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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?

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"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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Next Round

No pretense this time, no hint of a tease or anything that could be misconstrued as sexual. I would be a blank slate. The only perviness would come from the other side of this unwholesomely shaded rainbow.

I want to take a minute to talk about saving a bunch of money on car insurance.

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"Sign this and then we'll be together always!"

Is anything more boner-wilting than that sentence? Maybe if I had evoked Jesus instead of insurance, but even then it's a tough call. I sent out the reply to everyone and waited. This would do it. I was sure. I was so sure. You already know I was wrong, but for a moment I was positive this would end it.

"I'm confuse. What is I like it dirty to do with insurance"

This response wasn't so off-putting. The grammar is an issue, but I didn't tense my anus reading it. Maybe it wouldn't be so bad.

The next response came from the man who wants to have sex with his brother. It was a massive, poor-resolution photo of a lady in a very compromising position with his phone number. I was immediately rendered unhappy.

"Send me a Photo of You. I'll give you Such Bone."

Was that the title of a thesis? Did he even read the insurance email? On the upside, it had eliminated a number of responders. Only five people wrote back. I had even lost Samberg Stallone, and I was sure he was going to threaten to smother me in raw meat if I didn't do as he said.

This was the next response:

"Are we gonna screw o what?"

Thomas Morrison/iStock/Getty Images
"Sure Jaysus, my name be Screwy O'What! Touch my shillelagh!"

Irish sex? No. Just another grammatical butt cramp. Desperation was hanging by its final, frazzled thread. The miserable, gnarled boners of the Craigslist wastelands were becoming frustrated snuffling about the trunk of a tree that bore no hump truffles. Patience was waning like the libido of Hugh Hefner's newest shame sink.

Being a mentally deficient poop enthusiast was OK by Craigslist standards, but I knew the terrible truth of what direction I had to take this. If my goal was truly to find out what a Craigslist deviant found to be too much, I really had only one option left. You may think there were more -- proposing we have sex in a casket, suggesting I'd also enjoy giving a yogurt enema, things of that nature -- but odds are at least one guy would consider me his dream girl if I brought that up. And therein was the secret to putting a nail in this experiment's gross coffin (a coffin we would not be having coitus in). I had to not be a dream girl at all.

The End

"My name is Jerome. I haven't showered in a week. My lust python is a solid 5 inches of venom-spitting fury with dreadfully precise aim. I'm ready to get married. What's your number?"

Anna Kotowska/iStock/Getty Images
But pythons don't spit ... oh, I get it. Gross.

The sad truth of this world is that the most awful thing you can be in the eyes of a sex C.H.U.D. is the same kind of sex C.H.U.D., which is to say a man. I suppose that's very slightly tragic in its way, that these guys would happily have Virgin-Mary-cabin-poop sex with a batfish-lipped middle-aged woman, but a man is just ludicrous. Or was it? I got one reply to the five emails I sent out with that message from Jerome. Only one.

"No thanks, I'm not gay."

Guess who sent that message. Yes, it was the guy who wanted a threesome with his brother. I felt a pang somewhere deep inside, wondering if perhaps his name was Lenny and he wasn't allowed to spend time with bunnies. Did he have a brother, or did people put him in a small animal corral with a crusty, foul pillow that they called his brother? I had to send him one final message, the end to this tawdry tale.

"I think we should see other people. Goodbye forever."

Thus ended our relationship. The email address I used is now abandoned, the e-communication equivalent of a mental institution shut down and forgotten, only to be opened again for the potential horror movie atmosphere it will provide in another generation. What is too terrible for Craigslist? Nothing. Nothing is too terrible. Directed at the right audience, you will always find a taker for whatever brand of madness you're espousing. Is that good or bad? Well, it's often gross, but that's the only definite answer I can provide, and that's pretty relative. One person's gross is another man's threesome with his brother and a feces-lovin' lady friend.

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