Coming Up Lame at the Moment of Truth

Anyone with even a passing interest in this blog (hi, Mom!) knows one thing about me: I am all about the female derriere. You need a rim job or a face to sit on for a couple hours, ladies? I’ll do that shit like it’s my job. Because in many ways, it is.

But here’s something you may not know: I’m not really all that into screwing ass.

Not sure why, but doing a woman in the butt has never appealed to me. I’ll do it, sure. But like the guy who gets paid to film all those ridiculous Rob Schneider movies, I’m not really gonna like it.

This makes me an oddity to those females whose orbits I stumble into. They don’t understand how I could spend hours upon hours eating their asses but freeze up when given the chance to throw Little Ronnie McTavish (as my cock is sometimes referred to) in there.

It’s a paradox that many women mistake for false advertising. And it’s gotten me in trouble more than a few times.

Case in point: A few years back, I fell into something good with a female coworker. When we found ourselves out on the road on business, stowed away in shady hotels on the outskirts of town, we’d typically get liquored up and mess around for lack of anything better to do.

Needless to say, facesitting was a big part of the repertoire. And furious tongue-fucking.

But then there was that one fateful night. After a rather intense drinking bout, we stumbled back to her room, pausing only to make out clumsily in the elevator and down the hallway. Once alone, she lost her clothes in record time, leaving only her heels on (my Kryptonite, mind you). The smell of her skin and perfume and the booze in my veins and the way her ass felt as I dug my hands in good was overwhelming.

“I’ll do anything you want,” I remember muttering. “Anything.”

Taking the cue, she pushed herself loose from me, got down on all fours on the bed, arched her magnificent, impossibly round butt in the air, and said, “I want you to fuck me in the ass.”

This was the moment of truth. And like 9 year-old me, edging awkwardly out onto the diving board for the very first time, I felt the jitters. I got the sweats. A gorgeous, eager woman was offering her voluptuous hindquarters to my measly pecker. And seeing it all laid out before me, her hips waving back and forth enticingly, her heels catching what little light flickered through the curtains, I tried to make it happen.

But… I couldn’t. Not sure if it was the booze or the slowly encroaching hangover or my natural aversion to anal sex. I made an honest go of it, but Ronnie couldn’t seem to force his way in there, especially not without the rest of my body’s buy-in.

She kept wagging her hips and looking at me over her shoulder and throwing her head back in anticipation of the ecstasy. But I couldn’t deliver. After a few minutes, as the painfully obvious truth sunk in, she slumped over on her side. Still eager to please, I moved in, kissing her, trying to ply her legs apart to administer Ronnie the way I preferred (ie, vaginally).

But she wasn’t having it. Visibly disappointed (a look that seems to come naturally to the women I’ve bedded), she clamped her thighs shut, slipped from my grip, and curled up under the covers.

I tried to spoon. To entice. To beg for the chance to put my tongue to use for her benefit. By then, however, the moment was nuked. I listened to her snore for a bit, then collected my things and slipped back to my room.

The next morning there was a casual nod over breakfast. And to this day, there has been no further discussion of that night. Perhaps not surprisingly, there hasn’t been anymore sex between us, either.

If I take any lesson with me from that night, it is the following: When a woman tells you to fuck her in the ass, you fuck her in the ass. Otherwise, just grab your bat, ball and glove and go home. Cuz this game is over.


  1. Suzyn

    July 18, 2012 at 12:23 pm

    The last paragraph says it all. Might just be me, but I’d prefer a guy’s cock in my ass than his nose and mouth. Though I would not have turned down the oral, just to get something out of the deal.

  2. Stephanie

    July 19, 2012 at 11:10 am

    You know Ken, sometimes you just have to do something for the woman okay. The alternative is to keep a toy on you at all times. Then use that when she’s not looking. 😉

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