tagHow ToGuy's Guide to Casual Encounters

Guy's Guide to Casual Encounters


I'm no longer on the market, guys, but I'm re-posting this advice I wrote back when I was doing the Craig's List CE thing because you might find it helpful (or just funny).


Tips for men using the Casual Encounters section of Craig's List from a woman who has actually had sex with men from Casual Encounters on Craig's List.

"Yeah right you are so fake."

With one pithy, poorly punctuated sentence, Angelo Sloan Whitehead* violated two important rules for answering an ad in the Casual Encounters section of Craig's List: Be Anonymous and Be Engaging.

Be Anonymous

The person on the other end of your response probably isn't a grandstanding asshole planning to publicize your pathetic attempt at internet seduction to the entire world, but he/she/it might be: an auto-responder, an email address harvester, your wife, your best friend, your best friend's wife, your wife's best friend, your boss, your kid, your mother, a picture collector, or someone writing an article for Literotica. Email addresses are free. Go get one.

What name should you put on the account? Not your full, legal, unique one, that's for sure, Mr. Angelo Sloan Whitehead who works at a prominent west coast university and graduated in 1992. But unless your first name is Madonna or Fabio, consider using it. A fake name has to be corrected before she starts screaming it out in the heat of passion causing you to look over your shoulder to see who else is in the room. Or before she gets your voice mail, whichever comes first.

If using even your first name scares you, try an initial, a variation of your name, or a nickname. Whatever you do, don't use David or Peter. You all use David and Peter. If your name really is David or Peter, I'm sorry. 'Cause I'll never believe you.

The other thing you'll need is photos. You'll need two. Neither one of them is of your dick. Yes, I know you're proud of it and yes, I know you'd love to get a pussy picture back, and hey, I actually kind of like them. But most women don't and anyone who requires a picture of your dick is probably a guy who will either add it to his collection or send it off in answer to someone else's ad. (Since we both know you're going to take a picture of your dick anyway, I've put a sidebar at the end of this article with tips for doing it well.)

The pictures you really need are a face pic and a body shot (shirt off/shorts on). A general internet rule is: never allow your face and your body to appear in the same photo. Photo cropping software is free and easy to use, but if you're technically incompetent you can achieve the same effect by taking a picture of yourself in a mirror. Hold the camera close to your face and use a flash. That should render what's left of your face unrecognizable.

In casual encounters, the body shot is the teaser; the face pic is the closer. Your face pic should be recognizably you, which means you don't send it out until you're ready to be recognized. Until then, show off that headless torso.

Be Engaging

Now Angelo Sloan Whitehead thought he was OK in his fully-named, company-addressed glory because, after all, he didn't actually ask me to fuck him with a strap-on/call him Daddy/grind my pussy into his face/or make him wear women's underwear. He thought that answering my ad with "Yeah right you are so fake" was the perfect alibi. He wasn't interested in what I was offerring. No, no. He was merely a good internet citizen, patrolling the Craig's List boards and privately debunking any ad which appeared too good to be true.

Let's say you were Angelo Sloan Whitehead's wife. Would you fall for that? No. So Angelo Sloan Whitehead failed in his goal of answering my ad without committing himself. He also failed to get my (positive) attention.

As a man answering ads on Craig's List, this is what you need to know: women get a lot of responses. A loooot of responses. More than that even. Post an ad yourself and you're lucky to hear from anyone besides the spam bots. But women rule. Even in my backwater CL section, I can get more than fifty responses to a Casual Encounters post. With an inbox full of answers and more coming in every minute, I'm not looking for reasons to keep you. I'm looking for reasons to toss you. If you don't think an ad is for real, then don't answer it. But if you do answer it, answer it well. You've got a lot of competition.

The key to answering an ad well is actually reading it. It contains clues. Let's start with the subject heading: Do Me, Do Me, Do Me - w4m - 34 (North Bumfuck)

* w4m means this is a woman looking for a man. Don't write and ask her if she's a woman. She's already answered that question once and if she lied to Craig's List, she can lie to you.

