3 Craigslist Ads That Will Shake Your Faith in Humanity

Recently I used Craigslist to get myself invited to an orgy, and it was a blast in that way that being scared to your marrow is a blast. But it opened my eyes to something else beyond all the floppity wangs I saw in that man's house, which was this: There is a core of greasy weirdness on Craigslist. You can advertise damn near anything on that site. Time was, if you wanted anonymous sex, you'd pay for a prostitute or advertise in the back of a weird magazine like Denver Dong Fancy or Butter Puckers or whatever. Now, thanks to Craigslist, the market is wide open in more ways than one, and it's not enough to just say, "Hey, let's roll naked on a mat and see what gets lodged where." Now you can expand your fantasies to the furthest reaches of depravity. Is that good or bad? Who's to say? But it did make me wonder, is there a limit and, if so, what does it mean? Can you weird out people on Craigslist? What about the people who aren't weirded out? How far are strangers willing to go for a potential sexual circus ride? There's only one way to find out!


The best way to determine what's too weird for Craigslist is to carpet bomb the site. I wrote up three ads that I felt were off-putting but believable in that way almost anything is believable if you wish hard enough. Time for Ad #1:

I overestimated the number of ladies with a robot fetish in the New York area. If you're thinking that means I got no responses, you are incorrect. Two prostitutes replied to me, one of whom couldn't keep her fake name straight across two emails. I found this to be devoid of comedy and abandoned it immediately in favor of Ad #2:

A quick glance at Craigslist will demonstrate gay men outnumber straight women about 100 to 0. There are 100 gay men for every woman who is not on Craigslist. That meant gay was the way to go. I posted this ad confident I'd find some slightly left-of-center gay fellow, but I may have pressed my luck too much with the photo or the colorful description, as no one replied at all. New York is not balloon-sex country. I should have tried Florida. On to Ad #3:

A woman looking for a man. Actually, you'll notice, I clicked the wrong button without realizing it and made her a party girl -- she wants multiple men! That's my girl. I thought I'd have to be pretty exclusive for this to work, knowing as I know how likely dudes are to want to hump literally anything that may have even been in a room with a vagina once. What's gross enough to eliminate a large portion of the "normal" people looking for group sex on Craigslist? Poop.

The ad reads like it's written by a mentally disturbed person or an online comedy writer who should have tried harder. The first three sentences really push it, but the bit about dressing it like a doll seemed over the top. How over the top? Look here.

Also, the ending about "lips like a batfish" seemed like a game-changer, but no one mentioned it. Fourteen people replied. My heart sank a little with each new email. I guess I hadn't considered how a conversation develops between two strangers who only connected via a desire to have group poop fun. Have you ever considered that? I suspect not. And do you know how you'd initiate such a conversation? Well, let me tell you, there's a wide range of ways men broach this subject, and none made me feel better about this stupid idea, especially the one who posed with his penis wrapped around a can of Coke. Or the guy who looked like the hirsute bastard child of Andy Samberg and Sly Stallone who sent me five full-body nude photos while he stared longingly into the lens, as if to say, "My furry body is going to be the last thing you see before you die if you respond to this."

It was clear to me that my idea had backfired to a degree. I had not so much found out what was too awful for Craigslist so much as I'd found out what was too awful for me, and I had no one to blame but myself. My choices were to quit now, my triumph being a handful of pictures of naked men, or to persevere and try to win this battle of smuttery by turning the tables and making these guys uncomfortable enough to stop talking to me.


Everyone who replied was greeted with this follow-up message, regardless of what they said to me:

Wanting to make the most of life. My ultimate fantasy is to make love in prison. What are your special goals?

Michele Piacquadio/iStock/Getty Images
"Sweet, sweet fantasy, baby/When I close my eyes/You come and you take me/On and on and on"

It's disjointed and bizarre, but it's also a response that implies hope, yet danger. Prison? Why would I be in prison? That's a red flag, kids. A small handful of emails got an addendum to this message based on what they sent me first. For instance, one email asked me if I wanted to go upstate to a cabin to party with some Spanish men, so I asked what kind of Spanish, Spain or Mexico, and how many? Another fellow sent three pics of his penis and one inexplicable shot of him in his apartment facing away from the camera with a massive statue of the Virgin Mary clearly visible on his back wall. Like, easily 3 feet of the Mother of God rendered in plaster and paint. I asked if she'd be joining.

This response did not eliminate a single person. Everyone answered this with utter sincerity. Here's a sampling of the quality of responses:

"I wanna have a three some with my lil brother n an older women"

"I buy a prisoner costume sexy, and I police and in your bathroom have rough sex that you think"

"I want to gape your asshole"

There were others, but they were less polite. It was around the little brother threesome answer that I again began to question my motives for this article. What was the point again? To see if there was a limit to what someone would want to get involved in via an anonymous classified website. What exactly are people putting themselves out there for? This was my answer.

Photodisc/Photodisc/Getty Images
"I want to wear you like a wriggling, screaming flesh condom."

It's hard not to start judging people once you get this far into something. Admittedly, I was being deceptive, but at the same time, was I leading anyone on? Would any rational person have bought into what I was selling so far? Tough call. And is there any point in your life where wanting to have a threesome with your brother and a lady who puts clothing on poop is not something worthy of at least a little judgment? If we were standing on some cosmic scales, I felt that, karmically, I'd have the cleaner soul in this mess. It was time to hit a new round of responses to separate the wheat from the chaff, and I don't even know what the fuck chaff is. Like, I can guess, but if I stepped in a pile of it, I wouldn't say, "Oh, chaff!" or anything.

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Felix Clay

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