User blog comment:Miskos3/Fairy Tail Chapter 508: Pleasure and Pain, Review/@comment-86.70.179.73-20161031153436/@comment-30338537-20161031173334

Maybe Zeref had sex with someone in Alvarez and due to him considering the woman as a tool (in this case a tool to please himself), she didn't get killed right off the bat.

Besides, despite being self-loathing and having a death wish, he may occasionally feel the need to torpedo a woman every now and then. Love doesn't always have to be involved, as it is comparible to goign to a whore. Doubt many people would love the whore, you'd just go and do your stuff.