My middle child was like that... she would rather play side by side than with other kids (normal at that age), but when they included her she just did what anyone told her to. I sat back and watched for a few months. After all, she had her big sister to speak for her and didn't feel the need to voice her own opinions. Finally one day, she was playing with a group (sister included) and decided she wasn't going to be bossed around anymore. She told her sister what SHE wanted to do, and the other kids told her that they didn't want her playing if she wasn't going to play by their rules. Well apparently enough was enough, and she punched her sister (the ringleader) square in the face with her little fist. While she shouldn't have hit someone, I wasn't even mad, because it was the first time I had ever seen her stick up for herself. My point is, your son will come around in his own time when he decides that he wants things his way. The shoe WILL go on the other foot. Hopefully, with your guidance, he'll be taught there's a time and a place to assert himself... my daughter is now 'that bossy kid'... we're working on it ;)