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.