Club Caribe

Happy hour never began until 8 PM. Leaving your desk earlier was a sign of weakness. Un-seriousness. An interest in staying in your current position forever. But when it got going, it quickly got silly. Now ice was tinkling in the glasses and everyone was decompressing fast.

I was standing with my co-workers. Shelly was a slim, athletic brunette with a huge work ethic. She would work her way up or die trying. Toni was the gorgeous, brilliant, but manipulative one. I expected her to fuck her way to the top. Betty had a nice face, but she was frumpy and lumpy. I expected her to be a big success. She was my problem solver, which made her invaluable if not easy to look at.

I was two years senior to them, so I was the nominal leader on group projects. But in our giant meritocracy, any of us could crater, and any of us could zoom ahead. It made everyone edgy.

"I hear ya goin' to de islands next weekend, mon," said Shelley in not-very-good mock-Jamaican. I had been planning to spend the long weekend with my intended fiancée, Tiffany. I had bought the ring.

"Yeah...no. She just joined the other team," I said. "She knew I was getting serious and she thought it was time to announce. You know, to save me the anguish, right?"

"You're better off without her," said Toni. "What are you doing tonight?" She eyed me speculatively, like a lottery ticket.

Shelley had already started talking work with a colleague. Betty was the only one available to save me from Toni. It wasn't easy talking to her because she was constantly hunched over and looking at her shoes. She gave me a little smile and a chaste, arm's length pat, like I had just missed a foul shot.

"I really could have used some more notice," I whined.

"I'm really sorry," she said. "Why don't you go anyway? That place has a rep for being pretty wild. You could drown your sorrows and find a new friend."

I said I wasn't sure I could turn my emotions around fast enough. "I think I need a little tea and sympathy before I move on. I might just fly home." She said she understood, and we parted company after a few more kind words.

But later, as I was leaving, Betty materialized at my elbow and walked me out. We both lived nearby -- a necessity with our work schedules -- and we strolled through the city gloom in companionable silence. The rush hour traffic had faded and the evening drunks were coming out. She stood straighter as we stretched our legs, but unfortunately it just made her look pigeon-breasted.

We started talking about Tiffany, and after listening patiently to my story for a block or two she asked whether I had really felt Tiffany was the one. I considered that kind of impertinent, but it started me thinking. Tiffany had all the right superficial attributes. Beautiful. Pretty smart. Wealthy family. Good schools and connections. Excellent tennis. My parents hoped and expected I would marry her. She'd fit right in. Except for the gay part, I supposed. Was she a soulmate? Maybe someday.

"Hard to say," I admitted. "I don't want to dump on her. I really think this wasn't a choice she controlled. She was pretty distraught. She wished me well. But we had different interests, and understandably she seemed lukewarm in the sack."

We paused where our routes parted. "Would you like to come up to my place for a quick drink?" Betty asked. "Maybe a little company would do you some good right now."

I really didn't want to get involved, especially with a sack of potatoes like Betty. But to be nice, I accepted, despite our draconian non-fraternization policies. Also, I really could use the company.

And she seemed so innocuous.

She lived in two rooms in a stylish glass tower. She pointed me toward a liquor store and asked me to pick up a six pack while she took a few minutes to change.

I knocked exactly a few minutes later and heard a musical "Just a minute." But when the door swung open it revealed a creature of total, cosmic gorgeousness: big boobs, boyish hips, long, long legs, wavy golden hair that fell down her back, and a face to die for. Brilliant blue eyes. Fantastic smile. All wrapped in a tight tee, tiny cut-offs and nothing else I could detect. The outlines of her nipples swung around distractingly in her shirt. I felt weak, but I hastened to introduce myself.

She said, "It's me, silly!"

"...?" Me, being charismatic.

She looked down where I was looking, then looked up with a mischievous smile and shook herself. Her shirt heaved around like things lived in there. "Like them?"

I did. "Who are you and what have you done with my friend Betty?"

"I just cleaned up a little," she said as she ushered me in. "And please call me Liza. We're both Elizabeth, but I like to keep us separate." She took the six pack out of my hand and sat me on her couch. She grabbed two cans and sat at the far end.

"Multiple personalities?" I asked. "Should I run while I can?"

