Yet another thing I'd forgotten to document: Tuesday almost two weeks ago, I played with Winnie. A bit of bondage, some not-so-hard spanking and some breath control. I wasn't planing on the breath control, but noticed he started breathing heavily anytime I got close to his mouth. So I asked, he said it was ok, and I did it. And it really, really turned him on. So that was fun. :) Didn't push any boundaries or anything, just nice and easy.
After I'd untied him, he stayed small and quiet for at least a couple of minutes. That's an accomplishment I'm very pleased with, as he's usually very cocky. Your typica naughty sub, joking and teasing just about everyone, in the hope that someone will take him firmly in hand. While I understand the reasons behind his behavior, it sometimes gets a bit annoying. So when I finally was able to get him down, all quiet and subservient, it felt very nice.
We talked quite a bit afterwards. It's very rewarding the way he trusts me. He doesn't trust easily.