Pederasty is the sexual relationship between an adult male and a pubescing boy or a young man (corresponding to an age of about 12 to 20). In the news media, this term tends to be used incorrectly as a synonym for pedophilia, even though the latter designates the sexual attraction of adults to prepubescent boys or girls.

Before the 20th century, homosexual relationships with a more or less pederastic element were possibly the usual pattern of male same-sex love. In Ancient Greece, pederasty was an integral part of the mentoring of an adolescent by an adult. The sex, as shown by vase paintings of the time, mostly consisted of intimate touching of the younger male by the older or of a form of sex in which the older one rubbed his penis between the thighs of the younger one. This form of ritualized anal sex (FYI: intercrural intercourse, ie. intercourse between the thighs, does not involve the anus), again judging by the vase paintings, was to be endured by the youth without physical excitement. Real anal sex, that is sex involving anal penetration, was not allowed to happen to a free (that is, not enslaved) male and boys or young men who tolerated being penetrated were generally ridiculed.

The usual explanation given for the pederastic sex act as part of Greek education is that the Greeks believed that the semen of the older man transported his power and virility to the younger one, strengthening him. This belief in special powers of the male semen is nothing specifically Greek and exists in some New Guinean cultures, for example, as well.

The most important part of the mentorship by an influential older man for the youth was the aspect of social networking, thus it was considered desirable to have had many older lovers / mentors in younger years, both attesting ones physical beauty and paving the way for attaining important positions in society. Even after their sexual relationship had ended and the young man had married, the older man and his protégé would remain on close terms throughout their life.

In Roman times, pederasty lost its status as a vital part of education and was instead recognized as an activity primarily driven by one's sexual desires. The social acceptance of pederastic relations waxed and waned during the centuries, but was probably most highly regarded during the time of emperor Hadrian, who erected statues of his beloved and prematurely deceased Antinous throughout the Roman Empire.

The dawn of Christianity meant that pederasty became socially unacceptable, as the Bible condemned all forms of homosexual activities. Reality of course was a different matter---especially in monasteries pederastic and other types of sexuality were quite prominent.

The Renaissance not only revived the Roman and Greek art and literature, but the more open social climate, certainly at least in part based on the economical prosperity of the time, allowed more freedom in sexual ways, even if those strayed from what the Bible allowed. Both Shakespeare's sonnets and Marlowe's poetry, among others, revolve around androgynous beauties that seem to lie somewhere between boyish and girlish in looks and demeanor. Perhaps this special kind of beauty can be attributed to the boy actors, young boys who played all the female parts on the stage at the time.

In the 19th century, the gradual discovery of the sites of antiquity in Italy and Greece fueled a new interest, if not almost a hysteria, in these old civilizations, particularly in Great Britain and Germany. Accordingly, pederastic relationships again became en vogue in the life and work of artists, for example in poetry (Walt Whitman, Lord Byron, Johann Wolfgang von Goethe), literature (Oscar Wilde), art (Henry Scott Tuke), and photography (Wilhelm von Gloeden).

The end of the 19th century, marked by the trial against Oscar Wilde, more or less brought the end for the social acceptance of pederasty. This is exemplified by the Young Wandervogel movement, an organization similar to the Boy Scouts, but emphasizing a more romantic view of nature. Young Wandervogel was itself spawned by the Wandervogel movement and was quite open about its gay / pederastic tendencies, although this kind of affection was supposed to be expressed in a mostly nonsexual way. The founding of Young Wandervogel happened largely as a reaction to the public scandal about the erotic tendencies in Wandervogel, which was said to alienate young men from women.

Starting in the 1960s, the gay liberation movement made progress in having the laws against homosexual sex lifted that had existed in several countries. Also as part of the sexual revolution, the legal age of consent was lowered somewhat and usually set equal for heterosexual and homosexual sex. With a change in the homosexual beauty ideal from boyish to masculine, homosexual relationships tended to become more equalized in terms of age difference.

Today, pederastic relationships have a difficult, somewhat polarized social status. On one hand, the media capitalize on sex scandals that involve either pederasty of pedophilia, like the one in the Catholic Church, because people take an (perhaps partly voyeuristic) interest in these matters. On the other hand, sexual liberation and the presence of media like the Internet cause homosexual youths to discover their sexuality and have their Coming Out at a much younger age than before, and frequently they enter first relationships with males somewhat older than themselves, prompting mixed emotional reactions from their parents.

See also: List of pedophiles and pederasts.