Well octane and egirlky -
My wife wanted (still wants, I suspect) to watch me both give and take it in my backside.
Also doing her while getting it from behind.
Also oral both ways as well.
With her directing the whole thing like a movie...
It sounds extremely erotic, but I am not into pain - it's just not, well, necessary. When you can take it easy and just work your leisurely way to a mind-blowing orgasm why would you want it to hurt? Not judging, just stating an opinion...
So I think I would want to have some lengthy foreplay - plenty of anal massage (inside and out), making sure I am ready to "take it". There should be a definite sense of seduction - the overcoming of my inner "objections" with the overt use of sensual massage and teasing - just getting me so completely overwhelmed with sensation that I can't wait to have it.
I have had this - from a nurse before I was with my wife - who was REALLY great at it. I kept hoping she had a strap-on tucked away but that never happened.
Once I was really loosened up, I would take whatever direction was given and the whole "very gentle, very slow but very firm" fucking kicks in - I don't know whether I would have to wait for an erection or whether it would last through the penetration. When my wife has used the strap-on in the past that tends to vary.
Once I was being pumped for a while and my wife was able to watch as much as she wanted I would want to enter her.
I would need to get her ready just the same way octane describes - and her being able to watch in a mirror would be just the thing.
I suspect I wouldn't be able to last too long either - although there is the idea that once I had cum she would want to do me with the strap-on while I do the guy in the back.
She likes the idea of the prostate massage making me hard before I am fully recuperated - that she could "force" me to have another orgasm.
She's kind of bossy...but lots of fun.