I know being respectful of others is critical on sites like this. Everyone is weird to some degree, and we should tolerate each other's little armadillos. Uh may have the wrong word there, sorry. But you get the idea. Play nice, be respectful.
Having said that, a little lighthearted stroll along Weirdness Lane isn't harmful, is it? On the older site for alternative wrestling, Globalfight, seeing one amusing entry led me to do a keyword search. A guy wanted to "wrestle for steaks." The search found around a half dozen similar entries. I know a loser buys dinner challenge might make sense. But the interests outlined in the profiles strongly suggested the intent was that the loser would be well done, without an assist from a chef.
A guy wanted to do a brother versus brother match with me. Sounded good, until he said we needed to become blood brothers first, by cutting a finger a little and exchanging blood. I decided to remain an only child.
The times I was asked if I would ride a guy like a horse or a pig (think Deliverance - the movie, not the theological concept) didn't surprise me. But riding a guy like a turtle, super slowly? That request produced a disturbing mental image, with the part of the turtle head going in and out of the shell being played by an uncircumcised penis. I passed on terrapin pinning.
I get the almost infinite variety of gear possibilities, including the bizarre requests, with one exception. Nude except for a Hawaiian lei. That match didn't happen so I didn't get lei-ed.
A little online trash talking is great fun. But one guy went from "make you tap out" to "I'll unscrew the motel lamp light bulb and shove it up your ass, then squeeze your ass cheeks until it breaks." That seemed way too well thought out in advance.
I guess the conclusion here is that it's always okay to ask a possible opponent if a particular behavior would be acceptable, as long as the person asking does not respond to rejection with rudeness.