I truly believe that both of you would greatly benefit from reading the following book.
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True Selves: Understanding Transsexualism--For Families, Friends, Coworkers, and Helping Professionals
I purchased a copy for work and during a meeting where I announced my transition I said that this book will be on my desk if anyone wanted answers and of course said feel free to chat with me too. Both have happened and from feedback the book helped many come to terms with my transition that were unsure.