When Barry Met Sally

Barry took in what she said and concluded that it made a lot of sense. He had never really given it a lot of thought, but when he was Beatrice's age, did he really think he was suddenly going to change into a totally different person?

"But let's leave the philosophical discussion for another time," she said, rising to her feet and stepping back over to him. "Let's get you a little more comfortable," she added as she helped him out of his tie and jacket.

She tossed the jacket onto a nearby chair. Then she undid the tie and, holding an end in each hand, pulled his mouth to hers. The kiss was short but just as nice. Releasing one end of the cloth, she pulled on the other and sent it falling to the floor.

"Oh and by the way," she said, "my friends call me Bernie. Dave thinks that's unladylike too, but so are a lot of the other things I do."

If Barry had a comment, it was lost as Bernie kissed him once more, this time even more pleasantly. As their lips locked, her fingers began to work the buttons of his shirt, starting from the top and quickly working down to the bottom. When the last button gave way, she grabbed the shirt and pulled it down and off him. Her hands then gripped the edge of his T-shirt, pulling it up and over his head. It landed just to the left of his dress shirt.

"Very nice," she said as her hands ran across his now exposed, lightly haired chest. "Some women like hairy men, I like just enough to run my fingers through."

Leaving an erotic, almost electric tingle in their wake, Bernie's hands slid down to Barry's waist and loosened first his belt, then the zipper of his pants. Holding them up with one hand, she reached inside with the other and took hold of his manhood. Smiling in appreciation of its size and hardness, she slowly massaged it with her fingers.

"Also very nice," Bernie said as she felt it grow even firmer in response to her touch.

Still holding up his pants, the fifty-two-year-old guided Barry to the bed, setting him down on the edge. She quickly relieved him of both those pants and his footwear, leaving him with only the dark blue briefs he wore. Briefs with a quite noticeable bulge in the center of them. Reaching down, she ran a slow hand over that prominence, letting it rest a few moments before taking it away and walking a few steps away from the bed.

Bernie had only put on a pair of loafers when she got out of the shower earlier and a quick toss of each foot sent each of them flying to the far corner of the room. Her hand went to her own waist, undoing her belt and the clasp of her slacks, sliding them down and off her legs. All that remained of her outerwear was her blouse, which hung down to a few inches above her knees.

One button at a time, starting at the bottom, Bernie began to remove that as well. As each button gave way, she took a small step back toward the bed. By the time the last was done, she had climbed onto the bed and was straddling Barry's lap.

Barry reached up and parted the halves of the now open blouse, revealing the silky green bra beneath. To what was now no longer any surprise to him, he had watched her impromptu striptease with as much interest as he would one performed by the centerfold of the month.

Held within the cups of emerald silk were two medium-sized globes that at the moment occupied the center of Barry's universe. As his hands closed around them, he was struck by two thoughts. First, that they were slightly bigger than Sally's, and secondly, despite their age difference, they were just as soft.

Bernie shifted just enough that her blouse could slide down her arms and on to the floor. Reaching behind her back, she undid the metal clasp that held her mounds in check.

The thin material collapsed in Barry's hands, leaving a clear view of two dark pink circles, each which was capped by a short, wide tip. Lowering his head, the dark-haired twenty-five-year-old kissed first one, then the other, his nimble tongue tickling each as he did.

Bernie, in the meantime, was moving her satin-covered ass back and forth across Barry's crotch, massaging his already straining cock. Her hands held the back of his head, stroking his hair softly and helping guide his mouth to her breasts.

Back and forth they went, Barry suckling at her nipples and Bernie rubbing against his cock with her ass. The press of their flesh against each other was producing a rapidly rising heat within the both of them.

The rocking motion grew more pronounced with each repetition. Suddenly, Bernie threw all of her weight into one forward thrust and sent them flying back across the bed, one on top of the other.

Barry had barely time to take in the weight of Bernie against him before that pressure lifted as the older woman shifted position on the bed and pulled down his shorts. As she did, his now freed cock jumped to attention at its full six inch height.

