No! But I have come damn close a few times...my cock is large and sometime I will make a girl start to show blood before her main period starts....I have probably had a couple of dozen time where i eat a girl out then fucked her and then she start bleeding on my dick...thank god not in my mouth ...hell just three days ago it happened with my wife.
Now one of my friends has had it happen.....said he swallowed a blood clot!!!!!!!!