"Same brew, different mug," she said. "You know, don't mix work and play?" She was still having fun with me. She handed over a can. I could definitely detect a little Betty in her movements -- I thought. Economical, assured. Why hadn't I noticed that Betty was graceful?

No, this was impossible.

"But Betty -- Liza - why do you -- how do you -- look so different in the office?" I asked. "God, you could be a movie star. You're the most beautiful creature in the whole company."

"I could also be a weather bimbo, or a sex harassment plaintiff, or the girl that made it on her looks, or the dumb blond. I've been several of those things, and I can tell you it is harder than you would believe to be taken seriously as an attractive woman. So I dress down."

"Dress down?! You're a different person in there. You're shorter. You creep around. You have lumps and bumps and another 40 pounds. You need glasses and you waddle...."

She smiled approvingly.

"I just can't believe you're ... you."

"Glad to hear it," she said. "But let me ask you this. If I showed up as a sex bomb, would it help my career?"

"Well, you'd make a big splash and get recruited wherever you want. . . . and then I suppose guys would be all over you and making jokes behind your back, and then you'd be put in sales."

"See?" she asked softly.

I did. Sort of.

"I don't want to be immodest, but I can look in a mirror and I see my effect on people. The thing is, it's just luck. An accident of birth. Icelandic genes. It's not an accomplishment, just a gift. It doesn't make me a better person, but it might fool me into thinking I'm smarter and more interesting and funnier than I really am. And, it makes some women resent me and it means I have to turn away a certain number of guys. I often end up with the wrong kinds. A lot of good guys get intimidated and think I'm out of their league, and that leaves the egotistical assholes.

"So believe me, looking like this is a mixed blessing. Usually it makes life easier to hide behind Betty. On the other hand it can be fun to be Liza, like now. It's kind of a hidden superpower."

"I'll say," I said. "But how....?"

"Not hard. First, it never occurs to people that someone would make themselves less attractive, so they don't look for it. Negative make-up. A wig. Clunky glasses. Frumpy clothing. Padding. A chest constrictor, although that looks odd on me with...these." She gestured across her chest. "Different posture and gait -- those are tough, but you get used to it."

It was an amazing transformation. But I saw her point. "Why are you coming out, so to speak, with me?"

"I like you."

My rpm's redlined. "Why? I'm a corporate drone. An ordinary guy at best."

"Don't sell yourself short. For one thing, I know you well. You're a good friend to Betty, so I know you're not shallow and just after tits. You've been entirely fair to her even with Shelly and Toni hanging around your neck. You see right through Toni, but you're always kind and you don't speak badly of people, even when they might deserve it. Like on our walk just now. And you're thoughtful. And fun. So I like you. And I hear you're available at the moment."

"Available? Like, off work?"

She smiled kindheartedly at me. "Like, unattached. And you have a fun trip lined up, and an extra reservation."

Now I was dying. "So, you're after me for my resort reservation? That's preposterous. Plus, this is a sex-drenched singles-couples resort and we're barely on a happy-hour basis."

"No," she said, "I'm after you because I like you. And, I like sex. With boys, just to be clear. But you're right. We'd have to upgrade our relationship."

I suspect my mouth was hanging open. Her superpower had frozen me. She looked like she was having fun, but to be fair, she didn't seem to be mocking me.

"Do you want to stay for dinner?" she asked.

****

She uncorked some wine and whipped up a chicken dish. She could cook, by the way. She lit some candles and we dined overlooking her 30 mile view of ugly rooftops. We had more beer. She actually had several kinds in her fridge already. She eventually asked me if she could come with me to Club Caribe. She said she respected my need for time to shake off Tiffany's sudden change of heart, but she had to know soon because she would need to get tickets and tie off some work projects if I would let her come.

It didn't feel right to rebound from Tiffany so fast. But Liza was a perfect eleven. But I had been about to ask Tiffany to marry me. But maybe our relationship hadn't really been that deep. By contrast, I did know Betty pretty well. And I liked Liza, although since she was in another league entirely I couldn't expect to be besties with her. Maybe I was intimidated now. Maybe I should man up and not be. Maybe our non-fraternization policies only applied to Betty, not Liza. Maybe I should dither a little longer....

