What are the chances of pregnancy accruing if a guy sticks it in a few times then puts condom on during fertile week. No ejaculation at all that night?

Very High chances. There is a very high chance of getting pregnant this way.~60-85%. This is due to the fact sperm can survive in your vagina for a long time and you have no way of knowing exactly when you are ovulating. Even when we are helping women get pregnant we cannot tell the exact time. Please always use a condom for protection against STDs and for Birth control I recommend and IUD, or Birth Control pills.