Mary Henly arrested for wearing men’s clothing, “seeming to confound the course of nature,” 1692
Mary Henly, a female-assigned individual in Middlesex County, Massachusetts, was arrested in 1692 for wearing men’s clothing, the charges stated that such behavior was “seeming to confound the course of nature.”
Source: Elizabeth Reis, "Hermaphrodites and 'same-sex' sex in early America. In T. A. Foster, ed., Long before Stonewall: Histories of Same-Sex Sexuality in Early America (pp. 144–163, New York University Press, 2007), p. 152, citing Records of the Middlesex County Court, 1691-1692, vols. 1689-1699, n. p. as cited in Lawrence W. Towner,"The Indentures of Boston's Poor Apprentices: 1734-1805," Transactions, Colonial Society of Massachusetts, 43 (1956-1963), pp. 417-468.