He was raised outside of Boston and went to public schools for his education. Later, as an undergraduate, he attended the University of Vermont and then spent a year in France at the University of Nice.Stephen worked a series of unrelated jobs including teaching yoga, working at a hotel, a kindergarten, and manning an ice cream stand. He worked as a travel agent for many years before moving to Brooklyn in the 1980s. There he attended adult learning centers to take some writing classes before enrolling in Columbia University's writing program. The writer Stephen Koch gave him the idea to begin work on his first novel.

His stories, articles and reviews have appeared in Gay Community News, Bay Windows, the Boston Phoenix, the New York Times Book Review, Vogue, House & Garden, Details, Vanity Fair, Harper's, and Travel and Leisure, among others.

Stephen is an alum of the Ragdale Foundation.