In parts of Greece, pederasty was an acceptable form of homoeroticism that had other, less socially accepted manifestations, such as the sexual use of slaves or being a pornos (prostitute) or hetairos (the male equivalent of a hetaira). Male prostitution was treated as a perfectly routine matter and visiting prostitutes of either sex was considered completely acceptable for a male citizen. However, adolescent citizens of free status who prostituted themselves were sometimes ridiculed, and were permanently prohibited by Attic law from performing some seven official functions because it was believed that since they had sold their own body "for the pleasure of others" (ἐφ' ὕβρει, eph' hybrei), they would not hesitate to sell the interests of the community as a whole. If they, or an adult citizen of free status who had prostituted himself, performed any of the official functions prohibited to them by law (in later life), they were liable to prosecution and punishment. However, if they did not perform those specific functions, did not present themselves for the allocation of those functions and declared themselves ineligible if they were somehow mistakenly elected to perform those specific functions, they were safe from prosecution and punishment. As non-citizens visiting or residing in a city-state could not perform official functions in any case whatsoever, they could prostitute themselves as much as they wanted.

Transgressions of the customs pertaining to the proper expression of homosexuality within the bounds of pederaistia could be used to damage the reputation of a public figure. In his speech "Against Timarchus" in 346 BC, the Athenian politician Aeschines argues against further allowing Timarchus, an experienced middle-aged politician, certain political rights, as Attic law prohibited anyone who had prostituted himself from exercising those rights and Timarchus was known to have spent his adolescence as the sexual partner of a series of wealthy men in order to obtain money. Such a law existed because it was believed that anyone who had sold their own body would not hesitate to sell the interests of the city-state. Aeschines won his case, and Timarchus was sentenced to atimia (disenfranchisement and civic disempowerment).

By contrast, as expressed in Pausanias' speech in Plato's Symposium, pederastic love was said to be favorable to democracy and feared by tyrants, because the bond between the erastês and erômenos was stronger than that of obedience to a despotic ruler. Athenaeus states that "Hieronymus the Aristotelian says that love with boys was fashionable because several tyrannies had been overturned by young men in their prime, joined together as comrades in mutual sympathy". He gives as examples of such pederastic couples the Athenians Harmodius and Aristogeiton, who were credited (perhaps symbolically) with the overthrow of the tyrant Hippias and the establishment of democracy, and also Chariton and Melanippus. Others, such as Aristotle, claimed that the Cretan lawgivers encouraged pederasty as a means of population control, by directing love and sexual desire into non-procreative channels:

{{quote|and the lawgiver has devised many wise measures to secure the benefit of moderation at table, and the segregation of the women in order that they may not bear many children, for which purpose he instituted association with the male sex.|

Phaedrus in Plato's Symposium remarks:

For I know not any greater blessing to a young man who is beginning in life than a virtuous lover, or to a lover than a beloved youth. For the principle, I say, neither kindred, nor honor, nor wealth, nor any motive is able to implant so well as love. Of what am I speaking? Of the sense of honor and dishonor, without which neither states nor individuals ever do any good or great work… And if there were only some way of contriving that a state or an army should be made up of lovers and their loves, they would be the very best governors of their own city, abstaining from all dishonor and emulating one another in honor; and it is scarcely an exaggeration to say that when fighting at each other's side, although a mere handful, they would overcome the world.

In Laws, Plato takes a much more austere stance to homosexuality than in previous works, stating:

... one certainly should not fail to observe that when male unites with female for procreation the pleasure experienced is held to be due to nature, but contrary to nature when male mates with male or female with female, and that those first guilty of such enormities [the Cretans] were impelled by their slavery to pleasure. And we all accuse the Cretans of concocting the story about Ganymede.

Plato states here that "we all", possibly referring to society as a whole or simply his social group, believe the story of Ganymede's homosexuality to have been fabricated by the Cretans to justify immoral behaviours. The Athenian stranger in Plato's Laws blames pederasty for promoting civil strife and driving many to their wits' end, and recommends the prohibition of sexual intercourse with youths, laying out a path whereby this may be accomplished.

The myth of Ganymede's abduction by Zeus was invoked as a precedent for the pederastic relationship, as Theognis asserts to a friend:

There is some pleasure in loving a boy (paidophilein), since once in fact even the son of Cronus [that is, Zeus], king of immortals, fell in love with Ganymede, seized him, carried him off to Olympus, and made him divine, keeping the lovely bloom of boyhood (paideia). So, don't be astonished, Simonides, that I too have been revealed as captivated by love for a handsome boy.

