Working Vacation Pt. 01

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Rebecca poses as Greg's girlfriend at a work retreat, but...
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This has a slow build-up, and is concluded in a second part. This is the first of several (non-linear) exploits by the same heroine, so some amount of extra detail is included. Feedback welcome.

*

It was late Monday afternoon, and Rebecca and Amy were sitting near the window at one of their usual places—an upscale tavern specializing in import beer and thin-crust pizza—and talking about life. Amy emptied the last of the pitcher into Rebecca's glass.

That was unusual. Amy always wanted the last beer—unless she wanted something else.

Rebecca brushed a strand of her dark hair over her ear and took a drink. "Come on," she prodded. "Spit it out."

Amy twisted her lips, hesitated a moment, then said, "Greg called."

"That's..." Rebecca paused. "That's weird, isn't it? What did he want?"

Amy shook her head. "It's not that weird. We've been hanging out."

Rebecca shot her a look.

"Fine, we've been fucking."

"Amy—!" Rebecca sat up straight, looking around at anyone in earshot.

"Come on, Becca, it definitely isn't 'making love.' And I know for a fact that you're not quite the good girl you—"

Rebecca's death glare stopped Amy in her tracks.

"Okay, fine. That's not even the point."

"Thank Heaven. A point."

"The point is," said Amy. She paused for a drink. "I kind of promised I'd help Greg at work, and now I don't want to do it. He's, like, really mad at me right now."

"What was the promise?"

"It's this work retreat. Long weekend, drinks, socializing, dancing, going out. It's at some resort hotel place. The whole thing's paid for."

Rebecca sat back and rolled her eyes. "You're right, how unfair of him," she said. "That doesn't sound like something you would promise to do at all."

"Well, obviously, yeah," Amy shrugged. "But...there's this dance workshop this weekend. I paid like, two hundred bucks." She paused. "Non-refundable."

Rebecca's eyes got big. "You paid that much for a dance workshop? ...All right, fine, I support your insane choices, whatever. Why didn't you just tell Greg you had this other thing?"

"Because," Amy winced, "I kind of booked it after I told Greg I'd go with him? Like, the next day?"

"Amy, what the f—" Rebecca stopped herself. She almost never swore. "So, Greg goes alone."

"That's kind of the problem. Only spouses are paid for. Greg had to convince his boss to make an exception."

"Why does he want you to go in the first place?"

"Greg's boss is moving to a new department, and there are only a few other guys who can take over. Greg's one of them...but the company doesn't promote singles. I mean, Greg says they will," Amy emphasized, and then she shook her head. "But the founder hates it. Like, enjoy-it-while-it-lasts, hates it."

"Greg's up for promotion," Rebecca repeated, "And you promised to help him by making him look like he's in a committed relationship. Except now, you're planning to stand him up and waste company money." Rebecca sighed. "Look, you shouldn't have paid for the workshop, but if you want to help Greg, it's just a sunk cost."

"Please, Becca," Amy interrupted. "Don't do sunk cost right now. I know economics is kind of your thing or whatever—"

"My thing?" Rebecca sat back in her chair and folded her arms across her chest. "I'm just trying to help."

"I know. Sweetheart, I know you are, and I'm so glad you are," Amy said. She put her hand out to touch Rebecca's sleeve. "Really..." She looked around, hesitating, then continued in a lower voice. "I really have my heart set on this workshop."

Rebecca unlaced her arms to take another drink of beer. "Then what," she hissed, "were you thinking?"

"I didn't think I wouldn't actually have to go through with it," Amy said.

"This, from the woman who broke up with him after she—" Rebecca lowered her voice to a sharp whisper. "—after she convinced him to try a threesome with another couple."

"First off," Amy snapped, whispering frantically, "that isn't what a threesome is. Second, it was awesome and that isn't why we broke up."

Rebecca pursed her lips.

"Look, Greg's a good guy," Amy continued, "He just needs someone to make him look good. And you—economics or whatever, all that shit—that's totally your thing. And look at you—"

"Where is this going?" asked Rebecca. A knot in her stomach made her feel like she already knew.

"Seriously, look at you," Amy insisted. "Twenty-three, professional, ready to graduate...never goes out on weekends..."

Rebecca clenched her teeth. "I work six days a week."

Amy soldiered on. "Now, I can try to look good..." Her modesty was undeserved; she was adorable, half-Asian with straight black hair, fair skin and beautiful chestnut eyes. She got hit on almost constantly. "But you can make Greg look good. Smart, savvy, sexy, head full of business. These guys at his work—I've never even met any of them. They won't know the difference."

