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Boss Vegas

"A sizzling threeway in a sizzling town"

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Author's Notes

"When I team up with one of my ex-bosses against another, more formidable ex-boss, who wins? We all do!"

It's a Wednesday in August. In Las Vegas. Actually, it isn’t Las Vegas. Strictly speaking, most of the Strip where we are walking is in ironically named Paradise, Nevada. You call this shit Paradise? It's a hundred fucking fifteen degrees.

Later tonight, it will get hotter than that, though I certainly don’t know that yet.

On the plus side, there are mist machines every other block to cool us down. Also on the plus side, and in many cases on the very appealing plus size, there are half-nude showgirls standing in front of every casino to compete with the blazing sun for heat. How they don’t pass out wearing nylons on a day like today is a mystery of the universe.

I'm ambling with two former coworkers - two former managers, actually - Gina and Sherrie, whom I've bumped into at the conference I'm attending this week. We all used to work together, Sherrie as my first boss at the Firm, and Gina who managed me a couple of years later while Sherrie was climbing the ladder.

"Should we go back?" asks Sherrie. "It's just too damned hot out here." We switch directions and start walking back to our casino.

"Yeah, let's get some AC and some drinks!" exclaims Gina, grabbing my arm.

No, no, it’s not like that with Gina. She prefers women. Hell, I went to her gay wedding. When we worked together twenty years ago, at our very conservative company, there was no way she could have been Out about her sexuality, though she had confided in me. She even had to bring beards to company social functions to cover up her real self. The Firm was pretty backwards then, even for the times.

But the times, thankfully, have changed. Now Gina is married to a woman and fully Out, even professionally.

Sherrie has grabbed my other arm. Unlike Gina, whose sleek swimmer build is attractive but not quite my usual type, I really could go for fuller-figured, wider-hipped Sherrie. Already in her thirties even when Gina and I were the young guns at the company, she must be about sixty now. And still pretty fine looking, with gleaming eyes and straight, honey-blonde hair that’s probably dyed now but recalls the color it had in the old days.

We reach our hotel and leave the abominations of the Strip: the half-scale Eiffel tower, drive-thru weddings, pizza vending machines, car vending machines, fake Venetian canals, world's largest Ferris wheel, faux-British Fish and Chips shops, faux Southern restaurants, faux everything except the fucking heat, which is all too real. The Tiki theme of our casino hotel's bar somehow feels less forced, because it’s as expected. It’s about the most normal thing about this city.

We order some Mai Tais and catch up. I haven't worked with either Gina or Sherrie for a long time. Unlike Gina and I, who found our paths leading elsewhere, Sherrie has stuck it out. Now a Partner and VP, she runs half the Firm and probably makes over half a million, not counting the millions more coming her way when she cashes out her partnership.

I think Sherrie may have already had a drink before we hit the Strip earlier. She's not exactly slurring, but acting looser than I've ever seen her, cracking jokes, some of them mildly naughty, and just being a bit overly friendly. For my part, I’m soon feeling the Mai Tai course through my veins, making her look better and better.

Eventually, the conversation turns to how Gina didn't feel comfortable staying at the Firm so many years ago, and Sherrie goes on a fair bit about how she always thought it was unfair that people couldn't enjoy and explore their sexuality. She says she led a lot of the changes at the firm, going on perhaps longer than necessary about how much she loves her gay and bi employees, and how they even have a lesbian partner now.

"It was just so awful that you couldn't be yourself back in those days," she continues. "The Firm was just so stupidly uptight."

"Yeah, pretty sure I'd have been out on my ass if it became known that I so much as hooked up with someone of the same sex at a conference like this."

"Probably true. Now it wouldn't matter so much. Heck, there are probably a hundred guys Joe here could take up to his room,” she taunted, “and no one at the Firm would bat an eye."

Before I get the chance to formulate a retort, Gina gets a flirty gleam in her eye and lobs this one right back at her. "There are at least as many hot women you could take back to your room too, Sherrie. You know, if you ever wanted to try it."

Sherrie smiles and replies, "You're right.” She giggles a bit as she adds, “Sometimes trying new things is a good idea." Her eyes lingering a split second on Gina, she blushes and excuses herself to go to the restroom.

Gina leans in, talking rapidly. "Listen, a couple quick things while Her Royal Tipsiness is gone. First, are there any guys here you have your eye on?"