The myth of Ganymede's abduction, however, was not taken seriously by some in Athenian society, and deemed to be a Cretan fabrication designed to justify homoeroticism.

The 5th century BC poet Pindar constructed the story of a sexual pederastic relationship between Poseidon and Pelops, intended to replace an earlier story of cannibalism that Pindar deemed an unsavoury representation of the Gods. The story tells of Poseidon's love for a mortal boy, Pelops, who wins a chariot race with help from his admirer Poseidon.

Though examples of such a custom exist in earlier Greek works, myths providing examples of young men who were the lovers of gods began to emerge in Classical literature, around the 6th century BC. In these later tales, pederastic love is ascribed to Zeus (with Ganymede), Poseidon (with Pelops), Apollo (with Cyparissus, Hyacinthus and Admetus), Orpheus, Heracles, Dionysus, Hermes, and Pan. All the Olympian gods except Ares are purported to have had these relationships, which some scholars argue demonstrates that the specific customs of paiderastia originated in initiatory rituals.

Myths attributed to the homosexuality of Dionysus are very late and often post-pagan additions. The tale of Dionysus and Ampelos was written by the Egyptian poet Nonnus sometime between the 4th and 5th centuries CE, making it unreliable. Likewise, the tale of Dionysus and Polymnus, which tells that the former anally masturbated with a fig branch over the latter's grave, was written by Christians, whose aim was to discredit pagan mythology.

Dover, however, believed that these myths are only literary versions expressing or explaining the "overt" homosexuality of Greek Archaic culture, the distinctiveness of which he contrasted to attitudes in other ancient societies such as Egypt and Israel.

Greek vase painting is a major source for scholars seeking to understand attitudes and practices associated with paiderastia. Hundreds of pederastic scenes are depicted on Attic black-figure vases. In the early 20th century, John Beazley classified pederastic vases into three types:

• The erastês and erômenos stand facing each other; the erastês, knees bent, reaches with one hand for the beloved's chin and with the other for his genitals.
• The erastês presents the erômenos with a small gift, sometimes an animal.
• The standing lovers engage in intercrural sex.

Certain gifts traditionally given by the erômenos became symbols that contributed to interpreting a given scene as pederastic. Animal gifts—most commonly hares and roosters, but also deer and felines—point toward hunting as an aristocratic pastime and as a metaphor for sexual pursuit. These animal gifts were commonly given to boys, whereas women often received money as a gift for sex. This difference in gifts furthered the closeness of pederastic relations. Women received money as a product of the sexual exchange and boys were given culturally significant gifts. Gifts given to boys are commonly depicted in ancient Greek art, but money given to women for sex is not.

The explicit nature of some images has led in particular to discussions of whether the erômenos took active pleasure in the sex act. In most images of pederastic scenes the youthful beloved is pictured without an erection; his penis "remains flaccid even in circumstances to which one would expect the penis of any healthy adolescent to respond willy-nilly". One painting on a bowl from the Athens National Museum shows a pederastic scene where both of the figures have erect penises.

Fondling the youth's genitals was one of the most common images of pederastic courtship on vases, a gesture indicated also in Aristophanes' comedy Birds (line 142). Some vases do show the younger partner as sexually responsive, prompting one scholar to wonder, "What can the point of this act have been unless lovers in fact derived some pleasure from feeling and watching the boy's developing organ wake up and respond to their manual stimulation?"

Chronological study of the vase paintings reveals a changing aesthetic in the depiction of the erômenos. In the 6th century BC, he is a young beardless man with long hair, of adult height and physique, usually nude. As the 5th century begins, he has become smaller and slighter, "barely pubescent", and often draped as a girl would be. No inferences about social customs should be based on this element of the courtship scene alone.

There are many pederastic references among the works of the Megaran poet Theognis addressed to Cyrnus (Greek Kyrnos). Some portions of the Theognidean corpus are probably not by the individual from Megara, but rather represent "several generations of wisdom poetry". The poems are "social, political, or ethical precepts transmitted to Cyrnus as part of his formation into an adult Megarian aristocrat in Theognis' own image".

The relationship between Theognis and Kyrnos eludes categorization. Although it was assumed in antiquity that Kyrnos was the poet's erômenos, the poems that are most explicitly erotic are not addressed to him—the poetry on "the joys and sorrows" of pederasty seem more apt for sharing with a fellow erastês, perhaps in the setting of the symposium—"the relationship, in any case, is left vague".

