Earlier quoted context omitted.
It doesn't matter how many dates you've been on, if you do this and the person didn't want that you are committing an assault. You don't get a license to do something just because you invested some amount of time or energy into dating, saying otherwise is a direct promotion of rape (remember, the majority of rapes are committed by someone known to the survivor).
That advice is also for after you've been (consensually) kissing, fondling, fingering, etc. At some point the meaning of "sexual assault" will be so diluted it's meaningless.
Sexual assault is crystal clear, you can do whatever you want with your partner(s) with consent, nobody cares at that point. The minute you take past activity as a license to do what you want without someone's permission is the minute you cross the line into assault.