A few odd comments on here! But lots of good advice. yet no-one has mentioned using plugs! So I shall remedy :-) I'm writing a book on BDSM for submissives and I wrote a chapter on this.
After a bit of trying various ones, I think the best ones are the silicone ones - you can get them from Ann Summers. Buy a few in different sizes. Also buy coconut oil. It's is the best lube I have ever found plus you can eat it. Otherwise you will need lubes specially designed for anal that remain slippy and dont go all tacky. Dont use coconut with condoms.
I do this bit on my own. If I know anal is on the cards then I go somewhere quiet. Liberally cover the plug and insert. Take your time, twisting gently helps. It may take up to 5 mins or even longer to do this. The plug needs to remain in situ for a bit. For me it is ten minutes or so. Ensure you have lube on the outside of your body as that is where rubbing can happen.
Then when you are ready, lots of lube on cock and off you go!
Someone upthread said this is the one where the woman takes charge. Totally agree. Go slow to begin but once you are open and have done it for a few mins then you can subject yourself to a brutal ass fucking if that's your thing.
Some misinformation I'd like to correct
No; it doesn't feel like you are having a poo
No; there may be traces of poo on the plug but most waste matter is kept in the bowl
It may bring on the need to go to the toilet
No; you dont need to always go slow. Build up the pace gradually. Slow is key to avoid pain and to let the sphincter gradually stretch
Some of the best positions are actually women on back variations.
Put a vibe on your clit and you may well have one of the most earth shattering orgasms. Ever. I cant last more than 20 seconds without coming this way. I temporarily lose the vision around the edges of my eyes. You may also find that your legs stiffen as you cum. Totally normal and you will recover
As long as you are respectful of your body and dont over indulge, it is safe. Some people do anal training to keep themselves open all the time but I personally dont think it's the way to go. Even though I have been regularly doing it for 4 years or so, I still need to use a plug. I prefer it that way.
Piles issue? Well that may be caused by the type of plug, or rather what it is made out of. Or the sphincter not be properly stretched slowly. That's why I switched to silicone. No issues now
It is entirely possible to do anal dry. I have on several occasions. But best to use lots of lube first
But my one golden rule is that if the man wants anal and is totally unprepared to deal with the gunk, then I would not do it. Period. That's part and package of the deal in my book.