Paid Vacation

Reader Advisory: This one might belong in Humor.

Tracy leaned halfway into my office doorway and made the phone call sign. Being on the other line, I waved her off. Like any good new employee, she flaunted her body at me while waiting for my call to end.

The flaunting wasn't intentional. Tracy was quiet and shy. She was also smart and responsible and great at her job. She had only one tiny problem, which was that she was way too hot for accounting. Behind her bookish, black-rimmed work glasses was a really pretty face with big grey-blue eyes like searchlights, and below that was... well, a walking orgasm. Her body was self-flaunting. It constantly screamed 'fuck me' at the top of its lungs.

I was so sure my clients would suspect she wasn't on staff for her numerical talents that I almost didn't hire her. Now, though, just a few months later, I was glad I had. She was extremely conscientious and eager to please. She'd warned me that she didn't want a lot of responsibility; she had just moved away from toxic parents who criticized her every decision, and she still felt traumatized. But she was perfect for me, because she would do anything I asked so fast and flawlessly that she became an essential employee in just a few months.

Unfortunately, she was still distracting. Her bulging blouses, her lithe, willowy frame, her sculpted legs and perfectly shaped ass were impossible to ignore. But I couldn't afford to annoy her, so I scrupulously avoided showing even a flicker of interest. My self-discipline was magnificent. I was pretty sure she wasn't the type to enjoy a good stalking by a green-eyeshade type anyway. She probably spent her weekends jetting to Formula 1 parties so that her bf du jour could show her off.

"Yes, George, the prize for your hole-in-one is taxable income," I told the phone. "Just report the value of the car. Retail, I'm afraid. Any golf balls you found are technically taxable income too, by the way, and before you ask, no, you can't deduct the ones you lost."

The whining continued. I noticed Tracy was still leaning in the doorway, arms folded and staring at me, which was both entertaining and disconcerting. Disconcerting because she seemed to do a lot of staring, which made me edgy. Entertaining because her folded arms were just barely able to frame her boobs, which filled the opening completely. Her boobs were sensational -- not oversized, but startling on her slender frame. For her, I suspected, they were an embarrassment of riches. Her tight little dresses were, shall we say, constantly bursting with promise, and some days you could see the contents jiggling vigorously as she marched through the office on her urgent missions. Try as she might, she just couldn't project the right image for an accounting firm. Maybe I should let her go. Some day. It wouldn't be easy. Besides the obvious, she'd been referred to me gratis by my friends and clients, Joe and Sasha. I'd have to pay a stiff headhunter fee to replace her.

"You have Joe and Sasha at six, boss," she warned as I finally I hung up. "Sasha says they'll meet you downstairs." She made her usual memorable exit, demurely smoothing her skirt over her nicely rounded posterior. The short margin of fabric that hung beneath flipped energetically as her spike heels hit the floor. Her clothes seemed to be getting more entertaining as she got comfortable with the job. I should talk to her about dress standards. Some day.

'Downstairs' meant the first floor bar. Joe was a good guy, if a little heavy on the cigars, aged scotch, and testosterone. Before he got serious with Sasha I was his occasional wingman. Now, apparently, Sasha was taking me under her wing, which seemed only fair. I'd forgotten she wanted me to meet someone tonight. I'd been contentedly unattached while starting my firm, but Sasha had leaned on me hard this time. She thought she had the perfect match.

They always think they have the perfect match. They never do. Maybe it's me. I'm not at my best meeting people for the express purpose of romance. It's awkward and cringy and the success rate is abysmal. Besides, smart, hot girls don't like accountants. But I had to appease Sasha. She was terrific -- not stacked like Tracy, of course, but a cute, redheaded little ball of fire. Joe had a wild ride ahead of him.

****

"Dave," said Sasha with a straight face, "this is Tracy. I believe you've met."

"We know you guys must be itching to get your hands on each other!" crowed Joe. He's in finance. Nothing embarrasses him.

Tracy kept her eyes glued to the table.

"You sandbagged me," I said to no one in particular as I reluctantly slid onto the last stool at the hightop.

"You needed an intervention!" opined Sasha. She was a lawyer and knew better than to date an employee, frankly. "You're made for each other!"

Oh, this was going to be epic. "Tracy," I said, "they must have sandbagged you, too. Sorry."

