The Legendary Mrs. Olsen

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Which one is better? And who will choose?
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adamgunn
adamgunn
203 Followers

The hotel lounge was quiet that evening, not surprising for a Wednesday. A table with five out of towners drinking pitchers of beer, seven people spread out around the oversized horseshoe bar. One woman, not bad for a lady of her age, certainly over 40, possibly even in her early 50's. C-cup breasts under a white blouse, jeans, black pumps. You always noticed the shoes, women love their shoes. Big rock on the left hand, but that didn't bother him, a lot of women didn't care much when their husband wasn't watching. Great necklace and bracelet, she was classy. Long nose, thin lips, collar length blond hair, she'd be pretty if she smiled, but Tom hadn't seen that since she'd entered the place half an hour ago and ordered a drink.

Curt was moaning about Cindy, worse than usual. The bitch had invited him to dinner last Friday, supposedly to talk like adults about the divorce, then took him back to their (her?) apartment and fucked him like the dick he was. Then she'd kicked him out in the middle of the night, letting him know another guy was picking her up Saturday morning and driving out to a B&B. Another time up and down the yo-yo, and Curt didn't know whether he wanted to try and make another go of it or tell her to go to hell. Tom tried to tell him he was getting played, but Curt didn't want to hear it; served him right.

Once again Tom checked the blond out, and this time he caught her eye and held it for five seconds or more. "Hey, doesn't she remind you of Mrs. Olsen?" It was their high school chemistry teacher, a very hot babe. She had something the younger teachers didn't have, a sense of I-know-what-I've-got-and-you'll-never-get it. There were rumors she was putting out for the principal.

"Yeah, I guess so," Curt replied.

"You know, I'd still like to have a piece of her ass."

"She must be sixty by now."

"Maybe, but I'd still like it."

"You're sick, Tom."

Maybe he was but still, if he could get to Mrs. Olsen he'd take the chance. Maybe, just maybe, the woman on the other side of the bar would be a great substitute.

