Changing rear brakes, caliper boot wont go in smoothly

[97avy]

Hey guys! This is the first "real" job of done on my Avalon..Oil changes dont really count as real work. My rear brakes started squealing, and the pads were almost gone, so I picked up some pads from a local parts store. The rotors are good, so I was only going to change the pads.

While retracting the caliper piston (to make room for the new pads) the boot, will not go smoothly into the caliper, it will "pop a bubble out". After the 3rd try it finally went into the right rear caliper, but for the left rear, I cant get it to go in.. Has this happend to anyone before? Any suggestion?

Ive changed brakes many times on many cars, but never had this happen to me. I've dealt with seized calipers, but never had the piston go in smoothly, and then have the boot not. So its a first timer for me..

Thanks in advance everyone.

[silverxls]

i've seen that happen before. the rubber boots get old and brittle too, and won't fold back in properly. it usually means it's time to get new boots too.