It is said Naomasa was the only man Ieyasu, who didn't much like homosexuality, loved; though homosexuality was so common in samurai society at that time that it was regarded as one of a samurai's accomplishments, and being loved by a lord was the fastest way to advance (other examples include Nobunaga ODA and Toshiie MAEDA, Kagekatsu UESUGI and Naganori KIYONO, Masamune DATE and Shigetsuna KATAKURA/Sakujuro TADANO).
当時の武士階級では衆道は武士の嗜みともいわれるほど一般的であり、主君の寵童出身であることは出世への近道でもあったが（その例として織田信長‐前田利家など、上杉景勝‐清野長範、伊達政宗‐片倉重綱・只野作十郎が挙げられる）、直政は衆道をあまり好まなかった家康が唯一愛した男性だとも言われている。