The 10 Creepiest Craigslist Casual Encounters

#5. "Willing to please you"

Desired Demo:
Men who are into terrifying cross-dressers

"i am submissive cd willing to please. I have rented a residence in North Vegas, off Craig street. If interested please email me for a appointment. I am very willing to please you."

What We Can Assume:
That no matter how disturbing these photos may seem there are more than a few dudes out there who want a piece of that, because he/she/it is taking appointments. Additionally, it's been indicated that our cross-dresser lives in North Vegas. And while everyone knows what happens in Vegas stays in Vegas, few are familiar with the North Vegas slogan, which is: What happens in North Vegas will haunt your dreams forever.

Where It Went Wrong:
For someone who's not into female impersonators, there is so much wrong here. But even if that is your cup of tea, you've got to be taken aback by the doll photo. That's some crazy serial-killer stuff right there. Combine that with the freaky flowers-and-curls wig and any sensible person answering this listing would have to be at least a little worried about ending up in a freezer.

Chance of Getting Laid: 74%
On the other hand, it's Vegas.

#4. "Winter is coming; I want a cuddle buddy"

Desired Demo:
"Cute and cuddly" women

"I'll provide the rugged good looks and the high metabolism. You provide the cute and cuddly. Not looking for a one-night thing. I want all of the winter or when one of us finds someone better, whichever comes first. P.S. I won't have sex with you. I'm saving it. Period."

What We Can Assume:
First off, Mr. Cuddles is probably in the wrong section, because he's looking for more than a one-time thing and he's ardent in his declaration that there will be no sex. We can also assume that he doesn't have adequate heat in his home, as his winter-term relationship seems to involve you becoming his human space heater.

Where It Went Wrong:
We're not saying every woman on Casual Encounters is looking to get tore up, but this just screams LAME. You've got a picture of kittens, you've asserted that you're a 25-year-old virgin and the best descriptions you can come up with for yourself is that you have a "high metabolism?"

Chance of Getting Laid: 14%
No offense Mr. Cuddles, but you should consider eHarmony. If there's no ass play or misguided fantasy involved, Craigslist Casual Encounters has no use for you.

#3. "God, this never works......but is there a submissive lady out there"

Desired Demo:
Women who want to be manhandled by a lover with a questionable sense of style

"This is a recent picture of me taken four weeks ago ... Vanilla women is out of the question and I only do KINK women that have a drive and a need to be controlled and in a submissive relationship. We all have options and your is to be with a DOMINANT LOVER. I am DOM in a good way, I am not a beater, yell or threaten - any male can to that, we call them ass holes. A true DOM knows how to control by asking once and can give you a look that will melt you in one second."

What We Can Assume:
This guy likes to be in control. He knows what he wants and he's confident in his ability to melt flavors other than vanilla with a look that has been clocked at one second. Unfortunately, honing this incredible melting stare power has kept him from having time to get to the mall. Our best estimates track this tie to the Structure's 1992 spring collection.

Where It Went Wrong:
In the first line where he reveals that it's a recent picture of him. He may not be what we call "ass holes," but his pose and choice of neck wear are clearly giving off a heavy vibe of dork. And, it's not the sweet helpless sort of dork either. We're guessing that the annoying repeated capping of "DOM" is an indication our friend is desperate to act out a control fantasy that has something to do with being passed over for a manager position at the grocery store where he's a "professional" cashier.

Chance of Getting Laid: 38%
This is the sort of guy who quietly stewed his way through high school, managing to alienate any girl who bothered to talk to him. We don't see why a listing that gives off the same bitter vibe he does in person would make his chances any better.

#2. "Cum With Me"

Desired Demo:
Masculine gay men under the age of 35

"I'm a 33yo male ... I would like to find a MASCULINE male, under 35 ... I'm offering ot take you on a cruise to Hawaii (expenses paid for) with me that is round trip to LA."

What We Can Assume:
You want to know the last time a 33-year-old woman offered a young heterosexual man a $3,000 vacation for sex? Never. It just doesn't happen. So despite all the name calling, feelings of alienation and social discrimination, sometimes it is really, really awesome to be gay, like when you get extended a two-week Hawaiian vacation and cruise for a few hook-ups. Also, sometimes it's not that awesome to be straight, broke and desperately in need of a vacation.

Where It Went Wrong:
Honestly, the only thing wrong with this listing is that it evokes a great deal of envy amongst heterosexual males. The curious straight guy who happens upon this inquiry will inevitably ask themselves why they've been cursed with an attraction to the opposite sex when the best you can hope for in the women-for-men listings are 40-year-old single mothers looking to host dudes who enjoy big-bodied females at their mobile home.

Chance of Getting Laid: 97%
We're actually considering replying to this one. The only way this goes wrong is if he's full of shit and the cruise turns out to be a trip around the bay on his Uncle Remus' fishing boat.

#1. "SODOMY"

Desired Demo:
Women who are attracted to cult-leader types.

"Sodomy is the ultimate act of trust. You could really get hurt if you resist. But pushing past that fear, by passing through it, lite rally the joy that lies on the other side of convention ... If you're an atheist, you will get to know God experientially, from being fucked in the ass."

What We Can Assume:
Butt sex means a lot to this guy. Not many listings offer a spiritual experience, but the author of this one is doing just that. Photos of his torso display a muscular build, because no one wants to be reamed to a point where they "know God experientially" by someone who doesn't have a membership at Crunch.

Where It Went Wrong:
When the Archbishop of Ass-Nailing completely disregarded the fact that this is called Casual Encounters. The feeling you get after reading the listing is that an encounter with this guy is going to be anything but casual. In fact, it doesn't seem like a stretch to think his idea of foreplay includes some chanting and the sacrifice of a goat. However, it's good our anal missionary here is looking to convert nonbelievers using Craigslist. Taking his divine message door to door like a Mormon would be pretty creepy and probably illegal in most states.

Chance of Getting Laid: 52%
It's his unwavering belief that he should have anal sex with you versus your animal survival instinct. Really just a matter of whichever one gives out first.

Don't leave! Spread some holiday cheer with this e-card from and IFC's Whitest Kids You Know.


Recommended For Your Pleasure

To turn on reply notifications, click here


The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!