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The Internet contains so many ways to stumble across sex that we need special tools not to find it. Without SafeSearch even the most innocent Google inquiry can become obscenely biological. But there are sites out there, like Wikipedia, that want to both house all the knowledge in the world and stay SFW. This leaves them with the awkward task of finding pictures for sex acts that look more encyclopedic than pornographic, which may explain why Wikimedia contributors often decide to draw their own. But it doesn't explain why they're so hilariously awful. There are more biologically accurate pictures of Sonic the Hedgehog screwing BB-8. Brace yourself to behold the worst entries (in some cases literally) from Wikimedia's sex drawings.

Be warned: All links on this page are really, ridiculously NSFW.


This is more artistry focused on a genetic dead end than a gallery of castrati portraits.

1st slagman/Wiki Commons (NSFW)
The only other "auto" to twist itself that hard for fun is an Autobot.

The subtle details of this picture raise more questions than they answer. Why is this guy still wearing his glasses, for one thing? NOBODY's eyesight is that bad. And what about those sandals? They've been given more attention than his elbow and knee joints. Though, to be fair, he's got to have destroyed most of those joints to get this far. It just seems strange that someone short-circuiting everything human biology has ever learned about sex would be so worried about foot protection.

The picture's caption captures more pathos than a collection of Peanuts strips sucked into a black hole: "Looks like 69 position from some angles, but minus one participant." As if the complete absence of a partner was only a minor technical variation from the 69.

Whatever answers one can gather from this work, "1st slagman" clearly found them, disappearing after uploading these and only these images to Wikipedia. What happened? We examine the autofellating clues. He's cunningly worked out how to swallow any forensic evidence, but behold the pictures:

1st slagman/Wiki Commons (NSFW)

1st slagman/Wiki Commons (NSFW)

1st slagman/Wiki Commons (NSFW)

1st slagman/Wiki Commons (NSFW)

The increasingly unlikely series of positions forces us to conclude that this man has somehow twisted himself into a singularity.

Phone Sex

An online picture for phone sex defeats the point on more levels than Mario with a jetpack. A picture might be worth a thousand words, but these days a phone line means you almost certainly have an Internet connection, and that means you have access to infinite images of real sex. Or, if you're specifically into audio encouragement, you don't want a picture at all. Besides, a second-party drawing a doodle for third-parties about a fourth-party getting off while talking to a fifth-party puts more layers between you and sex than using one of those Russian nesting dolls as a condom.

None of that will have prepared you for this picture:

Pirategurl69/Wiki Commons (NSFW)

The sheer innocent joy of the picture means it has to be criminal. Especially since it appears on the Norwegian Wikipedia page for "Telefoonseks," which just sounds like an appallingly precocious educational cartoon. The inherent happiness almost distracts you from the conversation: That guy is talking about having big tits while rubbing his belly invitingly. So he's either involved in very progressive roleplay, or catfishing the hell out of some poor jerk(er).

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Before the Internet, artists still made statements about sex and exploitation through other media. For example, Manet captured the world-weariness of a fallen woman in "A Bar At The Folies-Bergere."

Have some culture before tackling the rest of this article.

The oranges represent the fact that the girl behind the counter is a prostitute and just as available for sale as the champagne she is serving. It is only a matter of time before she has to copulate with a man who means nothing to her.

But Manet's masterpiece of oil on canvas has nothing on "Cumfac_01.png." Maybe because he couldn't explicitly get a cock in there.

Kitetop at the English language Wikipedia (NSFW)
"Why is this?" -Manet

Image files are meant to store mere kilobytes of graphical information, not all the tragedy and horror contained within the human spirit.

The dead look in the woman's eyes elevates this image further by making you aware that you clicked this far specifically to see it instead of anything else ever created by humanity. Meanwhile, the sheer horror of being involved has apparently transformed the sperm into wallpaper paste. Maybe because anyone who can ejaculate while looking at this really should glue shut any orifice they're allowed into to remove the risk of reproduction.

