We have an older ten pound dog and a younger pup that is now 60 pounds. They were about the same size when we got the younger pup. We supervised them carefully as recommended above. We kept the younger dog on a long rope in the house at first for house training purposes, but it also allowed the older dog to get away from him if he needed to. The older dog did a great job socializing the pup & instructing him on what behavior is acceptable and what is not.
They still play together, but the smaller dog can back off the bigger dog with one growl. I found the smaller dog tugging on the larger dogs' ear the other day. I sometimes scold the big dog if it looks like he is being too rough with the little guy, just so he knows there are limits. The big guy is very attached to the older dog and now they sleep together every night. It is nice that they have each other when we board them (they sleep in one enclosure when boarded).