Liza rose, walked around the small table, bent over and planted a delicate kiss on my lips. I got a look right down her shirt at her unbelievable boobs swinging around. "I really do like you," she said. "I hope you believe me."

"Okay," I croaked, completely unencumbered by conscious thought.

"Great! We'll have so much fun! And so much sex, if you're okay with that!" She held my head in her hands and bent down again for a much more sensual kiss. "We need to get started on the practicalities. You should audition me. Is this a good time?" Her brilliant blue eyes sparkled until she snuffed out the candles.

"Audition?"

It couldn't be. It was incredible. I was supposed to audition the Rolling Stones for a kid's birthday party?

"You know. A trial run. But I want to ace it."

I still felt disoriented. "Ummm, you know, usually I'm a third date kind of guy. I want everyone to respect themselves in the morning."

She gave a slight frown and pursed her lips. On her, the expression was gorgeous. There was nothing she could do that wouldn't be sexy. "I thought so," she said. "But you've known me for years! Wait right here." She ran a finger down my chest, down to my belt, and she disappeared into her bedroom. I waited obediently. Frozen, again.

What just happened? First I was jilted, then I found I had been working with the sexiest girl I'd ever met and she wanted to audition for sex? With me? What had been in those happy hour drinks? In reality I was probably lying at the bottom of a concrete stairwell somewhere, drenched in my own vomit.

I didn't want to wake up.

She returned in black, but not much of it. It did go well with her golden, wavy hair. She had on a bikini that was basically a g-string bottom with a crazy top with tall but extremely narrow triangles. From the side all you could see was boob. It made her tits look larger than softballs. She posed in front of me. "Okay so far?" I managed to nod. Barely. She looked genuinely pleased. "I've never had the nerve to wear this in public before, but this trip would be my chance."

She extended both hands to mine and pulled me to my feet. Then she enveloped me in a full-contact kiss that took my breath away. While I was recovering, she undid my belt and pants. My steely dick popped out. She knelt before me, dodging it gracefully, and took it in one hand with a smile.

Liza -- certainly not Betty now -- had done this before. She inspected my dick unhurriedly, then fastened her brilliant blue eyes on mine as she opened her mouth. She placed the head on her tongue but didn't close around it right away. She ran her fingers up and down the bottom of my shaft. The sight was unbelievable -- that gorgeous face with my dick poised at the entrance of her mouth just begging to be shoved in, the bulging tops of her oversized breasts, the blue eyes seeming to beseech me for cum... I was all set to fuck her face...ohmygodohmygod ...

"Look out!" I said. And I shot in her mouth. I flinched but she held me and pumped me dry, which took approximately forever. "Mmmmmm" she said, and she smiled as she licked me off. I was mortified, but she said, "Don't worry. That happens to me all the time. Now we can get serious." She stood up, took my hand, and led me into her bedroom.

Despite her clever maneuverings, I still had the feeling that she must be auditioning me rather than me, her. I had probably flunked the first test. I had better stop being so passive. So I wrapped my hands around her slender little waist and gave her a long, hard, investigatory kiss. Her teeth were all perfectly even. Some people have all the luck. And her breasts were large and firm. They held shape even pressed against me. As we broke, I undid the back of her top and dropped it to the floor. Her nipples still pointed right at me. I ran my fingers up her ribs, palms up, and ended holding her tits. They stood so far out from her ribs that I couldn't even get my hand around the bottom half of each as I tried to cradle them. They were delightfully heavy.

She seemed at ease with my audit so far; in fact, she cupped my recovering dick and squeezed lightly and rhythmically. I reached past her wandering hand and ran a finger lightly up her slot. I was pleased -- maybe flattered would be the word -- to find she was wet.

I broke contact long enough to make a point of spinning her around and checking her out from all sides. She complied willingly but then pressed back hard against me from thigh to chest, and re-gripped my cock. "Do I pass?" she asked with a seriously worried expression. She could act, too.

We both knew she was spectacular and that she was going, but I was having a good time. "Well," I said while sliding a finger into her in one of the strangest conversational gambits ever, "probably. Would you bring this bikini?" She nodded enthusiastically. "I don't want to see you in anything boring!" I said, stroking her clit. She promised, and I said in that case ... we could resume the audition.

