Boylove in Ancient Greece was quite common between older men (lover Erastes) and boys (beloved eromenos), and was not unusual or frowned upon. The most common place where men would go to meet boys was the palaestra (the Greek word for their version of a gymnasium) where older men watched the young boys exercising. This being the case, only leisured aristocrats with time on their hands probably really engaged in homosexual affairs. Only when men carried on a relationship with a boy who entered adulthood was the man scorned.
Once a man had selected a boy from the palaestra, the next step would be to take him to the andreion, a sort of men's club or meeting hall. The youth received gifts, and the philetor along with the friends went away with him for two months into the countryside, where they hunted and feasted. At this end of this time, the philetor presented the youth with three contractually required gifts: military attire, an ox, and a drinking cup. Other costly gifts followed. In Crete, in order for the suitor to carry out the ritual abduction, the father had to approve him as worthy of the honor. However, according to Aeschines, Athenian fathers would pray that their sons would be handsome and attractive, with the full knowledge that they would then attract the attention of men and "be the objects of fights because of erotic passions."
Copulation with the pederast was a choice the boy could make; it was not required. Pederast/Catamite relationships were not monogamous; both boys and men were free to engage in as many of these such relationships as they chose. Typically, 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.
Pederasty was the idealized form of an age-structured homoeroticism that had other, less idealized manifestations, such as prostitution or the sexual use of slave boys. Paying free youths for sex was prohibited. Free youths who did behave as prostitutes and sold their favors, outside of the socially sanctioned gifts (See: Trochus/Hoop), were ridiculed, and later in life might be prohibited from performing certain official functions.
Pederasty as an institution in ancient Greek society assisted in forming strong life-long bonds between the erastes and eromenos, who often would go into battle together. It served as a type of apprenticeship where the adult male was expected to teach the young man or to see to his education, and to give him certain appropriate ceremonial gifts. The adult lover would assist in the process of the acculturation and integration of the youth into adult life. Pederastic (boylove) myths often depict the process of initiation and transformation of the boy into adult male life  through the allegorical "death and transfiguration" of the youth signifying that he was no longer a boy but a free adult ready to enter into the rank, responsibility, and privilege of adult society.
Vase paintings and an obsession with the beloved's appealing 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.
Anal sex is depicted, but far more rarely. The evidence is not explicit and is open to interpretation. Some vase paintings, which 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 perhaps seen as passive and unmanly for a free boy. Oral sex is likewise not depicted, or is indicated only indirectly; anal or oral penetration may have been reserved for prostitutes or slaves however to what extent such practices were engaged in by men and free youths is unknown.
- Stephen Batchelor: The Ancient Greeks for Dummies — John Wiley & Sons, 2008. — ISBN 978-0-470-98787-2