With the onset of adolescence in Book II, Augustine enters what he seems to consider the most lurid and sinful period of his life. He "ran wild," he writes, "in the jungle of erotic adventures...and became putrid in [God's] sight." In addition to his first sexual escapades, Augustine is also quite concerned with an incident in which he and some friends stole pears from a neighborhood orchard. Augustine deeply regrets both of these sins, and offers a few brief insights as to how and why he committed them.
[II.1-4] Though sinful in acting out his erotic desires, Augustine gives himself some credit, writing that "the single desire that dominated my search for delight was simply to love and be loved." Again, God has given Augustine only good properties, and it is his own fault for misdirecting those properties. In this case, the problem was that his love had "no restraint imposed [on it] by the exchange of mind with mind." Hence, pure love was perverted by its misdirection toward worldly things (bodies). Ideally, according to Augustine, sex is used only for procreation, and even then only in a relationship focused not on lust but on a loving, rational partnership (as he sees Adam and Eve relating before their fall).
[II.5-8] Having finished grade school at this point, Augustine was preparing to leave for Carthage for further study. His father Patrick had managed to raise funds for this, and Augustine praises him for trying so hard to educate his son. Still, he notes, his father had no proper moral concern for him--as was the overwhelming custom, education was seen simply as a means to worldly success.
"But in my mother's heart," writes Augustine, "you had already begun your temple." The Catholic Monica often admonished young Augustine against fornication, and he now recognizes that God was speaking through her. At the time, however, her warnings seemed "womanish advice which I would have blushed to take the least notice of." Eventually, Monica tends to lets Augustine do as he will, fearing that a proper wife at this stage would impede his chances for a good career.
[II.9-14] Augustine considers the theft of the pears next. What particularly disturbs him about this teenage prank is that he did it out of no other motive than a desire to do wrong. "I loved my fall [into sin]," he writes. The pears were not stolen for their beauty, their taste, or their nourishment (there were better pears at home), but out of sheer mischief.
Investigating this point further, Augustine again concludes that his actions simply represent a human perversion of his God-given goodness. In fact, each thing he sought to gain from stealing the pears (and everything humans desire in sinning) turns out to be a twisted version of one of God's attributes. In a remarkable rhetorical feat, Augustine matches each sinful desire with a desire to be like God: pride seeks loftiness (and God is the highest), perverse curiosity desires knowledge (and God knows all), idleness is really aiming at "quietude" (and God is unchanging in his eternal repose), and so on.
The underlying theme here is, again, Neoplatonic. For the Neoplatonists, all creation (the material world) has "turned away" from God's perfection, becoming scattered into a chaotic state of mutability, temporality, and multiplicity. God remains unchangeable, eternal, and unified, and creation always seeks (whether it realizes it or not) to return to God. Here, Augustine has argued that even sin itself fundamentally aims at a return to God.
[II.15-18] Book II ends with a consideration of the peer pressure on which Augustine partly blames the theft of the pears. The main lesson he takes from this is that "friendship can be a dangerous enemy, a seduction of the mind." Like love, it must be subjected to reason if it is to be truly good.