Over the weekend, Barry and I had a lengthy discussion concerning what to do next with respect to role playing. The conversation began when I asked him if he'd like to continue developing the "Corporate" Punishment scene was have been working with, or whether he wanted to move on to something new. As we worked through it, we decided that the current scenario has more potential that can be explored, so we decided to continue with it for a bit. Last night, Barry brought up the subject and told me that he has been thinking about where we could go with the scenario. He then completely surprised me when he said he would like to see us involve the first secretary (the one who had warned my new secretary) and or involve his wife along with his current secretary. After recovering from the surprise, I asked him how he planned to involve two women in the same scene. Of course, he had thought this through. He suggested that we take an overnight trip to Chicago, where we could enlist the aid of a professional disciplinarian or fetish escort, similar to what he did years ago. He was quite disappointed that I immediately said "No, we are not going to pay someone to do this sort of thing with us!"
This afternoon, I proposed a different solution to Barry. I asked him what he thought about my sister, Carol, playing the role of a second woman. Barry immediately protested that Carol doesn't even know that Susan spanks me. I then had to confess that Carol does know about Barry getting spanked. I explained that a month or so ago I had asked Carol to retrieve something from or bedroom for me and didn't realize that we had carelessly left several of our spanking implements on the dresser. Carol didn't miss seeing them and she began asking lots of questions when she returned from the bedroom. So, Carol knows!
Barry wasn't exactly thrilled about that development. However, he also didn't immediately rule out Carol as our assistant. That led to a discussion of how Barry would feel having Carol see him naked and spanking him. He wasn't sure, but he decided he would think about it. So, that's where it is at the moment. I suspect we will talk more later tonight or tomorrow.
I am also very aware that we had a disasterous situation a couple of years ago when Barry's sister was involved with his birthday spanking. She took over and gave Barry much more than he bargained for. However, that relationship is very different from that of my sister and Barry. I think it could work. My sister is certainly open minded and curious enough to probably want to do it. But, the final call needs to be Barry's. I suspect it may depend upon how badly he wants to be spanked by two women at the same time. That seems to be a major unfulfilled fantasy of his.
I will keep you posted ...