In general, Theognis (and the tradition that appears under his name) treats the pederastic relationship as heavily pedagogical. Theocritus, a Hellenistic poet, describes a kissing contest for youths that took place at the tomb of a certain Diocles of Megara, a warrior renowned for his love of boys; he notes that invoking Ganymede was proper to the occasion.

Vase paintings and references to the erômenos's thighs in poetry indicate that when the pederastic couple engaged in sex acts, the preferred form was intercrural. To preserve his dignity and honor, the erômenos limits the man who desires him to penetration between closed thighs.

Some vase paintings, which historian William Percy considers a fourth type of pederastic scene in addition to Beazley's three, show the erastês seated with an erection and the erômenos either approaching or climbing into his lap. The composition of these scenes is the same as that for depictions of women mounting men who are seated and aroused for intercourse. As a cultural norm considered apart from personal preference, anal penetration was most often seen as dishonorable to the one penetrated, or shameful, because of "its potential appearance of being turned into a woman" and because it was feared that it may distract the erômenos from playing the active, penetrative role later in life. A fable attributed to Aesop tells how Aeschyne (Shame) consented to enter the human body from behind only as long as Eros did not follow the same path, and would fly away at once if he did. A man who acted as the receiver during anal intercourse may have been the recipient of the insult "kinaidos", meaning effeminate. No shame was associated with intercrural penetration or any other act that did not involve anal penetration. This interpretation is largely based on the thesis presented by Kenneth Dover in 1979. Oral sex is likewise not depicted, or directly suggested; anal and oral penetration seem to have been reserved for prostitutes or slaves.

Dover maintained that the erômenos was ideally not supposed to feel "unmanly" desire for the erastês. Nussbaum argues that the depiction of the erômenos as deriving no sexual pleasure from sex with the erastês "may well be a cultural norm that conceals a more complicated reality", as the erômenos is known to have frequently felt intense affection for his erastês and there is evidence that he experienced sexual arousal with him as well. In Plato's Phaedrus, it is related that, with time, the erômenos develops a "passionate longing" for his erastês and a "reciprocal love" (anteros) for him that is a replica of the erastês’ love. The erômenos is also said to have a desire "similar to the erastes', albeit weaker, to see, to touch, to kiss and to lie with him".

Many of the practices described above concern Athens, while Attic pottery is a major source for modern scholars attempting to understand the institution of pederasty. In Athens, as elsewhere, pederastia appears to have been characteristic of the aristocracy. The age of youth depicted has been estimated variously from 12 to 18. A number of Athenian laws addressed the pederastic relationship.

Unlike the Dorians, where an older male would usually have only one erômenos (younger boy), in the east a man might have several erômenoi over the course of his life. Poems of Alcaeus indicate that the older male would customarily invite his erômenos to dine with him.

Greek pederasty was seemingly already institutionalized in Crete at the time of Thaletas, which included a "Dance of Naked Youths". It has been suggested both Crete and Sparta influenced Athenian pederasty.

The nature of Spartan pederasty is in dispute among ancient sources and modern historians. Some think Spartan views on pederasty and homoeroticism were more chaste than those of other parts of Greece, while others find no significant difference between them.

According to Xenophon, a relationship ("association") between a man and a boy could be tolerated, but only if it was based around friendship and love and not solely around physical, sexual attraction, in which case it was considered "an abomination" tantamount to incest. Conversely, Plutarch states that, when Spartan boys reached puberty, they became available for sexual relationships with older males. Aelian talks about the responsibilities of an older Spartan citizen to younger less sexually experienced males.

Historian Thomas F. Scanlon argues Sparta, during its Dorian polis time, was the first city to practice athletic nudity, and one of the first to formalize pederasty. Sparta also imported Thaletas' songs from Crete.

In Sparta, the erastês was regarded as a guardian of the erômenos and was held responsible for any wrongdoings of the latter. Researchers of the Spartan civilization, such as Paul Cartledge, remain uncertain about the sexual aspect of the institution. Cartledge underscores that the terms "εισπνήλας" ("eispnílas") and "αΐτας" ("aḯtas") have a moralistic and pedagogic content, indicating a relationship with a paternalistic character, but argues that sexual relations were possible in some or most cases. The nature of these possible sexual relations remains, however, disputed and lost to history.