"Haha, who doesn’t like a popsicle on a hot day?” I joke. Gina punches my shoulder at that one. I had confided my own heteroflexibility back when she came out to me. But it’s definitely something Sherrie couldn’t have known about when cracking that joke.

“Okay, maybe not you.” I jab back. “But I kinda have my eye on Sherrie. Or at least I did, until whatever that last comment was supposed to be. Maybe you have a better chance with her than I do.”

"Going for the older women now, huh?"

"Best kind,” I reply.

"Ok, second thing: I like older women too. Especially virgins.” She's obviously referring to Sherrie’s apparent lack of experience with women.

“I’ll be happy to step aside and let you initiate her into your little ‘club,’” I reply with a grin. “No shortage of guys at the bar that I could ‘initiate’ at a conference like this, like in Sherrie’s dreams.”

“That is not what I meant.” Gina’s grinning even wider and more mischievously than I am.

“Wait a ... are you suggesting we gang up on this sweet little old lady?”

She gives a really evil smirk.

“Oh, how naughty.” After a pause, I caution, “You do realize that a man would be present? Partaking in these festivities in intimate proximity to you?”

“I'm not completely disgusted by men, Joe. Like you, I can’t get enough of Taco Tuesday …” I shoot her a look for this trite food analogy, “… but I never hated Weiner Wednesdays.”

Her hand runs a few inches up my thigh as she says this. My mind shifts into overdrive trying to process this new development. First of all, is Gina not a full Kinsey Six? I, of all people, should have considered the possibility: come to think of it, she originally came out to me as bi, not gay. Knowing that gay people do sometimes initially come out as bi, perhaps I had subconsciously dismissed the bi angle too readily.

Secondly, I’ve never considered Gina’s sexual attractiveness, because she was locked away from that part of my brain in the dungeon of the Impossibilities Department, but now …

The Impossibilities secretary in my brain runs out of the elevator screaming, dashing down the hallway and flinging a file folder onto the front desk of the Opportunities Department. The receptionist quickly rubber-stamps the document inside, makes two copies, drops them into mail cylinders, and sends them - THOOMP! THOOMP! - through the hissing pneumatic mail tubes up to Speech Center and then Blood Flow.

They haven’t exactly reached the Digital Age back there, but they can still act pretty quickly in an emergency.

“So you’re looking to give Sherrie the full menu, then?” I reply, my trouser tenting simultaneously. “The Vegas buffet?”

“Well, just as long as you keep in mind that Sherrie is the main event tonight,” she cautions as we see Sherrie exit the restroom. She quickly adds, “And I’ll want her for the duration. How about you stick around until … well, you know, you have to take a male recovery break … and then you can excuse yourself?”

Fine by me. I quickly agree to this win-win situation as just as Sherrie returns, excusing myself to the restroom so Gina can work on her.

When I come back, both women are talking animatedly. Gina gives me a surreptitious wink, but no further indication of the progression of our plan. We continue talking about old times for another hour, drinks mostly worn off.

Except possibly in the case of Sherrie, who is still acting overly friendly, occasionally complimenting one or the other of us on something or other and touching a hand with hers. At a couple of points, she even runs her hand up my thigh.

Okay, that makes her the second woman to do that to me tonight - except the second time, Sherrie’s hand continues high enough to briefly contact my shortlimb. This leaves no doubt that I could bed her if Gina weren’t in the picture, but can we pull off the double feature?

The conversation turns to the hotel itself, and Sherrie describes the twenty-second story view from her suite, overlooking the Strip in both directions.

“Oh, I’d love to see it,” says Gina, giving my leg a nudge under the table to indicate the next phase in our diabolical double-team plan.

“You should come up, Gina. I’d love to show you everything,” replies Sherrie, a bit flirtily. “And you too, Joe,” she adds, appearing to compose herself. “You should both come up.”

She shoos us out of the booth, declaring, “C’mon, I’ve got a bottle of bubbly chilling up there, and the furniture is much more comfortable for lounging than this sticky little booth.”

She’s a little wobbly as we walk down the hall from the elevator, grabbing both of us around the waist for support. “Thank you for helping a little old lady back to her room,” she jokes.

Her room proves to be palatial, even by Las Vegas standards, with a view better than I’d imagined: downtown off in the distance, planes taking off in the other direction, and all the assorted architectural atrocities of pyramids, castles, desert canals, misshapen hotel towers and needles in between, lit up by a billion lumens of every color discernible to the human eye.