It was time for him to make a move.

~~~~~~~~~~~~~

The woman in the white blouse was ticked off. She couldn't stand her hotel room, so she'd headed down to the bar to at least have some noise other than the television. She waved to the barmaid, ordered an Absolut/tonic, two limes. Then she thought.

First, there was this stupid conference twelve hundred miles from home. Her new boss enrolled her in it, didn't give her a chance to talk her way out of it like she had so many times before. He'd caught on to her quickly, and even though she was the top sales rep in the district, he didn't let her run her own life the way Jerry had. She'd been bored during the morning meetings, slipped out in the afternoon and went to the Mall of America. Bought some jewelry and a sweet silky baby-doll. Maybe that would get her husband in the mood, he hadn't been really interested in over six weeks. And that was way too long, she was getting seriously horny even if she did bring herself off in the bathtub two or three times a week.

And he was getting on her nerves in other ways, too. Wanted to put in a new kitchen so he could cook for twenty people. That was okay, they could afford it and it would increase the resell value, but couldn't he just make the decisions himself and leave her out of it? So much talk about tile patterns and tint of woodwork and he even tried to get her to consult about the brand of oven as if she gave a rat's ass.

"Pour you another one, ma'am?" the barmaid asked. "No, I don't think so." Oh, how she hated being ma'amed. Looking around, she viewed the other denizens of this evening's dungeon. What was the Billy Joel line? Oh, yes, 'They're sharing a drink they call loneliness / But it's better than drinking alone.' The guy on the other side of the bar tried to catch her eye again. He was a little cute, not as much as his buddy who seemed sad about something, but even if she was thinking about getting picked up -- and she wasn't -- he was much too young. Not more than twenty-five she guessed, with his first big job, and he was a clothes horse. Thousand dollar suit, custom shirt, Armani tie. Bet he thinks he's god's gift, she thought. Catches his share of girls, then doesn't know what to do with them was her guess.

She went back to her brooding, this time about her daughter, just turned sixteen and had found out about boys. Once she discovered Kayla had her cherry popped, she had to take her to the gynecologist and get her put on the pill. Then they had to have the talk about how Kayla should limit herself to one boy at a time and make him wear condoms. Not that it mattered, Kayla was going to let it go in one ear and out the other. Damn it, the girl just didn't have any sense! Not that it was so different from what her mother had done in high school thirty years ago, but at least she'd taken reasonable precautions and hadn't gotten caught. It was funny, her husband still thought he was the second guy who ever had her, that summer after she graduated college. If he only knew . . . but then again, what he didn't know certainly didn't hurt him. And it pissed her off to know her daughter was getting laid on a regular basis, and she wasn't!

But Kayla just wasn't a smart girl. Oh, intelligent enough, she was keeping a B+ average, and she was great at taking tests, there shouldn't be any problem getting her into a good college. But the girl was amoral. Just that morning, before she went to the airport, she saw her tube of Dior lipstick in Kayla's hand. She confronted Kayla, of course, but she'd come up with a lie that she'd bought it with baby-sitting money. At least she had the sense to shrug it off and not make a big scene of it. And, of course, it wasn't the first time Kayla had stolen stuff. Kayla was spoiled, and it was mostly her husband's fault of course, but she wasn't completely blameless either she guessed.

Another glance around the bar, and this time the macho caught her eye. What, she wondered, would he be like if she ever did let him into her bedroom? Just an idle thought, it was never going to happen. Damn! She realized she'd let her eyes linger in his a little too long. And now he was coming over.

Tom didn't go directly to her, of course, he was much too suave for that. Instead he kept moving, heading for the men's room. But it didn't stop him from studying her as he passed, not ten feet away. Nice body, she must work out. And her complexion was duskish, she probably used a tanning booth. Bet she didn't have any lines, either, her teats must be as dark as the rest of her. As he used the urinal, he considered the possibility of another conquest, the oldest woman he'd ever had. He swigged a handful of water from the tap, quickly sucked a breath mint to mask the scotch.

On his way back, he enjoyed her rounded ass in the tight blue jeans. Approaching from the rear, he declared to the barmaid, "Tanya, get this lady another drink, won't you?" The barmaid was torn, the woman had turned one down already, but Tom was one of her biggest tippers. The lady didn't say 'no', so Tanya got down a clean tumbler and filled it with ice.

"I'm Tom." Confident, yet with that touch of sincerity women just ate up.

She smiled, gave a long look into his eyes as if to say 'you're sure you can handle this?' and replied with a handshake, "Gayle. Thanks."

"Mind if I have a seat?"

Gayle considered it, decided a little conversation couldn't hurt, motioned him to the stool beside her.

"And what brings you to this place?"

"A meeting at the convention center."

"Oh, you're from out of town then?"

"Philadelphia."

"What do you do?"

"Sales rep." Gayle decided to take a chance. "And you're a stock-broker."

Tom laughed, "Close enough, Financial Analyst. How did you know?"

"I'm a psychic."

"Okay," he played along, "tell me more."

"Let's see . . ." Gayle decided to go for it, if she embarrassed herself she could always just leave. "This is your everyday bar, you work in an office near here. The guy you left over there is your best friend, and you should bring him over here."

