Bouldin was born on September 28, 1838, in Charlotte Court House, the son of Wood Bouldin (1811–1876) and his first wife, Maria Louisa Barksdale Bouldin. His father was a prominent attorney, member of the, and a judge of the Virginia Supreme Court of Appeals from 1872 until his death.
Bouldin’s education began at Rough Creek Church in Charlotte County. He attended the University of Virginia from 1855 to 1857 and returned for one year in 1859 to study law with James P. Holcombe and John B. Minor. Bouldin began the practice of law with his father in Boydton, but on September 23, 1861, he joined the Staunton Hill Artillery and served as aduring the Civil War. Afterward he practiced law in Charlotte, Halifax, and Mecklenburg counties until 1871, when he moved to Richmond. There he practiced in partnership with his father and Hunter H. Marshall and later with James Alfred Jones until 1879. On December 9 of that year he married Florence H. Easley, daughter of James S. Easley, of Halifax County. Bouldin resided for the rest of his life in that county’s seat of Houston, later called Halifax. He and his wife had three sons and three daughters.
Constitutional Convention of 1900–1901
After the convention, Bouldin returned to the quiet practice of law in Houston, but in 1905 he succeeded William Leigh as commonwealth’s attorney after Leigh moved from Halifax County. Bouldin subsequently won election to a full term and was a candidate for reelection when he died suddenly at his home on April 11, 1911. He was buried the following day in the graveyard at nearby Saint John’s Episcopal Church.