He asked me for enforced male chastity play something like five years ago. I recognize a lot of what I didn't like in it (which wasn't everything, I had fun!) in threads here. Basically, he wanted me to use chastity as a kind of 'husband improvement program" with a lot of rules and punishments. I don't need more kids to raise and told him I didn't want to police him. We played on and off for maybe three years and then stopped because I went back to school and was just way too busy. So now I'm done with school, back on regular hours, and we started up again last week. I told him that this time, I'd only play if it's my rules, which are:
1) We play for as long as I want to play. If he wants to stop, then the game is really over and might never restart.
2) The default is that he can't cum. If I want him to cum I'll tell him, and otherwise I don't want him asking me. If I didn't say anything, it's no.
3) He wanted to use a cage for when I'm at work (I work at a hospital, he often works at home). Cages are not a turn-on for me. They're just so......so.....

So what I'm looking for, in two areas. First, I know he has all these ideas around me keeping him locked up for a month or more, but for me doing a week or two at a stretch is way more my speed. I almost never went past three weeks back when we played before. If I ask him, he just says it's up to me and that he can go longer than I'd think. But I'm not really interested in that (more in a sec), but I think shorter works for him anyway. When he's really wound up like this, a single orgasm doesn't even seem to wipe him out anyway.
And second, just trying to deal with sex in this game. I occasionally like oral, but for me sex is mostly PinV. When he gets too aroused (like from his kinks!) then he can't last or will start/stop, which is just frustrating. Sex for us is normally 1-2 times a week, and I'm not really up for making that once every month or two. J has suggested a strap on, but that would likely only work as a novelty for me, and it really needs to be realistic in feel. I have one dildo now (of about 20 I tried) that I like, mainly because it (once warmed up) feels almost exactly like the real thing.