Sasha cackled, as usual. She leaned forward to wink obviously at me. "We called her 'Titsy' in high school!" she confided to the whole restaurant. Sasha was a commercial litigator and one of those persons who spits out every single thought in their head instantly and without remorse. She was fun, but unpredictable and exhausting and a destroyer of confidences. Joe had assured me she was equally uninhibited in bed, which seemed completely believable.

Tracy put both hands to her face and arched over backwards with a quiet, "Oh my god!" The motion boosted her big, high boobs and scrunched them together, which looked insanely hot. There was nothing the poor girl could do that wasn't ridiculously, orgasmically hot.

"I guess it's better than Ditzy," I said. "Pleased to meet you again, Tracy, after all these minutes." She finally gave me a wan smile.

"The difference," explained Joe, "is that 'Ditzy' would never stick."

Tracy blushed again and asked me to pardon her friends. She'd been meaning to get new ones.

I hadn't realized Sasha and Tracy were old buddies. That explained how they recruited her for me. I could see they had some similarities. Sasha was smart, bold, forceful and apparently hot in bed. Tracy was quiet and shy but smart, too, and, did I mention, hot out of bed.

The problem was that Sasha had somehow mistaken me for a ladies' man, and now I was in way over my head. There was no chance Tracy had any interest in me romantically. If I couldn't squelch this somehow, Tracy would have to squelch it for me, which would be humiliating roughly forever. Time to save face.

"Hey, look, Sasha," I said, "it's nice of you guys to do this but really, we can't date. I can't get into a relationship with an employee. For one thing, it's harassment! You know that! And what if I have to fire her? What if she wants to quit? What if she's really good at the job but we break up? Tracy, I bet you agree."

Tracy inspected her lap, or at least the unobstructed portion thereof. She must be relieved I'd saved her from having to turn down her boss.

"Sometimes Dave lets workplace ethics get in his way," Joe apologized to her.

"Aw, c'mon, Dave!' Sasha implored. "How can you resist? Just look at her!"

"Sasha, how do I make a business decision about her if we're in a relationship? I'm happy to have drinks with you guys tonight, but I'm not going to date my own assistant. If anyone is offended or whatever, sorry. It's just not smart. Tracy, I like you a lot, but I can't afford to lose you at work right now." So much for our next salary negotiation.

We ordered drinks and group-chatted. As usual, it was hard to tell what Tracy was thinking, but the conversation was so good that three rounds went down before Joe and Sasha started taunting us about their upcoming vacation. I knew they had been planning to rent a budget cottage in the Caribbean, but there had been a long waiting list. Now, apparently, a last-minute cancellation had opened a better place for next week. Joe said he couldn't wait to see Sasha in the new swimsuit he'd bought her for Christmas. She swatted him and rolled her eyes, pleased but, amazingly for Sasha, embarrassed. This was obviously quite the swimsuit.

Joe put his arm around her and they kissed to make up. It went on for so long that it was hard to tell when the making up ended and the making out started. I was about to tell them to get a room when I saw that Tracy was staring at them intently.

Sasha finally surfaced and took a sip from her drink, looking flushed. "Nothing like a tropical moon, a beach, and a skimpy bikini to get the old hormones raging," she observed.

I shrugged. "Post lots of bikini pictures, Joe. It's your only hope for getting your followers into double digits."

But now, for some reason, Tracy was staring at me again. After a minute it got a little unnerving, like having cop on your tail. Sasha noticed and gave the appearance of thinking. Then she said, "Hey! Maybe you guys should come too!"

****

Tracy was still staring at me.

I blurted, "Gee that's awfully nice but it's a whole week together and we don't really know each other that well and there's no reason to think she'll want to spend a week with her boss and there's lots going on at the office anyway! You guys should stick to your plan. Have a nice time and get re-acquainted with yourselves. Or Tracy can go with you if she wants."

Joe said the offer wasn't entirely disinterested. The cancelled place was right on the water. They were thinking of taking it, but they wanted to share the extra cost. If Tracy and I came and paid our shares, it would work.

So that's what this was all about!

"I have no money," said Tracy, definitively. "I just moved to be closer to my new job. And there was no signing bonus." She gave me a look.

I leaned back, relieved. Although....

"Maybe you two can work something out," said Sasha.

"I have zero money. Z-E-R-O," said Tracy. "I just paid the security deposit and first and last month's rent on my new place. I can barely cover my drinks tonight."