"I can't believe you're asking this," Rebecca said. Amy was getting enthusiastic. "Please, Amy, don't say it—"

"Come on, Becca. Please. Go with Greg and take my place so I can go to the workshop."

Rebecca shook her head. "I have to work. I don't think I can get anyone to cover for me."

"That's complete bullshit and you know it. I told Greg you'd say that."

"You told Greg?!"

"Yeah, he didn't think you'd do it either. But look." Amy pulled out her wallet, extracted six hundred-dollar bills and fanned them out in her hand. "He bet me. He said if I could get you to take off work, he'd throw in for your time."

Rebecca lifted her eyebrow and shook her head. "And if I won't, smart girl...?"

"Well I'm still going to the workshop," Amy replied. "He only bet me three hundred. If I lose, I give this to him instead of you."

Rebecca laughed. "You really don't get the idea of a sunk cost, do you?"

Amy smiled.

"...Okay. Fine. Get another pitcher and we'll talk about it."

Amy skipped off happily. Rebecca felt a fluttering of nerves she never got used to—the feeling she always got when Amy, self-appointed trouble-maker, had been up to something. Like the time Amy sneaked onto Rebecca's phone, opened up her FriendZone app and messaged Rebecca's number (and winky emoji) to a guy Rebecca liked—a guy who just happened to be dating one of Rebecca's coworkers.

Or, most recently, Amy had secretly set up a dating app for Rebecca, complete with a fake name and an embarassing picture, and flirted with two different guys. That ended with Amy forcing Rebecca to wear a particular dress and go out for drinks at a new bar...where they ran into one of them (the one Amy thought was better looking) 'by coincidence.'

That had been a very unusual week. Rebecca had only told Amy that she wasn't planning on seeing the guy again—not that she actually had slept with him. As far as Rebecca was concerned, Amy didn't need more encouragement.

Rebecca, in Amy's estimation, was too much of a good girl, too bookish, too conservative, and didn't take the right kind of risks. Adventures—like the year Rebecca had dropped out of college to build houses in South America—apparently didn't quite count, because she hadn't—in Amy's phrase—"sampled the local wildlife." Which, again, not true. She simply felt no need to let anyone else find out.

That was the thing that Amy didn't understand—it wasn't swearing that bothered Rebecca, and she definitely wasn't bothered by sex. She didn't care if people thought she was a prude or uptight. That was the whole point.

Rebecca smirked.I'm a classy fucking bitch, she thought.And I have nothing to prove.

She smoothed out her skirt, crossed her legs, and finished her beer. Amy was coming back with the second pitcher.

"So," Rebecca said, "I'm listening."

* * *

After a few hours on the road, Greg hadn't gotten much farther with Rebecca than some awkward small talk. Rebecca had done her homework and already knew most of the details about Greg's job and family; she even knew his birthday. He, on the other hand, let his shyness get the best of him. As he turned his black two-seater into the resort's driveway and stopped by the valet stand, he realized he didn't know anything about her.

He racked his brains, and all he could come up with was a few months ago, when Amy set her up on a few dates, and both of them went pretty badly. He didn't know why. It wasn't much of an anecdote.

It was painfully clear that they hadn't ever been in the same room together without Amy.

She smiled and waved at the valet, put her hand on the latch of the door. "Well," she said. "This is it."

"Yeah. I really appreciate you taking time out of—"

She interrupted him by leaning over and kissing his cheek. Her hand fell on the leg of his khaki golf shorts and she squeezed his thigh. "There," she announced. "No big deal. It's fine to talk to me like your girlfriend. Come on—it's going to be fun."

Rebecca took the valet ticket and checked them in at the front desk. Everything was taken care of. The clerk gave her a map of the company's group buy rooms and circled Greg's name and room number, then informed her the bell staff would be along with their luggage as soon as they could.

It wasn't until the keycard clicked the lock open that Greg remembered the room only had one bed.

"Oh my god," Rebecca said. "This place is gorgeous." Rebecca went around the room, inspecting the fixtures and amenities.

"I—forgot about the bed. Sorry."

"What about it?"

"There's only one."

"Ehh," she shrugged. "You can sleep on the couch."

Greg nodded dutifully, but only because he couldn't argue. The couch was more like a loveseat. It was just big enough that he could fit on it, technically, but even petite Rebecca wouldn't be able to really stretch out.

Rebecca laughed at the look on Greg's face. "Come on, Greg, it's king size. I'm sure we'll be able to share. No big deal."