Excited Blowjob

Wikipedia is meant to be a reference guide edited by experts, not the Web-based version of an 11-year-old desperately proving that they do so know what "sex" means by scribbling on their notebook in the back of class. Because when that happens, you get this:

Svendora from nl (NSFW)
We're fairly sure that doesn't need to be pixelated.

Witness the daring lack of line work suggesting that the penis is actually ejaculating her lips onto her face, combining appalling body-horror with exquisite aim. The disintegrating breast would be reminiscent of Picasso, if the whole thing wasn't so unbelievably wrong.

This isn't a contribution to the repository of human knowledge. This is someone who had tracing paper and five seconds access to a porno magazine. Quickly drawing your own dirty pictures might have made sense 20 years ago, back when somebody with a computer couldn't see infinite blowjobs the instant they decided to do so. If this was traced from a real image, by someone who then deleted the photo, that means this picture is so bad it actively destroyed information about blowjobs.

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Impossible Male Masturbation

"M.C. Escher-bation" might seem like an appallingly painful and self-indulgent portmanteau, until you look at the act I am using it to describe:

Brallion/Wiki Commons (NSFW)
"To come where no man has come before!"

That poor guy is breaking his knees on axes our universe doesn't even have. I am sure at some point we've all gone to great lengths to get off, but those lengths were always measurable in Euclidean space. This guy is jacking off in a hellscape without any shadows to hide him, or help us work out the angle of that shelf he's semi-squatting on. Either he's knocking one out in Limbo or this is a tightrope walker with such bad sex addiction that he can't even wait until he gets to the other side.

The demented determination to masturbate across all possible boundaries also captures the spirit of the artist. That's because "Brallion~commonswiki" submitted this image to the Wikimedia "masturbation talk" page, which makes the Necronomicon Ex-Mortis look like Baby's First ABC. It's where Wikipedia editors have re-created most of the major religious schisms of history in one onanistic online argument. Some decried real pictures as lacking scientific merit. Others said the Internet didn't need more masturbation material. One proposed possible Kantian a posteriori arguments against masturbation, as if the only posterior involved in masturbation shouldn't be dat ass.

Alas, with such insane forces arrayed against him, even our 11-dimensional masturbator could not come through. He still lives on as a grim observer on the talk page, busily trying to distract himself from the madness the only way he knows how.

Nipple Artifacts

Great artists sometimes talk about subjects simply leaping onto the page, ethereal visions of such urgent beauty that the artist is only a conduit to creation. Obviously, they're lying. Art is really hard to do well. Especially when other parts of your body are also hard, as was clearly the case here. The artist -- no, the creator -- nope, the, uh, party responsible decided a woman licking another woman's nipple was the best thing ever and simply couldn't wait to create.

Kylejohnston at English Wikipedia (NSFW)
We'd rather pixelate this whole monstrosity, honestly.

No time to calm down! No time to learn how to draw! No time to tidy up all the telltale MS Paint mistakes that make the picture look like it's been lightly dusted in sugar. He had a vision of a woman who suffered a serious head injury just behind her hairline working her way down a viciously taloned Bride of Frankenstein in fishnet stockings, and the world needed it to exist ASAP. Also, you can't see it because of the pixelation (lucky you), but she thoughtfully used her own eyeshadow and neon pink lipstick to mark the location of her nipple on the melted mess of her chest.

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Bukkake Friends

The last time we looked into this abyss, Cyriaque struggled to comprehend the artwork of "seedfeeder." But that artist had so many more seeds to feed. Almost literally, in this case.

Seedfeeder/Wiki Commons (NSFW)
Her happy place is on the opposite side of the universe.

