conciliatory himself.

But Sally wasn't ready to give up so easily, not when she had one last card to play. A trump card she had held in reserve for the day she wanted Barry to do something he really didn't want to.

"I'll tell you what, love," Sally whispered into his ear as she pressed her breasts up against his chest, "you do this for me, and I promise that the next time it'll be just you, me, and any girl you pick. And when we're together, I'll do all those nasty things to her that I know you fantasize about."

Barry didn't respond right away, but Sally knew he was thinking about it. And if he was at least thinking about it, then she was already half way there. When he picked up the picture of Beatrice to look at again, she knew that she had won without him saying another word.

-=-=-=-

The following weekend, all the arrangements had been made and the two of them took a taxi to the Upper East Side and the condo where the Carters lived. Sally was totally impressed by the building, a luxury high rise with both a doorman and a desk attendant in the lobby.

She was even more impressed when, after getting off the elevator on sixteen, they found that the apartment they were looking for occupied almost a quarter of the floor. It had to be at least three times their apartment downtown.

"This is where a retired Cop lives?" Sally asked out loud as Barry rang the doorbell.

If the question had been intended as anything but rhetorical, Barry didn't have time to answer as the door swung open a moment later. The attendant down in the lobby had, after checking that their names were on a list of expected guests, called upstairs to let the Carters know that they were on the way up.

The first impression both of them had of the man in the blue golf shirt and black slacks was that the photograph Dave Carter sent them didn't do him justice at all. The phrase tanned, fit and handsome easily applied, as he was a man who had indeed aged well. Barry's second thought, as they were invited inside, was that he hoped Beatrice's picture had been just as unflattering.

"Can I offer the two of you a drink?" Dave said as he led the two of them through the foyer and into a spacious living room. "I had just poured myself a scotch."

"Scotch would be fine," Sally said, much to Barry's surprise since he had never heard her order one before. "A short one with just a little ice."

"Could I have a beer," Barry asked, drawing a cold look from Sally for being so plebeian.

"Sure, coming right up," the tall man replied as he stepped behind a waist high bar in the corner of the room, not seeming to find a problem with the request at all. "Heineken okay with you?" he asked.

"That would be fine," Barry replied, shooting a look back at Sally.

With a well-practiced hand, Dave poured Sally a quarter glass of scotch, dropping two ice cubes in as it filled. From a small refrigerator beneath the bar, he produced a frosted green bottle, which he emptied into an equally chilled beer mug.

"Here you go," he said as he stepped back around the bar and handed them their drinks.

"This is a really beautiful apartment," Barry said after he thanked him for the beer.

"Well I can't take any credit for that," Dave said, reaching back to the bar for his own drink, a double scotch, neat. "Beatrice's responsible for just about everything you see in here, decorated every inch herself. Speaking of which, she should be out any minute. She was still getting dressed when they called from downstairs."

It suddenly occurred to Barry that Sally hadn't said a single word about the apartment since they stepped inside. Normally, she was really had a passion for such things. In fact, except for asking for a scotch, she hadn't really even said a word. Since the moment she had laid eyes on the former Police Officer, she hadn't stopped staring at him.

She was obviously quite taken by the older man, in a way Barry had never seen before. Even down to asking for a scotch after he said he had just poured himself one. It was an attempt to impress him. That made Barry want to laugh. From the way Dave's eyes kept roving up and down her body, she hardly needed the drink to get his attention.

"That's a lovely dress you're wearing," Dave said in reference to the blue and white outfit Sally had on, "but not as lovely as the young lady inside it, of course." he added.

"Thank you, Dave," Sally said, sounding as if she was still a young girl rather than the sophisticated image she normally projected.

Then mention of clothing reminded Barry that with Dave in such casual attire, he himself felt rather overdressed in the suit and tie that Sally had insisted he wear. If he'd had his way, he'd be dressed the same way their host was.

"I hope I haven't kept everyone waiting too long," another feminine voice said from across the room.

All eyes turned in that direction as Beatrice Carter entered the room. Barry experienced a small disappointment as he saw that she matched her photograph perfectly. One thing the e-mailed image couldn't express, however, was the wide, infectious smile that lit up half the room. Wearing an open collared yellow blouse and dark blue slacks, she carried a noticeable warmth as she came close.

"Not at all," Dave said as he introduced Sally and Barry. "We were just having a little drink."

"Sounds good to me," Beatrice said as she headed to the bar herself, but not before going first to their guests and giving each a quick kiss on the cheek hello.

At the bar, the white haired woman took a beer from the hidden cooler and popped it open on the attached opener than had been screwed into the side of the bar. Instead of making use of one of the mugs as Dave had, she brought the bottle up to her mouth and took a long drink from it.

"Beatrice!" Dave Carter called out in admonishment.

"All right, I know it's unladylike," she shot back, "but if I can't be unladylike in my own home then what good is it. Besides, I'm sure our guests here weren't offended."

