Malcolm McKesson: Ballpoint Drawings and a Private Matriarchy

Malcolm McKesson (24 July 1909 – 5 February 1999) was an American outsider artist. He is known for ballpoint drawings he worked over and over, and for erotic fiction full of feminization, bondage, and matriarchal discipline. His wife was the poet Madeline Mason-Manheim. For decades he kept a middle-class public life and, in private, a world of androgynous figures, lady’s-maid training, and sadomasochistic devotion. Only late did he approach the outsider-art market that made his name.

He was born in Monmouth Beach, New Jersey, in the summer house of a wealthy New York family. Before he was eighteen he had done the Grand Tour of Europe twice. He later studied art history at Harvard. Deaths piled up while he was young: his grandfather in 1924, his eldest brother in 1927, his sister Mary in 1936. He entered Harvard College in 1933 and graduated in 1937. In the Second World War he served as a second lieutenant. In 1942 he married Madeline Mason-Manheim at Fort McClellan, Alabama. Back in New York he worked at the family chemical company until 1961. With Mason’s support he left business and made art in secret. To everyone else the couple kept an ordinary schedule: New York, summers in the Catskills, community boards. Friends did not know about the other vocation. Madeline Mason died in 1990. In 1993, three years later, McKesson went looking for dealers at the New York Outsider Art Fair. He did not necessarily call himself an outsider. He thought viewers who already responded to self-taught, visionary work might not reject his drawings the way a mainstream gallery would.

Matriarchy: Freedom in Bondage

His prose takes up gender identity, cross-dressing, and sadomasochism. The peak is the semi-autobiographical novella Matriarchy: Freedom in Bondage, published by Heck Editions in 1997 (ISBN 0-9638129-7-1). Harvard undergraduate Gerald Graham willingly hands himself to the stern Lady Gladys. She trains him to “curb his manly nature” and forces him into the clothes and role of the lady’s maid Rose. The house is a matriarchy because, as the book puts it, “in this house all things feminine are blessed, all things masculine are bound in slavery.” The training uses elaborate sexual bondage devices. When Gerald gives himself over completely, the narration slips from first person into third, a formal match for an ego dissolving under authority. For BDSM readers this is literary femdom and forced feminization, not a manual for a real scene. The ethics stay with the reader.

The book holds hundreds of fine ballpoint drawings. Figures with vague outlines turn, in dim light, into plump androgynous masses. The secret retirement years, the ballpoint, and the matriarchal SM story put him in outsider art and in erotic bibliography at the same time. Colin Rhodes’s 2002 essay “Fulfillments of desire in the work of a self-taught artist: the intimate existence of Malcolm McKesson” is a main scholarly way in. McKesson does not sit on the usual Sade or Sacher-Masoch shelf. He was a wealthy retiree who spent decades writing a private religion of feminine supremacy and bound masculinity, then briefly opened the door at an outsider art fair.