Huge thanks to Litero volunteer editor 'neuroparenthetical' for taking the time and effort to edit this final installment.
Please check the tags before reading: if cuckold stories aren't your thing, feel free to find another story.
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The following morning, Andy quietly packed his bag while his wife slept in. Before leaving, he leaned down to give her a kiss, but she remained fast asleep -- or at least appeared to to him. He watched her for several moments, feeling even more miserable about what he'd done the previous night: she must be so confused, he thought. With a sigh, he finally left their bedroom, headed downstairs, and went to work, dreading not seeing her again until Sunday night.
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-- 7pm at the Emerald Room --
Andy's heart pounded in his chest as he read Jenna's text. It was almost 5:30pm and he had begun to worry that she'd changed her mind.
The Emerald Room was a posh restaurant on the top floor of a twelve-story building, known for its rooftop dining and lounge area. Andy had only been there once before, and that had been for a work function. It wasn't the kind of place he'd typically go to -- the prices were in sharp contrast to its portion sizes -- but he had to admit it was very elegant and had an incredible view.
-- OK, he typed back.
He took his overnight bag to the staff bathroom and cleaned up a bit. He thought about changing, but decided against it, as he was already wearing one of his nicer button up shirts. He took a deep breath and looked at himself in the mirror one last time, feeling more nervous than he'd felt in a long time. Releasing a sigh, he turned and headed to his car.
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When he entered the restaurant, the hostess asked if he had a reservation. Andy suddenly realized he didn't know, but as he scanned the tables behind her he saw Jenna sitting at the bar.
"Right on time," she said, smiling as he approached her.
Her dress was both stylish and revealing, showing off her toned arms and ample cleavage. Her tattoos were visible, snaking up from her shoulders and disappearing into her neckline. Andy thought the contrast of her chic dress and her tattooed skin was incredibly hot, making her seem both mysterious and confident in such an upscale environment.
Jenna pulled him in and gave him a kiss on the cheek and a quick hug before sitting back down at the bar. "Our table should be ready soon." She signaled the bartender. "Let's get you a drink, shall we?"
"I'll have a glass of your cabernet," Andy said. "Anything California, please."
The bartender nodded and poured a generous glass of wine before sliding it over. Andy took a sip, savoring the taste, nervous about the evening ahead.
"Good day at work?" Jenna asked.
Andy found it strange to be sitting with Jenna telling her about his day, like they were friends or a couple. "Uh, yeah, I guess it was good."
When the hostess arrived to lead them to their table, Jenna slid from her bar stool and took Andy's hand, guiding him to their spot at the far corner of the outdoor patio.
The sun was setting, casting a warm glow over the city skyline as they settled into their plush dining chairs. Andy marvelled at the way the evening light shone on Jenna's tattooed arms, and couldn't help but stare at the intricate mix of dark and coloured ink that adorned her silky skin.
He wasn't sure what he'd expected from their dinner, but he was surprised at how much he was enjoying their conversation. He was careful not to bring up everything that had gone on the past few weeks, deciding there would be time for that later. For the moment, he wanted simply to enjoy their evening together and let Jenna take the lead.
When they finally finished their meal, the waiter poured the remaining wine from the bottle into Jenna's glass and set the bill on the table.
"So, Andy," Jenna said, smiling widely as she leaned back in her chair. "Have you been good this week? Did you do everything I asked?"
Andy's heart fluttered. "Yes. It wasn't easy, but I followed your instructions."
"Good boy," she said, patting his knee. "So tell me, how did it go when you told Abbie that you've fantasized about her being with other men? Wait, let me guess: I'll bet she was excited about it, wasn't she?"
"Well, maybe," he said, rubbing his chin nervously. "Yes, I guess so. I mean, I could tell it really caught her off guard -- but then she brought it up again later in bed."
"Ahhh, interesting," she said. "So what happened?"
Andy shifted uncomfortably in his seat. "Well, nothing actually. She was rubbing my -- well, rubbing me, and I was really, you know, ready, but then I told her we had to stop -- that I was too tired."
Jenna's expression was a mix of surprise and amusement. "Right, because no sex, like we agreed. And did she seem upset?"
"Well, yeah," Andy said, scratching the back of his neck. "Quite upset, actually and then a couple of nights later the subject came up again, and she was really getting into it, asking me more about my wanting to see her with another man.... and, well, it kind of happened again. She got me really worked up and offered to... you know... go down on me. And I told her I had to get up early -- that I couldn't have sex." Andy's face was bright red. He finished his last swallow of wine, feeling Jenna's eyes on him.