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I feel a bit nervous and dizzy. Maybe it’s vertigo from gazing out floor-to-ceiling windows two hundred feet off the ground. Maybe it’s just my excitement at getting closer to the moment of truth on the anticipated threesome. Or maybe I’m apprehensive about doing something to a woman who may still be intoxicated. I steady myself against the windowsill.

As Gina and I gawk out the windows, an eyeball on that new five-hundred-foot sphere blinking back at us from a couple blocks the other side of the Strip, Sherrie crosses the room to open a bottle of Champagne - yes, the real French stuff. Gina takes the opportunity to mouth the words, “She’s not drunk.”

Sherrie pours three glasses with remarkable deftness for a tipsy woman, bringing two over and setting them on the windowsill for me and Gina. She grabs the third glass for herself and slips up behind me, her right breast pressing against my back. Her warm alcohol-infused breath reaches my ear, “Spectacular, isn’t it?”

Yes. And that’s just one of her tits.

She pulls the same move on Gina, purring, “I sure hope you enjoy yourself up here, Gina.”

I notice that a couple of Sherrie’s blouse buttons have somehow worked themselves open while she was pouring the Champagne, revealing much of her deep, mature cleavage.

Sherrie proposes a toast and we pick up our glasses. "To old friends. Maybe we were just coworkers then, but tonight we are friends ..."

My dizziness and guilt simultaneously evaporate at the realization that Sherrie is not even slightly slurring her speech anymore. I can already see from the quick I-told-you-so expression Gina flashes me that she has already figured out what is just dawning on me now.

"To old times," Sherrie continues the toast, "and to newer, better times..."

Sherrie was always the smartest person in the room. And tonight, in this naughty town, it was her, not the casinos, that was gaming us. She faked drunkenness as an excuse to get friendly and touchy-feely with us and ultimately lure us both up to her boob-lair. She subtly and later openly encouraged both of us in our flirtations, even after it was clear both of us were in play with her. And having gotten us both worked up, she dropped the mic and took the most opportune moment possible to slip off to the restroom for us to “conspire” together. All along, she tricked us into thinking it was all somehow our clever idea.

"… And to being able to finally live our lives and do what we've always wanted to do,” Sherrie concludes the toast, setting down our glasses and pulling us into a big hug.

"Like this," she says, planting a quick kiss on my lips and then turning to Gina to do the same.

Her kiss with Gina, inches from my own face, lingers longer. Lips open, tongues dart and dance. I wrap my arms around Sherrie's wide waist from behind, kissing the back of her neck. "Mmmm, keep doing that, Joe," she encourages, still kissing Gina. Sherrie's curious hands are at Gina's blouse, unbuttoning, reaching inward and around to open the clasp in back.

"You ever?" asks Gina, helping with the blouse and bra removal.

"No, first time," says Sherrie, cradling Gina's boobies in her hand, marveling as she gently squeezes them. “I want you to teach me everything tonight,” she asks, bending down to take a nipple in her mouth.

“Doesn’t feel like you need much guidance,” murmurs Gina appreciatively, tilting her head back.

Meanwhile, I've been working on Sherrie's much fuller blouse and bra, cradling her soft, slightly wrinkly but very majestic mams in my hands, squeezing her nipples.

Sherrie leads us to the bedroom, lying back and letting Gina and me take the initiative, first both of us sucking on her big boobies, then Gina working her way down Sherrie's body while Sherrie reaches for my pants, undoing them and reaching for my straining stamen.

Soon Gina is tasting Sherrie’s twat, and Sherrie masterfully mouthing my manhood as I kneel next to her head.

“Oh, that is better than any man, Gina,” Sherrie moans around my meat, “but I want to taste you!”

Gina lays back for Sherrie to maneuver between her legs and chew cunt for the first time. Meanwhile, I get behind Sherrie and eat her out from the back. She presses her chest down against the bed to thrust her ass up and improve the angle of this two-hole taste treat.

Sherrie starts begging me to fuck her, so I grab a condom (packets left conveniently on the nightstand, further confirming the hypothesis) and plunge into her warm depths, enjoying another all-too-brief massage of her magnificent matronly melons while I plumb her passage and she continues lapping at Gina’s well.

Unfortunately, I am so excited I can only last a few minutes inside Sherrie, and soon find myself clotting the condom full of cum inside her crack.

