First off, I wouldn’t worry about grossness during a conversation about anal. But uh, I guess grossness warning on the below for anyone squeamish about talking about butt stuff and the related potential outcomes.

Shit happens, sometimes literally when you are talkin’ butt stuff, sometimes even despite multiple cleanses. Not saying you have to be into it when it does, but its good to be prepared for it both mentally (haha oops that’s my shit on the condom/strap/toy) and in terms of clean up (extra rubbers, tissues, toy cleaner, whatevs)

And for sure don’t do anal if you might have hemorrhoids, and maybe see a doctor too for that matter; I’m only familiar with them from a former partner having gotten them once but external ones are usually visually noticeable (or noticeable by touch if you don’t want to take a butthole pic but it’ll probs hurt.) They described the pain as extreme so you’d probably know if you had them but I’m guessing that’s not a guarantee? But yeah, any wound that could potentially open up and that is near shit is possible recipe for a really bad time, so probably doctor if you are worried about them.

I’m personally familiar with the sensitivity for wiping though; it hasn’t prevented me from enjoying a back door buddy so long as I’m mindful of not doing it for a little while after bleeding has happened. But I’ve found that I have that issue most often when my diet is terrible; a good clean diet with fiber (alternatively, a bad diet but with a multivitamin and benefiber can get a lot of the way there in my experience) can help with that.

Also as a reminder I’m just some non-doctor person on the internet who likes anal and has a pretty candid friend group so someone else may have better, less anecdotal input or experiences which contradict what has worked for me. I’m just hoping that sharing my experience with it might help others seeking to try it.