The view, which Bernie looked at appreciatively, didn't last long either. Before the discarded briefs could join the rest of the scattered clothing on the floor, Barry's youthful pride vanished into the warm recesses of her mouth.

"Ooooo" Barry moaned as he felt the wetness embrace him with an intensity he rarely felt from Sally.

Bernie bobbed her head a few more times as one of her hands closed on the base of his cock. She let him fall from her mouth, allowing it to stand tall once more before now just taking the crown back between her lips. Her tongue washed across the tip again and again, while her hand moved up and down its length, pumping it into her mouth.

A feeling of rapture spread from the tip of Barry's cock, down his shaft and across his stretched out form. The intensity of that rapture grew with each new heartbeat.

Up until this point, Barry had always prided himself on his sexual self-control. This time, with the passing of only a few fleeting minutes, he knew that restraint wasn't going to be enough. Experience overpowered youth and he felt barrier after barrier crumble until he exploded, sending the fury of that eruption into Bernie's mouth and down her throat.

Despite the wave of sudden euphoria that washed over him, a tiny fear shot across the forefront of Barry's consciousness like a lightning bolt. None of his previous lovers, Sally included, had ever let him come in their mouths. Once, early in their relationship, he had gotten carried away and didn't pull out in time, leaving the beginnings of an orgasm in her mouth. She had been so angry about it that not only did she not let him touch her the rest of that night, she had made him wait a month before they could again have sex.

Bernie didn't even give pause at the sudden explosion in her mouth. If anything, she seemed to relish it, going so far as to lick his cock clean after swallowing all that he could give.

Still, Barry felt the need to apologize when Bernie finally let his now drained cock fall free and sat up next to him. An act that totally puzzled the woman beside him.

"What are you apologizing for?" she asked as she ran a hand across her hair, straightening it out. "If I didn't want that to happen, believe me, it wouldn't have."

To show that she meant what she said, Bernie pressed forward and gave him a long, sensuous kiss. As their lips touched and she pressed her tongue deep into his mouth, Barry felt the slightly salty taste of his own orgasm.

"That, was for being so delicious," Bernie said as they parted once more.

At Bernie's suggestion, both of them moved higher up on the bed, to a position where they could both rest on the large pillows that were propped against the headboard. She also suggested they take a few minutes for him to catch his breath, an euphemism that became clear to him as he looked down at his near lifeless manhood.

"So have you and Sally been doing this long?" Bernie asked as she continued to run her fingers up and down his naked form.

"This is our fourth time," Barry replied, counting the menage a trois with Ray.

"Do you enjoy it?" she asked,

"Sometimes," Barry replied as he began to stroke her body as well, concentrating on her breasts, which had quickly become a fascination to him.

"Dave said that Sally arranged all of this," Bernie said, then asked. "Do you get to sometimes pick who you meet or does just she do it?"

"Sally pretty much decides it all," he replied, feeling a little ashamed at the admission.

"That doesn't seem quite fair," Bernie noted. "What if she liked the man but you don't care anything for the woman?"

Thinking of Bridgett Hiller, he was about to say that he made the best of what he could of the situation, then thought better of the idea. He didn't want Bernie to think that was what he was doing here, even though when the night started that was exactly what he thought he'd be doing. Nor did he mention that Sally had bribed him into coming tonight by promising a menage a trois with her and the girl of his choice.

Thankfully, Bernie didn't seem to expect an answer as she went on, saying that this was actually her first time.

"Really?" a surprised Barry asked.

"Yes, really," Bernie repeated. "In fact, you're only the third man I've ever been to bed with in my life."

That surprised Barry even more.

"Of course Dave's done this a couple of dozen times," she added.

Barry was sure he must've heard that wrong. How could this be her first time and the two dozenth or so for her husband? That was even stranger than his and Sally's relationship at times. Then it hit him, Bernie had said that she had two men before him, could that mean that Dave was her second husband?

"Heaven forbid," Bernie laughed when Barry asked just that. "Dave's not my husband, and as much as I love him, he's not really my type."

Barry was now even more confused. If he weren't her type, why would she have him as a lover. The answer was, she didn't.

