Crying upon awakening from nap

I teach at a Montessori School...we just enrolled a 3 yr old boy a couple of days ago, that was in an abusive school...he was just diagnosed with SPD a couple of days ago. I don't have many problems with him except when he awakens after nap. It is very difficult for him to go to sleep, and I just happened across applying pressure to his back to help him fall asleep. I just instinctively did it. (I was rubbing his back and when I did it harder, he calmed down) My problem is waking him up. He becomes very upset. He cries uncontrollably, when he gets to a certain point he wants his stuffed animal.

This is a classroom, so I am not allowed to give him his "lovie", as the other children will want theirs, too. I have thought about just allowing him to cry it out, but I'm not too keen on that idea unless it is the right thing to do. Can somebody give me some pointers? When I wake him up, the lights are already on, should I wake him slowly before the lights are turned on, maybe before the other children? Should I just give him the stuffed animal? I'm at a loss, and I don't want to try anything and upset him further...