Curt was watching the action, she waved him over. When he approached she greeted him, "Hi, my name's Gayle."

Curt opened his mouth in reply, was interrupted by Tom. "Don't tell her, she's a psychic. Let her tell you."

"Give me a break," Gayle responded, "real psychics don't know details, just generalities. Anytime somebody spouts off a specific date, they're phonies."

"I'm Curt."

"Nice to meet you."

"Curt, she's amazing," Tom said. "She knew we're analysts, and she figured out we work nearby. Tell us more."

Gayle had to giggle. This was turning out well. And Curt was pretty cute. Well dressed, but not over the top like Tom.

She decided to take the easiest route. "Well, you two are best friends, have been since middle-school. You're very competitive. One of you was the quarterback, one was the tight-end, and you won the last game in high school by a long pass. You're still arguing if it was a better pass or a better catch. Am I getting any of this right?"

"Close enough," Curt conceded, "We met as freshmen, and the sport was basketball. He was a guard, I was a forward. In the last seconds of the conference championship, I blocked a shot hard, he picked it up at mid-court, went to the basket and made an easy lay up."

"Yeah, right!" Tom interrupted, "there was a guy right on top of me, and I had to shoot the ball left handed." They looked at each other, the way guys who are trying to be macho always do, and then Tom asked her, "Got more?"

"Sure. You went to different colleges, and that way when the two schools played you could irritate each other. You still go to the games. Right?"

"I went to St. Cloud, he stayed at home at Metropolitan. Yeah."

"One of you, I don't know which, got a job at your firm and brought the other one in."

"It was me," Tom admitted.

"And, Curt, you're going through a rough time. Girl trouble? Got dumped?"

"Worse, divorce."

"Oh, I'm so sorry," Gayle commiserated, laying a hand on his arm. She honestly didn't know if it was meant to be suggestive or not. "Bad?"

"Pretty bad. Tom's right, she keeps screwing around with my head. But I've had it with her, it'll be final next month, and I'm moving on."

"Sure you are," Tom interjected, a little spitefully. "He hasn't made it with any other girl so far, and the bitch is setting new world fucking records."

"I'll be on my way pretty soon," Curt insisted, and Gayle agreed, "Yes, you will. You'll be fine. And once the girls find out you're okay, you'll be up to your neck in them." Curt smiled at her in disbelief, and she reminded him, "Remember, I'm a psychic."

The conversation moved on. Gayle shared with them a few details of her life, she had a husband and daughter, a little of her upbringing. They tried to guess her age, Curt missed her true age of forty-six by only a year, Tom underbid by nearly a decade. When Gayle was offered a third drink, she accepted. Forty-five minutes later, when the threesome was comfortable, Tom broke into it with, "So, Gayle, do you ever fool around?" He didn't know what her reaction would be, she might throw the drink in his face, but there's the old adage that if you don't ask . . .

Gayle just smiled, let a wistful mien cover her face, sighed, and then replied, "Of course not. I'm a Sunday School teacher." She knew, at least, the last part was true, and if you kept it to the past fourteen months, the first part was, as well. "But you do, Tom, and you're quite successful at it, aren't you?" Without waiting for a reply, she turned to Curt. "How about you? Before you got married, I'll bet you got your share."

"Enough," Curt agreed.

The conversation paused, Tom was at a loss. If Curt hadn't been there, he figured it would be like shooting ducks in a barrel. But she seemed to prefer Curt. Maybe he should throw her over to him, let him take the shot. But, damn it, she still reminded him of the legendary Mrs. Olsen, and he still wanted some of that.

For her part, throughout the hour Gayle had been thinking, considering, even perhaps beginning to plot. A long held fantasy reared its head, and Gayle didn't know if it was ugly or beautiful. If it chanced to happen this evening with these two beautiful boys she knew she wouldn't regret it. But on the other hand she was very much out of practice, and she didn't know how to place the invitation. Men are such cautious characters, and unless they, particularly Tom, believed it was their idea, they might spook.

"You know how I said you were competitive?" she began, and they nodded. "Well, I know one thing you've never been competitive about."

"What's that?"

"Sex. Oh, you two talk about your conquests, and tell each other how great the babes are, but you guys don't really know which one is the better lover, do you?" She got only blank stares, they weren't about to admit it.

"How would we know?"

"Well, you've never made love to the same woman, so you wouldn't. Actually, that's not quite true. One of you, again I don't know which, convinced a girlfriend of the other to go to bed with him. But you'll never tell, you don't want to hurt your friend."

Tom kept his poker face on. It was, of course, very true, and it was even worse than a girlfriend. Before Curt was married, after the engagement, he'd made a run at Cindy when Curt was out of town and scored. As they were lying in the sack after it was over, she'd said he was a much better lover than Curt was, but then again, he bet she said it to every guy she'd had since. It came back to haunt him every now and then, but luckily the bitch had kept her mouth shut as far as he knew. Funny thing, just a month ago Cindy asked him for a date but he was smart enough that he wouldn't touch her again with a ten-foot pole.

"So," Gayle continued, "You simply don't know which one is better in the sack, and, after all, wouldn't that be the ultimate bragging rights?"