Fortunately Gina is too busy moaning with pleasure, and starting to cum, to call for my ‘male recovery’ departure. I could kid myself that her excitement was enhanced by my thrusts repeatedly shoving Sherrie’s face into her vulva, but I’m sure it was mostly Sherrie’s newly developing oral abilities.

My male helplessness exposed but thankfully ignored, I sit out for a few minutes while the women sit up, kissing passionately with their legs alternating and their vulvas pressed together. I am privy to a beautiful alignment of mouths meeting mouths, tits meeting tits, slits meeting slits, and clits meeting clits. Sherrie finally ascends to her first orgasm of the night at this grinding of girlie genitals.

But it’s a plateau, not a peak. Sherrie is still manic with raw sexual need. Gina lies on her back and directs her to squat over her head on all fours for some serious muffin munching.

“Joe,” Gina mumbles from somewhere between Sherrie’s labia, “I don’t mind if you … well, you know …”

“Are you sure?”

“Yes, Joe, it’s okay.”

“So you’re okay if I go down on you and then enter you?”

Call me Mustafa, but if I’m going to bang a lesbian I really do need to hear the request three times.

Pulling her lips off of Sherrie’s lower lips, Gina articulates with mock frustration. “Yes, Joe, please put on a condom and insert your penis into my vagina,” prompting chuckles from us all.

I can hear Sherrie amusedly mutter, “God, you young people and your fucking consent rules.” Fortunately, laying witness to the ways of younger generations seems to sustain, not diminish, her excitement. She is still moaning and whining with pleasure at the twirling of Gina’s tongue.

I get between Gina’s legs, tasting her feminine folds and her sweet shaved snatch. It is exquisite.

All too soon Gina directs, “You can put it in now, Joe.” Okay, I am sure that I am not as good at eating a pussy as Gina’s usual partners, or probably even novice Sherrie, but I still can’t bring myself to just shove my dick into one without at least a perfunctory tasting.

“All right, this I’ve gotta see,” Sherrie exclaims while I unroll another condom. “Up close.” The women rearrange into a sixty-nine with Gina on top, presenting an opening as rare to male eyes, and dare I say as fragrant and beautiful, as the Kadipul flower.

I take my time, first pressing up against Gina’s neo-virginal opening, then very slowly pushing in an inch or so and withdrawing, checking with Gina to make sure she is okay.

“Oh good God,” I hear Sherrie mumble from beneath Gina’s cunt-convolutions. “Just shove it in already.” I don’t. I slide in a couple of inches, then back out. Then a bit further, and only them slowly sliding it all the way in.

Sherrie, meanwhile, despite her scoffing at my slowness, is showing herself to me a woman of as many talents in the bedroom as in the boardroom, sucking my balls and licking my plunging pecker almost maniacally, while giving Gina’s labia and nodule some frantic loving too.

I sure would like to have some more time with Sherrie and maybe even feed her some fresh-squeezed Joe-juice, but I know that particular act cannot happen tonight. Out of respect for Gina and her later enjoyment, I will keep Sherrie’s body semen-free.

I gently start massaging Gina’s medium mounds while I thrust inside her, surprising myself in bringing her to orgasm. Once again, not that I likely deserve the credit. I’m sure it was still Sherrie’s newfound slit-slopping skills that did it, but the fleeting thought brings me to my second climax and a second jizzbag full of cock-contraband.

And with that, I really am spent for a while. The ladies thank me for my participation, but also appear eager to explore each other without the penetrating male gaze, let alone the penetrating male protrusion. I take my leave for the evening, discreetly dropping the gooey balloons in the bathroom wastebasket on my way out.

Although I felt a bit of a third wheel in this encounter compared to the main event between Gina and Sherrie, I was certainly grateful to have witnessed that, let alone having been allowed to participate. Not that I wouldn’t have minded some time alone with Sherrie myself.

I awake at 6:00 am to fond memories and a raging erection. Just as I’m about to jerk off for the third time since last night’s encounter, my phone buzzes with a text from Sherrie.

“Gina just left for her morning swim.”

Before I can tap in a reply, she shoots me another message. “Thank you so much for the most incredible evening, Joe.”

Clearly in machine-gun text mode, she quickly adds, “I enjoyed the taste of a woman more than I ever imagined.”

“Thank you for including me,” I manage to squeeze in. “I’m honored to have been a part of it.”

“But I need to taste more of you too, Joe. Please come up.”

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Written by joe71
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