This is similar to a wandering eye, but applies to nipples. With a wandering eye, one eye looks in one direction, while the other, for unknown reasons, looks in another direction. With a wanering nipple, one nipple points in one direction and the other nipple is not similarly directionally aligned. This usually results from a bad boob job.
Man, she had a wandering nipple. I didn't know where to look. I think she must have had a botched tit job.
A wandering hype man is simply a random person on the street that likes to hype people up when the situation calls for it.
Those guys over there were being super loud last night.
Yeah they were playing a drinking game and a wandering hype man came up and started turning up with the rest of them and they all just went nuts.