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First hentai scene:
Lose to bandit leader in 3rd guild mission (lose virginity)
This is apparently key to sending you down either the light path (the boy Ruth (?) gets ill) or the dark path (you go bodyguard duty for an illegal casino).
Light path still has hentai in it.
Dark path is much seedier and nastier and has loads of hentai.
I think (not sure) you have to lose to the flower monster in the quest for cure for Ruth maybe. The end boss guy for that quest. Not sure atm but that sends you down the dark path.
Edit: I read a partial walkthrough, loads in japanese but some in english:
(SPOILERS)
http://www.ulmf.org/bbs/showpost.php?p=831521&postcount=203
btw, hentai scenes occur as animations in combat after you have lost your virginity. As combat moves by monsters.