She nodded gravely and started working my cock a little harder while pressing her tits on me and affecting an adoring smile. I stroked her back with one hand and her pussy with the other while kissing all over her face and lips.

Eventually she sat on the edge of her bed and took me into her mouth again, but I couldn't see her eyes and it wasn't the same, so I pushed her over backwards and entered her. She was tight, but what got my attention was the effect of my entry. She shivered, gasped and made little moaning noises on every instroke. She quickly started writhing and whimpering. I held her thighs and picked up the pace. Squishy sounds filled the room. She raised her hands above her head and gripped the bedsheets to better resist my thrusts, and her breasts started lunging up and down her chest. After only a minute she closed her eyes, arched her back, and froze for a good twenty seconds. Finally she gave a long "Mmmmmmmmmmm."

"Sorry, sorry..." she said. "It's been forever." I said we were even, and she smiled. We cuddled a while.

She said she guessed neither of us had passed our auditions. I agreed we needed more practice. "Ready when you are," she said. Girls. Sheesh.

We cuddled some more and discussed Club Caribe. I had heard wild things about the place and I wanted to be sure she knew what she -- we -- might be in for. I thought there might be a fair contingent of Spring break-type collegians as well as normal fun seekers. I secretly suspected Tiffany had chosen it because she thought there might be loose women there. But Liza said she could handle sexual situations, and rightfully so, I guessed. She said she would enjoy 'being Liza' for a while. We groped and stroked each other, but as usual we were exhausted from work, and eventually we drifted into sleep.

Her clock went off at 5:30. We went into work mode, dressing quickly. My options were limited. 'Betty' needed more time, so I kissed her goodbye and headed for the gym.

I had been clearing my desk for a month in preparation. Betty had a big project to complete, so she worked until midnight every night and we didn't have much fun. Also, she was ultra-careful not to blow our cover, and I took the hint. We barely nodded at each other all week.

****

We had booked early Saturday morning flights to the French Antilles, but Betty couldn't get on my plane. We shared a 5 AM ride to the airport and headed for our separate flights. We would meet when we landed.

Customs consisted of only a stern stare. Apparently vacationers and whatever they brought were all welcome. When I rolled out of the customs shed Liza was waiting at the pick-up point for the resort. She was wearing a modest, white calf-length dress that was tight only on top, and a lightweight cropped vest. She ran up to me, pressed her boobs against me, and gave me an excited kiss and a big smile. Then she looked around and briefly grabbed my crotch while staring at me with her big blue eyes. "Missed you!" she said. I assumed she was talking about a specific part of me. As Betty, she had seen me all week.

A few others were waiting for the jitney too. It was a young crowd, about half looking like college seniors and the rest young grads like us. There was already a buzz of anticipation and lots of skin.

Most noticeable was a bossy brunette who was organizing a small group of friends. She wore a pink terry chop top and matching hot pants, but her most noticeable feature was a pair of steely after-market domes stuck to her chest, the XL models. She had an otherwise forgettable figure and a good case of RBF. I disliked her immediately.

The jitney arrived. It had open-air bench seating and a keg of free rum punch to get the party going. We started to climb into the back seat when the brunette announced she needed it for her friends. We tried another seat but she said the same thing. She had about half the number needed to fill the jitney and I started to object, but Liza squeezed my arm and drew me over to where the young driver was enjoying a joint. As she explained the situation she squinted up at the sun and shrugged her vest off down to her elbows. Her big boobs, pointing right at the poor guy in the bright sunlight, were clearly visible through the tight white top, and the stretchy fabric outlined her tiny waist and her protruding nipples. She laid her most gorgeous smile on him. The guy had no chance. He hurriedly cleared off the rest of the driver's bench seat for us. Liza shrugged her vest back on and whispered to me, "And that's how it's done!" We rode in the front seat, getting the driver's running commentary, while the brunette and her buddies choked dust in the back.

The resort was nearby. For my big weekend with Tiffany I had booked a premium bungalow on the beachfront looking right at the ocean. It also overlooked the backs of many, many thong bikinis on the beach.

We lingered on our deck, and Liza asked me to point out the suits I liked most. Of course, there was a trend: an inverse correlation with size. She absorbed my tastes with interest. I wondered exactly what "being Liza" would mean, after so many months of being Betty.