The issue between Greg and Elaine began during their getaway week to Jamaica, the only “just-the-two-of-us vacation” since their first child was born.

Her parents suggested the trip as a good thirtieth birthday present to both of them. With all three kids in school, it was easy for them to take care of the siblings for the week. They, especially Elaine’s mother, were excited to have the children all to themselves.

Elaine had been sexually active since high school, and when she and Greg met in their sophomore year at UVM, she knew she had found “the one”. Greg felt the same. They fell madly in love. It took great effort to keep their torrid romance from derailing their academic careers.

They married after graduation, had two girls and a boy in five years, and settled into a nice life together in southern Vermont. Greg joined Elaine’s father in the highway construction firm that had grown into a monolith. Elaine worked in computer graphics for an advertising firm in Brattleboro.

Despite demanding jobs and kids, they kept physically active, and at thirty-two Elaine was still a tall, slender Scandinavian blonde, and Greg was still an iconic Viking.

It was after a particularly good morning of sex on their second day in Jamaica that Greg first broached the subject of inviting a man into their bed to share Elaine. 

His comment barely roused Elaine from her lovely postcoital haze. She was used to such nonsense. Since their early days together, Greg often spun perverse role-playing threads to get them both excited for another go. This one was new, so Elaine played along.

“How about our waiter?” she said. “He’s kinda cute.”

“Very handsome, with the darkest skin I have ever seen on anyone. He was sure taken with you, but he’s a few inches shorter than me; surely you’d want someone taller, more Usain Bolt-ish.”

“I dunno,” Elaine said with a bit of playfulness, “he has those broad shoulders, his thighs were thick, and did you see the package on him? I bet his cock is thick too.”

That little teasing while she stroked him was all it took to get Greg ready again. They “sixty-nined” before she started begging him to fuck her hard. It was an extra-intense missionary fuck with Greg ramming into her as if he was trying to kill her.

Elaine loved it. She stiffened and shook through her third orgasm of the morning.

Her sudden cunt-clamp on Greg’s shaft brought him home. He pulled out and went up her body in a jolt, getting her once between the eyes before almost gagging and drowning her in his second cum of the morning.

“That was nasty,” Elaine said, smiling while scooping the string of white gel from her forehead and casually sucking her finger. “That little dirty talk really got you worked up.”

Throughout the week in Jamaica, Elaine and Greg teased each other. One would point out a man, black or white, and say, “What about him?” They even engaged in some playful role-playing, imagining Jonny, their regular waiter at the resort, in bed with them.

The Jamaican weed, rum cocktails, and freedom from parenting, along with the couple’s teasing about sharing Elaine, led to the best sex of their lives, but nothing more. Elaine never took the sharing thing seriously. They returned home without taking any man into their bed. However, Greg’s talk of Elaine becoming a hot wife did not stop. It was becoming an issue.

Elaine found the bantering to be fun for a while. Sometimes after intercourse she would stroke and suck his expired cock while telling him things like, “Maybe it would be nice to have another man fuck me while I sucked you back to full missile alert.” It never failed to get his missile ready for a second round and often a third.

At the same time, Elaine remained a deeply romantic woman who loved Greg almost as much as life itself. She had absolutely no desire to give herself to anyone else, even if it was just physical. She also never again wanted to give Greg an excuse to have sex with other women.

She knew from their early days together in college, when their sexual wildness led them to play and swap partners with some close friends, that she didn't care for it. Not only did it get emotionally messy at times, but after the initial excitement of swapping, she would always rather have been having sex with the guy she loved.

Eventually, she grew tired of their role play always taking on the hot-wife or cuckold theme. 

One day at work, while creating super-realistic AI images for an advertising layout using the dazzling new AI program, Elaine came up with an idea to address the issue of Greg’s desire to share her. 

That evening, Greg again brought up the subject of sharing her. Elaine responded, allowing her exasperation to show. “The only way I would agree to it is if I could go out on my own and find a stranger to have sex with. If the man consents, I’ll send you photos and describe every lurid detail.”

Greg sat up immediately. “You mean you'd do it?”