Megara cultivated good relations with Sparta, and may have been culturally attracted to emulate Spartan practices in the 7th century, when pederasty is postulated to have first been formalized in Dorian cities. One of the first cities after Sparta to be associated with the custom of athletic nudity, Megara was home to the runner Orsippus who was famed as the first to run the footrace naked at the Olympic Games and "first of all Greeks to be crowned victor naked". In one poem, the Megaran poet Theognis saw athletic nudity as a prelude to pederasty, writing, "Happy is the lover who works out naked / And then goes home to sleep all day with a beautiful boy."

The legislator Philolaus of Corinth, lover of the stadion race winner Diocles of Corinth at the Ancient Olympic Games of 728 BC, crafted laws for the Thebans in the 8th century BC that gave special support to male unions, contributing to the development of Theban pederasty in which, unlike other places in ancient Greece, it favored the continuity of the union of male couples even after the younger man reached adulthood, as was the case with him and Diocles, who lived together in Thebes until the end of their lives.

According to Plutarch, Theban pederasty was instituted as an educational device for boys in order to "soften, while they were young, their natural fierceness", and to "temper the manners and characters of the youth". According to tradition, the Sacred Band of Thebes comprised pederastic couples.

Boeotian pottery, in contrast to that of Athens, does not exhibit the three types of pederastic scenes identified by Beazley. The limited survival and cataloguing of pottery that can be proven to have been made in Boeotia diminishes the value of this evidence in distinguishing a specifically local tradition of paiderastia.

The ethical views held in ancient societies, such as Athens, Thebes, Crete, Sparta, Elis and others, on the practice of pederasty have been explored by scholars only since the end of the 19th century. One of the first to do so was John Addington Symonds, who wrote his seminal work A Problem in Greek Ethics in 1873, but after a private edition of 10 copies (1883), only in 1901 was the work published in revised form.

Edward Carpenter expanded the scope of the study, with his 1914 work, Intermediate Types among Primitive Folk. The text examines homoerotic practices of all types, not only pederastic ones, and ranges over cultures spanning the globe. In Germany the study was continued by classicist Paul Brandt writing under the pseudonym Hans Licht, who published Sexual Life in Ancient Greece in 1932.

Kenneth J. Dover's seminal Greek Homosexuality (1978) triggered a number of debates which still continue. 20th-century sociologist Michel Foucault declared that pederasty was "problematized" in Greek culture, that it was "the object of a special—and especially intense—moral preoccupation", which was "subjected to an interplay of positive and negative interplays so complex as to make the ethics that governed it difficult to decipher". A modern line of thought leading from Dover to Foucault to David M. Halperin holds that the erômenos did not reciprocate the love and desire of the erastês, and that the relationship was factored on a sexual domination of the younger by the older, a politics of penetration held to be true of all adult male Athenians' relations with their social inferiors—boys, women and slaves. This theory was also propounded by Eva Keuls.

Similarly, Enid Bloch argues that many Greek boys in these relationships may have been traumatized by knowing that they were violating social customs, since the "most shameful thing that could happen to any Greek male was penetration by another male". She further argues that vases showing "a boy standing perfectly still as a man reaches out for his genitals" indicate the boy may have been "psychologically immobilized, unable to move or run away". From this and the previous perspectives, the relationships are characterized and factored on a power differential between the participants, and as essentially asymmetrical.

Other scholars point to more artwork on vases, poetry and philosophical works such as the Platonic discussion of anteros, "love returned", all of which show tenderness and desire and love on the part of the erômenos matching and responding to that of the erastês. Critics of the posture defended by Dover, Bloch and their followers also point out that they ignore all material which argued against their "overly theoretical" interpretation of a human and emotional relationship and counter that "clearly, a mutual, consensual bond was formed", and that it is "a modern fairy tale that the younger erômenos was never aroused".

Halperin's position has been criticized by Thomas K. Hubbard as a "persistently negative and judgmental rhetoric implying exploitation and domination as the fundamental characteristics of pre-modern sexual models", challenging it as a polemic of "mainstream assimilationist gay apologists" and an attempt to "demonize and purge from the movement" all non-orthodox male sexualities, especially those involving adults and adolescents.

As classical historian Robin Osborne has pointed out, historical discussion of paiderastia is complicated by 21st-century moral standards:

It is the historian's job to draw attention to the personal, social, political and indeed moral issues behind the literary and artistic representations of the Greek world. The historian's job is to present pederasty and all, to make sure that … we come face to face with the way the glory that was Greece was part of a world in which many of our own core values find themselves challenged rather than reinforced.

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• Media related to Pederasty in ancient Greece at Wikimedia Commons