Betcha Won't

Meg was rather subdued as she cleaned up and dressed herself, ready to leave. She'd come a long way, she thought, from the woman who'd got on the plane five days ago. Her objective-self wondered just how much farther she'd go – how low, perhaps, she'd stoop – before something signaled, 'Enough!' And through all of that, deep down quietly, a rather naïve innocence countered, 'Who's ever going to know?'

Quietly preparing to leave the protective confines of Mike's suite, she dug deep to put on a good face to go meet her travel mates for dinner. Their experiences had become so diverse they had little in common. She knew the girls disapproved of her – as they put it – 'obsessive gambling', but while she didn't need their approval, she still had to be social and civil.

At the door Mike bet once more that she wouldn't come back to see him on her final full day.

He lost; she showed. Meg arrived at his door wearing another skirt though not so short, and another blouse – conspicuously braless. After a warm good-morning kiss, Mike cut right to the chase. "Have you ever been fucked anally?"

Mike chuckled inwardly as Meg visibly flinched at his choice of words, still, she answered softly, after just a moment, "No. No, I haven't. We tried it once many years ago, but it was too much like work. Aiden never asked again, and I never brought it up."

"But you've always been curious, eh?"

"Am I that easy to read?" Meg shook her head heavily.

"I'll bet you another $1000 that you won't do it anally with me – how about that? We'll use lots of lubricant, and go very slowly – if you accept the bet, that is." Mike was staring at her, trying, once again, to read the nuances of her body language, of her eyes. "What do you say?"

"What the hell?" She gave a wry laugh. "In for a penny, in for a pound. You've already made me a prostitute."

"No, no," Mike protested, "You're not a prostitute. That would be no fun. I'd like to think I've merely helped to illuminate some of the true you – the sexy, savvy gambler – the adventurer, you're so used to keeping well in check." He cocked his head at her, "Don't you think?" Mike felt bad that she felt bad. This was no time for regrets; it was time for enjoyment – whether that be from taking bets and winning or fulfilling erotic desires.

They were quiet and still for a bit, both considering what had been said – and what hadn't. Then Meg stood and shrugged. "Okay, then," and she began removing her clothes. Mike stepped up and stopped her with a hug.

"You don't have to, you know. You've nothing to prove. We can stop right now – if that's what you want."

Meg leaned into him. "No," she whispered, almost purring. "Let's finish the game." And she kissed him warmly, before pulling away, disrobing, and climbing naked onto the bed. Mike swiftly followed suit, positioning Meg on all fours in the middle. Pausing, to appreciate the lascivious tableau, he slowly, gently inserted his right hand between her legs and began to caress her pussy – swirling fingers around her clitoris and drawing them back between her labia. At the same time, he reached over her back with his left hand to palm her hanging breasts, twiddling her nipples. Otherwise motionless, he kept it up until Meg's breath quickened, becoming shallow and ragged.

Eventually he moved back to kneel against her upturned ass, and, scooping moisture from her dampening pussy, circled and prodded her rosebud with his wetted fingers. Meg stiffened as he poked her anus, moaning in apprehension. Quickly grabbing the bottle of lubricant that he had had ready, off the nightstand, he coated the fingers of his right hand and swirled the slick liquid around her bum, dipping lightly from time to time – beginning the process of preparing her virgin sphincter.

Swirling his left hand about her clitoris, Mike continued to dip and twirl his fingers – first one, then two, then three – in and out of Meg's anus, until, with the distracting manipulation of her clit, she began to hiss and tremble. With a final poke and twist of his three fingers, stretching her butt-ring, he abruptly pulled free, and lined up his bobbing cock, seating it firmly against her rosebud.

For an instant both were still, then he started to push, slowly but inexorably, pressing against her innate resistance – pushing and retreating, causing her asshole to dilate – a bit at a time. Meg moaned, not knowing exactly what to do to ease the entry – not knowing how to relax those muscles. And Mike kept up the pressure – unrelenting, until, so gradually as to almost be in slow-motion, he popped past her resistant ring, his cock-head suddenly pulled through her sphincter. Entry was relatively smooth and easy after that, though still slow.