“I really don't know why you are so intent on me sleeping with another man, but if I'm gonna do it, that's the only way.” 

Greg sat silent for a long moment. “The guy would have to know you’re married and being shared, and consent to pictures for me or no deal.”

Elaine nodded. “Maybe I'd take a weekend alone down at the MGM casino hotel in Springfield, where no one would know me.”

Greg was excited. “Better yet, you can drive to Boston and stay at the Encore casino!”

“Those rooms are really expensive, aren’t they?”

“Don't care. When do you want to go? I'll book it right now. Then I am going to fuck you to within an inch of your life.”

Incredibly, Greg was able to get her a room at the Encore for Friday and Saturday night, Halloween. Three weeks away. Putting his hand over the phone, he asked, “Is that okay?”

“No! No way! I'm not missing Halloween with the kids!”

Greg stayed on the phone and secured a reservation for Elaine the following weekend.

“Okay, I’ll make sure my parents will take the kids.”

She lifted her nightshirt over her head, pulled the covers back, shook her hair loose, gave Greg’s excited shaft a little lick and suck, then a great titty fuck before straddling and sliding down on him, the whole time wondering if four weeks, one busy month, was enough to execute her plan.

Elaine began going into the office early, telling her boss and co-workers that she really wanted to discover the full potential of the new AI program. She started a private project and began feeding it typewritten information.  She instructed the program to search every photograph of the Encore casino, its restaurants, bars, lobbies, everything, including the rooms and suites with both daytime and nighttime views of Boston Harbor.

One morning, instead of going to work early, she tacked a white sheet to the wall of their bedroom.  She draped it over the headboard, so her bed and wall formed a white background. After placing her phone in the bracket she bought the day before, she used the timer feature to photograph her naked body in every position and from every angle she could imagine. She worked quickly, moving from standing and dancing in front of the bed, to sitting on the bed, to kneeling on the bed, to lying on the bed. Then she put on the deep magenta cocktail dress she would wear and took a few more photos so the program could replicate her dress.

During her lunch break at work, she loaded all the nude images into the private project.

The next day she scrolled through some headshots of male models from an agency the company uses for live shots, and selected three somewhat similar men for the program to amalgamate into her potential AI lover.

A few days later, she generated the first image of her with her “man”. It was a casual picture taken by a third party of “her” with her handsome fictitious lover’s arm around her waist. The realistic accuracy of the image was impressive even in the first version. By the fifth rendering, it was perfect.

The second picture she fashioned was a selfie set in an Encore hotel room. Her torso is naked, and her right arm is extended to hold the phone out. She smiles at the camera as the man kisses her cheek,  with his hand cupping her right breast.

The third is a POV shot of her face, her wide, gorgeous eyes looking up at the camera with the tip of a large, thick cock helmet just breaking the seal of her smiling lips.

By the end of the third week, Elaine had generated three short videos of her getting fucked missionary, doggie, and cowgirl. It took a good number of iterations, but Elaine was particularly proud of the frenzied, inescapable orgasm her finely pixelated body experienced at the relentless doggie pounding of her amalgamated lover.

She watched and rewatched the videos critically, tweaking them after each viewing. She fabricated herself rising to such extreme heights of ecstasy in the control of her handsome lover that she worried she might have gone too far. 

She tweaked the cowgirl video, to have it open with her riding his face to one orgasm before she began pogoing herself to another on his magnificent spire. Then she tweaked it again to amp up the voracity of their combined explosions. She knew it would excite Greg; hell, it even excited her!

The program quickly became so easy to use that Elaine was even able to create fabulous Halloween costumes for the kids and a great ‘Old Crone” costume for herself. She and the kids worked together assembling them in the evenings. They were a hit at school and touring the neighborhood on trick-or-treat night.

On Monday, Elaine arranged for that Friday off. She planned to go to the Encore that long weekend and just take advantage of time off and the luxuries on offer. She planned to even find time to go into Boston and shop.

Elaine continued arriving early at work to play with the video program in the days leading up to her big weekend. During the day, she was producing fabulous, eye-catching advertising photos for the layout department, but before anyone else arrived, she was entertaining herself by making some of the naughtiest pictures and videos imaginable. She even made one of her being gang-banged by her fantasy lover and three other well-hung men.

