Hmm, have you changed his food lately or added anything new? If he's a puppy, it sounds like maybe his glands may be irritated. If possible, you do want to
avoid getting in the habit of having a human empty them - bc, ideally, they shouldn't really fill up too terribly unless they're eating something that isn't agreeing with their system, or if there is something structurally amiss. Otherwise, a dog's nice firm poo should push out anything in the glands, thereby avoiding human intervention.