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I Was Banging My Boss And My Girlfriend And Neither Knew About The Other

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After double checking with my nondisclosure agreement and my therapist, I’ve been cleared to tell you all about my experiences as an intern with a Fortune 500 Company in the magical city of Miami. Well, just the fun bits, with all names changed to protect the innocent, of course.

Day one: I arrived punctually with the other intern, Claus, my blonde, German counterpart. We were living together in an apartment provided by the company and planned on carpooling the first few days until we figured out a schedule. We got out of my car and threw each other a final glance, checking each others ties and suits and mentally preparing ourselves for the first day of the next 6 months.

Satisfied with our appearances, we strolled through the front doors calm and casual. A very pregnant woman, Rachel, welcomed us and directed us to our respective desks and teams which were, unfortunately, at opposite ends of the office. With a handshake, we parted ways.

I introduced myself to the management team I’d be working with and was pleasantly surprised at how congenial everyone was, and how they all took the business casual approach to workplace attire. The office supervisor, James, came by to welcome me and assign me to my mentor. Beaming with pride he said, “You’re really lucky. You’ll be working with one of our best managers on our most expansive contract, Espiritus. I think Gabriella is running a few minutes late, but she should be here soon.”

At that moment, the team turned to me with the same doomed expression mirrored on each face. When James had left, their hushed voices showered me in condolences. Apparently, Gabriella was one of the team superstars, although the remaining descriptors ranged from “very particular” to “vampire hag,” none of which boded well for me.

I spent a few minutes consoling myself. How bad could this old woman be? Soon, shouting could be heard from the hallway.

“Where is my intern?!” I said a prayer, realizing I should have taken those minutes to run far, far away.

The voice could be heard rounding the corner. Soon enough, Gabriella had arrived and introduced herself. Frankly, my boner was confused; standing a little over 5’6” and at 28 years old, “Gabby,” my French-Italian mentor, was a total babe. I was reminded of Barney Stinson’s hot-crazy scale, wondering if this lady was likely to stab me with a fork. Taking the advice of my coworkers, I spent the next few weeks on my toes, always in anticipation, waiting for the crazy to burst through the pretty façade in a fiery flurry of fangs. I dotted my “i”s, crossed my “t”s and minded my “p”s and “q”s during that time and, thankfully, the crazy never came.

At the end of the first month, Claus and I were settling in quite well and we decided to see what kind of talent the city of Miami had to offer. Like all gentlemen, we made our bets on who could bring home the finest bit of ass. Claus chose the typical method of clubbing, and, with the advantage of his accent, he did fairly well. Lots of pretty things with slim waists and big boobs, but with a host of problems like chlamydia and daddy issues (debatable as to whether or not this is a problem, but I’ll leave that up to you).

But my secret to success? Volunteering at the local animal shelter. Girls swarm to animal shelters en masse to volunteer and play with puppies all day long. These will be the same girls pounding tequila on Friday nights, but, unlike makeup, their personality won’t rub off on your pillows. Skipping the details, I met a dime — let’s call her Melanie. I was hooked, and over the next month or so we spent a lot of time together.

About a month passed in this manner, flirting with death during the day and actually flirting with a girl at night.

Then one day at work, shit hit the fan. Espiritus was basically on fire and that week we were playing damage control. Seven o’clock on Friday rolls around and Gabby says to me, “I’m going to need to go over these documents with you today, but I can’t pay you any more overtime and I don’t want James to see me keeping you late. If I get you dinner, can you come over to work on these? I have server access from my home computer.” Free dinner and another hour staring at her thick booty? You bet your ass I said yes. She wrote down her address and asked me to come by in about an hour, allowing both of us some time to change.

I arrived at her place and was greeted by the smell of an exotic dish I still can’t pronounce. She called out from the kitchen, “take a seat, this will take a few more minutes. And feel free to change the channel,” referring to the movie droning about on the TV. I sat frozen, afraid to touch anything in case it caused a crazy snap. Soon dinner was prepared, and she brought the plates to the couch. We started talking, trying to delay the inevitable work and eventually got sidetracked by the movie. As the end credits started rolling across the screen, we noticed it was about 10. She apologized for keeping me so late, allowing me to leave. I bid her adieu and made my merry way home, preparing for a night out with Melanie.

Monday morning and I’m back at work. Later in the afternoon Gabby came by my desk. “Seeing as that we didn’t get everything done Friday as I had planned, would you be able to come by again tonight, maybe 7?” I had a date with Melanie but didn’t want to give this woman cause to stab me with the letter opener she was holding. I hesitantly asked if we could push it back about an hour. An odd expression flashed across her face, but it was so quick I thought I imagined it. She consented, “Why don’t you text me when you’re free? I try not to answer emails when I leave work.” We exchanged numbers and continued with our work.

That night, Melanie and I went rock climbing and got dinner at a local Latin café afterwards. On the drive home, she asked if I could pull over to the side of the road.

Fuck, the last thing I wanted was a girl puking ceviche all over the inside of my car. As I rolled to a stop and eased off the clutch, she grabbed my shirt and we started making out. A few minutes later and we’re in Blowjob City.