The best thing about this picture, "best" being an adjective I've now destroyed, along with the word "picture," is how all the men have considerately arranged themselves to one side, sitcom-style, so that the audience can see what's going on. Which is strangely out of character because consideration for others is not a defining trait of bukkake gangs. Though they're more diverse than most popular sitcoms. Not that I would know.

More disturbing is how the artist has somehow gifted the woman with an understanding of her situation. She could have been drawn in a magical fantasy land where the rain of man-juice is an enjoyable experience. But no. She knows where she is. She's not just ground zero of a gentleman juicing; she knows she's doing it for free on an allegedly educational website.

A Facial Proposal

Of all the sex acts that don't need a diagram, the facial has to be the most obvious. Anyone who can't work it out after hearing the word is an alien trying to trick you into revealing the secrets of this hu-man thing called "pornography." The only diagram you need for facials is one with red areas over the eyes, nostrils, and hair saying "DON'T BE A DICK WITH YOUR DICK."

Seedfeeder/Wiki Commons (NSFW)
"Oh, dear, OF COURSE I'll be your manly-milk sponge!"

Unlike the earlier facial artist, seedfeeder has gone all-in on the pleasure with the woman here, in more ways than one. She looks like he's just proposed instead of popping all over her. Which in fairness may be the last original wedding proposal mechanism left in the world, complete with a cunning role-reversal of who's kneeling. She's even got tears in her eyes, though that's more because of his aim than his intent.

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Repeated War-Hole

After a while any artist will try to start challenging themselves. They have to move beyond their own comfort zone, and when your early works involved fisting and finger-pulping double-penetration that can be a challenge. So what did seedfeeder do? Try a new perspective? Go on a retreat? Draw something that wasn't explicitly pornographic? No, they moved on to mixed-media, a porno-pop-art project drawing the same thing with different fill effects.

Seedfeeder/Wiki Commons (NSFW)
"DAS AYNYAL" ($58.99, some assembly required)

The first is a bold flat-color effect, as if someone colored instructions from IKEA. (And, like trying to put together a bookshelf, these instructions also look simple but can involve an awful lot of fiddling and cursing to actually complete).

Seedfeeder/Wiki Commons (NSFW)
After this the only place to go is the theoretical "B-nal."

The second is a daring extension into the third dimension. The same sexual lines (and the artist goes to great lengths to make sure they are sexual but definitely not sexy) are thinned, while the color advances through thick bands of flesh tone. Almost as if old 16-bit consoles really were trying to corrupt children the way parents thought.

Also, you are missing out on seedfeeder's attention to detail in the new image with the slight reddening of her ring because of our pixelation, which has made the resulting flowing-together digital sex-slurry infinitely more horrifying. Sorry.

All Peoples Coming Together

Thank the dear god Qetesh, finally one where the woman is enjoying herself. And you'd want to be enjoying yourself to become the organic engine block for a pork piston two-stroke engine.

Seedfeeder/Wiki Commons (NSFW)

The top guy is so devoted to her pleasure he's pounded his own hand to jelly and is still bracing himself with the floppy flesh-sausages to help her reach orgasm. We're getting a clearer view inside the artist than the woman, though: Most of these diagrammatic damsels are undecorated, but double penetration lady is suddenly wearing earrings and lipstick. Seedfeeder is clearly working through a few internalized stereotypes as well as X-rated acts.

It's worth noting this explicit portrayal of multi-penis intercourse has better diversity and gender ratios than both Marvel and DC movie universes. Though, ironically, not better than the DP movie. Something we're sure he'd enjoy.

Luke writes about The Worst And Best 'Star Trek' Games Ever Made, How 'DDR' Helped Him Rebuild His Broken Leg, and Nuclear Science-Fiction Sex. He also tumbles, and responds to every single tweet.

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See how Wikipedia members use page vandalism like gangs in a turf war in Wikipedia Hates Women: 4 Dark Sides Of The Site We All Use, and find more strange sex illustrations in The 6 Most Terrifying Sex Illustrations On Wikipedia.

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