"Oh, wow," she said. Her lips spread into a sly smile, and she started running her finger around the rim of her wine glass. "So tell me if I got this right: you asked her to sleep with another guy. She quickly got turned on by the idea and tried to have sex with you... and then you rejected her -- not once, but twice."
Andy sat up straight, visibly frustrated. "Now, wait a minute. I didn't ask her to sleep with another man. I just said... well, I'm pretty sure I just said I've imagined it -- you know, the idea of it -- not that I definitely wanted her to."
"I see," Jenna replied, "and you're sure that's how she understood it? I mean, you were there. I guess you'd know better than I would -- you know, that you were very clear that it was just a fantasy, and you'd never ever want her to be with someone else. Right?"
Despite the cooling night air, Andy felt a bead of sweat forming on his brow as his mind raced to remember exactly how the conversations had gone with Abbie the previous week. He was sure... well almost sure, that he didn't say he wanted it -- just that the idea of it was a turn-on. Thinking back, he'd been so nervous he couldn't remember exactly how he had phrased it. He did however, remember how quickly she had seemed to recover from her surprise -- how she'd seemed almost excited by his admission.
Andy looked over at Jenna, who was typing something on her phone, as if she'd completely lost interest in their conversation. He stared at her for several seconds before she finally looked up at him. "Oh, sorry," she said, tossing her phone into her purse. "I didn't mean to be rude. Anyhow, I'm sure it all went as you said it did. I'm sure she understood what you meant. And thank you for keeping your end of the bargain." She stood up from the table and reached for his hand. "I need a cigarette. Are you ready to go?"
After paying the bill, they made their way to the elevator and when the doors closed, Jenna leaned back against the mirrored wall, hands on the railing behind her waist. The seductive way she looked at Andy made his knees weak. Fuck, she's sexy.
"Come here," she said, head tilted slightly and biting her bottom lip.
Andy took a step forward, standing directly in front of her. The smell of her perfume was heavenly, and his cock began to stiffen.
"Kiss me," she said.
He only hesitated for a moment before he leaned into her and pressed his lips to hers. The kiss was soft, their mouths opening slightly at times, but with very little tongue. Jenna didn't even put her arms around him, just held tight to the railing behind her.
"That was nice," she said as he stepped back away from her again. As the elevator door opened, Jenna locked her arm through his and they crossed the lobby floor and stepped outside. She led him down the sidewalk and around a corner into the parking lot.  "I'm just over here. We can take my car."
When they reached her car, Jenna fished her cigarette pack from her purse. Andy stood a foot or two away, anxiety building in his chest as he watched her light the tip, inhale, and exhale a cloud of smoke up into the air. She took another slow drag, her eyes never leaving Andy's, but said nothing.
He shifted nervously as he watched her smoke in silence, as if putting on a show for him. His cock was rock hard, protruding almost painfully against his pants. He glanced down at Jenna's barely hidden cleavage and swallowed hard. He saw her raise her cigarette again, and his gaze quickly shifted back to her face, entranced by how sexy she looked when she smoked.
He finally broke the silence. "Umm, so what are we doing now?"
Jenna took one last drag, her cheeks hollowing deeply, before dropping her cigarette to the ground and grinding it out with her shoe. She moved into Andy, her breasts pressing hard against his chest. She slowly exhaled the stream of smoke from the corner of her mouth, her eyes still fixed on his.
Andy couldn't stop himself. He grabbed her hips and leaned down, kissing her soft lips, his tongue exploring her smoky mouth while he pushed her body against the cold metal exterior of the car.
Jenna moaned softly as they kissed before pulling finally away from him, a mischievous grin playing at her lips. She reached up and ran her finger down the bridge of his nose. "So cute," she said, as an adult might compliment an adorable child. She walked around to the driver's door, leaving Andy standing there with a raging hard on and feeling a touch of humiliation. Finally, he reached for the door and slid in beside her.
They were quiet for the entire drive, with just the faint music from the radio playing in the background. Andy glanced at the clock on the dashboard and noted it was just after 9pm. He wondered at first where she was taking him, assuming they would be pulling into a hotel parking lot soon, before he eventually realized they were exiting the downtown area. Minutes later, Andy began to recognize their surroundings, but stayed silent right up until they pulled into Jenna and Dean's driveway. Wait, what? She wants me to stay here? Right next door to my wife?
"Shit," he muttered, looking into her backseat. "I left my overnight bag in my car back at the restaurant."
Jenna patted him on the knee before opening her door. "Not to worry. We will figure something out."
