Cumming was born in west London in 1916. He trained at Hammersmith College of Art and at the Royal Academy Schools, where he won the Silver Medal for drawing. During the Second World War he served with the RAF and the Air Sea Rescue service in Malta, where he often drew portraits of his comrades in return for extra rations. Drawings from his sketchbooks, of life in besieged, wartime Malta, as well as a later oil painting of the rescue boat of which he was part of the crew, can be seen at the Imperial War Museum in Valetta. Following the war he worked as a freelance artist and illustrator before combining painting with teaching in 1950, when he became lecturer at the City of Oxford School of Art – exhibiting widely in Oxford and London, and receiving many private commissions. In 1960 he moved to Dorset, took up the post of lecturer at Bournemouth and Poole college of art. In 1979 he retired and moved with his family to Iwerne Minster in north Dorset, where he lived and painted until his death.