Barry signaled with a wave of his hand that was indeed the case. When he was home, he drank from the bottle as well. Beatrice's demeanor definitely wasn't what he expected from a woman her age. At least as compared to his mother and aunts. Sally didn't seem to have any impression at all, still having eyes only for Dave.

"We made some snacks that I hope you'll like," Beatrice said, "Why don't we have a seat while Dave gets them, then we can get better acquainted."

Dave headed for the kitchen as Beatrice guided their guests to two sofas that sat opposite each other in the center of the living room. She took a place next to Barry on one, leaving the empty spot on the other next to Sally for Dave.

With two platters in his hands, Dave reappeared a few minutes later and laid them out on the table in-between the couches. They spent much of the next hour munching on the snacks, having a few more drinks and becoming more comfortable with each other. In that time, Barry had just about every preconception he had about older people totally shattered.

Beatrice was telling a somewhat off-colored story that Barry found fascinating. With his attention totally focused on her, he didn't notice that only a few feet away, Dave and Sally had gone from trading tiny snacks, to trading tongues.

Neither he nor Beatrice even noticed when Sally reached down, unzipped Dave's pants and slid out his cock to play with. By the time the story ended, and both of them turned their attention toward the other sofa, Dave had his arms stretched out along the back cushion and his eyes tightly closed. Sally was now leaning over with her head in his lap and his cock in her mouth.

"I guess the playtime segment of the evening has begun," Beatrice said, her tone reflecting a small amount of what Barry took as embarrassment.

"What can I say?" Dave said as he opened his eyes and grinned.

"You could say that there are four bedrooms in this apartment for starters," she replied, her voice now containing an anger for him having complained about her drinking out of a beer bottle, "and that the two of you would like to make use of one."

Dave just smiled apologetically. Through it all, Sally hadn't even paused as she ran her tongue up and down the length of his cock.

"Oh forget it," the older woman said in exasperation as she turned back to Barry. "Why don't we leave these two to their fun and go find some of our own." she added, motioning for Barry to follow her to one of those bedrooms she had mentioned.

Rising from the couch, the dark-haired, twenty-five-year-old followed her across the room. Just before he passed through the archway to the hall that led to the master bedroom, Barry turned to look back at Sally. She had moved from the couch to the floor and her hand was now around Dave's cock, furiously pumping it in and out of her mouth. Her head was bobbing up and down as well, keeping pace with the movement of her hand. He watched her for a few seconds, then turned again and followed Beatrice once more.

-=-=-=-

Barry followed Beatrice down the hall and into the large master bedroom. As he stepped inside, he saw it was decorated in a colonial style, with large heavy oak furniture, dominated by an oversized bed in the center. A large double window on the far side showed a spectacular view of the East River.

The young man didn't have much time to take in much more as Beatrice abruptly stopped in the center of the room, turned around and placed her hand on his chest. Looking right at him, her smile seemed to be even brighter than before.

"You really are cute," she said, running her hand across his chest, playing with his tie.

"I think you're very beautiful too," Barry said, thinking something to that effect was expected.

"Liar," The white haired woman laughed softly. "I might have been once, but I'm not one of those movie star types who can spend all their time trying to look like they're still twenty-something."

As she spoke, her eyes flashed to a framed photograph on the closest dresser. Barry followed her gaze and saw an 8x10 of a young and indeed quite pretty Beatrice. Looking at it for a few seconds, then back at the older version before him, he realized that she was indeed still very attractive, but with a more mature beauty. He also realized that the longer he spent with her, the more his original one-dimensional assessment seemed to change.

"Beatrice, I think you're beautiful, and that's not a lie," Barry said, leaning forward and kissing her softly on her lips.

The kiss might have begun softly, but quickly grew in intensity as Barry felt her pressing against him. The sweet scent of her perfume caressed his senses, even as he felt her tongue press against and then past his lips, exploring the inside of his mouth.

"Wow," Barry said as their lips finally parted.

"Not bad for an old lady, huh," she said with a flourish, whirling around and landing on the bed, her body stretched out to give him a good look at her figure.

"I don't think you're an old lady," he said.

"You could've fooled me," she replied, "the way you were looking at me in the living room."

"What I mean is that you certainly don't come off as old," he said, trying to correct what he know knew was a mistake.

"Really," she said, lifting her head in his direction. "And what does an old person act like?"

Barry opened his mouth to answer, then found himself dumbfounded. He didn't have an answer. The other women he knew around Beatrice's age appeared in his mind and he suddenly couldn't imagine what they were like outside of the little niche he placed them in.

Beatrice laughed again as she sat up, enjoying the confusion on his face.

"Don't feel bad," she said, "when I was your age, I couldn't have answered that question either. Back then, I thought that anyone my age was just about ready for the retirement home. The very idea that they might have a life or even a sex life was just something I didn't even think about."

Twenty years later, and Barry would have to say that before tonight he thought the same way.

"Now that I am one of those people," Beatrice continued, "I keep thinking that I should feel older. Yet, despite the changes on the outside and a little wear and tear on the body, I still feel more or less like the twenty-five-year-old I once was. Just with more experience."