This doesn't quite seem normal. For the most part, a dog's anal glands should not need to be expressed manually (by someone else) unless there is something structurally wrong and they cannot express them on their own. They should express naturally if the dog is having good, firm poos - as the poo pushes against the glands and empties them. If, however, the poo is not always firm and/or the dog is eating a food that is irritating the system (and, therefore, overfilling the glands) - this can cause problems.
So, I'd look very closely at what you're feeding and consider if a switch might do some good. But also, bc what is happening with your baby (ie, possible loss of control) - I'd get it checked by the vet.
I would try to avoid getting into a habit of your baby needing manual expression - this can cause the glands to stop doing what they naturally do and become entirely reliant on humans to do it for them. In worse cases, it can damage the glands. I would try to see if you can get him back to functioning normally.