"Dave's my brother," Bernie said in explanation.

Three simple words, but enough for Barry to feel suddenly cold and pull back, putting a physical distance between him and Bernie's admission.

"Wait a second, Tiger," Bernie said in a strong voice as she watched him pull away, "don't let your imagination run away with

you. It's not what I know you must be thinking."

Wanting so much to give her the benefit of the doubt, Barry resisted the urge to keep going until he was out of the bed and paused to listen to her explanation. Although he couldn't imagine what it could be.

"First of all, let me start by saying that there's nothing going on between Dave and me that would be out of the ordinary for any other brother and sister," she began. "We're close, but not in that way."

Barry was listening.

"When your girlfriend pulled out his cock in the living room and suddenly decided to go to town on it, that was the first time I'd seem that part of him since I walked in on him playing with it when we were teenagers back in ..., well, lets just say before you were born."

Barry remembered the look on Bernie's face when she saw Sally blowing Dave on the couch. It seems that what he thought was a look of embarrassment, actually was just that.

Bernie went on to say that Dave and his now ex-wife had been swingers for years. They had separated a few years back for totally unrelated reasons. When Dave had first answered Sally's personal, he had done so under the assumption that his new girlfriend, also a swinger, would be his partner. Unfortunately for him, she dropped a bombshell right after that, trading him in for a younger model.

The story was becoming more and more interesting to Barry and he had already decided that he wasn't going anywhere until he heard it all.

So over their normal once a week dinner, Bernie continued, Dave told her what had happened. Some people might think it strange for a brother and sister to discuss each other's personal lives, but as she said before, they were that close and to be honest, she got a vicarious thrill when she heard about his adventures.

Dave had just told her that he was going to have to write Sally and tell her it wasn't going to happen and that was a shame because from what she wrote in her first letter, he thought she had to be one hell of a piece of ass. Then, as a joke, he turned to Bernie and said that, unless of course she wanted to play the wife-role, something she had done on more respectable outings when he would've been out of place without an escort.

The older Carter had indeed only meant it as a joke, so when Bernie had unbelievably said "why not?", he had quite literally fallen off his chair.

There had to be certain conditions of course, she said. Foremost, there would be no sexual acts between them, swapping mates was fine but this wasn't going to be an orgy. Secondly, if she didn't like the guy, either from his picture or when they met, then the whole thing was off.

Still in a state of shock, Dave had no problem agreeing to any of those conditions.

"So you're really Miss Carter," Barry said, thinking that he should say something but at a loss what that should be. The name on the apartment, which Dave said had been decorated by Bernie had been Carter so she must never have been married.

"Actually, I really am Mrs. Carter," Bernie replied. "I married a man who happened to have the same last name as I did. Saved a fortune on the stationary and monograms on the luggage," she laughed. "He was a dear sweet man who was somewhat older than me, but that didn't make a bit of difference. I loved him quite deeply. I'm afraid he passed on some years back, leaving me well cared for, but quite lonely nevertheless."

"I can see that," Barry thought as he looked again around the room and remembered what he'd seen of the apartment before. This time he noticed another photograph of Bernie and a man who looked to be around twenty years older than her. He couldn't guess what their marriage had been like, but they did look happy together in the picture.

"Yet I still haven't explained why I did this, have I?" Bernie remarked, and then proceeded to do so. "Well, when Dave made his little joke, and believe me, he never thought it was anything but, I suddenly had, oh I don't really know how to explain it, a sense of craziness I guess. Instead of hearing about my brother's sexual escapades, I wanted to have one of my own. Like I said, I've only been with two men in my life, my late husband and one before that. And at this point in my life, maybe I need a little craziness to just help me keep my sanity."

Bernie paused for a moment to study the expression on Barry's face. Normally she was able to read people pretty well, but this time she wasn't sure how he was accepting any of this.

"So I set the ground rules and let things take their course," she said as she drew her talk to a conclusion. "Dave would use the guest bedroom over on the other end of the apartment and I would use this one. The way this old place is built, we'd never even hear each other."

