most immoral thing you have done in the workplace
I hired an escort as a Project Consultant to my company so I could schedule “lunchtime blowjobs” and get instant pussy-on-tap and then wrote the whole thing off as a “project expense”.
Ah yes, those were the days…
I was in my late-20s, my first startup, the money started pouring in, so did the workload. 150-hour weeks for months and to the neglect of all else. We worked until the days and nights and weeks melded into one, then we went out, got hammered, got our dicks wet, and did it all over again.
I once saw a documentary, I think it was about Larry Flynt (or maybe it was Hugh Hefner). Legend had it that he got daily scheduled BJs from strippers/models, I can’t remember.
Anyway…
I get a call one day from Q. I was banging her pretty regularly for almost a year. We met in a club, she was a “sales agent”. She was no-holes-barred the very first time we went out. The next day, she called me and said “Darling, I need some shopping money” which I happily obliged.
Darling, after all the shit you let me do with your mouth last night ;)
That turned out to be her hustle: she was always free to “hang out” (her words) unless she had “other plans with a client”. You were expected to give her some “shopping money” after hanging out, just as she was expected to get on her knees at some point while hanging out.
Given my life at the time it was ideal.
I could work till 3AM, get hammered with my employees, show up at her doorstep drunk out of my head (after scheduling my arrival with her beforehand of course), and she would take me to her bed, undress me and blow my whisky dick till it was hard enough for her to ride me to sleep. In the morning, I left shopping money on her dresser table and it was back to “don’t call us, we’ll call you”.
So, I was pretty surprised when she called. But Q only calls me for one thing.
We meet for coffee in this bistro near my office. By “coffee” I mean “beers”. I remember when she showed up I was 1) happy that she still dressed to fuck even in the daytime and 2) that it was daytime — and it was the first time we’d seen each other outside in daylight.
Two beers down and some chit-chat later, she tells me she wants to “get out of sales”, she had to change apartment because some crazy ex-boyfriend was stalking her, her mother was sick back home, and yadi-yada.
How much do you need?
She said a number.
That’s a lot.
It wasn’t.
But there’s no free lunch in life. And speaking of lunch, I still hadn’t had mine, nor breakfast. Did I have dinner last night? I didn’t remember.
I was neck-deep in the final stages of my company’s first truly big project, my toothbrush was in the office, I’d been buying shirts every couple of days and throwing worn ones away for… awhile… and when was the last time I called my parents?
As always, maybe it was the beer talking, maybe it was her in that skirt that made me wanna hike it up and bend her over —
What’re you doing for the next few weeks?
Why?
Why don’t you come work for me?
She laughed. As we both had before, at night, when we were drunk, at this long running joke cum “hypothetical scenario” when she first told me she once worked as a secretary.
Sucking your cock? Q preferred the word “cock”.
And maybe reply some emails.
We laughed. But it was daytime. And we weren’t joking.
How much will you give me?
I told her I’d double what she was asking. Again, I reiterate: I was young, full of cum and pretty dumb with money. Or maybe it was the money that made me dumb. Either way—
I’m woken up one morning, about a week later, on my office couch where I’d been sleeping for weeks, and looking up Q’s legs in a short panty-peeking skirt — my suggested “what to wear to work” when she asked. She’s got coffee in one hand and she says “Good morning, Mr.____” sarcastically and we laugh. I have my coffee and she got down to taking care of my morning wood.
My employees (almost entirely guys) suddenly had a hot piece-of-ass strutting around in skirts and heels and her only job seemed to be eye-candy and having multiple meetings a day with the boss behind closed blinds. She was good for inspiring morale. And by morale I mean raging hardons.
I didn’t “schedule blowjobs” per se, but it was good for my “anger management”.
It’s impossible to lose your shit at a client on the phone as they rattle off last minute changes for things you’ve worked on for 6 months when you’ve got a girl on all fours in front of you with your dick in her mouth. That’s the closest I ever got to getting head while talking to a congressman on the phone.
Or you attend a meeting and a particular female client pisses you off, you get to channel all that rage into some hatefucking back in your office.
Some nights after especially long days (and there were more than a few of those), when she’d find me in my office, stuck in my head and in no mood to talk to anyone, Q would close the blinds, and without saying a word, quietly slip to her knees and slowly suck me (“like a girlfriend” she used to say) till I busted and regained the power of speech (which is a curios and wonderful opposite of sucking you till you’re speechless).
It was also a nice powertrip when she would sometimes peek into my office before heading off to lunch and ask, casually:
Mr. ____, do you need your cock sucked?
And I would answer, casually:
What do you think I’m paying you for?
Maturity is realizing sometimes the answer is “No”. Or, at least, “maybe later?”.
Strange times.
The project wrapped, she hung in there with me to the end, to her credit, even though I had paid her 50% upfront before it started. She said she was gonna move back home, open a salon with the money, and I didn’t hear from her again. She even changed her number.
A few years later, I ran into her at the club where we first met (I’d not been there for a while). Once again we got to talking but I didn’t ask what she was doing. After a few beers, she’s got me sitting on the toilet in the handicap stall while she’s on her hands and knees looking up at me:
I miss your cock, Mr. _____.
I watched her work that mouth, felt the familiar nuances of that mouth that got me through that crazy time all those years ago, and tried not to feel sad.
I gave her some shopping money after she was done rinsing her mouth, and left.
That was the first and only time I directly handed her money (it had always been through wire or the dresser table).
That was the last time I felt the compulsion to see her again.
The lessons of this story:
- Never date a hooker. A lesson I seem impervious to. Even today.
- Never run a company like a frat house. A lesson I learned pretty quickly with my second company after the first one tanked (surprise surprise).
