Artist Malcolm McKesson was married to poet Madeline Mason for 48 years but never had sex with her–or anyone else, for that matter. “It just wasn’t something I was interested in,” McKesson says. Of course, he’s not counting those few times in Germany at the end of the war, with the little boy sitting on his uniformed lap and the tingle of arousal just sort of sneaking up on him. If you want to speculate about that, well…”I’ve found that if I hold a cat I get the same feeling,” he says.

Not to say McKesson hasn’t had a sex life. He has, and at the age of 87, has still. But except for the anomalies already mentioned and a few episodes of, say, stripping, binding, and dancing in empty churches, it’s mostly been in his head, in the dense ink drawings he’s been doing for the last 15 years or so, and in his recently published autobiographical fantasy novel, Matriarchy: Freedom in Bondage. There he exists in a permanent state of submission and arousal–a beautiful boy poised somewhere between innocent youth and the full flower of womanhood.

McKesson was born into privilege, his daddy being a cofounder of the pharmaceutical giant McKesson & Robbins. Raised in post-Edwardian opulence on Manhattan’s Upper West Side, he attended private schools, graduated from Harvard, met his wife at a debutante ball, served in the army during World War II, and went into the family business. It should have been clear sailing, but from the time they cut his curls and took him out of those white linen dresses boys wore until they were ready for knickers, something was out of whack. The only thing McKesson excelled at was failure. Uncomfortable in his own body, yearning to be a woman “just for a day” (and occasionally dressing like one), he was a miserable student, a disappointing husband, and a hopelessly inept businessman who quickly drove a company his father set up for him into the ground. While his wife collected awards for inventing a new sonnet form, palled around with the Roosevelts and the Junior League, and published prose under male pseudonyms, he struggled to eke out a living as an animal caretaker for a cancer research project using…cats. After that he took what he calls a worse job–teaching art in New York City public schools. Finally, in the early 60s, his mother relieved him of the need to support himself and his wife, and he began to live as an artist.

For a long time McKesson took landscapes and buildings as his subjects, but all the while he was thinking about ways to use the human figure in his work. In the 1980s he began the obsessive drawings of his fantasy life that have become his oeuvre. Influenced by an unforgettable glimpse of S&M illustrations that circulated among German soldiers during the war and by a lot of time spent looking at etchings, his distinctive style evolved–a murky ground of crosshatched scribble that gives rise to semiluminous humanoids engaged in ritualistic scenes. The limbs hang like marionettes, the bodies are round and white as snowmen, the faces anonymous as death’s heads. “They’re all me,” says McKesson. On the back of each drawing he would jot an explanatory title: “Little mistress and her slave play together,” or, for a figure handcuffed to a wall for a whipping, “Young man being prepared for marriage.”

In 1994, about the time a friend took him to the New York City Outsider Art Fair, where he was “discovered,” McKesson began to string these title fragments together for his genteel, if not quite proper, coming-of-age novel. Gerald, a young man who senses he should have been a girl, has grown up in Manhattan under the thumb of a domineering mother. The year before he is to enter Harvard, he meets an older woman, Gladys von Gunthardt, who is even more powerful than mama. She takes him into her home, renames him Rose, dresses him alternately in women’s clothes and a bondage version of a page boy costume, and trains him to be her slave. Once his “manly nature” has been “curbed” by physical punishment, the action mostly consists of Gerald parading around in tights and high heels while the mistress takes her tea. This is so much fun that he persuades his sister to flee their parents and join von Gunthardt’s household. The mistress teaches her to whip her brother and promises to set them both up as artists. In the end, Gerald/Rose and the mistress marry, with the groom coming down the aisle (a la Dennis Rodman) in a long white silk gown. Everyone is ecstatic and fulfilled.

In real life, McKesson’s only sister died young, “of depression,” he assumes. But in Madeline Mason, who died in 1990, he had–at least on some level–the flesh-and-blood incarnation of his dream dominatrix. As for freedom, he found it when he was able to declare his bondage to art. He thinks his experience is “not uncommon,” and that people will be glad someone came out with it.

McKesson will be at the Henry Boxer Gallery booth at Outsiders Inside, the outsider, visionary, and folk art fair being held this weekend at 847 W. Jackson, 3rd floor. British cultural historian Tony Thorne will lecture on McKesson at 2:30 on Saturday. The fair runs from 10 to 8 Saturday and 10 to 6 Sunday; admission is $5. Call 773-281-3705 for more information. –Deanna Isaacs

Art accompanying story in printed newspaper (not available in this archive): Malcolm McKesson photo by Hirokuki Ito/ “Presentation” photo.