* 34 is her age, c.f. "lying"

* North Bumfuck is her location. For large cities such as NY and Boston, you can also get location information after you click on the link by looking at the top of the page. (e.g. "new york craigslist > brooklyn > casual encounters >" tells you that this person posted in the Brooklyn section)

Now let's read the ad itself. It also contains clues. Like what she's looking for. This is an important section to read. Don't respond to the woman who's in town for one night only with a dissertation on becoming friends first. Don't assume the woman who wants to spank you will also want to be spanked. Don't imagine that she'll have so few replies she won't mind that you're actually old, fat and married when she was looking for young, skinny and available.

Send her what she asks for. If she asks for your weight, your age, your wrist measurement or your zodiac sign, provide it. It proves you read the email and aren't just sending a form letter. (I can tell when you use copy and paste, and you go straight to the trash for it.) If she asks for a photo, use your body shot. Write between three and ten sentences. "ne pics?" is a bad answer, but so is your philosophy of life, your negative expectations, or any list of demands. Your goal is to make it past round one. You can get picky later.

If you make it past round one all you have to do is not screw up. Once all the other guys have screwed up, you win. Here are some suggestions for not screwing up:

* Answer emails promptly, especially emails with photos attached. She's considering sharing her body with you. She wants to know you'll enjoy it.

* Don't ask for more than your allotted two photos (one face, one body). It suggests either that you're not convinced by what you've seen so far or that you're only looking for wanking material and will never actually put out.

* Be flexible. If you're married and are only allowed out of the house at 2:30 am every other Tuesday, you should have said so in your first email.

* Be enthusiastic but respectful. You're looking forward to fucking the shit out of her and yet . . . you know it's completely up to her.

* Be only a tiny bit raunchier than she's being. If she tells you that you have nice eyes try to keep your response above the neck. At least above the belly button.

* Keep the conversation goal focused. When can you meet? Where can you meet? What would make her feel more comfortable about meeting you? A phone number is always a good touch.

* When you do meet, take her for a drink, not coffee. Sex doesn't start at Starbucks.

* Don't be late. You're just giving her a chance to change her mind.

One last tip: if you get eliminated at some point during the process, don't give up completely. Wait a week or two and email her again. By now she's realized that the ones who look good are losers and the ones who sound good are liars and she doesn't even want to talk about that one guy. A nice, sane, flattering email and you could be right back in the running.

Be Safe

So, you actually won. You're actually meeting an actual woman for actual sex! Ah, the sweet life. All your troubles are over. Pussy heaven, here you come!


If you think your biggest worry is how much fatter she'll be in real life than she was in her photo, you're wrong. It's not only women who get fucked over when they only wanted to get fucked. You may be bigger, but she may have friends. Make sure someone knows where you're going, who you're meeting, and when to expect you back. Always meet in a public place and if you head back to her place, call or text someone with the address or her license plate number. Carry minimal cash and some ID and leave the rest of the wallet at home.

If she gives you a sob story about needing money and how she doesn't normally do this, she normally does this. Remember that you were on Craig's List because you were too cheap to pay for a real dating site. Don't blow your savings by paying for sex.

Most importantly, use a condom. What's that? You don't like condoms? Oh, how original. Gee, I never heard that one before. Sure, go ahead and stick your unprotected dick into my pussy. You're the first one I've ever let do that, I swear. Just you and all the other guys with really poor judgement who happen to not like condoms.


The Craig's List mantra: If you can't get it up, keep it up, and shut the fuck up with a condom on, then maybe you shouldn't be trolling for sex on the internet.

Now I know what you're really worried about and it's not even on the list. This, for some reason, is the number one Craig's List nightmare - not that she might be fat, ugly, diseased, a mugger, a prostitute, an undercover agent, or someone you know - but that she might be: a MAN! I'm going to tell you why you don't need to worry about this. First, you're not going to send any photos you'd be ashamed to have appear on the evening news (the key to which is the separation of head and body). Second, you're going to meet this person in a public place.

