Mom's I need your help, bedtime question, C.I.O?

Ok I rock my 1yr old to sleep at the same time every night, he brings his blankie and pacifier and wants to be rocked, which was working out fine until just recently, he wants to rock but it takes a good hour or so for him to finally fall asleep, he puts his feet in my face, he touches my face, plays with my hair until, I fuss and he closes his eyes and goes to sleep. I'm thinking about maybe just starting to put him in his crib and let him fall asleep but I know he will cry and I will feel guilty. Do you think maybe its time I try just putting him in his bed? How should I handle him crying if I do this?