One school of thought is that a child, who is raised with diversity, will become much more accepting of diversity in others. Frankly, I do not buy into that, for if the child is "raised" with it, it is not diversity. It is the norm. When he/she gets old enough to see that other families may not be the same, the other families have the "diversity." Creating a child who is accepting of diversity is a function of learning and watching what the parents do when faced with outside diversity. The fact that dad may wear a skirt and cook the meals and Mom does the routine maintenance on the car is perfectly normal when it is Mom who generally ferries the child to and from activities. Now, I said I "don't buy into that." That is, I do not buy into the fact that it makes the child more accepting of diversity. But I do accept that what the child is raised with as "normal" will be "normal." We raised our youngest with Dad "dressing" upon occasion. It was the "norm" in our household. (And it was not questioned until he reached his teen years. I am not sure we did well with it then, but I would hope that today's experiences we would do better.) I currently know of several families in which the children are regularly even out with dad dressed. They have been raised with it all their lives. It is normal to them. "Normal is good," but the concept that it makes them more accepting of diversity is invalid.
Other families wait until the child is "mature enough to handle it." That is a "subjective" call on behalf of the parents unless the child has been exposed to "gender discussions" all of its life. If "gender talk" has been going on for many years, and the child has been exposed to other gender issues, you might have a reasonable handle on how it will be accepted by your child. However, you are throwing in an "unknown," as this IS "Dad." And "Dad" is already a preconceived notion in the child's mind. So, while you may have spent many years in discussion on gender issues, it takes on a new life when you introduce "Dad" into the equation. Age and maturity evaluations go out the window...and objectivity! This child already has a life experience of who and what "Dad" is, and it does not necessarily mesh with gender issues. Understand that to a child this age, "diversity" in today's norm, may equal "Cool" in our vernacular. But the jury is still out on just how this will impact in the future.
Ok, I have tackled the two most obvious choices. Either raise the child with the crossdressing, or wait until "maturity" sets in. And on both counts, I have given you the negative side that can result
Let us approach this with a different frame of mind. What do YOU expect to gain by telling your child that you are a crossdresser? Let me digress here a moment. I was five months pregnant with my first child when my father was killed. This was devastating, not just from my perspective, but from the perspective of my unborn child. This child would never know "Grandpa." And Grandpa would never have a chance to hold this child. As "Daddy's little girl" I had dreamed of the day when I could "present" my newborn child to "Grandpa," and now it was never going to happen. FOUR months was all I needed, but was not going to get it. Life sometimes deals lemons, and that was what I had gotten. One day I woke up and realized that neither the child nor the grandparent was going to realize this loss. It was all about ME! I was the one feeling the loss, not either of them. And with that revelation, I have since looked at things with the philosophy of "What do I expect to gain/lose from this?" When I could realize that it was all about ME, I found that taking alternate paths was a viable choice. So, let me ask you. What do YOU expect to gain from telling your child that you are a crossdresser? Our greatest motivation is what AFFECTS US, not others. And, that applies equally to our children. So, stop here. Honestly look at yourself and consider what it is that YOU want to achieve by telling your child that you are a crossdresser? In most cases, unless there is an "accidental" discovery, the decision rests solely in YOUR hands. And so does the motivation. (And do not discount that that "accidental" discovery could still be of your own manipulation.)
The child is not asking for this information. At birth, the child is not stating a preference for one life style or another. In adolescent or "mature" years, it is still all about what YOU are wanting. NEVER has the child raised the issue of a crossdressing father, it is all about YOU.
Gypsy Rose Lee had one. Shirley Temple had one. Jon-Binet Ramsey had one. Yes, we are talking about "stage mothers." These parents vicariously wanted to relive their own life through the lives and experiences of their children. When I hear of a crossdressing father of a pre- or adolescent daughter, and who suddenly "breaks ranks" with the perceived agreement with the mother of this child, deciding that the 13-14 year old daughter now suddenly has a "need to know" of his crossdressing, I shudder! Dad, get hold of yourself! As much as you might like, you cannot vicariously live the experience of being a "young teen-aged girl" through your daughter! She cannot tell you how tender her budding nipples are. She cannot explain how her womb begins contracting in cramps with an upcoming menstrual flow. And as much as you would like to "hear" how this feels, you are doing your young daughter a terrible disfavor!
This is the one time in her life that your role as "Dad" is most important! As she begins to develop sexually, anthropologically (i.e. from all of her natural genetic and environmental learning's,) she is also starting to develop a concept of what an ideal "mate" will be. YOU are that role model...either positively or negatively. YOU hold the key to her choices in a mate for the rest of her life. It is in YOUR hands as to what she perceives as an "ideal." It is perhaps your MOST important role as a father to a daughter. You do not know that. You have never been a daughter. You have no idea of just how important the role your display will mold her choices many years from now. But they will! Your fidelity to her mother, your work ethic as pertains to profession, your financial acumen, your reliability factor, your stability, your physical prowess, your mechanical or technical abilities, your educational level, and your emotional involvement will ALL shape the person she picks as a mate. Your role as "role model" is your biggest challenge in raising a daughter! I am not saying that should she pick a crossdresser as a mate, it could be the biggest mistake in her life. I AM saying that crossdressing is such a minor aspect to her future happiness. You need to focus on what really need to be the defining aspects in her seeing you as an "ideal mate." And then going out and seeking those same attributes.
The bottom line is that YOU hold all the cards. You choose what and when to introduce this into your child's life. THEY did not pick to be raised with it. THEY will have some of the same issues as your wife if you wait until adulthood. And if YOU choose to vicariously live through your daughter, you could be doing her the biggest disservice of your and HER life! Just recognize, what is it that you want to achieve in telling your children. And then think about what is actually achievable! The jury will be out for a VERY long time, and you may not know the verdict until 40 or 50 years from now.