Let the dice decide how your night will go.
Assumes couple is comfortable with plugs in both of their asses and woman is comfortable with anal but man is not comfortable with strapons or dildos.
See Advanced version for couples fully comfortable with anal play:
https://naughtygrin.com/luvdice/64382See Beginner version if man is not comfortable with anal play:
https://naughtygrin.com/luvdice/64459
Are you sure
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YES
NO