This paper describes a digital interactive book targeted at 10-14 year old boys which aims to educate about how the voice develops during puberty. The contents are based on a conventional print book for adults. The D-book has an advocacy as well as educative role—it attempts to argue in a “boy friendly” language that singing is part of a rounded and fulsome boyhood. It has had to consider carefully how this might be communicated to a potentially skeptical young audience. “Boy friendly” literature has been condemned by the critics of right wing recuperative masculinity politics. The paper therefore critiques the picture of boyhood that has been conveyed and discusses the justifications for the compromises that have been reached.