Tiferet Ḥatanim
Roni Weinstein is interviewed here (Hebrew) about the 17th c. Italian sex and marriage manual Tiferet Ḥatanim. Weinstein, the author of Marriage Rituals Italian Style: A Historical Anthropological Perspective on Early Modern Italian Jews, thinks that Tiferet Ḥatanim may have been the first book of its kind.
This Hebrew editions seems to have been preceded by an English edition titled, Juvenile Sexuality, Kabbalah, and Catholic Reformation in Italy:
Tiferet Bahurim by Pinhas Barukh ben Pelatiyah Monselice.