The 10 Creepiest Craigslist Casual Encounters

Craigslist is great for finding a used bike or cheap tickets to the ballgame. Oh, and also for posting pictures of your genitals and telling the world that you're a "bottom."

If you're confused, you've probably never checked out the "Casual Encounters" link in the Personals section of Craigslist. Recently, CRACKED did just that and turned up a list of the best requests for no-strings-attached nookie from across the country. And don't worry, for your emotional health, we've excluded the listings that feature stranger junk.

#10. "Bottom for rape fantasy tonight/tomorrow"

Desired Demo:
Violent homosexuals

"Submissive bottom here looking for one or more aggressive guys to come by late tonight or early morning. I'm staying at the Bensalem Hampton Inn. Room door will be unlocked and I'll be asleep. Just walk in, drop your shorts and bury your dick in my jock-strapped ass. Safe play only!"

What We Can Assume:
This is pretty cut and dry. We have a submissive bottom, who wants one or more guys to enter his hotel room and sodomize him while pretending that the act is actually being carried out by force. Thanks to the torso picture we also know that this fellow seems to be somewhat athletic, which may explain why he sleeps in a jockstrap.

Though ... this may not be as simple as that. This could easily be one creative man setting up another man for an unexpected ass raping.

Where It Went Wrong:
Unlike some of the other solicitations featured, we are genuinely concerned for this listing's author. Maybe this is prudish, but it seems dangerous to let the world know the exact hotel where you'll be staying, that you plan on leaving the door open and that you expect to be brutalized. Not everyone is into rape. Some people are more into robbery and gay bashing.

Chance of Getting Laid: 67%
It's really just a matter of who gets there first, the sexually frustrated gay men, the homophobes or the cops. It's also possible that this is one of the cruelest pranks ever perpetrated using the Internet.

#9. "Clein man looking for clein woman for tonight"

Desired Demo:
"Clein" women. Whatever that is. Perhaps he's German?

"tomarow weekend! im reed if you are must have pic! i got pic check it out!"

What We Can Assume:
That whatever educational institutions this man has attended have failed him. Any attempt to read this listing will confound even the most skilled codebreaker. However, we can glean from the photos that the author has studied a martial art, wears a referee jersey while tending to small children and competes in bicycle races. It doesn't seem like much of a stretch to speculate that his dad is just barely out of the frame of the bicycle race, having just let go of the seat of his bicycle.

Where It Went Wrong:
Where do you start? First off, any "clein" woman looking for a hook up needs to understand this strange secret language to communicate her interest. For regular human females, the logistics of using email to set up a place to rendezvous with a guy who has no grasp of the written word or any understanding of basic syntax will seem daunting. And, if that's not enough to scare them off, he mentions tonight, "tomarow" and the weekend as times he's available. Sounds like our little buddy here isn't the most popular mental defective in Houston.

Chance of Getting Laid: 28%
We're assuming that this is about the percentage of women in Houston that don't know that you can purchase Karate Gees with Black Belts on the Internet for a few hundred dollars.

#8. "Pregnant (expecting mother)"

Desired Demo:
Knocked-up ladies

"Thanks for reading this post. I am a well built and drug free gentleman with a strong sexual drive. I have a desire to be with an expecting mother(Pregnant)and want to make this fantasy come true. There is something so beautiful about pregnant women and I would love nothing more than to please one. I play no games and ask that you do the same."

What We Can Assume:
Right away, we know Damion is a polite guy. He opens by offering thanks for reading his listing and signs off with "sincerely" just to let you know that he's not kidding about wanting some pregger's poontang. He does mention that he plays no games, which probably means breast-pump bingo is out of the question. From the photos, we can also note that while not chasing women with child, Damion hangs out in abandoned train yards and old water-damaged barns.

Where It Went Wrong:
Clearly, the photos are pretty damning. Had Damion went with a single photo, one might think, "Weird, he looks kinda gay." Combine the two and any single, horny pregnant woman in San Diego will probably move on. They've got enough problems without introducing a sexually-confused lover into the mix. Also, "I am also a massage therapist" is doing Damion no favors. Roughly three out of five guys who post attest to being massage therapists. Basically, it's code for, "I promise to provide half-assed foreplay before wanting to bang."

Chance of Getting Laid: 13%
Any pregnant woman cruising the Craigslist casual encounters has enough on her plate. She probably doesn't need the heaping second helping of mommy issues this guy's clearly bringing to the table.


Desired Demo:
Age and body type have intriguingly not been specified.

"im a 23 male brown hair blue eyes 5'11 160 lbs attractive athletic and im looking for a woman to have drinks tonight and mabey do a lil oral play in the car i love to eat pussy email or im me on yahoo at garglemygoods i have more pics ill buy the drinks NO MEN"

What We Can Assume:
By leading with all physical attributes including age, hair and eye color, height, weight and the description "attractive athletic," we know this guy is proud of what he looks like. The fact that he wants to meet up for a drink and exchange oral sex in a car, well, that leads one to believe that he probably lives with someone. If it's a girlfriend or wife, that's one thing. If it's his parents, that's kind of sad, plus it might mean the car he's proposing to make out in is owned by his folks. If any bodily fluids are spilled, be prepared to be handed a Wet- Nap.

Where It Went Wrong:
He requests that interested parties contact him via IM using the screen name "GargleMyGoods." Any woman looking for a discrete gentleman may find this a bit lacking in subtlety. Meanwhile, he completely forgets to give any sort of indication about what type of woman he's looking for, which gives off the impression that he'll pretty much let anybody gargle his goods. The fact that he spells maybe, "mabey" not once, but twice is also somewhat troubling.

Chance of Getting Laid: 32%
His discretion and apparent total lack of standards help make success a sliver more likely then for Damion up there.

#6. "Safe fisting bring intense orgasms......Getting to be popular fun!"

Desired Demo:
Women who like their sexual organs to be treated like the African monkey trap.

"Experienced gentleman with smaller hands, looking for a woman who enjoys being fisted ..... curious newcomers welcome as well. If you've been there and done it, you already know and understand what's written below ..."

What We Can Assume:
What follows that quote is about 150 words describing "fisting" in extreme detail (You can click on the pic for the full ad, if you must). The verve he uses when rolling out the numbered steps of the process makes it evident that this guy will approach a possible encounter like some sort of demented camp counselor demonstrating macrame.

Where It Went Wrong:
The header reads "Getting to be popular fun!" C'mon now, if a woman is considering letting a guy go wrist-deep, it's probably not because everybody else is doing it. More than likely, it's not the type of experience she wants to have just so she can share the story at the watercooler with her fisting-enthusiast co-workers. Also, he might want to edit the tidbit about it taking "1-2 days for vagina to return to original state."

Chance of Getting Laid: 7%
If the whole fisting thing doesn't scare you off, we're assuming the unsettling drug-dealer-from-a-1980s-PSA vibe ("C'mon kid, all your friends are doing it. Don't be a chicken.") will do the trick.

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