"Maybe you can work something out anyway," said Joe, "like a salary advance or something. Frankly, Dave, you should just take her! She could be your arm candy. She'll upgrade your social status 100%, which it desperately needs."

Sasha cackled so loudly the whole place stared. "You should take her just on the chance you'll get laid!" she declared at the top of her lungs.

For a few seconds, you could hear a pin drop.

"I don't pay for that. And Tracy probably doesn't get paid for that either," I said. That didn't come out exactly right.

"You pay when you take a girl out on a date, right?" asked Joe. "And then maybe you hook up, so it was worth it? Why is this any different?"

"That's ridiculous!" I protested. "Totally different case! First, I'm her boss! And, this is a whole bunch of dates! So no, she's charming, but this obviously can't go anywhere. Right, Tracy?"

Tracy had been looking at me. Now she just turned back to Joe and Sasha and waited.

"Dave," said Joe patiently, "you could just hook up while you're down there and then call it off when you get back. It would be worth it! She'd be the hottest girl you've ever dated by a factor of ten!"

Everyone turned back to me.

"On behalf of my pathetically few exes, thanks a bunch! And how do you just call off something like that? Anyway, who says she wants to hook up with me in the first place? So back off! No offense, Tracy," I hastened to add. "Any guy would love to date you, but these people are crazy."

Tracy just looked back to Joe and Sasha.

"See? That's exactly the point," said Joe, conveniently disregarding all logic. "You're right, any guy would love to date her. Any guy would think she's worth every penny. If you knew for sure you were going to hook up with her, you'd take her, right? You'd be jumping out of your skin by now."

"So, here's the deal then, Dave," said Sasha, suddenly pretending sobriety. "You don't have to pay her way unless you guys hit it off, but if you do, her trip is on you. You'd pay her way if you were already a couple, so it's only fair for you to pay if you end up one. If it doesn't work out, Joe and I will cover her share." She turned to Joe. "I'm sure they'll hit it off once they get down there." She cackled again. "Remember the bikini problem?"

"Wait, wait, wait," Joe said, "that's way too vague, counselor." He downed the rest of his brew and waved for another round. "The Finance Department wants some certainty. What triggers a payment? What does 'hit it off' mean, anyway? There has to be a standard. Does Dave pay if they catch the feels? Snuggle? Kiss? Do they have to have a sleepover?"

"What bikini problem?" I asked.

Sasha looked cross. "It has to be more than a kiss if it's going to cost him a lot of money! That's expensive, even for Tracy. He'd never let her near him on the chance she might kiss him!"

"Expensive? Are you kidding?" Joe was incredulous. "Just look at her! She's worth $2,000 a night, easy."

I expected Tracy to flinch or scream or something. But, nothing.

"That would be for full service, though," Sasha pointed out. "Dave, you need legal representation here. Your finance buddy is trying to skin you alive." She looked back at Joe. "Let's just be blunt and say 'hit it off' means Dave has a happy ending."

Another pin dropped.

"It can't be just one, though, come to think of it," barked my lady lawyer, who was apparently a pit bull-shyster mix. "Like, just one happy ending, and Dave pays for Tracy's whole trip? That's not fair. There has to be proportionality." She wiggled her eyebrows at me. "If Dave's gonna pay for the whole trip, Tracy would have to provide full service for the whole trip, like a sugar baby or something. It's only logical."

We all looked back at Joe. Uncharacteristically, he seemed flustered, so we all looked at Sasha. Against all expectations, she was quiet, too. In fact, everyone was really quiet. Finance and Legal had hit an impasse. The whole thing was going nowhere. I was relieved. Sort of.

Tracy finally broke the silence. "OK," she said.

****

"Uuuhhhhh...." That was me. "No, no, no, no, that's ridiculous! I'm too young to have a sugar baby!"

"Yeah, but you'd do it if it was Tracy, wouldn't you?" pursued Joe. "She's a living sex doll, man! And, Sash, it would be the deal of the century for him! He'd pay a dollar right now just to feel her up for sixty seconds, right?" He looked at me to see whether I would deny it, but I didn't want to insult Tracy. Also, it was true. "So that's a dollar a minute,... which is $1,440 a day, over $10k just for a week of casual groping. That's way more than her whole trip costs, and he'll be getting unlimited access!"

"Unlimited access?" I blurted.

"Well, when you put it like that..." Sasha began.

"Uhhh, guys... " That was me again, conflicted.

"OK," said Finance, "Deal?"

