Preperation for anal sex

[clumsy123]

Hi, I'm new here so I'm sorry if I accidentally break any rules or anything, I don't mean to!
I'm biologically male, and I am interested in anal sex, however I have only had it once before and it wasn't the best experience. Despite later practice with a toy I have never been able to achieve insertion very far without pain, and I'm worried about the possibility of cleanliness and accidents when sexual intercourse arises.
I guess my question has two parts:
1 - what should I be doing in the long run to prepare my body for anal penetration? Should I practice with toys, if so how regularly, etc
2 - what should I be doing to prepare in the short term (i.e. day of)? Should I douche, take fibre pills, something else, or a combination?
I know this could be a subjective thing, but I've found a lot of conflicting and often incredibly impractical advice online, so I'm hoping for some perspective from real people who practice what they preach!

[Sam W]

Hi clumsy123,

In terms of practice, I would say that can be helpful in the sense that masturbation more generally is. That is, experimenting with anal stimulation helps you learn what does and doesn't feel good, and things like how much lube you need or how slow you need to go in order for it to be pleasurable. But you can't really practice on one day, or several days, and expect that your body will still be ready for anal stimulation days or weeks down the road. Part of that is that the anus and rectum are muscles; they tense and relax, and they have a resting state, rather than being something you can permanently stretch out.

In terms of in the moment preparation, I like the way this article breaks down what to consider when it comes to having safe, pleasurable anal sex: Anal Sex Lowdown. As far as douching goes, while it's up to you whether it would make you feel comfortable to do, it's not necessary in order to have anal sex; anal sex involves the rectum, which isn't where fecal matter is actually stored.