I Had Sex With My Boss’ Son

Fresh faced and confident, I was ready to take on the corporate world as a university graduate—at least after I enjoyed my summer. I picked up a part-time job to pay for my binge drinking during the “warmer” Canadian months. The job paid well and didn’t require me to think very hard with a hangover. A few months passed, I made some friends, and thought I knew everyone at the company—until I met Jake.

As I was getting ready to leave work one night I passed by someone I thought was a delivery guy or tech support (he was dressed extremely casually in a legal office), so I didn’t introduce myself. Days passed and I kept running into him sitting in the same spot where he’d be filling out paperwork, not repairing machines. I still wasn’t fazed by him.

One afternoon, Mike, my Seth Rogen lookalike of a coworker, decided to introduce us, though he left out Jake’s title. From that point on, I started making small talk with Jake everyday and we got to know each other slowly and carefully. Seth Rogen would make the occasional ‘stop flirting with each other and fuck already’ jokes, but I didn’t understand why. Weren’t we just friends?

Being ridiculously oblivious to crushes and hell even my own feelings, everything on my end at this point was platonic. One day, I strolled into work to find that Jake wasn’t in his same spot at the same time and I started to feel anxious and pre-diarrhea-ish, wondering where he was. Then it hit me. Oh no! Did I have a crush? What? How?! Why didn’t anyone tell me? I hadn’t even thought of him in that way, was he even attractive?

That same evening Jake had vanished from my life for what felt like days but was actually only seven hours, we had a work mixer and it was mandatory for all employees to attend. I promised myself I wouldn’t be that drunken coworker who hooks up with the coat check guy and began getting dolled up for the event. As soon as I walked in the posh bar, I felt a rush of panic because I realized although I had met everyone I had only really gotten to know Jake and Rogen. I made my way to my boss, delivered an awkward hug to her and hit the open bar hella hard.

I ordered a double vodka 7 and finished it in what I thought was a record time. Just as my bare glass hit the bar counter Jake greeted me. Okay, I’m not being dramatic but he took a cliché 80s movie 180° turn in terms of appearance. I was staring at a Bradley Cooper-looking God, wearing a crisp white shirt. He was draped subtly in a cologne that could make me wet and staring at me with his piercing blue eyes (I had never noticed till that night). Although I was standing in front of a man who now made my ovaries explode, I was glad I wasn’t totally shallow with my crush since I had liked him pre-80s makeover.

We talked, and talked, laughed, made fun of coworkers and dra(aaaaa)nk. We got lost at the bar just him and I to the point where people were asking him to leave me for a second and mingle. The comments came but we ignored ’em. I started to notice that everyone seemed to know Jake. I mean everyone, all 500 employees.

He stayed by my side all night since I expressed many times that I hadn’t made any friends since I began working (cool of me right?). I finally bit the bullet and flat out asked Jake what his position at the company was, how he knew everyone and what was going on. He couldn’t possibly own the place, he was at most 27 years old.

“My mom” he said. Huh? His mom? What about her—

“Hi dear, who’s your friend” said Beth, the owner of the multi million dollar company. She grabbed her son, Jake’s arm, and he politely introduced me as the new employee. She asked if she could take him away for a minute and I terrifyingly agreed. I downed 2 more vodka 7s in the 10 minutes he was gone. I was crushing on the owner’s son. I wanted to sleep with the owner’s son. I drank another. Jake asked me to hit up some after party when the mixer ended and “hell yes” was more or less my answer.

Well needless to say we drank more at the club, touched and danced up on each other a little. After repeat top 40s raped our ears, we headed to an after-after party (because those exist) at one of Jake’s friends’ apartment. We all remained in the upper level of the loft until slowly one by one everyone cleared—except me and Jake.

Our distance began closing in on each other as we said tedious, flirtatious things that if spoken in daylight would be humiliating. Suddenly his hand was on my hip pulling up my skirt, I grasped his neck and we moved into each other with the first kiss, aggressively with a bit of urgency yet with all the time in the world. His mouth, sad to say, was where cigarettes and liquor lived, but I didn’t care. My skirt, hanging around my waist like a pool toy and his hands exploring what they should (my vagina!). FYI to set a bit of context we were awkwardly standing in an empty, brightly lit room with a floor full of people below us and no door to close the entrance.

With the grab of my arm he pulled me into the washroom which was in the condition of a frat house. I ripped my skirt off, unbuckled his pants and like a horny 9th grader I began giving him a hand job as he fingered me. We were banging into the sink, shower, and toilet while stumbling about, we didn’t want to lose contact with each others bodies.

Jake, the supposedly gentle, sweet mama’s boy now had me bent over the sink still fingering me as he reached for a condom. I attempted to continue jerking off his wonderfully circumcised dick but I’m really not that coordinated and I think it seemed as though I was reaching for his wallet.

“No!” I moaned.

“No?” he asked.

“We can’t, I don’t usually do this” I lied through my moaning. He inched his 7 inches into me, hesitantly in case I was serious. And like a violent animal I arched my back off the sink and shamelessly yelled “FUCK ME!!!” With that Jake was no longer a sweetheart and we both became dirty, sexually aggressive freaks.

I called for him to “fuck me harder” and he called for his ego to be stroked “yeah, you like that?!” He thrusted perfectly and we moved together, rattling the gross sink harder into the wall and knocking the mirror into a crooked position. Coming close to a simultaneous climax, I heard my name being called in the distance by a friend. Things moved harder and faster and I could feel his body produce beads of sweat. Again my name was called as we were cuming to the end to which I responded with a “YESSSSS” in a seriously pornographic voice.

“Yes, yes I’m coming!” I screamed as I searched for my clothes in a now apocalypse looking washroom. “Well that escalated quickly” I claimed, awkwardly of course. He kissed me and we adjusted each others’ clothing to seem natural and not all post-intercourse. We made our way downstairs and it seemed as if half the people had left. I grabbed my coat thinking I got away with having sex in the close proximity of his friends and some of my coworkers. “Bye guys” I said as I made my way to the door.

“Bye Petra” said Jake right before he kissed me goodbye in front of too many people. Shocked and slightly humiliated I ran out the front door to Uber my ass home with my friend.

I went home to over analyze, over think and message the group chat about what had happened. I planned out in my head how awkward it would be at work. The next morning when I walked into our staff room I realized I was the only awkward one. I giggled my way in like a schoolgirl which is unlike my monotone self (picture a slightly happier April from Parks and Rec).

Jake was fine, as if nothing had happened but with a slight sense of secrecy about him. Wait. Why was he so cool about this? Did he go home to over analyze like I did?? And that’s when I realized that although this was my first time getting it on with a coworker, this definitely was not his. Aside from eventually owning the company, he didn’t only know everyone due to his relationship to his mom—he fucked half the office.

Over the course of the next few months of my employment, Jake and I had only a few similar moments but nothing close to us going on actual dates or being functional outside of sex. I moved on from the idea of us and eventually left that job (for another, better career).

I realize now I fell for a fuckboy’s dick and yes the sex was good but overall it could have been a risky situation. I also should add it became a known thing within the office—from his mother, to my manager to my co-workers. Not exactly the classiest of ways to go out but hell, it was fun while it lasted!