The anticipation of Elaine’s foray into becoming a hot wife kept Greg constantly hard and eager for sex until Elaine cut him off the Tuesday after Halloween.

Greg’s excitement remained undeterred. He insisted on taking Elaine to their favorite restaurant on Thursday evening, where he presented her with a brand-new, sexy clubbing dress.

When she opened the wrapped box and lifted the dress, she was mortified. The short, backless, silver lamé dress was sexier than anything she would feel comfortable wearing. More importantly, the pictures she generated with her magenta dress would need to be redone.

“You want me to wear this?”

“You don’t like it?”

“I could wear my magenta dress that you like and just put a ‘fuck me’ sign on my back.”

“That is kind of the point of this weekend, isn’t it?”

“But…”

“I want you to look intimidating, so only the most confident men approach you.”

“So, rich assholes.”

“No, sexually confident.”

“So, hung assholes.”

Back at home, Greg had her try on the short silver dress.

“You look Marvelous!”

“Yeah, yeah…actually, it does fit nicely,” turning this way and that in front of the mirror.

“You are still the sexiest woman I know.”

“Well, you are the sexiest man I have ever known. I still don't know why you want me to do this.”

“Because I think it will uncover the untapped sexuality in you.”

“Oh, I think you have already thoroughly plumbed the depths of my sexuality. Anyway, I do like it. Thank you. Not so sure I’ll have the nerve to wear it, but I’ll take it along. 

“Please wear it. You look beautiful and classy and hot in it. Now take it off.”

“I will, but you don’t get to touch me until Sunday night, when I get back.”

“Oh, come on, the kids are already at your parents’.”

“Okay, BJ only.”

As soon as Greg left for work the next morning, Elaine put on the dress and took a selfie and another six photos to feed into her little AI project before anyone else arrived at the office. She had arranged for Friday off and didn’t want others to find her there.

Incredibly, within twenty minutes after arriving at the office, she had the new AI-generated photos of herself wearing the silver dress on her phone. With twenty minutes to spare before anyone else showed up, Elaine was locking the office and heading to Boston.

If anything could end Greg’s foolish desire for her to fuck other guys, Elaine thought, the AI videos surely would. If they proved too much for him, or if the whole weekend overwhelmed him, like Elaine hoped it would, she could show him that the entire AI charade was made up.

On the downside, if Greg enjoyed the pictures and videos and it fed his appetite for more, she would still probably confess that it was all AI and that if would be as close to her being with another man as she would ever get. She would just put her foot down, and he could never ask her again.

Casually scrolling through over a hundred TV channels, Elaine reclined into a pile of pillows propped on the king bed in her room at the Encore. It was only 3:30 in the afternoon, but she was under the covers in her panties and T-shirt. She was going to enjoy her downtime and order room service.

Then Greg called, FaceTime. “What are you doing in bed?”

“Relaxing,” Elaine lied. “I'm just about to take a shower and put on my makeup before I slip into that gracefully slutty dress you got me.”  “Oh,” Elaine said with a sexy smile, “and I’ll try not to lose that five hundred dollars you slipped into my suitcase at blackjack tables.”

“I figured if you're gambling, no one will think you're a hooker. So have fun!”

“So thoughtful. That’s why I love you. Maybe you should have thought of that before you bought the dress. Love ya’ Bye.”

“I love you too. Have a good night.”

“Oh well,” Elaine thought to herself after ending the call, “I’ll put on the slutty dress and go play some blackjack.”

The table was cold. Ten minutes after sitting down at a busy blackjack table, Elaine already lost a hundred bucks. Three of the other players left. One man remained at the far end of the table, to her right.

They each slid a chip forward. The dealer dealt the cards face up. Elaine had two eights. She split them and drew a six. She glanced at the man. His lips were pursed. She scratched for another and again drew a six and a four. The man smiled. The other eight was topped by a Queen. The man smiled, then held on a seventeen.  Expecting to lose again, Elaine was about to move off the stool when the dealer busted. She settled back down.

Forty minutes later, Elaine finally did slide off the stool, up three hundred dollars.

