Don't get a one-size-fits-all things, or a simple S/M/L... You'll never find something that fits right.
maturemetal dot com sells custom cages, but they are expensive - they do, however, provide good tips for measuring.
If you go on Etsy and search "The Guardian" they have a $59 option that you can choose custom sizes. I recently got one of these and it's actually incredibly comfortable, although it does kind of have a pinch point.
I wouldn't wear a chastity device overnight until you know it fits well and how your body reacts - that said, don't worry about a 'keyholder' for now.
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