SHERRILOVE answered question 4/30/2007 If Your Son Wants A Sex Change And His Therapist Suggests Allowing Him To Try Dressing As A Girl This Summer, Would You Allow Him To? If So, How Feminine Would You Permit Him To Look? If your son really wants a sex change, than dressing like a girl should be no problem for him. Try girly jeans and tanks for starters. Take it slow.