Mike ensured his rod was well lubricated, as his dick crept gingerly into her dark passage – two centimetres forward one back – gentle, but persistent, until he felt his thighs against her buttocks. He held still for a moment, in deep, bottomed out – literally and figuratively – before beginning to withdraw. Pulling back until he could feel his knob up against the inside of her anus, he began to stroke – setting up a leisurely in and out rhythm.

Meg was surprised how quickly the initial discomfort dissipated, and, in short order, found herself beginning to join in. Mike could feel her rectal muscles tighten and release as he established his rhythm. She relaxed as he pushed in and gripped as he retreated, holding him tightly on his backstrokes, so that he couldn't escape. Soon Meg was moving her hips in counterpoint, rocking back against his intrusions, and pulling on him as he drew back.

And so they both enjoyed a slow see-saw, both being somewhat worn out, Mike especially having had more action in the past two or three days than in the previous two months – much more than he was used to; nevertheless, their rocking gradually became more urgent, faster, more energetic. As they accelerated, Mike reached over Meg's back to, once again, cup her hanging breasts, first palming, then pinching her nipples. The attention to her tits stoked her building arousal. Mike could feel the building heat through her ass. He pulled back to upright, for a bit, with his hands on her hips, assisting her participation in the ongoing rhythm; then he reached around her hips to strum her clitoris, once more, spreading the juices from her dripping pussy, adding moisture to the lube surrounding her stretched rosebud.

His manipulations accelerated Meg's building pleasure, which, in turn, pulled Mike higher and higher, closer and closer to his apex. It had been a long and gradual, inexorable journey, but with a final rush of sensation that set off explosions behind his eyes, Mike felt his cock swell even more, before jerking and twitching and squirting gobs of cum into her warm ass. Meg could feel his spasms. She could feel the liquid spurts gushing into her fundament – more so than she had ever felt vaginally. And her orgasm was forcefully ignited – triggered by the feel of Mike coming in her. A low rumbling orgasm, it was, too, rather than the sharp and peaky climaxes she was used to.

Mike gasped and cried out. Meg groaned and whimpered in response, the moans of their dénouement joining in unison, a sort of sensual harmony. Suddenly enervated, Meg collapsed onto her front, with Mike covering her – both of them panting and puffing. When she'd finally caught her breath, Meg looked back over her shoulder. "A girl could get to like that," she observed, smiling wryly.

While she was in the shower he saved all the files onto a USB thumb-drive. Then he hooked up the laptop to the TV and had some of the video running when she emerged from the shower.

"So," Mike asked brightly, "whaddya think?" Meg was visibly worried, but silent. "I mean, how do you like seeing yourself on TV?" Nodding toward the screen, he snickered, "How much do you think that's worth?"

"That's blackmail," she gasped.

"No it isn't," Mike replied casually, but a desolate look of betrayal came over Meg's face. She suddenly looked as if her spirit had just crumbled inside her and fallen like sand to her feet.

"Ha!" she laughed mirthlessly. "here I thought we were having a shared adventure – but it turns out to be nothing but a crude trap!"

"No. Hold on, pet. I'm joking! Really! I wouldn't seriously try to blackmail you – honest. That was just a joke – just getting a rise. Not real." He shrugged, his palms upraised. Meg looked unconvinced, although, perhaps slightly less devastated. As she stayed silent, Mike went on. "I am filthy rich, you know. I certainly don't need to extort money from you!"

"I was just playing – part of the game." He watched her silently, detecting, perhaps, a slight release in her taut shoulders. He started again. "Hey, I know, for a fact, you can't bring more than ten thousand dollars cash into Canada without declaring it, and I assume something similar applies in Britain." He paused, tried to give her a reassuring smile. "You've amassed what? Fifteen, twenty thou? I don't know. I've completely lost track. Do you know what your total is?" Meg shook her head and shrugged, mutely, so Mike went on, "Anyway, it might be kinda hard to explain if you have to declare too much, eh?"