“Have you ever played craps?”

The man from the blackjack table was behind her. He hadn’t said much while they were playing, but enough for Elaine to know it was him. When she abruptly turned, he almost bumped into her.

“Oh, sorry.”

“It’s okay, my fault,” Elaine said. He backed up a step, giving her space. She replied, “No, never have. I don’t know a thing about it.” 

“It’s more playful than blackjack, more exciting.”

“My husband says you can lose money pretty fast.” Elaine wanted to make a statement that she was married.

“He’s right, especially when you don’t really understand the game. It goes the other way too. I’ve lost big, but I’ve won big too. Luck seems to play a bigger role.”

“I guess that’s what makes it exciting.”

“Yeah, I guess. You seemed to bring luck to both of us at the table there, so I was wondering if you would want to join me in tossing some dice?”

Elaine looked up at the man, an inch or two taller than Greg, leaner, more like a swimmer than a linebacker like Greg. In an instant, it occurred to her that while he didn’t really look like her AI guy, the same instructions she gave the program, could have produced him. It made her smile involuntarily.

“Is that a yes?” The man said.

She nodded slightly, and when the man offered his arm, she took it. “Steve.”

“Elaine.”

It sounded like a party as they approached the busy craps table. The party quieted as the crowd parted to make space. Even though Steve was maybe six or seven years older than Elaine, he was still younger than the others, whom she guessed were in their fifties.

“I’m Steve, and this is Elaine, and she is something of a good luck charm.” He put his arm around Elaine's shoulder possessively. “At least she’s been for as long as I’ve known her.” His confidence was impressive.

As if in a roll call, each of the others stated their names, and before long the party was back in full swing. One woman complimented Elaine’s dress. The men nodded their agreement.

A cocktail waitress came by and took drink orders. Steve ordered a Scotch and Elaine requested champagne.

At one point, after taking a turn at throwing the dice, Steve caught one of the men putting his hand on the base of Elaine’s back, right where the scoop of the bareback dress met the crest of her ass. Elaine reflexively pulled forward, pushing into the table.

Steve leaned closer to the man and said just loud enough for the man and Elaine to hear, “You can look, but you can’t touch.”

The man pulled his hand up and held it there for a moment as a gesture of compliance.

Steve remained a complete gentleman. Other than when he put his arm around Elaine’s shoulder during the introductions, Steve never actually touched Elaine.

They had pooled their chips together and placed bets as a couple, with Steve directing. At first, in the first half hour, their small stack of chips was reduced by half.

Then the table turned. In another half hour, their chip stack was back to where they started. An hour later, the stack had already tripled. It was not even quite seven o’clock.

Because they were having so much fun, it didn’t seem that long to either Steve or Elaine, but at nine-thirty, after two unlucky rounds of bets, Steve finally said: “We’re out, time for dinner.”

The dealer changed out their chips for fewer chips of higher denomination.

They had exactly nine thousand dollars. Before arriving at the cashier cage, Steve insisted they had both started with the same amount, even though Elaine thought she had only half as much when they pooled their chips. He directed the cashier to count out two equal stacks, nine five-hundred-dollar bills each. He handed one of the stacks to Elaine. “Thank you,” she said as she folded it and put it into her tiny clutch.

“Dinner at the overpriced steakhouse?”

“Gladly, I’m starved, but Dutch.”

After ordering, Steve finally asked the obvious question, “So what brings a beautiful woman to the Encore all by herself?”

“You first.”

Steve told her he was scheduled to be on a plane home to San Francisco by then, but skunked on a business deal that failed to close before the day ended. So he thought it might be fun to spend the weekend at the Encore.

Elaine pointed to his hand. “You have a wedding ring, any kids?”

“Two boys, fourteen and twelve.”

Giddy from the excitement and the champagne, Elaine told Steve her whole story.

“How disappointing,” Steve said when she finished.

“You were expecting sex?”

With a smile and a slight nod, Steve said, “I have been enjoying your company.”

There was a brief, silent pause as the two looked at each other. Genuinely flattered, Elaine shyly hid a smile. Steve failed to hide a mischievous one.

