Dudefile #88 – The Craigslist Casual Encounter Oral Sex Dude

Dear DW,

So here’s the story.  This warm weather we’ve had lately has had me really wanting to go, go, go.  As in sex.  I have a boyfriend-ish who lives 7 hours away that I haven’t seen in 6 months.  Before that, we rarely, if ever, had sex.  And when we did it was terrible! Boyfriend-ish also once said I could have sex with other guys.  New boy knows all of these things because I told him.

On to new boy.  I found him in the casual encounters section on Craigslist.  He had an ad saying he just wanted to perform oral on a girl and this sounded good to me.  I replied, sent a few pictures. And a short while later, he drives an hour to come to see me.  He ends up staying for 6 hours.  I climax 7 or 8 times (which is totally a record for me) and he does once (whoops…)  We do everything but have actual sex and kiss (this feels weird to me given my whole situation). Though most of our time is spent on sex, we spend a good deal of time laying around the house naked and talking.  And we kinda hit it off just on the talking alone….Like if it was a first date, you’d definitely be super-excited for the next.  Aside from the sex (which was great…he really liked it too I think), I had a really, really fun time just hanging out with him.  I think he did too–or why would the last hour have just kinda been like getting-to-know-you talk?

Now I wonder if I’ll see him again.  I’m pretty decent looking and think he was pleased/excited about it.  I’d say I’m maybe a 7 or an 8 and he’s a 5 or 6.  He also said this whole meet a stranger and go down on her thing is something he only does on the side occasionally. He doesn’t tell anyone about it and lives a pretty basic normal
generally good boy life outside of it.   This wasn’t his first time doing it.  He’s done it quite a few times but never spent the amount of time that he did with me so he says.

So-my questions are: Is this some weird boxed-off sex thing that he wants to keep in its place (ie-not seeing a person more than once)? Is he not interested in pursuing it because I have a boyfriend-ish that I’m still pretty attached to in a lot of ways?  Is he completely interested given that he drove an hour to see me, stayed for 6, and then drove an hour back?  If he is interested in just seeing me again, how would he be acting?

This whole encounter happened 2 days ago.  Right after he left my place-I sent him a text saying I had fun. That I was sad to see him go. He replied-I had a great time, take care!  (Take care means I won’t see you again or for a while–right?) So I say We should do it again sometime.  He says I would like that!  The end. The next day I sent him another  text saying that I had a really great day. That he basically performed a public service. He responds-Glad to help!  His responses are always so short and lame.  Am I obsessing over them too much?  Do they really mean as much as I’m reading into them?  Is he playing games by NOT contacting me very much?  Because it’s driving me crazy!

He really seemed to like me when he was with me.  But now he seems distant.  Again, it has only been 2 days.  But how many before I know he’s not really interested in it?

Dude. Please tell me!




Hi Frisky,

First of all, congratulations on having a successful Craigslist encounter. Seems like the ones that make the news have a lot more mortal danger and a lot less multiple orgasms. Not to sound like your grampa, but the DW hopes you’re taking some safety precautions when you’re meeting these hour-drive, on-the-side, “I swear I’m a normal guy” pussy lickers. Public settings, friends know where you are, that sort of thing. 

As for your questions, let’s just throw your boyfriend-ish out of the equation. Mr. Anonymous Cunnilingus couldn’t give less of a shit about that other dude as long as he’s headlong into your hoohoo. And frankly, you don’t seem to care much about him either. Infrequent, terrible sex. Haven’t seen him in months. He’s told you to go ahead and bone other dudes. Why bother? That’s a pretty tenuous connection even for boyfriend-ish

So what are we really looking at? You signed up for a casual encounter and that’s exactly what you got. End of story. If you’d met this dude on a dating site and he said he wanted you to be his gf 4evs, the DW would be writing you an entirely different letter. But you didn’t. So here goes.  

The thing that’s supposed to be great about “casual encounter” type setups is this. The sexy thing you want to do is discussed, you do the sexy thing, you go home. No muss, no fuss. The dude doesn’t have to spend all night wondering if you’re just milking him for free drinks and have no intention of fucking him. You don’t have to think a guy is wonderful, fuck him, and then realize later he would have said anything to get you to spread your legs and grab the headboard. You make a deal, essentially. An orgasm contract. Contract is executed. Finis. You wash your hands of the situation, metaphorically and, if it was fun, literally, and you move on.

So, as confused as you are about what Mr. AC is thinking, the DW guarantees Mr. AC is even more confused by you. He had a good time with you and your vagina, but there are no more terms to your contract. It’s over. To Mr. AC, you’re starting to act like you posted an ad for Aaron Eckhart, not a casual encounter. He’s being as polite as he can, but every time you text he’s thinking, “Uh-oh! This isn’t what I signed up for!” Maybe you’re going to stalk him. Maybe you’re going to track him down an hour away and make a scene at his work. Maybe you’re going to call his wife and tell her that her husband is a cheater cheater pumpkin eater. The terse responses you get from Mr. AC are far from “lame” in his eyes. To him, you’re starting to get lame. He’s thinking, “Don’t you know how to handle a casual encounter, rookie?”

And that’s about that. Has nothing to do with you. Maybe Mr. AC likes posting his ads for the thrill of anonymity and spontaneous nature of one-nighters. Maybe he’s a little pent up in real life and these jaunts give him some kind of pussy eating superhero alter-ego, patrolling the hot city nights for unsatisfied women with shitty boyfriends who give shitty head. Maybe he’s a practical lad who’s simply hit upon an efficient formula for getting up close to as much fresh ass as he can.

Whatever it is, though, a casual encounter is what he signed up for and that’s what you signed up for, too. That’s why he kissed your crotch, but didn’t kiss your face. No feelings or entanglements. Dudes are literal, and get extra literal when it comes to responsibility-free boning because responsibility-free boning is 1) something they want more than they will admit to you in most situations and 2) something they almost never get to have.

There’s absolutely no intrigue for you to find here, no love story to grow through the cracks in the casual encounter sidewalk. There is only some Grade-A facefucking. Which, if you think about it, is nothing to sneeze at. Which is good, because sneezing could cause a terrible facefucking accident. But I digress.

Here’s to finding a dude on OKCupid who has casual encounter-like skills.


the DW

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2 Responses to Dudefile #88 – The Craigslist Casual Encounter Oral Sex Dude

  1. TheHumanScone says:

    have you ever noticed on HUNG that Aaron Eckhart obviously actually has a tiny cock? You can tell by the way he walks, by his zero-package pants, by his whole smiley-guy oeuvre. So why did they cast him? I heard they wouldn’t even screen test Jonah Falcon, who is this shlubby looking guy trying to get into acting who also just so happens to have a 14 incher. Google him. Anyway, wouldn’t he have been perfect in that role? Why does the guy have to be good looking if the whole series revolves around cock? It would have made that show interesting, instead of the pile of crap it is. Just, you know, an opinion. Go DW!

  2. Hung is actually Thomas Jane of “The Punisher” non-fame, but point taken. Aaron Eckhart has been periodically filling sensitive boyfriend roles from Erin Brockovich straight through to that cooking movie with Mrs. Michael Douglas.

    And the DW absolutely did Google Jonah Falcon, which is apparently his real name. Here he is on The Daily Show with Samantha Bee.

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