I dont understand what you mean by the second part!
BlankCanvas,
I have not tried it, and forget about the second part I dont know how to explain it.
If your foreskin is tight it is reasonble to be concerned about your foreskin getting stuck. Sometime foreskin do get stuck behind the head. When that happens it is called paraphimosis. You can look it up on the Internet.
You say your foreskin goes back part way and then rolls up on top of itself. This suggests to me that you probably have a short frenulum that is preventing complete retraction. The frenulum is the connectiive tissue under the head that connects the head with the foreskin. That condition is called "frenulum breve". When you are hard and you pull your foreskin back, does the head bend down toward the ground? If it does that suggests that you probably have frenulum breve. You can also look that up on the Internet.
You can clean out your foreskin without retracting it by using a rubber bulb ear syringe. This is used for cleaning out ears but it also works great for foreskins. Just pull your foreskin forward and insert the nozzle of the bulb syringe inside and squirt. Water will squirt back into your foreskin and clean it out. You can wash out all of that accumulated smegma.
if you use some lube and start to move the skin back and forward your foreskin will
loosen up enough for you to retract over the glans. try to soak it in warm water and then
pull the foreskin by the tip outwards and then pull back over the head. My friend does this and
he is happy now.