I'm trying to find a fic from quite early on (pre-Cas/Apocalypse/etc):
It was one in which Dean somehow ends up kinda daring Sam to take/hold an enema for a certain amount of time, possibly by telling him that he manages it. I think it was mostly non-sexual, although Dean makes Sam lay on the bathroom floor naked while holding the water, which he fails to hold and releases just before the timer Dean had set goes. After he'd cleaned up they went to bed (separately), at which point Dean is thinking that Sam's about to discover that he'd adulterated the water with mineral oil and he was going to be feeling it (leaking?) in the night.
Anybody recognise this?