Depends on how long ago you played. Updates 9 and 10 really finished off the first part of the game while adding new girls for punishment. 11 started the next "chapter" with more girls and school expansions.Speaking of, it´s been a while since I played. Is there only new stuff in updates, or is something added to the start of the game? Is it worth replaying from the beggining? (I have saves)
I would say it might be worth a restart to get everything to happen in order, plus it will refresh your memory coming into the next update.