Here's the thing about public places: they tend to be full of men. One guy more or less isn't going to hurt you. You'll be looking for a woman. You won't see her. This will be sad but it won't kill you. If a guy approaches you, you'll tell him he must have the wrong person. You won't go home with him. You won't accidentally have sex with him and become gay. See how easy that is?

Now please go back to worrying about whether she'll be fat, ugly, diseased, a mugger, a prostitute, an undercover agent, or someone you know. And bring condoms!

Be Sure

Despite the fantasies, machismo posturing, and letters to Penthouse, not all men actually enjoy casual sex. And many of you suck at it. Before you get some poor woman all hot and bothered and then fail to come through, ask yourself the following questions:

* Have I had casual sex before?

* Did I enjoy it?

* Am I too afraid of getting caught to actually go through with it?

* Do I find most women sexually attractive or do I need an underwear model to get it up?

* Am I pretty proud of my cock? Do I mind showing it to strangers?

* If it takes more than 5 milliseconds to get a condom on, do I lose my erection?

* Can I cum with a condom on?

* Can I cum in more than one position and without my partner knowing the secret handshake and pass phrase?

* Do I enjoy oral sex and other forms of foreplay?

* Am I likely to last long enough to make this worth the effort?

* Do I imagine that the reason I don't fuck like a porn star is because I don't have a porn star for a partner and that once I find the right woman I will suddenly enjoy performing oral sex, last longer than five minutes, learn new positions, go several times a night, plus my dick will grow two inches?

This section comes at the end because it's where you should start. It's OK to not be built for casual sex. It's not OK to waste the time and attention of the one woman on Craig's List who was actually going to come through for some lucky guy. Do her and your fellow man a favor and stay home with your wife, your girlfriend, or your porn. Polish your technique, practice jerking off with a condom on, and maybe someday you'll be ready for your very own Casual Encounter.

Good Dick Pics

I don't know why so many women are so anti-dick pic. A little sneak peek is a good thing. Nothing worse than that first disappointing look at sub-standard equipment. Then again, maybe they're just disgusted by the quality of the photos they get. I know I am. Guys, please:

* Take your pants all the way off; don't just push them down far enough to get to the goods. Nothing says "I'll be zipped up and out the door before you even know I was there" like a guy who can't get undressed for the money shot.

* One word: foreshortening. Don't take a picture of your dick pushed straight out in front of you from above. It looks like it's about 2 inches long and has no head on it. Try to get the camera eye-level with it from the side.

* Keep your hand out of the shot as much as possible. Your hand is subtracting length.

* Be hard. All the way hard. How does this not go without saying?

* Other women with unrecognizable faces. Oh she loved it. Gee, I bet I'll love it too. Too bad I can't see it because it's buried in her mouth/pussy. Hey, maybe I should fuck her. She looks like a good lay.

* Other women with recognizable faces. Like you've got a chance in hell of getting near me with a camera.

* Learn to measure. You don't get to start from your anus. We know you're lying anyway but when you send a measurement and a photo in the same email, we have proof.

* Hair. Now I'm not one to endorse the prepubescent look but if the hair is crawling up the shaft, it's time to get out the weed whacker. If nothing else, shaving will add an inch.

* Ugly-ass ones. Why are you so proud of these? I'm talking shrivelled, bumpy, tiny-head, discolored, crooked. Maybe some things should be a surprise.

* Big, well-formed, smooth cocks at hard attention attached to gleaming tan torsos with washboard abs. Sigh. Thanks for the photo but your email goes straight into the trash. Guys who send male model quality photos don't show up and fuck because the photo came from a porn site and the guy who sent it is either 80 or 12, a priest, a woman, gay, or all of the above, can't get an erection or is too young to have them, or is in prison.

If you really do look like a porn star and are still, for some twisted reason, chasing down tail on Craig's List, please send additional photos, preferably with my name and your phone number on a sign held sufficiently close that I can read it but not blocking any of the good bits. Thanks.


*not his real name because I'm not that mean

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