Below are OPINIONS from the WikiAnswers Community.

  You know deep inside this is not normal behavior for your son and most young men don’t go around dressing up like a girl. It’s time to sit down with your son and ask him straight out if he feels he is gay. He may not know what he is at this point and there is no shame in that. He may simply be a “cross dresser” which means he likes to wear women’s clothing. I just saw a program on cross dressers and the men led perfectly normal lives … were married, had children, went to work and once he was home, the kids were in bed, he dressed up in women’s clothing. Some of the wives accepted it and lived with it and others couldn’t cope with it.

Whatever happens, be blessed he’s alive and healthy and if gay, support him all you can, and if he wants to dress up in women’s clothing in private then accept that, but it’s highly dangerous for him to dress up like a woman for the summer. His peers could be very cruel and harmful to him. I don’t think your son realizes this.

Try talking your son into seeing a psychologist to straighten out his thoughts (not straighten out who he is inside!)

  Start small. Dress up at home, maybe go shopping dressed up like a girl. Maybe a weekend trip full time as a girl. And sure, why not spend a summer as a girl while he can still pass for one. Get lots of pictures.

Your approach and handling as appropriate would/should vary depending on how old your son is. However, as a lifelong transvestite I am quite certain that no matter what his age, if he has asked to dress as a girl all summer, he already knows very well “what it is like” and he likes it very, very, verrrryyy much! I would also guess from his request that he is at least 13 years old. If so, he is old enough to already know what he wants and he is probably wondering whether he is a transvestite or a transexual. He could not pick a better age to get the answer to that question. In my opinion, here is the bottom line: Eventually he will indulge in crossdressing somehow, someplace, sometime and the sooner the better by his deepest desires. If your son was going to drink alcohol and smoke pot no matter what, would you not prefer that he do so at home under your watchful eye, rather than someplace outside the house with people you do not know and may never meet? Consider yourself facing that question because that could be your and his reality. You have two options: 1) the WRONG one: disown him, or 2) the no-brainer RIGHT one: embrace him and his crossdressing desires with all your love and support. If the social wisdom and maturity level of our society had been what it is today when I was his age, and my mother had been able to know about and embrace my crossdressing desires, I would have stayed out of a heck of a lot of trouble, felt good about myself growing up, probably would have gotten straight A’s all through school and been the picture of absolute success, happiness and wealth from then on.

There are two broad classes of boys who crossdress. One are simply crossdressers (which has replaced the older term, transvestite) and the other are transsexuals. Crossdressers enjoy experimenting with wearing the clothes of the opposite gender. This can start about age 4 or 5 but can arise at any time. Usually, crossdressers come from families where the mother has a stronger relationship with the son than he has with his father and where women are seen as the dominant gender. Sometimes, the son gets the impression that the mother wanted a girl instead and there are instances in which a boy may be crossdressed by such mothers at an early age. By contrast, transsexuals feel they have been born into the wrong body. Research indicates that this “gender identity” is formed in the child’s brain before birth and that the child has what is known as Gender Identity Disorder (GID). This is a lifelong disorder and if not treated, sometimes leads to suicide if the child’s depression is severe. A mental health professional, preferably as psychiatrist, can diagnose GID, and there are established procedures for dealing with this disorder.

  Why not let him dress like a girl for summer if he wants to experience it? Though if he is 12 or older I think he already knows why he wants to do this and feels like a girl anyway.

  This is wrong, boys are boys they should not dress in girls clothing. If my son asked me if he could do this, I would say no and we would have a very serious discussion on how wrong it is if he is younger than 16.

  Give him some time to think about it. If he still wants to then let him try for one day. You should let him borrow your clothes the first day, and if he tries it and still wishes to dress as a woman, you could then by him his own clothes. Like the first answer stated, you need to be careful.