Meg shrugged, then nodded. She could see his point – now that she could think again. "So how about a straight deal? No blackmail. No implicit or explicit threats. Simple. I'll leave you with ten grand, plus extra pin money for the duration, and I'll get the rest of your – er, accumulation to you over the next six months or year or whenever. Okay? Really, I think that's best for you. You know what they say, 'What happens in Vegas stays in Vegas! Here." He handed her the USB key. "That's all the files. Wordlessly Meg nodded again, pocketing the drive, and, to be honest, not believing she'd ever see him again.

At his door, she turned back to face him. "Thanks – I think." She chuckled, "Yeah, thanks. You saved me. I believe you really did." Mounting on her toes, she leaned in and gave him a smoking hot kiss.

"It's been a slice!" he quipped.

"Yeah," she observed, drolly. "A little bit of 'out of the pan and into the fire', I think."

Then, with a quick "Bye," she turned, scuttled to the elevator, and was gone.

"You made out pretty well, though," Mike whispered to the empty hallway, leaving the double – or was it triple – entendre hanging.

––––––––––––––––– Epilogue –––––––––––––––––

Back home, once more, in Birkenhead, Lancashire – just across the Mersey, through the Birkenhead Tunnel, from Liverpool, Meg tried, with limited success, to resume her regular, mundane life. She told herself that she wanted to put Vegas out of her mind, and concentrate on her husband, her job, her friends. But over the following six – eight months, she managed to watch the video files two or three times. And she found them even more strangely alluring than her daily fantasies – memories of the incident, in which she sometimes changed details slightly, trying out slight differences in the scenarios.

Watching herself – her lewd self – on the computer monitor – when her husband was away on business – all those many, many weeks later, had been almost frighteningly arousing – causing a sudden and vise-like contraction in her genitals – squeezing enough moisture to soak the crotch of her panties, before, even, she could push them out of the way and spread her engorged lips, swirling the natural lubricant over her vulva and across her clitoris. Her orgasms, every one of them, were violent and strong and long. Meg was amazed, still – at herself, at her response, at the situation, at everything that had transpired. And she was frightened by the keenness of the thrill even the reliving of the event still afforded her.

It had been over six months since her Las Vegas excursion when Meg received an email from Mike, to her private account. It was simple enough: a few of the less risqué pictures and one word; "Remember?"

Curious, and more than a little concerned, she made a single word reply. "Yes?" Most of the meaning, she felt, lay in the question mark.

As she hadn't warned him off that email address, Mike plunged right in. "Remember – yes! I can't seem to forget! I am in the Liverpool area for a few weeks and I would dearly like to see you – reminisce about our time together in Vegas; make a few 'friendly wagers', perhaps. I'm staying at the Radisson Blu Hotel on Old Hall Street in Liverpool. Let me know when we can meet for dinner and drinks. Cheers. Mike."

Meg was stricken. What should she do? Ignore him is what she really should do, but could she. The memories of herself – how she'd let go – of the peaks of arousal, the ecstasy, the roiling sensual miasma, flooded back. Echoes of her sensory overload fogged her consciousness, leaving her in a muddle of indecision. Fortunately, for her, her husband failed to pick up on her sudden consternation. He was, as usual, preoccupied with work. Finally, after musing a day and a half, Meg sent a terse reply. "Okay. How about Tuesday – noon?" Mike replied immediately, "Awesome!" and gave her the suite number and parking instructions.

Exiting from the Birkenhead tunnel onto The Strand, Meg felt increasingly confused; after all, this was not Vegas. Apparently 'what happened in Vegas' had chosen not to stay put. As the 5-Star hotel came into view, she felt her stomach tighten, and her pussy dampen. After leaving her car with the valet, who was expecting her, she entered the elevator woodenly, and ascended to the top floor – her otherwise petrified body trembling. She studied herself in the mirrored wall. She still couldn't decide whether the clingy sheath dress and heels made her look classy or tarty – but it was too late now, as the elevator's ping signaled the penthouse floor.

