Funniest story you've read. Both on Lit and off:

[NoTalentHack]

Here on Literotica, What Dreams May Come by @ThatNewGuy had me laughing out loud at several points. College girl hooks up with her crush, has great sex, and then...

And now here we are together in his bed. He's sound asleep, with his arm draped over my side. His hair, disheveled from sex, is sticking out every which way, and somehow it makes him look even more adorable. He looks so comfortable underneath that lush down comforter. He's utterly content, without a care in the world.

And he's snoring.

So. Fucking. Loudly.

It's basically 4.3K words of her desperately trying to sleep and/or contemplating smothering him with a pillow while steadfastly refusing to take on the social anxiety burden of just getting up and leaving. Highly recommended; I even included it in the afterword of one of my darker LW stories as a palate cleanser. Hell, everything he writes is great.

In terms of the funniest book I've ever read? This one is very situational. I was visiting a friend in London 20-odd years ago, and she took me to the V&A. We ended up wandering around for a while, finally coming to a "Live in Victorian England" exhibit. There were a selection of children's books there with... very Victorian England ideas in them. That wasn't the funny bit, though.

One of them had used an old-fashioned typeface, the kind where the "s" looked like "f". The author regaled us with tales of "pretty dreffef," "lovely green graff under a blue fky," and, the thing that broke us, "whale fifheries." Because there's nothing that Victorian children need to know more about than whaling, especially with a font that reads like Sylvester the Cat.

 

[HordHolm]

Oh god yes. The electroshock and the wildlife photos.

I was about 19 when I read Indecent Exposure for the first time and it really was an introduction for me. I found it hard to comprehend that someone would actually be allowed to write a sequence as funny as the nitro, the honey-covered condoms and the ostriches. It was also one of those profound moments when I realised that literature was so very, very much more than anything 'they' would allow you to read in school.

 

[yowser]

I've enjoyed Wodehouse over the years, Blandings Castle more than Jeeves, tales which are dazzling, daffy and delicious.

On Lit shawalphamale has done a lovely, very funny X-rated Jeeves at https://www.literotica.com/s/oh-jeeves

 

[TimDEnchanter]

The funniest story that I have ever read here may not be up anymore, or I just can't find it. It was in LW -- which back years ago was not a cesspool -- and started out with a husband being concerned about discrepancies in his wife's explenations of unusual events. He, very vividly, imagined her having an affair and took vacation time from work to follow her.

Sure enough, she was lying to him. And she was seeing a man. There was another imagined sex scene as the husband built up his resolve to arm himself and confront the two in flagrante delicto.

He bursts into the room, gunfire ensues... She wasn't cheating on him... Well, she wasn't having a sexual affair. She was a Soviet spy. (Did I mention that the story was set in the Regan years?)

 

[AwkwardMD]

Funniest on Literotica: I'm bad at ranking stuff, but I did very much enjoy White Castle Christmas ("funny" on its own tends to feel a bit empty but this one has a bit of heart to back it) and also AwkwardMD's "Terrible Company", which is just good silly D&D-style adventuring fun.

A short excerpt that makes me happy every time I re-read it. The premise is that Terrible Company, my group of awful and perpetually unsuccessful adventurers, were captured in chapter five by a large number of bards, who had grouped together in mutual self interest to form a gang.

Val <Female Orc Fighter> had dragged, tossed, beaten, and chased all of the bandits out of their own camp by sundown that first day, leaving behind a sprawling trove for the five of them to pick over. In the week that followed, they were able to amass a sizable bonfire every night from the useless crap they'd found: a pile of curved arrows taller than Ayen, dozens of bolts of cloth for each of a dozen different shades of green, enough glitter glue to drown a pack animal. A fresh hell each time they went into a new quarters, or opened a new crate.

They found two young peacocks in a pen near the back of the camp, kept for no better reason than for their feathers. According to the personal journal of the head bandit, peacock feathers were his method of choice for signifying promotions and showing favoritism, as well as denoting status among the rank and file. They found a waiting list for feathers, nearly four feet long, with intended purposes ranging from 'De-Drabification of headwear' and 'Calligraphy isn't the same without flair' to 'Fan Dance Tuesday' and 'Boondoggle', although Ivy <Female Human Bard> insisted the word meant something very different to bards.

That journal included, among other things, lengthy essays on the dire economic conditions which had lead so many bards to uproot themselves for a life of fabulous crime, as well as a sonnet outlining the head bandit's thought process for the selection this particular location for their camp. Ultimately, that decision hinged on an adjacent field of wild daisies the author had found, and later made love in, during an eventful LSD trip; the details of said trip were elsewhere chronicled in an as-yet unperformed one man show entitled 'Getting Incestuous with My Inner Child'. Val promptly burned the extant copy, unread, "For the greater good."

 

[MillieDynamite]

I read a Fanfic based on the old-assed movie Where the Boys Are. It cracked me so much that I had to watch the movie. It wasn't bad, almost good. But not nearly as over the top as the Fanfic, and even the sad parts about the rape and its aftermath in the story were funny as shit. Not so much in the movie.

 

[MelissaBaby]

I just read this, and it was really funny. I can see why won, it was so well done. You really captured the mood of a lonely Christmas eve, and how kind people can be.

Thank you. If it was a movie, the tag line in the ads could be "A very funny story about loneliness."

 

[Candy_Kane54]

Additionally, "The Mouse That Roared" and the next two books, "The Mouse On The Moon" and "The Mouse On Wall Street" were all hilarious.

 

[Bramblethorn]

The funniest story that I have ever read here may not be up anymore, or I just can't find it. It was in LW -- which back years ago was not a cesspool -- and started out with a husband being concerned about discrepancies in his wife's explenations of unusual events. He, very vividly, imagined her having an affair and took vacation time from work to follow her.

Sure enough, she was lying to him. And she was seeing a man. There was another imagined sex scene as the husband built up his resolve to arm himself and confront the two in flagrante delicto.

He bursts into the room, gunfire ensues... She wasn't cheating on him... Well, she wasn't having a sexual affair. She was a Soviet spy. (Did I mention that the story was set in the Regan years?)

Reminds me of this sketch:

 

[Two21B]

"Not Guilty" by Harddaysknight is a very funny story here on Lit. https://www.literotica.com/s/not-guilty

Off site, Stephen King's short story "L.T's Theory of Pets" is a very funny addition to his collection "Everything's Eventual."