son cross dressing

My 5 yr old son has been sneaking into my underwear drawer and trying on my bras and underwear then hiding them so I won't catch him doing it. I have had several loving discussions with him explaining that I don't want him in my things etc, but really I am very concerned about the behavior. He says he likes the "softness" but I think there is more to it. He can't explain why he keeps doing it even though he knows I don't want him to. He seems to be sensitive and can cry easily although not at school or around friends. He is well liked with peers of both sexes and very bright (reads at 4th grade level , excellent in math also. He started kindergarten this last year). In all other aspects seems happy and well adjusted, confident. When I confront him, he starts to cry and promises not to do it again. I've changed my drawers to make it more inconvenient for him but it still continues and i feel it is becoming a compulsion.  I also find the sneakiness disturbing as he is pretty open otherwise. How do I handle this? Thank you

[Kevin Kennedy, Ph.D.]

The focus should be on his disobedience, on his failure to adhere to your directions. Let him know that, should there be a repeat of his going in your room without permission (for whatever reason) he will receive a time out (probably around fifteen minutes) and lose a privilege (something that he particularly favors). Given that his overall developments appears to be positive, I don't think you need to focus on the specifics of the behavior. Should the straightforward limit-setting fail to curb the behavior, seek an evaluation by a pediatric mental health clinician.

[f13]

A related discussion, autism and cross dressing was started.