I have several suggestions for funny stories, however they are all short. But, you did say you would take any lengths, so here are my favorite funny stories.

Date Night. Dean/Cas Summary: It's date night, and not hell or high water is gonna ruin that. http://deancastiel.livejournal.com/1670233.html#cutid1

Supernatural Romance. This is Gen actually, and one of the funniest things I have ever read. Summary: Announcing the release of the twenty-fifth book in the Supernatural Romance series by Carver Edlund. http://cupidsbow.livejournal.com/418915.html

Prince Castiel and the Quest for 100 Orgasms. Dean/Cas Summary: Castiel knows about how gladiators can win their freedom by winning 100 fights, so Castiel has decided to operate under the assumption that if Dean has 100 orgasms, he might let Castiel go. http://luchia13.livejournal.com/274949.html

Start Quoting Shakespeare and We're Done. Dean/Cas with a side of Sam/Gabriel. A/U Summary: In which Dean has the hots for a librarian named Cas, Cas may or may not have the hots for a mechanic named Dean, and Gabriel joins Sam in the peanut gallery in the hopes that he might just get to do a horizontal tango of his own. http://archiveofourown.org/works/244582

Put on Your Dancing Shoes Dean/Cas. Summary: Dean needs a favor, Castiel is the ideal fake boyfriend, and the Winchester/Campbell clan... helps.
http://archiveofourown.org/works/180892

Accidents Will Happen This is Gen and the main character is an outsider. Summary: Some Goth teenagers accidentally resurrect John Winchester. No, seriously. http://archiveofourown.org/works/35067

As for crossovers, I know of a really good one with the Marvel Universe. It is a two story arc called: Dean Winchester, Agent of SHIELD.
Level 6. Summary: Dean is beginning to think that a stint as Tony Stark’s bodyguard is just a rite of initiation. This is Gen as far as Dean is concerned, however it is Tony/Bruce. http://archiveofourown.org/works/1092559
Things We Lost in the Fire. Summary: Over the years, Dean thinks he may have lost just as much as he’s gained. He means to change all that. This has a bit of Dean/Natasha, but it doesn't do into details. This is not a funny story.
http://archiveofourown.org/works/1359166








Edited 2015-04-13 11:04 pm (UTC)

Thanks!!

Pissedoffeskimo's Funnies (http://archiveofourown.org/works/1567235/chapters/3325892) never never fails to make me giggle. It's Wincest.

There is some suspense/action in glovered's Mountie Duck (http://glovered.livejournal.com/77068.html), but it's mostly a hilarious and schmoopy romp. Jared/Jensen (30,000 words)

The Incestuous Courtship of the Antichrist's Bride (http://fleshflutter.livejournal.com/102268.html) by fleshflutter is much lighter than it sounds. :) There is some angst in there, too, if I remember correctly, but happy ending for sure. Sam/Dean (48,000 words)

some shorter faves

I Wanna Hold You Til I Die (http://lazy-daze.livejournal.com/468887.html) by lazy_daze: first-time Wincest (4600 words)
The Koala Conundrum (http://de-nugis.livejournal.com/110258.html) by de_nugis: "Dean knows too much about koalas and tops the hell out of Sam. It ends well." Wincest (3800 words)
The Time Dean Was Sam's Girlfriend (http://fleshflutter.livejournal.com/5457.html) by fleshflutter: bodyswap, genderswitch, humor. Sam/Jess, Sam/Dean (11,041 words)
Ergonomic (http://archiveofourown.org/works/1415413) by sobrecogimiento: humor, pranks, first-time Wincest (19,301 words)

And astolat's SPN x Harry Potter crossover Old Country (http://archiveofourown.org/works/164479) is great and long, but there is definitely some angst and suspense there. Sam/Dean (40,639 words)

For one of them being an angel:

Kant's Dove (http://tryfanstone.co.uk/kantsdove.htm) by jay_tryfanstone: "In a dystopian paradise angel Inquisitor Samuel and rogue human Dean are uneasy allies. Together, they could knock their world from its foundations, but both of them have secrets to keep." There is a happy ending, but this is not a fluffy fic. angel!Sam, Sam/Dean (34,000 words)

Reanimated (http://tigbit.livejournal.com/81373.html) by tigbit: "n which Jared manages real estate in Heaven and Jensen works as Hell’s attorney in Death Trials. Extreme ambiguity and a distinct lack of beer push Jared to accept a different kind of job in a hotter, more southern locale. The boys meet. Hi-jinks and grocery-stealing in Hell ensue. Featuring saints on book tours, love on trial, after-life bureaucracy, and sin. Surprisingly not as cracktastic as it sounds." Very funny, some angst, happy ending. angel!Jared, Jared/Jensen (80,000 words)

Sorry, I don't have very many long schmoopy fics saved, but I hope you can find something you like!

Second THE INCESTUOUS COURTSHIP OF THE ANTICHRIST'S BRIDE. Hysterical.

One of my favorites when I'm feeling down-and-out is the wonderful leonidaslion's SAM WINCHESTER AND THE TERRIBLE, HORRIBLE, NO GOOD, VERY BAD DAY. Sam-centric, 14K+ words, funny and schmoopy. Very visual, the whole thing plays out in my head.

http://archiveofourown.org/works/181646

dean tries asking cas to prom: Coordination (https://archiveofourown.org/works/4253940) on ao3