hmmm, all very good questions.... throughly means to the point he could barely function. It was a planned playtime, that way he would be sure to be clean and prepped. As far as time, I think we were at it about an hour. Tried various positions and a couple of different dildos. We have a long clear one that seemed to be hitting the right spot but he couldn't quite get "there" if you know what I mean. We tried something new last night that I think we both liked and that seemed to take things to the next level. I turned around and leaned against the bed, he then was able to move back and forth at his own speed / depth with encouragement from me. We also worked on him continuing to move through spasms. Usually when I am behind him doing the fucking the spasms push "my cock" out. Ohhh another reason he may have gotten close to a handsfree sissygasm is that it has been several days since he was allowed to cum. Sunday was 77 edges with no happy ending (any idea why 77?), Monday was edges with two ruined orgasms. So last night he was definitely wanting to cum! But again no happy ending.. Maybe tonight will be the night - or not ;-)