i am new to reloading pistol cartridges

i do however reload plenty of rifle just none in the unnecked variety

here are some picts of the problems

step by step of process

#1 new round (federal)
#2 once fired round
#3 cleaned/lubricated/resized
#4 expanded (where problem starts)
#5 - 11 bullet and crimped ( as you can see very messed up)

close up of # 4,5, and 6


cartridges do not fit in pistol when complete(not that i would fire them in this condition any way)