Even with the panty stealing, I can't think of an incident where Akatsuki just did it to get some kicks, or went out his way. Every time its happened, its been a response to someone challenging him in some kind of way, like the maids challenging him when he was leaving and the beach contest where girls where trying to strip him.
I see it more as a humorous "I'll get you before you get me" kind of thing.
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