"Deal," said Legal. They shook.

"I'm no lawyer," I said, "but I think your contract is missing an important party or two."

"Dave, not everyone who works on a big project signs the contract," said my ferocious counsel. "The accountants sure don't. Now get in there and make me proud!"

Four eyes turned toward me. Then six. There was a long silence as everything sank in.

****

I cornered Joe while the girls powdered their noses. "Joe, this is beyond awkward! Tracy must be doing this just to save you guys money. You're taking advantage of her!"

"Hey, don't look at me. Sasha's the matchmaker. I'm just in finance. You're getting a bargain."

"But Tracy doesn't really know me at all, outside of work!"

"Oh, I bet you guys know each other pretty well. She's been with you what, three months now? And you forget we introduced you at a party last year, when you were in kind of a work trance starting your new firm. So I'd just go with the flow, man. Unless she's not hot enough for you."

****

The girls returned, whispering between themselves.

"Better get your plane tickets, Dave," warned Sasha. "The flight to romance leaves Friday."

"And pack light," added Joe. "Thanks to your legal mouthpiece here, you won't be spending much time with your clothes on."

"I want to talk to Tracy without any mouthpieces," I said. "See you later." I took Tracy by the elbow and frog-marched her to a booth across the bar. We sat across from each other.

"Tracy, what the hell? What are you thinking? Joe and Sasha are manipulating you just to save themselves a buck, and you're letting them!"

Tracy started tracing patterns on the table with her finger, not looking up.

"Come to think of it, it's worse than that. They're pimping you out! I pay, they profit, you get screwed! Do you really want to be hooking for them?"

"Don't you like me?"

"Well, . . . yeah, of course, you're fantastic, but the whole thing is just too awkward."

She gave it some thought. "... Well, for me it's a free vacation that I could never afford..... maybe you just don't like the idea of a sex vacation? Or maybe just with me?" She wouldn't look at me at first, but then she leaned forward and questioned me silently with those big, grey-blue searchlights.

She suddenly seemed more sympathetic. Also, the motion had pushed her boobs forward and was stretching her dress over them tight as a drum. In my imagination she was kind of presenting them to me. That must have turned my brain off, because I was beginning to see things her way. "I don't really have that much experience with sex vacations...," I started aimlessly.

She gave me a nice smile.

****

Tracy reported that we'd had a meeting of the minds. Sasha cackled and clapped, and Joe wiggled his eyebrows at me. "Jeez, man, wish I were you! She's the hottest thing ever! No offense, Tracy. I hear you're good at accounting, too."

Sasha looked just a bit miffed. "Joe, seriously? Maybe this wasn't such a great idea. Are you going to spend all next week drooling over her? 'Cause if so I could bring my own arm candy." The air was suddenly chilly.

"No, no, hon. You're the best!" said Joe, quickly and unconvincingly. We all knew that as a sex object, Tracy was world class.

"Well," Sasha continued, still sounding annoyed, "I hope I don't regret this whole thing. If these two are getting it on like minks all week, there's going to be lots of annoying fucking going on. It's going to be fucking annoying, actually.... Maybe we should do something to liven it up for us, too, babe."

"....and that would be?" Joe was intrigued.

"I could be your sugar baby, too! We could make it a sex vacation for everyone!"

Joe looked puzzled. "You're already my sugar, baby! Nothing would be different."

He had a pretty good point, I thought. But Sasha was ahead of us. "No, actually. Right now, I don't spend every waking minute anticipating your every sexual desire and submitting to your every whim. But sugar babies do whatever you want, before you even know you want it!"

"How will you know what I'm going to want, before I want it?" Joe seemed honestly puzzled.

"Tracy and I will figure it out. We want to be good sugar babies. We'll just need to spend a little time strategizing together. Trace, are you free Wednesday afternoon?" She looked at me, not Tracy.

I took a deep breath. "I'll give her the afternoon off," I said. "It sounds important."

****

Sasha swung by the office late Wednesday to pick Tracy up for their strategy session. They came by my desk on their way out. Sasha asked if I had any special requests. For a moment it didn't register, but then I waved them off. I was still having a hard time with the whole concept.

Sasha looked disappointed. "Well, we'll do our own research on the internet, then. Could we borrow your laptop? What's your password?" she asked with an evil grin.

I considered my browsing history over the last few years. "Absolutely not," I muttered, pretending to be busy.