I can't remember exactly how old I was the first time I put a finger into my own ass, but I remember liking it. I was probably 15 or 16. I was so guilt ridden about it after the fact that I walked around the house for hours torturing myself with the idea that I was probably gay as a result. What other implication could there be for a man to inserting something into his ass? As airheadedgenius pointed out, it's difficult to escape the power play implications with anything involving a man's behind. For a man, putting something into someone else's ass is macho; putting something into your own hindquarters is a lilting defeat. The alpha versus the limp-wristed beta.
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