Lots of funny things happen in my roleplays. and it's honestly hard to pick one out of everything and remember it since so many memories come back and I am sure I am missing some. I did just wake up.
Most recently a character had his underwear stolen, she refused to return it. A struggle followed and then she pointed out his collection of Disney movies to stun him while she escaped! It made me laugh a lot because he is a rather large, rough man covered in scars and not exactly the type you'd expect to watch Disney things. The whole scene had me smiling the entire time.
One of my biggest, baddest guys was trying to coerce the group into withdrawing and leaving him be for his plan to succeed. The PCs were, in true PC fashion, having none of it and obviously passed the pretty hard difficulty check to be unfazed by the threats.
Resorting to violence, then, my big antagonist revealed a stationary automatic 50 cal machine gun and pulled the trigger: it jammed on the second shot. The group made short work of him after that.
There are a lot of funny stuff that comes up, most of it's unintentional. I've even experienced stuff like SHOVED IT IN. (LOL) @Skyle
The funniest that was well written and put together was a cum filled condom. So imagine a Minotaur with a huge ass dick pounding a condom wrapped cock into your characters stomach, because the neck just wasn't long enough. Then cumming enough to expand the condom, and make taking it out practically impossible. The condom was released off his dick, but they tied it around my character's throat with a knot and then left.