She's The Boss

My name is Ken. I work in Boston. And I totally want to have sex with my boss. Good morning.

My boss is about 51 years old. Blonde, roughly 5'5". Prolly 100 pounds soaking wet and holding a sack of potatoes. She is a mother of four from one of the city's affluent suburbs. And, holy mother of god, I want to bury my face between her legs with an intensity that I imagine only guys who've been in prison for twenty years can comprehend.

Why do I wanna bone a woman who is roughly ten years younger than my mother? Because it's my boss, dudes. Sure, she's also an incredibly hot 51 year old professional who has her hair done on Newbury Street and depends on a team of twenty five Vietnamese women in Newton to keep her nails appropriately-chiseled. But, dude, fucking the boss? That's gotta be bonus points the likes of which my feeble mind could never comprehend.

It's also never going to happen. Because she's the boss. And she didn't get to be the boss by throwing herself at young, goofy, pale Irish dudes.

Not that there isn't something there. We've been on countless business trips together, during which jokes about sex and making out and getting fingered fly fast and furious [that last one being a story she told me about her high school prom that had me up all night in my hotel room jerking off to the dulcet tones of CNN]. Once, while we were setting up our company's booth at a trade show, she bent over and inadvertently backed up squarely against my crotch, then stood there for a beat, noting, "Hey, I hope you at least buy me dinner after this." And, voila, I had enough masturbatory fuel for, oh, ten months.

But, again, fucking the boss is simply not going to happen. For one thing, she's too smart. And I'm too goofy. Although I would like to assure her that letting me bone her in the Executive Conference Room wouldn't shift the balance of power. In fact, it would probably make me an even better employee, as I see it.

Perhaps, in the dark recesses of her mind, she's thought of this as well. And is even considering throwing me a bang before her retirement. In any event, I'll be here waiting for the Boss. Biding my time by shagging the 22-year old Haitian cleaning woman.