Fucking My Boss

”Fascinating.” I thought to myself. “Despite years of sexual conquest and taboo fucking, you’ve never slept with my boss.” And such was my inner dialogue as I slipped out the back door of the coworking studio in which our little startup was housed. As I drove like hellfire back to my place to wait for his knock on my door.

Part I

At the time, my boyfriend and I were on a break. I was 29 and augmenting my time as Alyx by working on a project. The scope of my endeavor was broad enough that required the type of focus and organization one can only attain (well, mere mortals at least) in a dedicated office space. So after signing a lease with a co-working studio, I went in to claim my desk. And it was on this first day that I first became aware of him. It was the day our lives first intersected.

There I sat in my new environment, doing that thing we all do when presented with a new work space I was organizing. Whiteboard there. Pens over here. Inspirational kitsch on the wall. Stapler … 

I was fully immersed in trying to decide how often I would use my stapler and, therefore, how near I should place it to my right hand when I heard his laugh. Goofy and boyish, his was a loud one. Then I looked up to find that he was, in fact, devastatingly good looking.

Loud and hot and married. “You have a type.” I admitted internally.

So the day progressed and I settled in. And as I settled, I felt and then found his eyes upon me on more than one occasion. We remained aware of each other as the days passed until the moment he approached me at last. I was engrossed in the screen before me when I heard, “Hi, I’m ______ What brings you here?” He beamed down at me. His tone was that of a salesman, so I was hardly surprised by his answer when I turned his question back upon him. “Hi, Eric. I’m ________. What brings *you* here?” He sized me up, then laughed that laugh. “Well played” he conceded.


And then we talked. About his job, my project, the space .. we just talked.

Within a months time, as we continued to talk, I found myself conversing with my boss. He’d brought me on board as a ________ researcher, and I was happy. I had a job that I enjoyed, I was still being Alyx, and I was able to enjoy having to converse with and report to this totally bangable man on a daily basis. Just looking at him made me wet. Made me want him. He would take a call with a client, sit at his desk, execute intricate conversations, and eye fuck me all the while.

We tried to be careful and to do the right thing. He even went so far as to work from home more frequently in order to physically avoid me. (He later confessed this.) But in the end, virtue lost to raw animalistic desire.

Part II

We met after work to discuss a new project and take inventory of my first month. Taking shelter in the air conditioned bar, we had a drink as we chatted. He coached me on how to - as he put it - “hide my light under a bushel just a bit”. He explained that even though I dressed appropriately and demurely, my mannerisms and confidence were exceedingly threatening to my timid, unassured female colleagues.

“You just need to play a role. Play the role of a woman who is not so self aware and in charge. Play the role of a woman who doesn’t know who she is, and who doesn’t particularly like who she is. Just think of it as a game.”

I wanted him. I have always enjoyed fucking my mentors, and I wanted him. So I digested his wisdom over another drink. And then I felt brave. Daring. Confessional.

“Look.” I told him. “There is something you need to know about me. It factors into why I am working for you .. what i am doing at this point in my life .. why I am so, as you say, confident. Why I exude whatever I exude.”

I paused…

“I am actually an escort. Men pay me to be hot and fun, and I go to Chicago for a week or so every month. I don’t work here. That is why i have to work remotely now and then, as we discussed.”

His face lit up, and he exclaimed that he knew there was “something about me”.

I was dripping inside my lace panties as he bit his lip and stated, “I have so many questions …”

PART III

Suddenly, we were in his truck. One hand was on my thigh and his other on my cheek as he kissed me with fire. I let him pull me in from the passenger seat. And then I was on top of him. “What are we doing?” we asked in unison, breaking away just long enough to utter those words. And then back to the physical sensations of our lips and curves and hardness.

“No, really. What do we do now?” I asked.

He sighed and rubbed his eyes. “I don’t know. I don’t know. My wife … I’ve only done this once before. It was right after we married .. things weren’t looking good. We had a big fight, and there was this woman … Fuck. I don’t know. I feel like a bad person, but I can’t not want you. I can’t look at you and hear your voice and talk to you and not want to fuck you. And fuck your mind.”

“I’m not going to make you do anything you don’t want to do. If you want to be good, be good. I want you too Clearly. But … I don’t want to be the person to lead you astray. If you are going to do anything, it is because …”

He pulled me in, and I was silent as his lips explored mine.

And then we drove to my apartment, where I exited alone. Alone and wanting him. Alone, wanting him, and knowing full well that this was not the end of our indulgence.

PART IV

He didn’t show up at work the next morning. I asked our developer if he was out sick and was told that he’d decided to work from home. I was distracted, horny, and just a little worried. I knew that as a sex worker, maintaining an actual employment history was of paramount importance, and I couldn’t help but worry that the previous evening had set me up for termination.

I retreated to my workspace and absent mindedly set about working on a mock-up. I paid zero attention to the task at hand and ended up going down the rabbit hole of typeface, background image, button color and gradient … Gone was my low-fi project. I jumped right into finite design and it was terrible.

Unable to torture myself further, I went outside to clear my head. My phone pinged.

It was _____. “I want you. I stayed home because we can’t do this. But I want you. Meet me.”

“Where?” I replied.

“Your place.” I gave him the address.

I tore back into the building, muttering something about being late for a doctor’s appointment I’d forgotten and being back in a few hours. I gathered my handbag and keys and was gone.

I arrived at my apartment before he, and nervously paced as I waited for the knock which eventually came. I let him in, and he pushed me against the wall with such a tender force. I was somehow naked now, fumbling at his pants. Our foreheads slammed into one another at one point, causing us to laugh like awkward high school kids. Upon a later debriefing session, we would both admit to being incredibly nervous and feeling a bit awkward. But that did not stop us.

I will always remember laying on my bed, his fingers buried deep inside me. Gently, slowly working them in and out as I touched myself with one hand, his hardness with my other. Seeing him explore my body and feeling his cock respond sent me over the edge again and again that afternoon.

And when I turned my focus on him at long last, it did not take long. My hands and lips were all he needed to explode all over his chest and neck. I licked up every drop and then kissed his lips. He did not ask me to stop.

PART V

And so we carried on like this for a few months. Our routine was set: arrive at work, text at work, sneak out from work, fuck, go back to work. It was a game of which we never tired. We kept at until a move and a reorganization came between us.

In the end, it was only he and I, the CFO - his best friend - and the developer in a small and chic industrial office.The other two quickly grew suspicious, so we decided to sever ties.

(Although he continued to attempt to rescind his severance, up until the day I left them.)