I heard a buzzing and my eyes turned into dinner plates — Gabby was calling. It was nearly 8. I had to answer the phone, my hand over the microphone so she wouldn’t hear Melanie slobbing on my knob. She asked if I’d still be coming over as it was getting late and she hadn’t heard from me. I confirmed that I was going to make it, citing my delay as traffic on the Palmetto Expressway. The trip concluded at Swallow Station and I hurried Melanie back home.

I arrived at Gabby’s apartment, dinner was ready and the TV was droning again. I apologized for the delay and enjoyed my second dinner of the night in silence. Afterwards, we began our work in earnest, with a few “inappropriate” messages from Melanie to keep the monotony at bay. By midnight, the work was wearing on us and our attention drifted back to the movie on TV.

Again, the end credits gave my cue for departure. Again, I said farewell and the door closed in my face, however as I heard the deadbolt sliding into place a thought occurred to me. I paused and mulled it over in my mind the way a sommelier might sample a wine. Fortune favors the bold, and I figured I’m going to die young anyways.

I knocked on Gabby’s door again, and she answered with a dejected face. I froze somewhere between asking if she was okay and continuing on my intended path. She gave a look as if to challenge what I was doing and the words rolled off my tongue, “This wasn’t just coworkers finishing up a project after work, was it?” That same look flashed across her face again and she said, “What is that supposed to mean?”

Needless to say, I nearly crapped my pants, but I was going to be in a thunderstorm of shit if I didn’t do something. “I don’t think you just invited me here so we could work on spreadsheets.”

She cackled.

I died a little on the inside.

She replied, “Actually, it was mostly for spreadsheets. But maybe we can do something about those sheets in my room,” and threw me a wink. I’d give her an 8/10 for the pun; I’ve heard better, but it was a huge relief considering the circumstances. She invited me back in and soon found she was fond of roughhousing. Normally I’m not a huge fan, but, as she was essentially my boss, I relented.

I woke up in her bed the next morning with the evidence clear on my neck; it looked like Leonardo DiCaprio post bear mauling in The Revenant, teethmarks showing on my mottled skin. Realizing it was 7 a.m., I hurried home to change for work, ignoring the prying questions and exclamatory remarks from Claus. I ran into work, dodging people and ducking behind my monitors, and pulling my collar a little higher. Gabby came in fashionably late with a smirk on her face.

I was hoping to avoid people the rest of the day when James came by my desk. “Hey Tony, do you want to come with us to the quarterly meeting at Espiritus? You’ve done… oh my goodness, what’s on your neck?!” His guffawing drew unwanted attention and commentary. The snickering ended with, “Tell your vampire to take it easy on you next time!” Gabby heard this and bared her teeth at me in mock playfulness.

I went home that day to find Melanie had come over and Claus had invited her in. She had made me a little care package for my upcoming road trip with Claus and wanted to drop it off. She remarked on my neck and I lied, saying something about an allergic reaction. She hinted against exclusivity a week prior but care packages don’t say “I’m not interested in commitment with you.” After she left, I explained everything to Claus, who was curious about what was going on considering our gentlemanly bet. He asked what I’d do about it. I told him I’d figure it out after some reflection.

It took about a month of reflecting, during which I relegated each girl to her own nights of the week. You may call me a scumbag, but I call myself a strategist. In the words of Sun Tzu, “If you know the enemy and know yourself, you need not fear the results of a hundred battles.”

My time of reflection came to a startling and screeching halt all at once. I was out one Saturday night with Melanie, Claus, and his lady friend when a drunk Melanie cornered me. The words out of her mouth were “When are you going to ask me to be your girlfriend?” In my drunken stupor I panicked and a questionable case of “caring about her feelings” forced my mouth to say “Yeah… I was going to do that when we had some alone time, but I guess now is as good a time as any.” I heard the sound of my prison cell door slamming shut and the key to my freedom being thrown away.

That Wednesday, Gabby had equally wonderful news for me. She dragged me aside at the office and said, “I was offered a 2-year position at one of our European offices. I get to teach new managers coming into the company. I’ll be leaving in 2 weeks.”

Not too bad, right? Here comes the kicker.

“I’ll be making enough that I can pay for your flights to come see me. You can come visit once a month and between semesters, or more often if you’d like.”

I was about to speak when the pregnant office assistant, Rachel, came around the corner and said there was “something pretty waiting for me at the front desk.” I took the opportunity for reprieve, “One second, Gabby. Let me see what this is about.” However, Gabby was equally curious as to what could be waiting for me at the front desk.

Lo and behold it was Melanie. She had packed a bunch of snacks with a handwritten letter for me because I was “looking particularly gaunt recently.”

Gabby lashed out, the incredulity transforming her voice, “What is this? Who are you?”

Melanie piped up, “Oh! I’m his girlfriend!”

The dam had broken and the crazy poured out like the biblical flood. A modern Noah, I looked up to God one last time in full anticipation of my death.

Gabby roared. Melanie shrieked. I vomited. Needless to say, it was a very messy ending.

Image via Shutterstock

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Harhko, Esq.

Son of The Most Interesting Man in the World. Has a weakness for single malt scotch and older women.

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