Of Pussy And Pals

In keeping with the theme of my last few posts, I wanted to share a story about a time in which my adventures with “taken” women actually went less than stellar. Navigating the seas of women can be rough, but never as much as when the other man is a friend, and the woman is a dunce.

The girl in question—we’ll call her “Caprice”—is what I’d call a social climber, though in this instance, she was more of a social lateral mover. Caprice met my friend, whom we’ll call “Duane”, after one of her girlfriends was invited to hang out by a co-worker of ours. I wasn’t around when this went down, but by the time I met her, Duane and her were already dating…more or less (more on this later).

It was at another social gathering with the same group of friends that I first met her. For Caprice, I think it was pretty much lust at first sight. I would have needed to be partly blind to miss the fact that she was eye-fucking me the entire night.

(Jeebuz! What is it with me always attracting sluts? Does my resting asshole face also read as an “I love sluts!” face?)

When the night wound down, and I was getting ready to split, Caprice asked to borrow my phone. Apparently, she’d left hers out in her car, and “needed” to call it to check her inbox. Now, maybe I have too much sex on my mind (it’s true), but I totally took this as her making a move on me. If you’re not convinced by the things that sex-crazed Jack tells himself, though, then consider that Duane was nearby, and his cell phone was sitting on the coffee table right in front of him. If you’re still not convinced about my assessment, then…keep reading.

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The Combat Zone Hookup, II


Last time, on Jack’s TMI Blog, I was left with a mind full of worries, and fingers smelling of vagina. My newest acquaintance, “Alexa”, asked me to come to her trailer so that I could lay some pipe, but there was one little problem: Military personnel were not allowed in the civilian areas. After almost 8 months without any sexual contact, though, trivialities like “rules” were not about to dissuade me…

When I finally arrived back at the big tent, my rack mate, “LCpl Wallace”, greeted me. “Rayner! So how’d it go, man?!”  He’d actually seen Alexa and I hanging out on a previous night, and like the big, clueless asshole that he was, yelled to wish me luck. He knew I’d met her that night, also. “Smell my finger…”

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“Have you ever been punched in the face?”

Several years ago, while hanging out with two of my female friends and catching them up on the drama in my life (lies, there is no drama), one of them asked me if I’d told the other about a certain crazy story. The title to this post? That’s what she asked me after I’d shared my story…

This story stars the same “head shaker” that I wrote about in “On Discretion“. This story precedes that one, so I won’t blame you for thinking that this instance might explain part of the reason why he ran his big mouth. From here on we’ll call him “Smith”. Since the heroine will come up again, we’ll name her as well. We’ll call her…“Christina”. Christina was a known floozy. She’d already fucked at least two of us, myself included (and here is that story), and according to the co-worker’s girlfriend that introduced her to us, she even tried to fuck her once. Everyone at the office knew about this already. It was a thing of legend. So, yeah. Not exactly monogamous relationship material, one would think. Anyways, I caught my female friend up with this background info, then got on with the story…

One day, word got around that Smith had begun talking to Christina. When asked about it, he told the rest of us that he was going to “make her fall in love with me, then break her heart”. This was a recurring joke of Smith’s. He liked to play up the narrative that he was heartless. Anyways, we laughed it off and assumed he was just going to “hit it and quit it”, which made sense, being that he was well aware of her reputation by this point.

About a week later, several of us took one of our multi-vehicle trips to lunch. While parked and eating inside of my work vehicle, with one of my supervisors sitting next to me, Smith came up to my window. There was some small talk and then, in a very casual, nonchalant manner, I asked “So…is Christina’s pussy still tight?”

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On Discretion

Discretion is something that I think those of us who live non-monogamously should practice, and I do mean every type of non-monogamy.

watched this video recently, in which the late Patrice O’Neal tells a story that basically amounts to him being falsely accused of rape because someone had a big mouth, and it took me back to a few times in my life where my lack of discretion almost got me in big trouble, and to others were my discretion kept things from turning worse than they did.

The one that sticks out the most, as an example of trouble brought about by my lack of discretion, was the first time that my then-girlfriend and I had sex (we’ll call her “Liz” from here on). In the spirit of discretion (Haha. Gotta make up for that time!), I will be keeping some of the details vague: She worked at a swanky hotel whose bar my then co-workers frequented, and her job had strict rules against fraternizing with customers. They’d all met her long before I did, and were telling me all about how hot she was for a while before I finally met her.

When I did, it was pretty much lust at first sight for the both of us. She had me look her up on MySpace (that should give you some idea as to how long ago this was) and after a few weeks of writing each other and occasionally talking on the phone, I somehow convinced her to meet me at her job on one of her days off (Aside: I have a tendency of underselling my seduction skills. I like to think it keeps my head from getting too big). I was kind of stuck there until my co-workers got out of work, so I couldn’t meet with her elsewhere, and the situation demanded that I struck right then and there, when the iron was hot. So, I snuck her in through one of the side exits so that none of her co-workers would see her, brought her up to the room, and we had ourselves a fuck that I still remember fondly.

If you’re thinking “But Jack, that was sneaky as fuck! How much more discreet could you have been?!”

Lots. Things are about to get scandalous, just you wait.

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