Decisions decisions! You drive a hard bargain - but then I'd expect that. As a sub it would depend on whether this was a first meeting with you or meeting after a while, because I'd know I'd been able to cum recently - like the day before - in both cases. In which case I'd be pretty sure I'd click in good time and take the cock cage for a week.
If this was part of a longer session where we'd met up and I'd already had some time in the cage, say the meeting at the end of the week above, then I don't know. My maso side says have a decent cum and take the punishment but we all know that after the orgasm the maso side - mine anyway - takes a back seat and lets me get on with whatever mistake I've agreed to. I'll probably take the cum and the polishing after either week one or two and hope that I get soft enough quick enough so's you can't get to the cock head quite so easily. Some hopes......