Thomas had his will prepared by his attorney from Pikeville in July
1865, he signed with his mark (X). He most likely was in very poor
health and was obviously concerned about the welfare of the family of
his recently deceased son, David.
. Will of Thomas May, Sr. 
Witnessed: July 12, 1865
Filed: Will Book B; pg. 65-66; November 4, 1867
Signed by his mark (X)
Pike County Court October Term 1867
This day the last will and testament of Thomas May Sr. was produced in open court and proved by the oath of R. T. Burns, which was examined, approved by the court and ordered to be filed and recorded in the proper book which is as follows to witt (Viz).
In the Name of God Amen
I, Thomas May, being advanced in age and feeble in boddy but Sound in mind and memery, do make and publish this writing as my Last will and Testament.
First I desire that all my debts be paid.
Secondly, I will to Thomas May, Alice May, Hatler May, William May  , David May, Fanny May, Mary Elizabeth May, Children  of my son David May, and to Mary May his wife or widow, all the lands I own from my Randall grass field or sugar orchard up Robinson Creek and its branches, Except the piece or tract heretofore deeded by me to Thomas May, son of my son David May. It is my will that said Thomas shall have an Equal Share besides the tract heretofore deeded to him by me. So far as the said Mary, wife or widow of my dear son David, is concerned, this will is only to her a Dower interest in said land for her natural life or during her widowhood. Should she marry, it is my will that the whole of said lands go to said children.
Thirdly, it is my will that all the other lands I own including the house and farm I live on shall, at my death, go to my dear wife Dorcas during her Natural Life, and at her death I devise  said land to go Equally to my Children or their heirs.  To wit, Reuben May, Thomas P. May, Cynthia Marrs, William J. May, Samuel May, Dorcas Owens, Henry May, John May, Harvey May, Salley Adkins, Polley Harman and David May. Should my dear wife Dorcas depart This Life before I do, then at my death it is my Will that the Lands above mentioned go to my said children or their heirs as above directed. It is my will that David or his heirs shall have an equal share in said Lands - notwithstanding that already willed to them on Robinson Creek.
Fourthly, I will to Each one of my dear children, except David and Reuben, any amount they may or do owe me. The debts owing to me by my sons, Reuben and David, I do not will to them, but desire that the same be paid into and become part of my Estate.
Fifthly, I will to my dear wife Dorcas, should she survive me, all of my personal property including House Hold Furniture, Kitchen furniture and any money debts that may belong to me or be owing to me at my death. Should my dear wife Dorcas depart this life before me, then I desire that all my personal property, including House Hold and Kitchen furniture and any money belonging to me or debts owing to me be Equally divided among my said children or their heirs. The above devise to my dear wife is upon condition of her remaining widow. Should she marry again she is to have just what the Law allows her.
Sixthly, this will is not to apply to a certain piece of land layed off for my daugther Dorcas Owens and sold by her to my son Thomas P. May. I have given up said piece of land to Thomas and should I die before I make deed to him I desire him to have the same said tract lying from the cross fence by the well where Swinny lives up Shelby Creek running with the cross fence to the top of the Hill and then with the top of the hill.
Seventhly, I hereby appoint my son, Thomas P. May, as Executor to execute and carry into effect this, my last will and testament.
Given under my hand this July 12, 1865.
Attest Hibbard Williamson  Clerk