It sounds like clickbait, but this is the honest, straightforward truth. I'm not talking about expensive sex toys or rigorous stretching and dilation routines (though I can coach you through those, too).
I'm talking about a bidet. Specifically, a bidet with a warm water connection. That's it!
Generally speaking, pleasurable anal sex is the result of a sufficiently relaxed (warmed-up) hole and enough consistent lubrication to avoid any unpleasant friction. (Obviously some people enjoy anal pain and friction, but this post isn't really for y'all unless you would like to experiment with an alternate methodology.) So, if we are going to get fucked in the ass, we either need to rely on a conscientious top who will take the time to get us prepped and ready for smooth and easy penetration, or we need to accept that this world is filled with unconscientious tops that we will need to prep ourselves in anticipation of.
A warm water bidet is like a pressure-variable hydro massage for the asshole and surrounding erogenous areas. The more things that go in and around your asshole, the more accustomed your asshole becomes to allowing things in and around it without a reflexive tightening response. Bidets can act as an anal massage and also gently clean out the rectum, creating a shit-free environment for fingers, dicks, and toys that when done properly can eliminate the need for an enema (if you're looking to get fisted or fucked by more gigantic objects, I'd recommend a more thorough clean-out than what a typical bidet can offer, but that is a different blog post).
It also bears mentioning, this is a good way to experience anal pleasure if you live in a situation where you can't have traditional sex toys around. Washing one's ass is basic hygiene and honestly I don't understand why they aren't a standard appliance in any bathroom with plumbing. (Actually I do know why – bidets were historically associated with prostitutes, and so they went out of favor so respectable people could distance themselves from women practicing good hygiene. Because some people are so whorephobic they would insist on nations of unclean asses. Anyway.)
I write this because a number of clients over the years who are new to bottoming have expressed shame or insecurity because, while they do know what they want, they feel like they don't know what they are doing. I appreciate this honesty, because I get to remind them that by reaching out to a professional and expressing their desires and asking for help accessing those experiences, they are making it happen for themselves. Sometimes it feels like we don't know what we are doing, but we actually just need to reach out to someone who can show us how. And some of the things that can make the biggest difference are both easy and discreet.
In my opinion, an important early stage of getting comfortable getting fucked is getting comfortable with your relationship to/with your ass. Our assholes can hold stress, trauma, memories, and feelings, but it can also release all of those things from our bodies. Remember to start slow, start simple, and make your bum the squeaky clean temple of worship it was born to be.