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Originally Posted by Charlatan
My son played dress up with he was two or three and he'd wear dresses. He's 13 now and wouldn't be caught dead in a dress. That said, a group of girls put nail polish on him recently and he's still wearing that (although it's quite chipped).
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Your son is playing along because he thinks he'll get some if he plays along with the girls who are flirting with him.
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Originally Posted by sapiens
Back to the OP: What kind of harm will be caused by letting a boy wear a dress?
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I never wore dresses, but I was always the kid who enjoyed being weird and standing out. My parents tried to guide me toward acting more normally, but I wouldn't have any of it. I had very few friends through elementary and middle school, making a few more friends, mostly fellow nerdy or weird outcasts, along the way. In high school I ended up with a big group of friends who, looking back, accepted that I hung out with them (to the extent that my mom would let me hang out with the weird people,) but never really liked me. I always had high hopes of being successful and I figured that the people who said that being myself was the way to do it were right.
Those people were full of shit. I made no new friends in my first year of college and made no progress in life. My second year, I saw that one of my friends from high school was in the Student Government room and I went in to say hi, I never left. I was quiet at first, but slowly I started acting like a "normal" person, keeping my interests but adapting to social norms that you have to fit into to be around normal people. Over the next few years I realized that I should have tried a bit better to fit in. My parents told me what I had to do but never fully explained why (my dad worked long hours and was tired when he got home, my mom did most of the raising the kids but never really understood me, what I got from my dad was the stuff that helped me the most because he understood more about how to get me to understand than my mom did.)
Did I enjoy being the weird kid when I was? Hell, yeah. Would I do it again? Fuck, no! If I could go back and do it all over again, I'd spare myself the verbal and physical abuse of other kids, being a social outcast, and if I did it just a little differently, I'd still have the friends that I'm still in touch with today and wouldn't have wasted so much of my life. There should be some individuality, but there are basic things you have to do to get by. The parents need to explain to the kid that individuality is important, but there are certain things you just have to do. If he hits puberty and it's looking like he's genuinely transgendered, that's when they need to get him professional medical consultation and psychoanalysis/therapy to help him either deal with living as a man or prepare him for a big change when he's an adult.