The Legendary Mrs. Olsen

“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.”