Play with the goal for him not to cum too early. Each roll must be completed or the other player gets to do their choice. You need a toy for each of you and a butt plug. Lube will also help. Shower together before play and have a drink while playing. Each roll you do all 3 actions before rolling again. She will probably cum during this so have him choose how he wants to cum including position and hole. He can also choose to cum inside or on her. She must end with however he wants. You must play at least 7 rounds before finishing: if uncomfortable with anal you may skip those and roll again.
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