So, today this happened:
We've had his big boy bed set up for a few months now, but I've been delaying the inevitable assuming that the transfer would be long and hard for both of us. I pictured dragging him screaming into the bed, closing his door, listening to long hours of crying while he fought sleep in a new environment and finding him asleep on the floor next to the door. In reality, he asked to take his nap there this afternoon, he cried a bit when we first closed the door, but less than 20 minutes later we found him asleep in the bed.
Bed time was even smoother. (Knock on wood-I realize we have a full night ahead of us)
Part of me wants to jump for joy that the transition seems to be going so smoothly. The other part of me is ready to scoop him up and rock him to sleep again. It seems like just yesterday we put him in his crib for the first night. He fit the short way and each time I lay him down, I would rub his back and wait for his deep sighs and heavy breathing. Two years later I'm fighting back tears as I sneak into his big boy room and listen for the same things.