Since I last posted, Barry continues to have increased libido with respect to me (as opposed to masturbation). I firmly believe that Devotional Sex and his chastity device play a key role in this. Since Valentine's Day, he has frequently made efforts to pleasure me (sometimes too often, but I love seeing his desire). He has also not complained about his chastity device, I suspect because he knows he needs that type of control.
Interestingly, last night he broached the subject of pegging with me. He shared how sexy our Valentine's Day experience was with respect to him having the dildo in his bottom. In his words, "it enhanced everything else I did". He asked (almost begged) if I would consider pegging him in the future, even if it didn't result in an orgasm for him. I was a bit surprised, but also pleased with his confession and sharing of need.
I didn't answer right away. I told him that I needed to think about it. After I did so, I came back to his request and shared with him that I would happily consider it. However, I then told him what I was thinking. I suggested that I would use a strap-on dildo to peg him and provide him with a very special experience if he would agree that Carol and Helen would be invited to witness the event. My line of reasoning was that I needed to explore and challenge Barry's degree of submissiveness. It seems to be very strong and this challenge to him would tell me how strong it is.
To my surprise, Barry immediately agreed. He didn't even think about it! My sense of his submissive needs were immediately confirmed.
Soooo, this morning I called Helen and invited to her to come over for coffee. She accepted and we had a very interesting conversation. I shared with some of my discussion with Barry and asked her if she would be willing to again be a witness to what would happen. I didn't know what to expect, since I don't think Helen even knew what "pegging" meant when I started to talk with her. However, she quickly, and excitedly, agreed. She is a very interesting and open woman. I still needed to talk with Carol, but I knew she would love this, so Helen and I set a tentative date of tomorrow evening. I suggested that we have coffee and dessert together, and Helen immediately offered to bring the dessert.
Later today, I called Carol and shared my plans with her, including some of my thoughts about what I would like her to do. She was immediately "all in".
So ... tomorrow evening we will gather. And, Barry is in for some surprises that may challenge him. I think he will like them, based upon what I have observed about his submissiveness.
We shall see ...