"That would be a switch," Barry said under his breath, remembering his and Sally's previous encounters.

"It never occurred to me that your girlfriend and Dave would jump the gun, so to speak, and let things get so out of hand," she finished, "I tried to make a joke of it but yes, I was a little embarrassed when it happened."

"There are a lot of things you could do to put a little craziness in your life," Barry said, "why this?"

"For lack of a better answer, I guess I could say I wanted to do something for my brother, but that really wouldn't be totally true," she said. "If that was all there was to it, I could always have just hired an escort for him to act as his partner. Like I said, I really can't fully explain it, but maybe I was just feeling horny after so long and thought meeting a nice young man to fuck would be fun."

Barry grinned sheepishly in response.

"And speaking of a nice young man that I'd like to fuck," Bernie said as she reached down and lifted his now half erect cock in her hand, "If you're still interested, I think your friend here is just about coming back to life."

Barry spent less than a second thinking about it. If Bernie's explanation was a little bit strange, it wasn't enough to matter.

"Well if that's the case," he said with yet another grin, "then I think one of us is just a little bit overdressed."

Bernie looked down at the green panties that still covered her sex, then lifted herself just far enough off the bed as to be able to slide them off. As they joined the mixed pile on the floor, she spread her legs and gave Barry a good look. What he saw was a tightly trimmed gray and white bush, which, aside from the hair color, looked just like any other he had seen.

Reaching down, Barry ran his hand across the triangle, finding it wet to the touch. Slipping his fingers inside, past the twin folds of Venus, he reached her pearl and began to massage her sensitive spots. One could say that, given her age, it had long ago ceased being priceless, but that was something that the young man would greatly contest.

"That's nice," Bernie said as she leaned back and closed her eyes, content just to float in a pleasing haze for a few moments.

Barry continued to gently rub her clit as, beginning with her neck, he began to kiss his way down her body. Down he moved, leaving a shiny, wet trail until he caught up with his fingers. Then he added his mouth to the pleasures washing over the woman below him.

"Oh that's even better," Bernie said, her eyes still tightly closed.

Going down on a woman had never been high on Barry's list of favorite things. Still, he appreciated the fact that if a woman did it for him, it was only right that he reciprocate. A lot of men he knew didn't see it that way.

Soft moans filled his ears as Bernie voiced her enjoyment of his efforts. Unlike Sally, who often complained that he wasn't trying hard enough, the woman between whose legs he now labored seemed to appreciate the effort. If only as an appetizer of what was to come.

More time passed until Barry was confident he had done the best he could with what he considered his limited skill in this area. Filled with an enthusiasm that he hoped Bernie shared, he went from the appetizer to the main course. A meal he hoped would be satisfying for the both of them.

Taking hold of his hard cock, he pressed it at the entrance to her womanhood and entered her with only the slightest of resistance. The way had been well paved by his labors and her own high level of excitement. One within her, he moved back and forth slowly, each time rising a little higher on the up stroke and moving deeper on the downside.

"Oh yes," Bernie said even louder as she opened her eyes and enjoyed a feeling too long absent from her life. "I have missed this."

It didn't take long for Barry to develop a rhythm as he lifted her legs up over his shoulders to gain even better penetration. His pace quickened, as did the level of Bernie's response; a response measured by the level and frequency of her encouragement.

Her eyes totally fixed on the young cock sliding in and out of her, Bernie grabbed her breasts and massaged them, pressing against her nipples as well as the soft flesh around them. Her body rocked in time with Barry's vigorous entries, adding to the forces building within both of them. She felt more like a high school girl on prom night than a mature woman with almost thrice her years.

The dark-haired young man also found himself in a state of approaching bliss that felt like it could go on forever. Drawing on a reserve of energy that unexpectedly presented itself, Barry now found that self-control that had failed him earlier. He was determined that he would hold out until Bernie had her own climax. If not before him, then at least with him.

The second proved true as only moments before he felt he was going to have to admit defeat in that desire, Bernie let go and climaxed explosively. It was her first orgasm that hadn't been self-induced in years, and her body responded accordingly.