I have given Gregory many hand spankings by now. I love spanking him, and I love doing it with my hand. I generally like to touch his butt, but spanking his butt is one of my favorite things to do. It´s such a personal and emotional thing. I feel close to him while spanking him, and I love that during these spankings he lets me do with him pretty much whatever I want to ;-)
A little while ago I gave him one of those hand spankings, but then I completely changed my modus operandi. I told him to get up and show me his butt plugs. He was quite surprised by my request, but did as I told him. He presented all the toys he owns and I chose one and told him to insert it into his pretty butt.
He looked at me a bit stunned and asked: "Now?"
And I only smiled at him and said: "Yes, now. I wanna watch you inserting it and I wanna watch you wearing it."
I could actually see his face turning red. He could not hide his embarassment. And for some reason the fact that he had to insert it himself made it mentally even more challenging for him. It is one thing to use a butt plug in the privacy of your home and alone. But letting me watch was obviously a bit difficult for him.
He did as he was told though and I enjoyed his show. I was on the bed, fully relaxed, while he was presenting himelf to me completely naked, with an ass still red from the spanking, and butt pluged.
It was so much fun for me, but I could tell that it was quite difficult for him. I will never forget the sign of relieve on his face when I finally allowed him to take it out again.
I asked him yesterday: "can we do something like this again? I know you did not like it too much at the time."
And his reply was:"Sure. It was good. Embarassing butt good ;-) ".