What It’s Like To Bang Your 50-Year-Old Boss

At the age of 12, I made a conscious decision to move away from my safe, secure, netball-loving, ice-cream eating, girlfriends, and become best friends with the ‘bad girl’ in my class. Hand in hand, we ticked-off the following, at least two years ahead of everyone else in our school year: smoking, drinking, shoplifting, piercing, blow-jobbing, boning, and pregnancy-scaring. We were there first, and my God, did we ride that glorious wave of high-school notoriety.

Now, while she left school, got married and had kids (yawn), I entered adulthood with a very clear, albeit varied, list of things I wanted to accomplish in my young, free, early-twenties years (which basically included everything from acid to anal). Fucking someone old enough to be my dad? Yep, that was definitely on there.

So I don’t want you to be under the impression that my entanglement with an older, married colleague was some kind of great love affair. Oh no. The whole thing was completely pre-mediated on my part, out of a combination of boredom, curiosity, and the desire for a great big tick on my sordid ‘to-do’ list.

It goes without saying; if you’re female, under 25 and work for a large-ish company, it is very easy to have sex with an older man. You aren’t special. He will not leave his wife for you. You are most likely one of many hot-messes saved in his phone as ‘Dan Work’ or ‘Mark Golf’. The tricky part is to make it about more than just sex. For it to be legitimately classed as an ‘affair’, we’re talking dinner, drinks, secret rendezvous in obscure parts of the city where you won’t be seen, and if you’re really lucky, sleazy gifts from Agent Provocateur.

So you need to make him fall for you, at least a little. Don’t ‘put out’ on the first date, and do not make your move at a work event. Show him you’re smart. My affair with Stu* began with an exchange of sassy emails, where I simultaneously stroked his ego, but also made it clear I had absolutely zero respect for his authority (did I mention he was my boss?). Think along the lines of, ‘I am fully aware that you could fire me at any moment, but I couldn’t help noticing the Bukowski book on your desk. Are you perhaps going through a mid-life crisis, Sir?’ This shit is too easy.

It wasn’t long before he invited me to have dinner with him, under the guise of it being a totally normal, not-weird-at-all, work thing; ‘I have a reservation at so-and-so restaurant on Thursday, but my friend has cancelled, don’t suppose you want to come? We could talk about (insert name of bullshit project here)’. 

I don’t want to bore you with the gory details, but three weeks later, we’re fucking in a hotel room.  And yes, it was fun, for a very short time. But it was also the dumbest thing I’ve ever done. 

The fantasy wore off fast, for both of us. There were no longing looks across meeting rooms, no cryptic post-it notes left on my desk, and absolutely no close-encounters in the stationery cupboard. Instead, my ‘lust’ (if I can even call it that) rapidly turned to loathing. I was constantly checking his calendar to see when he was most likely to be in my part of the office (and working out how I could avoid being there when he was), I felt sick at the sight of him eating the packed-lunch his wife had made him, and I desperately wanted to tell someone – anyone – else at work about it, in some sort of weird attempt to try and lessen my burden.

For his part, he clearly hated it pretty quickly too. He stopped giving me anything interesting to work on (so I wouldn’t have to talk to him, ever), his emails became curt to the point of rude, and, oh yeah: he stopped booking hotel rooms for us to have sex in. 

There was no clear-cut ending. It just became very obvious to both of us that we’d fucked-up. I made it my number one priority to get a new job, and he gave me a glowing reference two months later. 

So, I guess I got my tick. Go me. Fortunately, I didn’t give a shit about that job, but if I had, that could have been a major career screw-up for… a screw. And then there’s the ‘w’ word. At the time, I consoled my guilty soul with; ‘That’s his problem, he’s the married one’ and ‘I’m probably not the first, and I definitely won’t be the last’. But seriously? That was a really shitty thing for me to do. I betrayed the sisterhood, big time. 

So if, like me, you find yourself contemplating a work/boss/affair fantasy, I beg you to exercise those demons via the safety of Pornhub. 

Or maybe get a new job. At a convent.

*Do I really need to say that’s not his real name?
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Words by Maisie Louise. Photo by Katya.

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