"Really?"

Rebecca shrugged.

"Huh. Wow. I really am sorry, though. I guess when I booked the room, it was supposed to be me and Amy, and then—"

"Seriously, it's fine. We're supposed to be dating! And stop thinking about Amy so much."

"No, I appreciate it. Thanks for letting me drag you along." He couldn't stop himself from grimacing. "Her and I aren't...I don't know what we're doing. But I thought, if she came this weekend, we might—ah, I'm just stupid to even think that."

"Hey! Look, she's my friend, but she is a flighty bird. And she's not here for you. New rule: don't even talk about her. This weekend is just us."

"I feel dumb."

"Hey, don't talk like that. You're a great guy! You're my weekend boyfriend! Come on, I wouldn't have come on this trip if I didn't think we'd get along."

She fell sitting on the bed, her pleated skirt flouncing around her legs. "Let's change the subject. I was thinking we should try to make this a little less first-date-y. I have a plan."

"Let's hear it."

"That's not part of the plan. If we've been dating for—?"

"A year?"

"Exactly one year—no—yes. It's our anniversary. If we've been dating for a year—I forgot what I was saying. Anyway let's just go for it. Like trust exercises in theater class, except with a fake relationship and we've only got an hour. Rule one: casual. No big deal. No lovebirds stuff."

"Got it."

"But hold my hand, get me drinks, that stuff. Here, hold my hand."

They held hands and stared at each other for about ten seconds before they both started laughing.

"Ha, okay. Now touch my leg."

"What, like...?" Greg reticently put the back of his hand against her shin.

"No," she said, coyly. "You weren't very subtle in the car, staring at my legs the whole way. So—" Rebecca took his hand and, biting her lip, placed his hand up against her thigh. She hesitated for a second, then pulled his hand toward her inner thigh.

"We can't have you looking like you never touched my legs," she said.

"I should have stared at your boobs," Greg replied, and withdrew his hand.

"Ha!" she laughed, and pushed him away. "Okay. Now, um...fantasies."

"I don't know."

"Just name something you'd be a little embarrassed to tell anyone. Then we'll have secrets. It's better than looking like two strangers who accidentally got into the same car."

"Why not just regular secrets?"

"Because I don't want to hear some story about something you feel bad about. Something a little spicy. Pick something."

"True?"

"Of course."

"Well...I'm kind of—I'm kind of curious about polyamory. I think it's interesting."

"What's that?"

"Like when you have a relationship where the people are honest about also dating other people. Like loving many people."

"So, swinging."

"It's not supposed to be. I think swinging is more like casual hookups, but this is supposed to be more—I don't know. Less random."

"I don't think I could do that," said Rebecca. "That's like this blonde girl at my work, Hannah. She's dating this guy I used to like and I'm pretty sure she cheats on him almost constantly. What do you like about it?"

"I dunno. Flirting is fun. I like the idea of not always going out to eat with the same person. A little variety, you know, in bed. What about you?"

"Monogamy," she sighed. "It gets me soooo hot."

"Hey!"

Rebecca laughed.

"Come on, I told you."

"No," she laughed. "I don't want to give you any ideas."

"Oh, man! Come on!—Just a hint. Just give me a hint."

"Okay," Rebecca relented. "A one-word hint. Let me think. Hm. Alright, ready? The word is: s—"

There was a knock at the door, followed by a voice in the hallway: "Luggage is here, sir."

Greg groaned in agony. After that, even though he begged and begged, Rebecca kept laughing and insisting the word was 'suitcase.'

* * *

The roar of the blow-dryer had been going on inside the bathroom for long enough to make Greg nervous about being late to dinner. He sat on the tiny leather couch and rehearsed his elevator speech with some bullet points on a notepad.

At last the noise stopped and was replaced with a silence so complete, he pulled on his suit trousers and shoved the crib sheet in his jacket. Then he paced for five minutes.

"Ready when she's ready," he muttered to himself. "Everything she's doing in there is a favor for me. Keep it together, Greggsy. Don't even have to be there for—"

He checked his watch. It was still an hour before dinner.

"Hey, Greg?" she called through the bathroom door.

"No rush!" he yelped back.

"Uh, okay," she said. "Come in here a second."

Greg pushed the bathroom door open a crack, and asked, "May I come in?"

He saw just her face reflected in the mirror—she was gorgeous. Her chestnut brown hair was arrayed in bangs with longer locks sweeping down her cheeks; in back, she'd pulled it back into an elegant tress that revealed her neck and shoulders. Greg was surprised she'd managed the look so quickly.

