What do you think? (Sorry a little long)

So July 20th I had an appointment for my birth control options, and my period started that day too! My doctor told me about Kyleena IUD and said if I wanted she could insert it that day. So I let her. My boyfriend and I have always used condoms and still want to go continue... But he wants to try not pulling out anymore. So he would finish inside of me (with a condom on, of course). Do you think this is safe? What about no condom?