In my experience, I actually bled three times on different occasions. 1st was when it was my 1st time being penetrated. 2nd time was when I had a bigger one. 3rd was when there's no preparation and my vagina got a cut. So it's possible to bleed even if it's not your 1st time.
I hope someone uploads better translations soon, dgmr im really thankful for the speed but I am really lost in the sauce plot wise.