In short, yes. For the rest of their lives to some extent. In the absence of the proper structures of extracellular matrix telling your body that this thing is supposed to exist, it treats it like a wound and tries its best to heal it.
Now there is a certain point at which the dilation schedule becomes much less intensive and more livable, but it's typically a lifelong thing.
Once tissue engineered vaginal implants become a thing for transwomen, this might change. But with existing tech, that's the way it is.
