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Malcolm McKesson was born in Monmouth Beach, New Jersey at the summerhouse of his wealthy New York City family. He completed the Grand Tour of Europe twice before turning eighteen, and these trips piqued his interest in art history, which he later studied at Harvard University. His grandfather died in 1924 and his eldest brother in 1927.
McKesson graduated from Harvard University in 1933 and experienced another death in 1936, this time that of his beloved sister Mary. He served as a second lieutenant during World War II, marrying poet Madeline Mason at Fort McClellan, Alabama in 1942. Upon returning to New York, he began working in the family chemical company. This he would do until 1961, when with Mason’s support he was able to retire from the business world and devote his life to his secret creation. Other than his early retirement, the couple led a conventional middle-class life in New York City, summering in the Catskills and serving on the boards of a variety of community organizations; none of their friends could ever have guessed at McKesson’s other life.
Madeline Mason died in 1990. Three years later, McKesson approached dealers at the New York Outsider Art Fair. Although he did not necessarily think of himself as an outsider, based on the other work he had seen there, he felt that here was an audience that might appreciate him.
Template:Review His writing explores themes of gender identity, transvestism, and sado-masochism. All of these are developed in his magnum opus, Matriarchy: Freedom in Bondage, a semi-autobiographical erotic novella that has been compared to such classics as Venus in Furs and Story of O.
Matriarchy follows the sexual transformation of Harvard undergraduate Gerald Graham, who willingly subjects himself to the authority of the stern Lady Gladys. She teaches him to "curb his manly nature" by forcing him to take on the role and costume of a lady's maid named Rose. The house is a matriarchy because, as Lady Gladys explains, "in this house all things feminine are blessed, all things masculine are bound in slavery" (McKesson 1997, p. 46).
Gerald's first transformation into Rose is described thus:
"From a closet she removed some padded silken forms. These were strapped tightly to his shoulders and waist, adding a more feminine shape to his thighs, breasts and buttocks. In this upholstery Rose was indeed a proper woman prepared to assume the black dress, the slip and the elegant apron of a serving maid" (McKesson 1997, p. 34).
Much of Gerald's training also involves elaborate sexual bondage devices such as the "Walking Machine." This consists of two horizontal bars, the lower padded and at crotch-height and the upper with a collar in the middle of it. Gerald is fitted in high heels and fixed into the device, which "rolls with greatest ease and steadies my body at the neck and at the crotch. If I miss my footing, it is painfully disciplinary" (McKesson 1997, p. 32).
Interestingly, the narrative voice shifts from first person into third person as Gerald subjects himself more and more to his lady's authority.
He is also given a bondage device to wear while away at Harvard, so that he can never truly forget his mistress. She straps him into "a tight belt strapped around his waist... attached [to] a kind of suspender which passed over each shoulder and through the belt at his pelvis. This done, she moved the cord down to his thighs, looped it around his legs and tied them into a tight knot high up his thighs near his crotch. She felt the scrotum and was satisfied that all was smugly bound" (McKesson 1997, p. 73).
At the conclusion of the work, and the conclusion of Gerald's training, Lady Gladys and Gerald are united in a symbolic marriage. He repeats the pledge: "I, Gerald Graham, surnamed Rose, do hereby submit myself, body, soul, and spirit, to the will and pleasure of my great mistress Gladys, to serve her all the days of her life. In token of this pledge, I herewith place my hands in hers in total submission" (McKesson 1997, p. 170). She replies, "Now you are a man because you have your mistress... Together we shall do great things in the world" (McKesson 1997, p. 171).
Matriarchy is illustrated by hundreds of intensely worked ballpoint drawings. While McKesson was presumably in a state of great sexual excitement while crafting them, they are not pornographic in the least. Figures are defined vaguely, modeled by voluptuous and androgynous masses. The scribbles and hatch marks that make up the figures are also reminiscent of the chiaroscuro technique, and all of the scenes appear to take place in dim lighting.
- McKesson, Malcolm. (1997). Matriarchy: Freedom in Bondage. Heck Editions. ISBN 0-9638129-7-1.
- Rhodes, Colin. (2002). "Fulfillments of desire in the work of a self-taught artist: the intimate existence of Malcolm McKesson." Journal of the Association of Art Historians. 25 (5), 649-675.