Mike welcomed her effusively, giving her a quick, warm hug before stepping aside and welcoming her in. After showing her around the executive suite, and giving her time to admire the view – she could only go through the motions, given her current emotional haze – he sat her down with a drink, and some room-service snacks. Mike chatted amiably, while Meg remained wary; but slowly Meg's tension dissipated and she eventually found herself relaxing. Amidst the non-threatening chatter, the conversation veered subtly back to their shared history, until, in an unguarded moment, Meg confessed that she still had all the video files on USB, and, indeed, had watched them from time to time when she was alone.

And then the switch had been tripped. They quickly got down to what they both knew they were there for. "I'll bet you a hundred pounds you won't take off your panties and give them to me as a souvenir."

Picking up the game more or less where they'd left off, it was not long before they were naked and involved. Kneeling between his thighs, and sucking on his cock, it surprised Meg how easily she surrendered to the excitement of the 'faux gambling'. She 'won' a bunch of 'friendly wagers' throughout the afternoon, before Mike put out the final bet. "I'll bet you – whatever – twenty-five hundred pounds, that you won't let me sodomized you again."

Meg was silent for a minute. She recalled the novel sensations, the eventual delight of their last anal congress in Vegas. However, this was the first time he had referred to it as sodomy. Irrationally, she knew, she wasn't sure she liked that. Turning the tables slightly, she replied, "I accept your proposal for full-on anal sex. Accept eagerly!"

It would be her first since Vegas, Meg admitted, and went on to explain, as she was arranging herself on all-fours in the middle of the king-sized bed, she hadn't been able to figure out how to get her husband to try it without raising suspicion. Then her attention was seized by the cool application of lubricant to her backside.

Mike swirled lotion around her anus, slipping and prodding, and darting his fingers up and over her clit from time to time. His other hand played with her hanging boobs, twiddling and pinching her nipples, eliciting moans of building pleasure from Meg, as she dipped her back and rocked her hips gently. Lining up his tool, Mike took it very slowly, but, when she couldn't wait any longer, Meg facilitated his intrusion by thrusting back against him. Once full inserted, they shared a dynamic rhythm of push and pull, grip and release, until a rise in Meg's temperature, signaling the onset of her climax, initiated Mike's ignition sequence. The simultaneous orgasm hit them so hard, ricocheting between them, they had trouble remaining upright, and crashed into a trembling, sweating, panting, smiling tangle on the bed. The room was silent, but for the sound of breath being caught. The crisp tang of sweat and cum filled the room.

Then the afternoon was gone. After showering together, Meg reluctantly got dressed. Neither she nor Mike had bothered to actually keep track of the amount of her 'winnings' – but it was all a sham, anyway – a carry-over from Vegas. "It's got to be at least ten grand!" Mike said, producing a bankers' bundle of bills. "And you're worth every penny!" Catching the darkness pass over Meg's eyes, he hastened to add, "Not that I'm suggesting you're a prostitute. This is all just winnings, eh?"

As she accepted the proffered money, Meg still felt conflicted – torn between carnal desires and moral expectations. They stood for a few awkward moments at the door, before sharing an oddly chaste kiss.

"Bye."

"Bye."

After a heart-beat pause, Mike whispered, uncharacteristically unsure of himself, "Can I see you again?"

Moral conflict flaring once again in her psyche, Meg stared at him – shocked. But, she thought, society's mores were obviously flexible, whereas her base temptations were unwavering, so it was her primal spirit that prevailed. "I'd like that," she replied with a shy, sly smile. Turning, she stepped into the hallway, taking, as she left, her 'winnings', to squirrel away in her secret 'Mad-money' account. Flipping a final glance over her shoulder, she breezed, coyly, "Email me."