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Over the course of history there have been a number of pederastic relationships between adult men and adolescent boys which have become part of the historical record. In some of these cases one or both members are notable historical figures, while in other cases the individuals involved are only minor personages, often remembered only for this particular aspect of their lives.

Though all of these relationships are by definition homoerotic in nature, the individuals involved do not necessarily identify themselves as homosexuals. The nature of the relationships have ranged from overtly sexual to what is now commonly referred to as platonic, sometimes out of religious principle.

Limitations of the historical record

In the pre-modern and modern West, their equivocal status has made pederastic relationships difficult to document, since it was in the interest of both participants to keep the relationship secret. According to historian Michael Kaylor,

ince in Victorian England ‘homosexual behaviour became subject to increased legal penalties, notably by the Labouchère Amendment of the Criminal Law Amendment Act of 1885, which extended the law to cover all male homosexual acts, whether committed in public or private’, expecting ‘verifiable data’ concerning their unconventional desires is the ultimate scholarly presumption.

Another obstacle to the documentation of such relationships has been the destruction of "incriminating" personal and public records, either to "preserve the honor" of the individuals involved, or as retribution against their perceived transgressions.

Nevertheless some of these relationships have become public knowledge, usually because one of the members disclosed it as part of his artistic production, or because the relationship came to the attention of the authorities and the legal record was preserved. In recent years, with the greater public acceptance of homosexual expression, such information has become somewhat easier to come by, especially in those cases where the relationship is no longer illegal.

Known or presumed pederastic relationships

In the following list the couples are listed in chronological order, and the name of the older partner precedes that of the younger. Although many more men are known to have engaged in such relationships, only those instances in which the name of the younger partner is known are included. In keeping with various traditions which allow (and actually privilege) chaste pederastic relationships (See Philosophy of pederasty and Nazar ila'l-murd), included below are also relationships in which there is evidence of an erotic component even in the absence of actual sexual relations. The more famous partner is usually the older one but not always so.

Middle Ages

• Waliba ibn al-Hubab and Abu Nuwas
  • Waliba was a teacher of poetry to his beloved, who was to far surpass him in talent and renown. He took the young man (b. 756 C.E.) to Kufa, where he lived an openly gay and bohemian lifestyle, to live with him as his apprentice. Abu Nuwas went on to become a prolific writer of mudhakkarat (boy love) poetry.

• Roger de Pont L'Evêque, Archbishop of York and Walter
  • According to John of Salisbury, Roger had been involved with a beautiful boy who, upon growing up, regretted the relationship and blamed the Archbishop, who had the young man tried and had his eyes gouged out. When he persisted with his accusations, he had him tried again and hanged. The scandal broke in 1152, and Roger escaped his deserved punishment through the efforts of Thomas Becket.

• Mahmud of Ghazni and Ayaz
  • The two, sultan and slave, are paragons of male love in Islamic culture. Their story depicts the power of love of a man for a youth, where the king becomes a slave to his slave. Mahmud appointed Ayaz ruler of Lahore in 1021.

• Ibn Ammar and Muhammad Ibn Abbad Al Mutamid
  • In 1053 the 19-year-old poet Ibn Ammar was appointed tutor to the 13-year-old future ruler of Sevilla, with whom he promptly fell in love. Separated from the boy by his father, they were later reunited but eventually fell out. Al Mutamid killed his old lover with his own hands in 1086, only to then give him a sumptuous funeral.

• Muhammad Ibn Abbad Al Mutamid and Saif
  • "Henri Peres tells us: 'Sodomy is practised in all the courts of the Muluk al-Tawaif. It is sufficient to point out here the love of al-Mutamid for Ibn Ammar and for his page Saif...'"

• Raoul II, Archbishop of Tours and Jean, Archbishop of Orléans
  • Raoul appointed his adolescent lover (also known as "Flora") in 1097 to the post in Orléans over the vehement objections of other prelates.

• Ailred of Rievaulx and Simon
  • Ailred, the abbot of the Cistercian monastery of Rievaulx who was in his mid-twenties in 1135, was in love with a young monk named Simon, about 14 years of age. The relationship is thought to have remained chaste.

Pre-modern period

• Mehmed II and Radu cel Frumos
  • While a hostage at the Ottoman court in the 1440s, Radu (whose epithet, "cel Frumos" means "the Handsome"), younger brother of Vlad III the Impaler, became the beloved of the Sultan, after first refusing his favors and wounding him with his own sword.

• Marsilio Ficino and Giovanni Cavalcanti
  • Ficino lived with the youth at his villa for many years, only separating briefly in 1473, occasion of ardent love letters.

• Leonardo da Vinci and Gian Giacomo Caprotti da Oreno (Il Salaino)
  • An attractive youth with beautiful hair who delighted and exasperated Leonardo ("ladro, bugiardo, ostinato, ghiotto") Salai entered his service in 1490 at 10 and remained for thirty years. His master spoiled the boy with money, food and clothes, and used him as a model for his Saint John the Baptist, a painting related to an erotic charcoal drawing by the artist. Leonardo's physical and emotional attraction to other males have been identified in his art. His relationship with Salai has been seen as homoerotic since the Renaissance, by such writers as Gian Paolo Lomazzo, Walter Pater and Kenneth Clark who, writing in the 1930s, stated that the relationship between the two was of a kind "honored in Classical times and partly tolerated in the Renaissance.".

• Babur and Baburi
  • According to Babur's autobiography, some time around the year 1500,

    In those leisurely days I discovered in myself a strange inclination, nay! as the verse says, I maddened and afflicted myself" for a boy in the camp-bazaar, his very name, Baburi, fitting in.... From time to time Baburi used to come to my presence but out of modesty and bashfulness, I could never look straight at him; how then could I make conversation and recital? In my joy and agitation I could not thank him (for coming); how was it possible for me to reproach him with going away? What power had I to command the duty service to myself? One day, during that time of desire and passion when I was going with companions along a lane and suddenly met him face to face, I got into such a state of confusion that I almost went right off. To look straight at him or put words together was impossible.... In that frothing up of desire and passion, and under that stress of youthful folly, I used to wander, barehead, bare-foot, through street and lane, orchard and vineyard.

• Benedetto Varchi and Giovanni de' Pazzi
  • Varchi's first love affair, around 1525, was with Giovanni, the adolescent son of a local aristocrat. The father had Varchi knifed upon finding his son stole out of the house to spend his nights with his lover. Varchi survived to have other lovers.

• Nicholas Udall and Thomas Cheyney
  • Udall, headmaster at Eton College resigned in 1541 after confessing to having "committed buggery" with his pupil, for which he spent a short time in Marshalsea gaol.

• Pope Julius III and Cardinal Innocenzo Ciocchi Del Monte
  • the 16th-century historian Onofrio Panvinio asserted that Julius was "puerorum amoribus implicitus" (entagled in the love of boys). The future pope "picked up" (the phrase is used by the Catholic Encyclopedia) the illiterate 13 or 14-year-old street urchin in 1547, and the resulting scandal almost cost Julius the election to the papacy, becoming a stap

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