Well, you're sort of right about the Principal. Like you, it's a long time since I played that scene so I just checked; Jessica initiates the spanking bit but the Principal suggests the cheerleading uniform. I still find that whole situation a pretty sad stereotype though. She may well be a good journalist, but too often resorts to using her sexuality as a short-cut to success.
That is why I prefer her relationships with Christian, Heather, Mr Parker Tommy, and so on, where the flirtation and exploration is just that.