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Dragons having sex with cars is an internet paraphilia and art subculture based on sexual intercourses between automobiles and legendary creature dragons.
The fetish was allegedly invented by John Martello, a Furry artist who has a particular interest in Dragons. He created the first images in May-June of 2004; as far as is known, there were only three images created at that point:
Where and when these images were originally posted by Martello remains unknown, though based on his other NSFW dragon artworks, it can be inferred that these were not created as a joke. The assumption is that they were, in some form, made specifically as sexual fetish images, whether for himself or as a commissioned artwork for someone else (commissioning custom artworks is a common practice in furry fandom).
These images remained unknown to a wider audience until February of 2007, at which point a user of DoodleDraw.com found these images.
DoodleDraw.com was a Oekaki BBS similar to the still-running 2draw.net, and owned by Jay Stile, best known for the 4-chan precursor shock/porn site stileproject.com (later being sold and now functioning completely as a porn tube site). Being part of StileNet, DoodleDraw was thusly an NSFW, anything-goes Oekaki board, and many perverse images were drawn there. Rule 34 was just becoming a popular meme at this point, and DD users were happy to use their skills to propagate any ridiculous things they could find or come up with. When Martello's images were posted to the board, there was a certain level of disbelief that anyone could possibly have a real dragons-fucking-cars fetish because there was no backstory or credit to Martello that came with these images. Naturally, DD users decided to make as many images of dragons fucking cars as possible because, well, "Rule 34".
After having made these images, the DoodleDraw users posted them to many other forums as well as 4chan for giggles. In the following months, "dragons fucking cars" became a popular meme, though it was totally devoid of any backstory or relation to DoodleDraw, much like Martello's original images when they came to DoodleDraw. At some point, Martello must have seen DoodleDraw's homage to his perversion, and ended up making two or more images later which made it into the lexicon of the dragons fucking cars phenomenon:
Dragons fucking cars became reasonably well known in the following years, though it didn't seem to become a full blown meme until the now-famous subreddit was created by /u/jymotion. Here are some images from 4chan from 2010 and 2011 (a full 4 years after most of these images were created) where the posters still only possessed strictly Martello and DoodleDraw images:
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