I've played twice with Mondage since the last time I wrote. We've been pushing some bounderies (all with T's permishion obviously). Monday, I shaved him, which he found odd but eventually came to accept. I think he looks much better this way. Cleaner and more neat in every way. Besides, I wasn't going to go anywhere near his ass when he was all hairy and such. So shaving was just something that needed to be done.
And yes. His ass. That's one of the things he said early on that he didn't want to play with.. And one of the things I decided early on that I'd make him come to terms with. He's got some.. issues.. with his sexuality. The standard "sex = dirty and bad" routine. However, we're working on overcomming that. Late in December, or perhaps early January, he told me that he might have changed his mind on the ass being a no-go zone. I'm happy he came to that realisation on his own. I didn't push him into it, it was a (relativly) natural developpement. That's a good thing.
Anyhow, this Monday, after shaving him and tying him up and doing that regular stuff, I started stimulating his anus opening. I used a gloved, well lubed finger. Not only did he accept it, he said he enjoyed it. That was a significantly better reception than I'd expected. Not long after, I had first one and then two fingers well planted deep in his ass. I did not expect to get that far with him so fast, but was very pleased that I did. While I said it felt very weird, he also said he enjoyed it. The sensations made him horny. That was really a great step towards a more liberal, accepting and exploring sexuality. He did well that day.
Later in the day, I whipped him with licorice strands. Or kinkorice, as we call it. The strands kept breaking on me. I need to get me a propper whip sometime soon. Anyhow, I whipped him all over the body, trying to push him into crying. Pushing him hard enough to have him break down a little, but not so hard as to get codeworded. It took alot of work, but we got there. He was gaged all the time, and having him sobbing and crying with the gag, knowing it was me who caused it.. Knowing he COULD have stopped it, but chose not to... Call me insane, but that was really sexy. It's interesting to observe that pushing him to crying was easier with tickling than with pain..
He didn't come during that play session, and I forbade him to ejaculate in the days following. I'd see him again five days later, Saturday. The last two nights before seeing me again, he was also told to somehow stimulate himself, but not cum. He chose to use bondage, not surprisingly, and although he was very tempted, he did as he was told. He didn't come.
Yesterday, we had a few other BDSM friends over. I started out with tying a friend of ours into a hogtie, and then tying up Mondage in a hogtie right next to her. He's fantasized about similar situations, and although it wasn't exactly what he wanted, it got close. Later on, after everyone else had left, I continued playing with Mondage. Did some neat bondage on his arms, making a corset-like tightening mechanism that enabled me great controll on how tight his arms were bound. I'll post pics soon. I also did a bit of spanking, on the "sweet spot" where the ass becomes the inner thigh. I wasn't rough with him, just wanted to see if I could have him enjoy it.. But he's still not thrilled about that. I also carefully snapped my fingers on his balls, hit really near them etc. He took it, it didn't hurt him, but he was really nervous. Guess CBT still lies some way in the future. Hehe.
We ended the night with Mondage in a hogtie, a ball gag in place and my thumb up his ass. There was almost no breath controll, just the stimulation of the bondage itself.. And my thumb up his ass. And he came! Feeling him cumming FROM THE INSIDE, now that was a real power trip! His muscles contracting, his pulse, I could feel it all. Very, very cool. Will definitly do that again!