Apparently it’s from an adult game called Another Chance, made by Time Wizard Studios. They also created this meme (source is here)
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It looks like imsrryboris renamed themselves to imsrryoisin because I found what appears to be the same post that you found, but under this account: https://imsrryoisin.tumblr.com/post/693084592352247808/trans-unity
Their twitter was also renamed from imsrryboris to imsrryoisin.
Kaos is the show you’re thinking of.
The Longest Joke in the World is the Nate and lever reference (well worth the read).
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An animation from Obarski / Kiszkiloszki: https://www.facebook.com/watch/?v=1767596029979438
They cite their reference material as: Chroniques de Jehan Froissart (Froissart's Chronicles), Bruges ca. 1470-1475, Bibliothèque nationale de France: http://gallica.bnf.fr/ark:/12148/btv1b84386043/f167.item
They have a longer animation, with the one above included, here: https://www.facebook.com/story.php?story_fbid=1663615227058317&id=1663615227058317
Non-Facebook links to both: https://files.catbox.moe/pjfava.mp4 https://files.catbox.moe/o7qul7.mp4
Edited to fix Facebook link and added non-Facebook links.
Probable source: https://www.deviantart.com/hearte42/art/The-Emperor-357892316
It’s been posted all over the Internet but this is the oldest version I could find. There’s news articles about it too, such as: https://www.huffingtonpost.co.uk/2013/03/11/stars-wars-emperor-palpatine-babys-ultrasound-scan-picture_n_2852674.html
Apparently the woman from the greentext was known as “plastixfangs” online. She deleted a significant amount of her content, but random porn sites still have some of her posts. For example, https://pornpics.click/@plastixfangs (NSFW)
Source of the top left image is dakimomkura (twitter link) (non-twitter link)
Source of the top right image is Little Caesars (non-twitter link)
Source is imizu
Non-twitter link (site is NSFW)