What is the ruling on supplicating with the words: "O Allah, make me the first of my family to die"? And is it permissible to say: "O Allah, do not deprive me of my family, nor cause me grief concerning them," or "O Allah, let me enjoy my family for as long as You grant me life"? And is this considered an transgression in supplication?

It is disliked to wish for death due to a hardship that has befallen a person, unless one fears temptation concerning their religion. Wishing for martyrdom is not forbidden; rather, it is recommended. As for praying for a long life for one's parents and for oneself to die before them, it is permissible, but it is contrary to what is most preferable. What is most preferable is to pray for what benefits one in the Hereafter, because lifespans are predetermined, and "had you asked Allah to protect you from punishment in the Fire, or punishment in the grave, it would have been better and more excellent." It is most preferable to pray for oneself and one's parents for forgiveness, mercy, and happiness in this world and the Hereafter, and to ask Allah for patience and contentment with His decrees.