At some point Jereme Rogers decided his talent on a skateboard would also translate to a successful music career. He did have an instant audience at his disposal. The results have been less than what he might have expected.
Rapping about sex is a fine line. More often than not it just comes across really uncomfortable for teh listener.
Lil B, Odd Future et al can get away with ridiculous sexual braggadocio because of their lo-fi approach to it. Similarly when people just go over the top, the comic element takes away some of humanity away from what is usually an intensely personal act.

And, like bragging in general, if you’re a really good rapper, with good production, you can say what you like. because it’ll sound good so who cares, right?

J. Casanova kinda misses the mark on everything, yet I still feel compelled to watch him. He’s entertaining and I can’t help but feel it’s all an elaborate ploy, an in-joke that he hasn’t shared with us, the viewer just yet. Check out the soundboard and the election speech. It has to be a set-up to an epic reveal.
Jereme Rogers Soundboard. Seriously.