Wait until they're mostly undressed, and preferably in a semi-private place. Otherwise, it's kind of inconvenient.
If you have a set of rules for this sort of thing that are rigid, I think you're robbing yourself of opportunity for enrichment. It depends entirely on the situation, and the person. Wait until you're BOTH comfortable, or at least willing to set aside some of the discomfort for fun or adventure, or love...
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Time flies like an arrow, fruit flies
like a banana.
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