Very carefully and with copious amounts of lubricant
I’ve yet to venture into that desolate land
My wife said she doesn’t fancy it but would give it a go if I wanted, trouble is, because I know she isn’t keen I just go soft whenever I try , so until she asks me to do it because she wants I don’t think it will ever happen 
Lots of lube, dont be stressed, clean up before
My wife licks and puts her finger in mine. I do the same to her. Need to ramp it up. Want to try pegging and milking my prostate.
Lube me up and have your way. I love it.
My wife has tried it with previous partners and doesn’t enjoy it, so even though I’m interested it’s off the table.
I have found if you can rub the anus the clitoris and penetrate all at the same time it’s the trifecta of jackpot. Work up to it, tease with it by going close but not touching. Make sure your fingers are lubed. If she is on top she can rub her clit on your stomach while you’re inside her and then you can reach out to her anus.
I like to lick it more or less how you taught in this lesson.
I love doing anal play on my wife and she loves receiving it. I really want to experience it but I’m having a hard time pushing through the discomfort.
Never done it, maybe later down the line with my partner
Haven’t had a partner who wanted to do it. I think the size of my penis makes them apprehensive. And I get pretty bad hemorrhoids sometimes so I recoil at being touched there.
My ex loved anal play. If you use lube and good hygiene, there’s nothing to worry about. Of course with new partners I approach it very cautiously.