Rebecca smirked at him in the mirror and nodded, then turned back to her lips with a cosmetic pencil. Her eyes were glittering, enhanced by wisps of smoky black.

Greg pushed open the door slowly and went in. She'd pulled on a tight, cherry red quarter-sleeve minidress with a subtle and elegant pattern that drew the eye along her hips and shoulders. It was hitched together in the back, but the zip was open down to the small of Rebecca's back. A thin, lacy band of black lingerie interrupted the curve of her spine, just below her shoulder blades.

"Would you mind?" Rebecca asked, concentrating on the mirror. "This is why I can never wear this silly thing."

Greg took the tiny zipper pull between his finger and thumb and lifted, but all he accomplished was hitching up the hem of her skirt about a centimeter.

Rebecca paused to look at Greg's reflection. "Is it stuck?" A glint of gold caught his eye at her ear.

Greg shook his head, and braced her hip with his palm. Pressing his thumb against the base of her spine, he tried again, and the zipper eased upward to the clasp at the eminently kissable nape of her neck.

Rebecca stepped into two glossy black pumps. Though still petite, she stood a few inches higher, with her back curved sensually, and her feet arched, flexing her slim, shapely calves and well-toned thighs. This was the most beautiful woman he'd ever spent an evening with.

"Do I look okay?"

"Yeah," said Greg. "Totally."

* * *

In the lounge area, the owner—called Chuck, behind his back—had his hand on Rebecca's shoulder, patting her with paternal approval. In his other hand he had what could not have been his first scotch. "That's fine, that's just fine," he said.

The three of them stood in a triangle, with Greg frozen in horror at the far end while Chuck asked her how many children she was planning on. At one point, Chuck also joked about whether Greg needed the promotion because Rebecca wanted an even bigger wedding.

Chuck derailed Rebecca's conversational diversion toward at least one of her two majors. "A fine mind is a great help, and in the end it all comes down to the M-R-S. Family!" he snorted.

"Family, I couldn't agree more," smiled Rebecca. "That's why we're here."

The tautology struck Chuck as deeply profound. "All that and pretty face, too," he smiled. He patted her shoulder a few more times. "That's fine, that's fine. Why don't you run along and see if you can find someone to get you a spritzer, while Greg and I talk a little shop."

Rebecca giggled when Chuck kissed the back of her hand. She pecked Greg on the cheek and squeezed his arm to encourage him—and wish him luck. Then she turned, gave Chuck a beaming, hate-filled smile, and pranced away.

* * *

Rebecca stood alone, gazing out the window and absently swirling the second act of a double martini in a crystal cocktail glass. She had managed to order a drink from the bar by herself.

Dinner should have started already, but no one told the men in the most expensive suits. As keenly as she wanted to, she resisted talking to anyone. Anything she said would have to be about Greg.

After this, he'd owe her more than just a few introductions. It could wait.

She scanned the room to check on her date, hoping to get an ETA on some dinner rolls. Chuck had led him off somewhere. In Chuck's place stood a tall, lean blond in a gray suit with a circle of laughing sycophants. A short, beefy man turned his head and walked off, rolling his eyes.

The blond slapped the suit next to him on the shoulder, and swept his arm (and his drink) outward in an open gesture, one that said: Am I great, or am I great?

He was definitely full of himself, but when his bright green eyes flicked up to catch hers, and he broke out in a grin—well, she couldn't really blame him for being so confident.

Rebecca turned back to the window. Her face was flushed. She could feel the heat in her cheeks, and hoped the dress would hide it a little. Wondering if the blond was watching her, she shifted her weight self-consciously and started counting to sixty.

She didn't make it past thirty before she felt footsteps coming up behind her and saw a ghost of the blond's reflection in the window. He planted himself beside her and said, "Hi. I'm Tyler."

"Hi, Tyler."

"Are you with the company, or—?" He didn't wait for an answer. "I'm in line for promotion."

"Good for you. Tyler."

"That's a gorgeous dress. It looks great on you..." He paused, let that thought land. "What was your name?"

She made him wait for a second, enjoying his direct approach. Then she turned and smiled back at him. "Rebecca."

"A gorgeous name. It matches your dress."

"Thanks," she said. She had no idea what he meant, and she guessed he didn't either. Standing this close to him, she could make out the light stubble on his chin—not quite shadow, since he was blond, but just enough to give him a trace of a rugged edge. "And no," continued Rebecca, "I'm not with the company."