Every time I want to give Lion an orgasm I think I should just do it. You know, the long buildup and then the orgasm. But now it feels like there’s pressure to edge him first. Tease him and edge him every other day. Tease him further than last time. There’s always the possibility of a ruined orgasm. Then there’s the possibility of whatever we had the other night which was more than a ruined orgasm. Then there’s last night which was beyond that. I pushed him way too far and he didn’t get his orgasm that he had been anticipating for eleven days.
He’s disappointed. I’m disappointed. We tried again about an hour later, but whether it was really not possible or he was just too upset, I couldn’t get him hard again. Maybe we could try in the morning, but Lion has never been a morning sex kind of guy. In this case, that really sucks because we’ve got a seven hour drive ahead of us and he’s wild and he’s disappointed and I’m mad that I disappointed him and now I’m awake at 5 in the morning writing this and you can imagine how much fun this drive will be.
The worst part is that for a few minutes he thought I was actually trying to push him too far. Why would I do that when I know he’s been waiting eleven days? Why would I do that when he specifically said he didn’t want to come a day early because he was looking forward to “a big send off” for our last trip? I should have just played with him enough to get him excited and then given him his orgasm. Nothing fancy. But I feel pressure to make it fancy. I don’t want him to have a boring orgasm after waiting so long and with him anticipating “a big send off”.
He’s been telling me how much better I am at edging him and how interesting it feels to have multiple ruined orgasms. Do more. Do it more often. He says I’m starting to enjoy things. I think I’m just getting more confident that I can do what he wants and not hurt him. And then something like this happens and the rug is pulled out from under me again.
I’m sure he’ll read this and think we should just stop or that I want to stop. I’m just irritated that I disappointed him and for what? So he could have a better, less vanilla orgasm? Yeah, that worked out. I know I can make him come tonight, but it was supposed to be last night. And I was already thinking about making him come tonight anyway.
I think I’ll go back to my less confident way of doing things. In some ways I feel safer with my insecurities.