This is a good topic, but even hypothetically it would really need some clarification. The biggest question I would have is the age of the boy. You say you would both be aware of the others cd'ing, but is this a 7 or 8 year old that is saying I'm a girl. A thirteen year old with raging hormones that wants some lace panties, or maybe 17-19 year old that wants a skirt and top. There are just so many variables here, but i would try to be supportive in any case.