“Can I see the AI images you created?”

“NO!” Elaine blurted too loudly for the quiet restaurant.

“Might be helpful to ensure they are convincing.”

Another silent pause hung between them.

“Then again, I guess it doesn’t matter; being deceitful is the problem,” Steve said.

“I just want to give Greg what he wants.”

“But you’re not, not really; you’re deceiving him.”

“For his own good. I figure once he sees my AI pics of me with another man, he will get jealous and stop bothering me about it. Besides, you’re the one here willing to cheat on your wife.”

“We both travel for our jobs; we have an open agreement. We don’t go looking for it, but if opportunity presents itself…let’s just say we’re not bound to confess, but if we do, it’s all cool.”

They sat in another silence for a while before Steve continued. “You might be confused about what Greg really wants, what he really needs. When he says he wants to share you. I’m pretty sure it’s more for him than you. He’s proud of you. The few times I’ve seen my wife with another man, it excited the hell out of me.”

“You swapped or swung or whatever it’s called?”

“In our early days together, before kids.”

Elaine remained silent; she wasn’t about to confess about her and Greg in college. 

“He picked out that dress, didn’t he?”

Elaine remained quiet. She actually felt what Steve was saying about Greg’s desire Qwas true; she just had never wanted to accept it. Oddly, the realization made her feel sexier than ever.

“Yes. He actually bought it for me, surprised me with it last night.”

When the waiter asked about dessert, Elaine realized she hadn’t even noticed the dinner plates were already cleared.

Uncharacteristically, she ordered a Crème Brûlée and a coffee. So did Steve. Elaine rarely has dessert, but she wasn’t ready for the evening to end.

Besides, she liked Steve, and by now, if it weren’t for being married, she would already be in his room taking his cock down her throat.

Steve took her hand in his and, as if beginning goodbyes, told her how much he enjoyed spending the evening with her. He gently caressed the back of her hand, his thumb sliding between the knuckles of her index and middle fingers as the tone in his voice deepened.

“There is one scene that I can’t stop imagining ever since you told me about your AI tryst videos.”

Elaine tried to pull back on her hand, but it went nowhere as Steve tightened his grip. He brought his other hand up to her forearm. She relaxed, and Steve’s thumb continued softly over the mounds and clefts of her knuckles.

“The scene would open with a frame-filling close-up of the silver material of your dress as you prop up your phone while it’s recording.

“When you back away, it becomes apparent the phone is aimed squarely at your center, but you turn and take another step away, and your beautiful round ass undulates in a final step towards the bed.”

The gentle movement of Steve’s thumb on the back of her hand, the subtle glide of his fingers along her arm, and the calming depth of his voice drew her into the scene.

“Standing at the bed, your full height fills the frame. Do you realize how stunning you look in that dress, how your bare back is a sight in and of itself?

“A man’s voice is recorded, but the words are unclear. You respond by peeling one side of the dress off your shoulder, then the other, and work the form-fitting material down until it is a silver puddle at your feet. No panties. You step one stiletto from it, then the other, and kick it to the side.

“Another step towards the bed and a man’s arms encircle you. You remain still for a moment as he palms your butt cheeks, before you lift one heeled foot onto the edge of the bed, revealing the top of a dark-haired man’s head between your legs. The man repositions his arm to stroke the soft flesh of your raised thigh.”

Steve separated Elaine’s middle finger from her index and ran his thumb along the side of it.

“Another inaudible murmur from the man is recorded. You lower your raised foot and turn your naked young body full frontal towards the camera. The tall confident stance of your perfect body is breathtaking. You lean back, and the top of the man’s head reappears between your thighs as you widen your stance and bow your knees outward to settle onto the man’s face.”

“Steve, stop!” Elaine said as she jerked her hand away into her lap. “Please stop.”

Steve watched her flushed face intently, awash in the radiance of her eyes, the impossibly brilliant shimmer of her hair in the low restaurant light, and the silent scream of her subtly heaving chest.

Elaine brought her hand back onto the table, then the other.  She lowered her eyes as she took hold of his hands. When she again lifted her face towards his, she half-whispered, “Your room or mine?”