"Okay," Tom bit, "assuming we want to know, how do we go about finding out?"

"I think you would have to make love to the same woman and let her be the judge. You shouldn't have any problem finding a girl that would have sex with both of you, would you?"

"I guess not. There's enough sluts out there."

"Ah, but that's the rub, isn't it?" Gayle commented.

"What do you mean?"

"Well, the referee has to be a pretty good lover herself. After all, you wouldn't get somebody who doesn't know the rules to officiate a basketball game, would you?" Nods all around.

"So," Tom said, "We get a woman who knows how. Okay, that's still doable. I mean I know some girls who know the ropes. There's Sue, I bet she'd do it. Would that be okay with you?" he asked Curt.

"But wait a minute," Gayle interrupted before Curt could agree -- she could see Curt was interested in the woman they were talking about. "I assume you've been out with her a number of times, haven't you, Tom?"

"Well, she's sort of a fuck buddy, yeah. But she plays the field."

"That wouldn't be fair to Curt. You've had Sue plenty of times, she knows you in and out, and so she lets Curt do his thing once, maybe even twice. So she's comparing two things that aren't really equal. She might even pick Curt because he's new, and you're a known factor." This got to Tom, he could see what she meant.

Curt picked up the chain. "Okay, we need somebody neither of us have ever had before. That could be tough, other than a hooker."

Both Gayle and Tom agreed together, "That wouldn't do, she'd just say it was the one who tipped better."

"Yeah, I know," Curt continued. "And then, what if the girl was in the mood one night and the night when the other guy got her there was something wrong or something, like she had a headache?"

"Good point," Gayle agreed, "you both have to make love to the same woman on the same night. But even that wouldn't be good enough. Let's assume the first guy really does it to her, gets her hot and bothered. Well the second guy gets this woman who's completely worn out. That's not fair, is it?"

"Nope." This time, it was Tom talking. Gayle looked at both of them, knew she had manipulated them into just the mood she wanted. It was time to seal the deal. And then Tom walked right into the trap. "It has to be a threesome. One girl, the two of us, winner take all."

"And neither of you could know the woman before that night. Otherwise, it wouldn't be a good survey."

"Man, that's tough," Curt observed, then he turned to Gayle. "Have you ever done this?"

Wistfully. "A long long time ago." A pause.

"Tell us about it."

"Not all that much to tell, really. This was before I got married. My boyfriend had a friend who I thought was hot, and he came over one night. My boyfriend encouraged us so we got it on. My boyfriend just sat around for awhile watching us, then he joined in. We had him back a few more times. That guy could really screw me!"

"No shit!" Tom exclaimed, "And your boyfriend didn't mind?"

"Uh-uh, he got into it."

"So you've had lots of experience then. You know, it sounds like you'd be the perfect woman to judge which one of us is better."

Gayle just laughed. She hoped the two boys thought it was from disbelief, but in actuality the mirth was caused by Tom's step into the trap. "Oh, come on! I'm almost old enough to be your mother."

"No, you're not. And besides, that just means you know what a great lover is."

"Oh, that I do . . . I do." She looked Tom directly in the eye, held his gaze. "I know you're interested, you've been checking me out all night." Then she turned, "How abut you, Curt? If you don't think I'm attractive . . . ."

"Hell, no," he proffered. "You're a very hot milf. I'd love to get it on with you."

"You sure?"

Curt put a hand on her thigh, under the table, rubbed it up and down her leg. "Yeah, very sure. You want to do this, don't you?"

"Can't say it doesn't appeal to me. Okay, so if we go ahead with this, what are the rules?"

"You make them," Tom decided, "what ever you say is good enough for us." Curt nodded his agreement.

"Okay, you asked for it." Gayle knew, of course, that Tom had gone for the presumptive close, and that she very willingly had agreed. The two men were as good as buried inside her right now. "And what's the bet?"

"Our usual for a big one?" Curt asked, and Tom accepted. "It's dinner, at the restaurant of the winner's choice. Loser pays."

"Sheesh. What do I get out of it?"

"It'll be tomorrow night, and you get to be the guest of honor."

Gayle thought about it for a minute, rubbed her chin. "Sounds fair to me."

Curt added, "And you can have the winner all to yourself later."

"We'll see about that, maybe neither of you will get a passing grade," she jabbed humorously.

"Oh, I'll pass, don't worry about it."

Gayle laughed once again. "Very well, no time like the present?"

The three rose simultaneously from the table, Gayle waited while the boys paid and tipped the barmaid and they marched to the elevator. As it rose the threesome was quiet, each lost in anticipation. When the room was reached and they were in private, she told them, "Okay, first, a kiss from each of you. I've never had a good lover who couldn't kiss. Flip a coin to see who goes first." The toss went to Tom.

He grasped at Gayle, kissed her hard, using a lot of tongue. She allowed it, feeling the heat permeate from his body, and when his hand slipped to her bottom and crept into the crack between her legs, she didn't protest, in fact she let him drag her closer. She knew from the kiss Tom wanted sex with her, badly, but she felt it was more an advertisement for what was to come than what already was. After some time they broke, Tom asked with a smirk, "So, how was it?"

"I've had better," she critiqued. "You were a little too aggressive, and it was supposed to be just a kiss, not a grope." Then to Curt, she said, "Your turn."

adamgunn
adamgunn
203 Followers