I have sat down with him and told him that the only part of this that is roleplaying, is the part where I ruin his life. I told him the blackmailing is more of a game, and I would never actually show those pictures to anyone. He was put at ease by this, I seem to be the mix of safety and threatening that works. I just don't have a lot of ideas for blackmail, it isn't something I ever needed to do.

~Miss Sadi Stick

When it comes to blackmailing, cameras and video are like the cream and sugar to your coffee!!! I'll give you one suggestion but thats it, let your devious imagination run wild :D

Get a nice, cute little hidden camera device and plant it in the bedroom or wherever you are doing your scene. Let the scene be as humiliating as possible, HE ESPECIALLY HAS TO SAY SOMETHING THAT IS SO UTTERLY HUMILIATING INTO THE CAMERA WITHOUT HIS KNOWLEDGE OF BEING CAPTURED ON CAMERA! Then when its all over, viola :) BLACKMAIL c'est bon no?